3rd CQM Annual Meeting Abstract Book

Transcrição

3rd CQM Annual Meeting
Abstract Book
01-02 April 2016
Funchal, Madeira Island – PORTUGAL
Abstract Book
Editor
Centro de Química da Madeira
Address:
Centro de Química da Madeira
University of Madeira
Campus da Penteada
9020-105 Funchal (Portugal)
Website: http://cqm.uma.pt
Twitter: http://twitter.com/UMa_CQM
Facebook: http://on.fb.me/gqSeD9
LinkedIn: http://bit.ly/LinkedIn_CQM
Edited by
João Rodrigues
Catarina Silva
Rosa Perestrelo
Énio Freitas
Organizing Committee and Secretariat
Catarina Silva
Rosa Perestrelo
Énio Freitas
ISBN
978-989-20-6547-2
The content of this publication can be used on the condition of full acknowledgement and citation of the source.
(March 2016)
2
01-02 April 2016 | Funchal, Madeira Island - PORTUGAL
Index
About CQM ............................................................................................................................................... 5
Program .................................................................................................................................................. 11
Oral Communications.............................................................................................................................. 15
Nanotechnology in the fight against infectious diseases - The case of Dengue and Zika ...........................17
Understanding lipid/carbon interaction for the rational design of biomaterials ........................................18
Optimizing selectivity in the development of a chromatographic method LC.............................................19
Volatomic fingerprint of breast cell lines .....................................................................................................20
PEGylated PAMAM dendrimers: extent of cell uptake, endocytosis mechanisms and final fate ...............21
Non-invasive approach to establish the volatile metabolomics pattern on asthmatic children ................22
Biodegradable Amine-modified Dendrimers as Drug/Gene Nanocarriers - Preliminary Results................23
Azedas (Rumex maderensis) as a dietary source of compounds with activity on digestive enzymes
linked to type II diabetes: an in vitro study ..................................................................................................24
Blue fluorescent PAMAM dendrimers for biomedical application ..............................................................25
GC-MS on profiling passion fruit volatiles. An effective tool to discriminate between species and
varieties ........................................................................................................................................................26
Facile synthesis of hybrid DNA/cationic polymer films ................................................................................27
Caffeoylquinic acids as enzymatic inhibitors, from in silico hypothesis and target acquisition to in
vitro mechanism of action ............................................................................................................................28
Microextraction and analysis of bioactive compounds in food matrices from Madeira Island ...................29
Ultra-high Performance Liquid Chromatography method development for determination of
oxidative stress biomarkers caused by hyperhomocysteinemia..................................................................30
A concise history of Kurdish Jewish mtDNA lineages through the assemblage of HVS-I, -II and -III
gene sequences ............................................................................................................................................31
Brewer’s spent grain as a source of ferulic acid ...........................................................................................32
Antifungal activity of Helichrysum devium extracts .....................................................................................33
Preparation of a new family of poly(alkylidenamine)s dendrimers with different functional groups........34
Generation 0 and 1 of new PAMAM dendrimers with different terminal groups. Synthesis and
characterization ............................................................................................................................................35
3
Simultaneous quantification of carotenoids and tocopherols in tomato by LLUSAE/UHPLC using PDA
and FLR detection .........................................................................................................................................36
Electroactive properties and biological applications of electrospun PVDF polymer ...................................37
Authors Index ......................................................................................................................................... 39
Participants List....................................................................................................................................... 43
4
About CQM
Governance Structure
Executive Committee
João Rodrigues | Scientific Coordinator
Helena Tomás | Materials Group Director
José S. Câmara | Natural Products Group Director
Management
Emília Pimenta | Project Manager
Énio Freitas | Secretariat
Bruna Pereira | Director of Communication
Paula Andrade | Administrative and Technical Staff
Permanent External Scientific Advisory Commission
Professor José Martinho Simões
Full Professor FCUL- Faculdade de Ciências, Universidade de Lisboa, Portugal
Professor Gordon Cragg
Retired Chief, Natural Products Branch, National Cancer Institute, USA
Professor Makoto Fujita
Full Professor, Department of Applied Chemistry, University of Tokyo, Japan
5
Organizattional Structure
6
3rd CQM Annual Meetin
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02 April 2016 | Fuunchal, Madeira Island
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Vision and Mission
Our Vision
Making the CQM a renowned research institution in the field of Natural Products and Materials.
Our Mission
CQM – Centro de Química da Madeira/Madeira Chemistry Research Centre – constitutes a central element
in the promotion and enlivening of R&D activities in the field of Chemistry and Biochemistry in the
Autonomous Region of Madeira, Madeira Island, Portugal. CQM is firmly interested in the development of
advanced training, partnerships with national and international institutions, offer of services to the
community and in the popularization of science.
Our Philosophy
To be a relevant part of a scientific community that performs world-class research aimed at improving the
scientific knowledge and the well-being of the Society.
Working Areas and Research Groups
CQM is organized in two interdisciplinary research groups – Materials and Natural Products –
developing its R&D activities in the fields of Analytical Chemistry, Food Chemistry, Health, Materials,
Molecular Modelling, Nanochemistry, and Phytochemistry.
Our Logo
The CQM logo is composed of different colored petals, each one
representing various areas of chemistry and biochemistry working
together to improve scientific knowledge and contribute to the wellbeing of Society.
7
CQM Com
mmitments and Princiiples
ws the ruless of Fundação para a C
Ciência e a Tecnologia
T
(FCT-IP), thee European Charter forr
CQM follow
Researcherss and the Co
ode of Condu
uct for the RRecruitment of Researchers (Commisssion Recom
mmendation,,
Brussels, 11
1.3.2005, 200
05/251/EC) since
s
2008, b
being comm
mitted to the
e principle off equity in employment
e
t
and selectio
on based on
n merit.
ws the Code
e of Conductt from the U
University off Madeira an
nd is strong ly committe
ed to all the
e
CQM follow
European regulation related to the ethica l, legal and
d social aspects (ELSA
A) and gov
vernance off
ology, name
ely with the COMMISSIO
ON RECOMM
MENDATION of 07/02/20008. CQM alsso voluntaryy
nanotechno
follows thee Code of Conduct
C
for responsiblee Nanoscien
nces and Na
anotechnoloogies researrch and the
e
opinion of the Europe
ean Group on
o Ethics in
n Science and New Tecchnologies concerning the ethicall
Nanomedicine.
aspects of N
c
att CQM is in close collaboration withh the local Hospital,
H
and
d
Part of the research thaat is being conducted
c
faciliity at CQM aallows the biiological eva
aluation of tthe develope
ed materialss
the existence of a cell culture
mpatibility studies,
s
genee delivery studies). In pa
articular, aduult human sttem cells are
e
at Madeira (e.g. cytocom
d in the studies with th
he authorizaation of the
e Local Ethiccal Committtee and respecting the
e
being used
national and European rules.
8
3rd CQM Annual Meetin
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01-0
02 April 2016 | Fuunchal, Madeira Island
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- PORTUGA
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CQM – mo
ore than 10
0 years of proud
p
Histo
ory: Building now ou
ur dream fo
or the nextt 10
adeira Chem
mistry Research Centre (CQM) was founded more
m
than a
The Ma
decade ago by a haandful of Ph..D. researche
ers with the firm desire to establish
h
nter in the fiield of Chem
mistry at the
e
an internationally reecognized research cen
University of Madei ra. The Center, which iss regularly eevaluated byy a panel off
upport throuugh highly competitive
e
international expertts, receives financial su
ms granted m
mainly by the Fundação para a Ciên cia e a Tecnologia (FCT))
program
ARDITI, and
a by Euro
opean fundin
ng agencies.. As a result oof all the sciientific workk
develop
ped within th
he Center, th
he support and
a servicess it provides to industry,,
and its numerous
n
sscientific dissemination activities (“A
A Química é Divertida”,,
Bridging
g the Gap” a nd “ScienceShop”), CQM
M has amasseed a large body of workk
over the
e past decaade being considered
c
a Center off reference both
b
at the
e
regionall and nationaal levels.
Taking into
o consideration the exxperience an
nd knowled
dge of the founding m
members of CQM, new
w
strategies w
were defined
d for the gro
owth and deevelopment of the Cente
er for the neext five years, always in
n
the contextt of the Autonomous Region of Maadeira. We aim
a to enhan
nce the quaality and visibility of the
e
research do
one in the Center, contributing to th
he strategic and interna
ational posit ioning of the Universityy
of Madeira (UMa), the Region
R
and the
t Country..
With reseaarch falling under two
o key policcy areas, namely Natu
ural Produccts, and Ma
aterials, the
e
multidisciplinary CQM research un
nit has man
naged to pu
ublish since 2004 over 2263 papers in specialtyy
journals. Also, both re
esearch line
es have estaablished strong interna
ational collaaborations with
w
severall
research en
ntities and universities in the Maccaronesian Region,
R
as well
w as in C
China, India,, and Brazil..
Acco
ording to a bibliometric studyy
cond
ducted by FCT, and taking into
o
acco
ount all areaas of scientiffic expertise,,
the productivityy of the CQM per FTE full-ttime equivaalent (18.42
2) over the
e
perio
od of 20088-2012 was one of the
e
high
hest in the ccountry. Inde
eed, 53% off
the papers publlished in the
e considered
d
od, were in tthe top 10%
% of journalss
perio
specialized in the strate
egic areas off CQM resea rch, while 30
0% of the pa
apers were p
published in the top 5%..
ber of citatio
ons per FTE o
obtained byy CQM clearly
y stands outt from all oth
her research
h
Furthermorre, the numb
centers in P
Portugal. In the
t most reccent internaational evalu
uation condu
ucted by FCTT, the CQM got
g 22.5 outt
of a maximum of 25 po
oints. Based on these reesults our Ce
enter has clearly demonsstrated that despite stilll
nd located i n an outerm
most region of Europe, it has been possible to
o
being very young, smaall in size an
004.
achieve thee dream thatt began in 20
ly 60 researcchers (includ
a
ding 15 Ph.D
Ds.,13 Ph.D. sstudents and
d 16 Masterss
Made up off a team of approximate
students), w
with 34 papers publishe
ed in 2015 ( including on
ne paper in the journal Chemical Reeviews), and
d
with ca. of one million of euros off contracts aand grants obtained
o
lastt year, CQM is now sought after byy
nd researche
ers from all around
a
the w
world.
students an
he CQM is no
ow facing its greatest c hallenge - growing
g
in a
Having passsed the initial phase of creation, th
sustainablee manner. Ho
owever, as CQM
C
coordin
nator since 2006,
2
and as one of its foounding me
embers, I am
m
convinced that we willl achieve our aims as a result of the
e efforts of all
a team mem
mbers, partiicularly with
h
3rd CQM Annual M
Meeting
01-02 April 2016 | Funchal, Madeirra Island - PORTU
UGAL
9
the inspiring enthusiasm of the younger ones. I also believe that through the implementation of our
strategic plan, thinking out of the box, we will continue to serve the Autonomous Region of Madeira,
playing a crucial role in research and technological development, training people, creating jobs and
contributing to open the doors of the region to the world.
University of Madeira, Funchal, 1 of April 2016,
(João Rodrigues, Scientific Coordinator of CQM)
10
Program
Friday, 01st April 2016
9:00
9:30
Participant Reception
9:30
10:30 Opening Session
10:30
11:10 [O-2] Nanotechnology in the fight against infectious diseases the case of dengue
and zika
Carla S. Alves, Helena Tomás, Miguel A. R. B. Castanho and João Rodrigues
11:10
11:30 Coffee-break
11:30
11:55 [O-16] Understanding lipid/carbon interaction for the rational design of
biomaterials
Joana M. Vasconcelos, Federico Zen, Daniela Angione and Paula Colavita
11:55
12:25 [O-20] Optimizing selectivity in the development of a chromatographic method LC
Rosa Patela and Sandra Cachopo
12:25
13:55 Lunch
13:55
14:20 [O-19] Volatomic fingerprint of breast cell lines
Catarina Silva, Helena Tomás and José S. Câmara
14:20
14:40 [O-13] PEGylated PAMAM dendrimers: extent of cell uptake, endocytosis
mechanisms and final fate
Ana Olival, Rita Castro, João Rodrigues and Helena Tomás
14:40
14:55 [O-8] Non-invasive approach to establish the volatile metabolomics pattern on
asthmatic children
Pedro Berenguer, José S. Câmara and Irene C. Camacho
14:55
15:20 [O-14] Biodegradable amine-modified dendrimers as drug/gene nanocarriers Preliminary results
Mara Gonçalves, João Rodrigues, Yulin Li and Helena Tomás
15:20
15:45 [O-1] Azedas (Rumex maderensis) as a dietary source of compounds with activity on
digestive enzymes linked to type II diabetes: an in vitro study
Vítor Spínola and Paula C. Castilho
15:45
16:05 [O-3] Blue fluorescent PAMAM dendrimers for biomedical application
Cláudia S. Camacho, Helena Tomás and João Rodrigues
11
16:05
16:20 Coffee-break
16:20
16:35 [O-18] GC-MS on profiling passion fruit volatiles. An effective tool to discriminate
between species and varieties
Priscilla Porto-Figueira, Ana Freitas, Catarina Cruz, José A. Figueira and José S. Câmara
16:35
17:00 [O-15] Facile synthesis of hybrid DNA/cationic polymer films
Rita Castro, Pedro Granja, João Rodrigues, Ana Paula Pêgo and Helena Tomás
17:00
17:20 [O-7] Caffeoylquinic acids as enzymatic inhibitors, from in silico hypothesis and
target acquisition to in vitro mechanism of action
João Serina, Paula C. Castilho and Miguel Fernandes
Saturday, 2nd April 2016
12
10:00
10:30 [O-9] Microextraction and analysis of bioactive compounds in food matrices from
Madeira Island
Jorge Pereira and José S. Câmara
10:30
10:45 [O-12] Ultra-high performance liquid chromatography method development for
determination of oxidative stress biomarkers caused by hyperhomocysteinemia
Liliana da Silva Rodrigues, José Sousa Câmara and Helena Caldeira Araújo
10:45
11:00 [O-21] A concise history of Kurdish Jewish mtDNA lineages through the assemblage
of HVS-I, -II and -III gene sequences
Catarina J. Cruz, Sara C. Gomes, Alexandra Rosa and António Brehm
11:00
11:15 [O-5] Brewer’s spent grain as a source of ferulic acid
Pedro Ideia and Paula C. Castilho
11:15
11:30 Coffee-break
11:30
11:50 [O-10] Antifungal activity of Helichrysum devium extracts
Sandra Agrela, Paula C. Castilho and Irene C. Camacho
11:50
12:15 [O-4] Preparation of a new family of poly(alkylidenamine)s dendrimers with
different functional groups
Dina Maciel, María de los Ángeles Múñoz-Fernández, Helena Tomás and João
Rodrigues
12:15
12:30 [O-6] Generation 0 and 1 of new PAMAM dendrimers with different terminal
groups. Synthesis and characterization
Nádia Nunes, João Rodrigues and Helena Tomás
12:30
12:50 [O-17] Simultaneous quantification of carotenoids and tocopherols in tomato by
LLUSAE/UHPLC using PDA and FLR detection
José A. Figueira, Priscilla Porto-Figueira and José S. Câmara
12:50
13:05 [O-11] Electroactive Properties and Biological Applications of Electrospun PVDF
Polymer
Xiang Yao, Ana Olival, Pedro Pires and Helena Tomás
13:05
13:20 Closing Session
13
Oral Communications
15
16
[O-2]
Nanotechnology in the fight against
infectious diseases - The case of Dengue and Zika
Carla S. Alves1, Helena Tomás1, Miguel A. R. B. Castanho2 and João Rodrigues1
1
CQM - Centro de Química da Madeira, MMRG, Universidade da Madeira, Campus da Penteada, 9020105 Funchal, Portugal
2
Instituto de Medicina Molecular, Faculdade de Medicina, Universidade de Lisboa, Lisboa, Portugal
Dengue and zika are considered to be amongst the fastest growing re-emerging diseases to
date, with more than half of the human population presently at risk worldwide (1). Considering
this impact on public health, several strategies have been developed over the years to limit the
further spread of such vector-borne diseases (e.g., application of vector control methods). Of
crucial importance in the move towards the eradication of these diseases is the development of
novel medicines targeted directly at their causative agents, namely the dengue virus (DENV) and
the zika virus (ZIKV). Research here is ongoing and is focused on unraveling the mechanisms
associated with infection. Viral, vector and host factors have all been shown to be important
elements in disease transmission and are thus considered as potential targets for therapeutic
intervention.
In this presentation, the impact of infectious diseases on Global Health and the role of
nanotechnology-based tools in the fight against these diseases will be discussed. Progress in the
development of intervention strategies targeted specifically at dengue and zika will then be
highlighted, with focus finally being placed on the development of a nano-based therapeutic
agent that targets the initial stages of viral entry into host cells.
References:
1. World Health Organization (2014) A global brief on vector-borne diseases. WHO:1-54.
Acknowledgments: This work is supported by the Fundação para a Ciência e a Tecnologia (FCT) through the CQM
Strategic Project PEst-OE-UID/QUI/00674/2013. C.S.A. acknowledges the Associação Regional para o
Desenvolvimento da Investigação Tecnologia e Inovação (ARDITI) for a Post-doc Grant (002458/2015/132). The
Bilateral Agreement between Portugal/India (FCT/DST 2013/2015-Ref. 441.00) and RED CYTED 214RT0482 (Project
VIHVACD) are also gratefully acknowledged.
17
[O-16]
Understanding lipid/carbon interaction
for the rational design of biomaterials
Joana M. Vasconcelos, Federico Zen, Daniela Angione and Paula Colavita
School of Chemistry, Trinity College Dublin, College Green, D2 Dublin, Ireland
When a biomaterial is exposed to biological fluids a series of events occur on their surface after
implantation, starting with small biomolecule adsorption in the first seconds followed by cell
adhesion after a few minutes.1 The ability to control the first layer of biomolecules adsorbing on
the biomaterial surface is critical for preventing undesirable bioresponses such as thrombosis or
infection. Proteins and lipids are an example of biomolecules that adsorb on the biomaterial
surface after implantation. It is known that protein adsorption plays an important role as they
regulate cell adhesion and receptor binding; also, lipids can modulate surface-protein
interaction and determine the performance of biomaterials.2, 3 Understanding how lipids and
proteins interact with materials and which is their role in determining biocompatibility is
important to prevent undesirable bioresponses. Here we report a comprehensive study on the
interactions between model lipid assemblies and carbon surfaces using a combination of
spectroscopic and fluorescence methods. The adsorption of phosphatidylcholine (PC) /
phosphatidylserine (PS) liposomes onto amorphous carbon surfaces was investigated regarding
buffer composition and surface chemistry. Infrared Reflectance Spectroscopy (IRRAS)
measurements indicate PC/PS liposome adsorption on amorphous carbon (a-C) and hydrogendoped amorphous carbon (a-C:H) surfaces, while oxidized amorphous carbon (a-C:O) shows no
adsorption when a monovalent ion solution was used as a buffer. When a di-cation was added as
a counterion, the adsorption of PC/PS is seen for all a-C surfaces. Atomic Force Microscopy (AFM)
was performed in order to understand the type of adsorption on amorphous carbon surfaces. It
was showed that PC/PS adsorb on a-C surfaces as a mono/bi layer of phospholipids depending
on the surface chemistry and buffer composition. Finally ζ-potential measurements on a-C
surfaces gave insights about the electrostatic interactions between PC/PS liposomes and a-C
surfaces.
References:
1. Buddy D. Ratner, Allan S. Hoffman, Frederick J. Schoen and Jack E. Lemons, Biomaterials Science, Elsevier
Academic Press, London, 2 edn., 2004.
2. M. Malmsten and B. Lassen, Colloids and Surfaces B: Biointerfaces, 1995, 4, 173-184.
3. H. Lorentz and L. Jones, Optometry and vision science : official publication of the American Academy of
Optometry, 2007, 84, 286-295.
Acknowledgments: This work has emanated from research conducted with the financial support of Science
Foundation Ireland (SFI) under Grant Number 12/IP/1273.
18
[O-20]
Optimizing selectivity in the development of a chromatographic method LC
Rosa Patela and Sandra Cachopo
Waters Portugal, Edificio Atlantis - Avenida D. João II, 44 C, Fracção E, Parque das Nações, 1990-095
Lisboa, Portugal
e-mail: portugal@waters. com
In the process of development of chromatographic methods, which can be completed in weeks
or months depending on the complexity of the objectives, there are different stages tunable to
reduce time spent, increase productivity and get a result of enormous quality. The main
objective is to maximize the resolution (Rs) inherently UPLC technology, combining the reduced
particle size with a low-volume scattering, and further with parameters which modify the
selectivity and retention as the mobile phase and different column chemistries.
Therefore, the objective of Waters in this presentation is to show clear and simple new chemical
fillers based on both ligands with alternate selectivity and innovative particles with various
technologies that expand the range of available columns (BEH, HSS, CSH, CORTECS). And as for
the detection (Detector QDA), have very simplified tools to track each chromatographic peak to
ensure unequivocally robustness and confidence in the results obtained in the development of
methods for LC in different analytical applications.
Acknowledgements: ©2016 Waters Corporation.
Waters and The Science of What’s Possible are trademarks of Waters Corporation
19
[O-19]
Volatomic fingerprint of breast cell lines
Catarina L. Silva1, Helena Tomás1 and José S. Câmara1,2
1
CQM - Centro de Química da Madeira, Universidade da Madeira, Campus da Penteada, 9020-105
Funchal, Portugal
2
Faculdade de Ciências Exatas e da Engenharia, Universidade da Madeira, Campus da Penteada, 9020105 Funchal
Breast cancer (BC) remains as the most prevalent oncologic pathology in women having huge
psychological, economic and social impact in our society and the current diagnostic tools
present limited sensitivity and specificity. Nowadays, there is no single screening test that is
totally reliable and a number of tests can be combined to help an early breast cancer detection.
Metabolome analysis emerge as a powerful tool of information about the biological processes
that occur in the organism using several biofluids as a mean to discover new biomarkers or
disease diagnosis. The use of cell culture metabolomics allows the discovery of novel biomarkers
of pathological conditions and investigation of the metabolic pathways that produce them. The
aim of this work was to identify volatile organic metabolites (VOMs) being emitted or
metabolized by human mammary epithelial cells (HMEC) when compared with breast cancer
type as a mean to better understand the origin of metabolites from cells. Their establishment
relied on gas chromatography with mass spectrometric detection (GC–qMS) and solid-phase
microextraction in headspace mode (HS-SPME). It was possible to identify 46 VOMs in cell lines
analysed, belonging to several chemical families, namely alkanes, aldehydes, ketones, acids,
alcohols, among others. From these, 2-pentanone, 2-heptanone, 3-methyl-3-buten-1-ol, 1,2,4trimethylbenzene, ethyl acetate, ethyl propanoate, and 2-methyl butanoate were detected only
on cell lines headspace. Multivariate statistical methods were then used to verify the volatomic
differences between oncologic and normal cell lines in order to find related volatile metabolites
that could be associated with breast cancer, providing comprehensive information on volatile
metabolites as potential cancer biomarkers.
The characterization of these volatiles using GC-qMS approach is feasible and will contribute to
increase our knowledge about the cancer etiology and consequently improve the diagnostic
tools.
Acknowledgments: Catarina L. Silva acknowledge the Portuguese Foundation for Science and Technology (FCT) for
the PhD grant (SFRH/BD/97039/2013). The authors also acknowledge the Portuguese Foundation for Science and
Technology (FCT) through the CQM Strategic Project PEst-OE-UID/QUI/00674/2013, MS Portuguese Networks
(RNEM/2015) and HCV - New INDIGO EU Project (FCT reference: New-INDIGO/0003/2012).
20
[O-13]
PEGylated PAMAM dendrimers: extent of cell uptake,
endocytosis mechanisms and final fate
Ana Olival, Rita Castro, João Rodrigues and Helena Tomás
Nanomedicine approaches can be applied in cancer treatment by making use of different
nanomaterials as delivery vehicles for drugs. These nanomaterials should be designed to escape
clearance by the mononuclear phagocyte system (for this, they are often functionalized with
polyethylene glycol, PEG) and be able of overcoming several other biological barriers to reach
their target inside cancer cells, such as the cell membrane barrier, after preferential
accumulation in solid tumour tissues through the Enhanced Permeability and Retention effect.
Dendrimers are amongst the nanomaterials investigated for anticancer drug delivery, and in this
scope it is of extreme importance to understand their interaction with cells [1,2].
The objective of this project is to evaluate the influence of PEGylation on cytotoxicity, extent of
cellular uptake, endocytosis mechanisms and final fate of poly(amidoamine) (PAMAM)
dendrimers with amino termini. For that, generation 4 PAMAM dendrimers (G4) were labelled
with rhodamine B isothiocyanate (RITC) and conjugated with PEG arms at different ratios. The
studies were performed using the NIH 3T3 cell line. The obtained preliminary results point out
that there seems to be a correlation between the number of PEG arms in the dendrimer scaffold
and cytotoxicity (assessed through the resazurin reduction assay), as well as cellular uptake
extent (by measuring rhodamine fluorescence intensity in cell extracts). Assays using known
inhibitors for specific endocytosis pathways revealed the existence of mixed mechanisms of
entry into the cell. Subcellular fractionation showed evidences that the dendrimers can
accumulate in the nuclear fraction which is particularly noticeable for the higher dendrimer
concentrations used. These results were corroborated by fluorescence microscopy through colocalization of the labelled dendrimers with fluorescent organelle markers.
References:
[1] Duncan, R.; Richardson, S.C.W. Mol. Pharmaceutics 2012, 9, 2380-2402.
[2] Zhao, F.; Zhao, Y.; Liu, Y.; Chang, X.; Chen, C.; Zhao, Y. Small 2011, 7, 1322-1337.
Acknowledgments: We acknowledge the support of the Portuguese Science Foundation (FCT) through the project
PEst-UID/QUI/00674/2013 (CQM, Portuguese Government funds), and PTNMR-2015 (NMR Portuguese Network). A.
Olival acknowledges the Instituto de Emprego da Madeira for the Period of Training at CQM. R. Castro
acknowledges FCT for the PhD grant SFRH/BD/87465/2012.
21
[O-8]
Non-invasive approach to establish the
volatile metabolomics pattern on asthmatic children
Pedro Berenguer1, José S. Câmara1,2 and Irene C. Camacho3
1
Funchal, Portugal
2
Faculdade de Ciências Exatas e da Engenharia, Universidade da Madeira, Campus da Penteada, 9020105 Funchal, Portugal
3
Faculdade de Ciências da Vida, Universidade da Madeira, Campus da Penteada, 9020-105 Funchal,
Portugal
Asthma is one of the most common childhood disease in almost all developed countries. Its
incidence and prevalence in Madeira Island is high, 11% for 6-7 years old children and about
10% for 13-14 years old children (ISAAC’s study in 2002). Although the excellent advances in
medicine, there are no specific diagnosis method to detect asthma in childhood. Thus, better
understanding of its biochemistry can lead us to new techniques to its identification in patients
at an early stage. In this regard, the aim of this work is to evaluate the potential of a non-invasive
sampling procedure combined with solid phase microextraction (SPME) technique, gaschromatography-mass spectrometry (GC-MS) and multivariate statistical analysis (MVA) to
identify urinary volatile organic metabolites (VOMs) from atopic asthma patients in pediatric age
and healthy individuals as potential biomarkers of the disease. The most SPME influencing
extraction parameters were optimized using a univariate experimental design. An exhaustive
screening of the VOMs found in urine of asthma patients and healthy individuals was carried out.
Sixty two VOMs were identified and distributed by chemical families: alcohols, furans,
naphthalenes, organic acids, terpenes, ketones, benzenes, phenols, sulphur compounds and
miscellaneous. The obtained data matrix was submitted to MVA namely principal component
analysis (PCA) and stepwise linear discriminant analysis (SLDA) using a set of 55 VOMs. PCA
didn’t provide us an obvious separation while SLDA was responsible for 98.6 % of crossvalidated grouped cases correctly classified. Among others, ketones (e.g. 2,4-dimethyl-3pentanone, 4-heptanone, 2-heptanone and dehydro-β-ionone) and indole play an important
role in differentiation among asthmatic children from healthy individuals. Some of these
metabolites are linked to oxidative stress, but other pathways cannot be excluded.
Acknowledgments: The authors acknowledge the Portuguese Foundation for Science and Technology (FCT)
through the CQM Pluriannual base funding (Project UID/QUI/00674/2013) and MS Portuguese Networks
(RNEM/2014) for the financial support.
22
[O-14]
Biodegradable Amine-modified Dendrimers
as Drug/Gene Nanocarriers - Preliminary Results
Mara Gonçalvesa, João Rodriguesa, Yulin Lib and Helena Tomása
a
b
East China University of Science and Technology, Shanghai 200237, People’s Republic of China
The synthesis of dendrimers for biomedical applications gained importance since the mid-80s.
There are several dendrimers which are commercially available including poly(amidoamine)
(PAMAM), poly(L-lysine) (PLL), 2,2-bismethylolpropionic acid (bis-MPA) and poly(propylenimine)
(PPI) dendrimers [1]. PAMAM dendrimers are perhaps the most studied family of dendritic
polymers. On one hand, due to their well-defined structure and multivalency, they are promising
candidates for drug or gene delivery. On the other hand, their high toxicity, low solubility, as well
as low biodegradability prevent them from being perfect delivery systems [2]. In this respect, the
use of bis-MPa based systems seems to be more advantageous than PAMAM dendrimers since,
in contrast, they are expected to present low toxicity, high water solubility and biodegradability
[3, 4]. Due to these reasons, they are achieving a special attention from researchers all over the
world.
In this work, bis-MPA dendrimers are being studied as possible carriers for drug and/or gene
delivery. In a first approach, the dendrimers were modified at the surface by replacing the
terminal hydroxyl groups for amines. Afterwards, the obtained dendrimers were characterized
by 1H NMR, 13C NMR, and by the TNBS (2,4,6-Trinitrobenzene Sulfonic Acid) assay for evaluation
of the extent of amine substitution at the surface. Other studies are ongoing, such as their size
and zeta potential analysis, DNA complexation ability, gene transfection efficiency and capacity
of carrying drugs.
References:
[1] M. A. Mintzer, M. W. Grinstaff. Chem Soc Rev., 2011, 40, 173-190.
[2] H. Wang, Q. Huang, H. Chang, J. Xiao, Y. Cheng. Biomater Sci., 2016, 4, 375-390.
[3] N. Feliu, M. V. Walter, M. I. Montanez, A. Kunzmann, A. Hult, A. Nystrom, M. Malkoch, B. Fadeel. Biomaterials, 2012,
33, 1970-1981.
[4] J. Movellan, R. Gonzalez-Pastor, P. Martin-Duque, J. M. de la Fuente, J. L. Serrano. Macromol. Biosci., 2015, 15, 657667.
Acknowledgments: This research was supported by Fundação para a Ciência e a Tecnologia (FCT) with Portuguese
Government funds (from the CQM Strategic Project UID/QUI/00674/2013). FCT is acknowledged for the PhD grant
SFRH/BD/88721/2012 (M. G). The Portuguese Nuclear Magnetic Ressonance Network – PTNMR 2015 is also
acknowledged.
23
[O-1]
Azedas (Rumex maderensis) as a dietary source of compounds with activity
on digestive enzymes linked to type II diabetes: an in vitro study
Vítor Spínola and Paula C. Castilho
Funchal, Portugal
The present study was designed to investigate the composition of Rumex maderensis L.
(Polygonaceae), a wild leafy-vegetable growing in Madeira Island (Portugal). A total of 86
polyphenols (about 70% C- and O-flavonoids) and 9 compounds of non-phenolic nature (organic
acids, lignans, and oligosaccharides) were identified by HPLC-ESI-/MSn analysis. Quantification
data showed variations on the phenolic profile of different morphological parts (flowers > leaves
> stems). Also, quantitative analysis of L-ascorbic acid (L-AA) and oxalic acid (OA) was carried
out, revealing high amounts of both organic acids. In vitro inhibition assays towards enzymes
linked to carbohydrate and lipid metabolism (α-glucosidase, α-amylase and lipase) were
performed. Our study supports consumption of R. maderensis as a good dietary source of
phytochemical antioxidants or functional food material with potential impact on sugars and
lipids absorption.
Acknowledgments: V. Spínola is grateful to Fundação para a Ciência e a Tecnologia (FCT, Portugal) for a Ph. D. Grant
(SFRH/BD/84672/2012). This research was supported by FCT with funds from the Portuguese Government (Project
PEst-OE/QUI/UI0674/2013) and the Portuguese National Mass Spectrometry Network (Contract
RNEMREDE/1508/REM/2005).
24
[O-3]
Blue fluorescent PAMAM dendrimers for biomedical application
Cláudia S. Camachoa, Helena Tomása and João Rodriguesa
a
Despite its unique properties and several applications in the biomedical field as nanocarriers for
delivery of drugs/genes and bioimaging, Polyamidoamine (PAMAM) dendrimers have a
limitation, a weak intrinsic fluorescence, that could be achieved through the labeling of
fluorescent molecules on the surface of the dendrimer. However, this limitation can be explored
as reported in the literature [1-3].
In this work, different generations of amine-terminated PAMAM dendrimers (3, 4 and 5) were
treated with ammonium persulfate (APS). Afterwards, the synthesized compounds were
characterized by different techniques as NMR, UV-Vis, Fluorescent and IR. It was also studied the
effect of pH and time and tested the cytotoxicity in vitro culture with fibroblasts cell line
(NIH3T3).
Preliminary results indicate that the dendrimers treated with APS have a very intense
fluorescence/absorption compared to the pure dendrimer, displaying a blue colour
luminescence when irradiated at 366nm. The NMR spectrum revealed a shift of two peaks
correspondent to the protons of the peripheral amines. In the FTIR it is possible to verify that the
bands of methylene groups become weaker after modification with APS; the bands
corresponding to amides I and II shift slightly and, the band related to the hydrogen bonded NH
of the amide group it becomes broader due to overlap with the band of ammonium ions [1].
And accordingly to the cell viability tests in NIH3T3 cell lines, the APS-treated PAMAM
dendrimers are less cytotoxic than pure dendrimers.
References
[1] Wang D.; Imae T.; Miki M. J. Colloid Interface Sci. 2007, 306, 222-227.
[2] Lee, W.I.; Bae, Y.; Bar, A.J. J. Am. Chem. Soc. 2004, 126, 8358-8359.
[3] Kesharwani P.; Jain K.; Jain NK. Prog. Polym. Sci. 2014, 39, 268-307.
Government funds through the CQM Strategic Project PEst UID/QUI/00674/2013and the NMR Network – (PTNMR2015). We acknowledge the continuous support of our work by Vidamar Resorts Madeira.
25
[O-18]
GC-MS on profiling passion fruit volatiles. An effective
tool to discriminate between species and varieties
Priscilla Porto-Figueiraa, Ana Freitasb, Catarina Cruzb, José A. Figueiraa and José S. Câmaraa,b
a
Funchal, Portugal
b
Faculdade de Ciências Exatas e da Engenharia, Universidade da Madeira, Campus da Penteada, 9020105 Funchal, Portugal
Passiflora L. is originally from the tropical and warm climates of South America, although it is
nowadays cultivated in many other latitudes with suitable conditions for its grown. Passiflora L.
fruit, known as passion fruit, is a rich source of vitamins A, C and D, alkaloids, carotenoids and
flavonoids. The composition in different bioactive compounds makes passion fruit a very
interesting functional food. To gain insights on the volatile composition of Passiflora L., passion
fruits from nine species and varieties produced in Madeira Island (yellow, purple, lemon, orange,
pineapple, peach, tomato, melon and banana) were investigated by headspace solid-phase
microextraction (HS-SPME) followed by a GC–qMS and multivariate analysis (MVA). HS-SPME was
optimized in terms of fibre coating, extraction time, ionic strength and sample weight, in order
to achieve the best extraction efficiency. Following this optimization, all the passion fruit
samples were analysed and more than 150 volatile organic metabolites (VOMs) belonging to
different chemical groups, namely linear and branched esters, terpenes, alcohols, fatty acids and
carbonyl compounds, were identified. The major VOMs identified in all samples were ethyl
hexanoate, ethyl butyrate, β-pinene, cis-β-ocimene, cis-3-hexenyl acetate and hexyl hexanoate,
but significant differences in the volatomic profiles among the nine samples have been
obtained. The corresponding data matrices were submitted to principal component analysis
(PCA) and the obtained VOM patterns were able to differentiate all the passion fruits analysed.
Acknowledgements: The authors acknowledge the Portuguese Foundation for Science and Technology (FCT)
through the CQM Strategic Plan - UID/QUI/00674/2013, the MS Portuguese Networks (RNEM/2015), and the FEDER
(Transnational Cooperation MAC 2007-2013 Program) through AVC-MaC-CV (MAC/3/M251) Project for the financial
support.
26
[O-15]
Facile synthesis of hybrid DNA/cationic polymer films
Rita Castroa, Pedro Granjab, João Rodriguesa, Ana Paula Pêgob and Helena Tomása
a
b
INEB - Instituto de Engenharia Biomédica, Universidade do Porto, Rua do Campo Alegre, 823, 4150-180
Porto, Portugal
The physical-chemical properties (e.g. charge and base specificity) of deoxyribonucleic acid
(DNA) make it an important material for use in diverse technological fields, such as in diagnostic
devices [1] and charge conductivity systems [2]. DNA films can also have interesting applications
and have been prepared by several methods, like chemical immobilization on gold or polymer
surfaces [3], UV cross-linking [4], and layer-by-layer assembly in combination with cationic
polymers [5].
In this project we developed a unique method to prepare DNA/cationic polymer films through a
self-assembly process. First, poly(amidoamine) (PAMAM) dendrimers (monodisperse highly
branched macromolecules, having a well-defined structure/molecular weight and possibility of
functionalization) [6] were used to obtain transparent, resistant, flexible and relatively stable
films. For this, salmon DNA and PAMAM dendrimers with terminal amine groups (which are
protonated at physiological pH and capable of interaction with DNA's phosphate groups) were
used. These films were studied using different procedures and techniques in order to
understand their composition and internal organization.
Following this approach, other polymers were assayed for the possibility of obtaining hybrid
DNA/polymer films using the same experimental methodology. Chitosan and poly(allylamine
hydrochloride) (both linear) and polyethylenimine (branched) were selected due to their
molecular structure and cationic nature. The results of these studies will be presented and
discussed.
References:
[1] H. U. Khan, M.E. Roberts, O. Johnson, W. Knoll, Z. Bao. Org. Electron., 2012, 13, 519-524.
[2] Y. Okahata, T. Kobayashi, K. Tanaka, M. Shimomura. J. Am. Chem. Soc., 1998, 120, 6165-6166.
[3] L. A. Chrise, G. U. Lee, C. E. O'Ferrall. Nucleic Acids Res., 1996, 24, 3031-3039.
[4] M. Yamada, K. Kato, M. Nomizu, N. Sakairi, K. Ohkawa, H. Yamamoto, N. Nishi. Chem. Eur. J., 2002, 8, 1407-1412.
[5] K. Sato, J. Anzai. Molecules, 2013, 18, 8440-8860.
[6] R. Esfand, D.A. Tomalia. Drug Discov. Today, 2001, 6, 427-436.
Acknowledgements: We acknowledge the support of the Portuguese Science Foundation (FCT) through the
projects PTDC/CTM NAN/112428/2009, UID/QUI/00674/2013 (CQM, Portuguese Government funds), and PTNMR2015 (NMR Portuguese Network). R. Castro also acknowledges FCT for the Ph.D. grant SFRH/BD/87465/2012.
27
[O-7]
Caffeoylquinic acids as enzymatic inhibitors, from in silico hypothesis
and target acquisition to in vitro mechanism of action
João Serina, Paula C. Castilho and Miguel Fernandes
Funchal, Portugal
Caffeoyquinic acids (CQAs) are polyphenols, classified as hydroxycinnamic derivatives, common
in plants and foodstuffs. Coffee is the main source of CQAs to which the slimming action of
green coffee is attributed.
To evaluate this hypothesis, in silico studies of the inhibitory activity over digestive enzymes
were performed.
Previous in silico results showed that CQAs bind preferably to the NAD(P)+ site of
oxidoreductases in the glycolysis pathway.
Despite the fact that the binding affinity of the ligands was lower than the cofactor’s, this
mechanism of action has never been reported.
Considering that:
- the literature on enzyme inhibition is only focused on inhibitory potency,
- these ligands do not exhibit toxicity by themselves or through their inhibitory effect and
- the in silico results pointed to an unusual mechanism,
in vitro assays were designed to put these results to the test.
The results from these in vitro assays show that these ligands can function both as inhibitors and
activators, depending on concentration. This mechanism of action explains not only the inhibitory
potency of these ligands but also their lack of side effects in vivo: they are able to reduce
glycaemia but do not cause hypoglycaemia.
Acknowledgments: Thanks are due to FCT for CQM Project UID/QUI/00674/2013
28
[O-9]
Microextraction and analysis of bioactive compounds in
food matrices from Madeira Island
Jorge A. M. Pereira1 and José S. Câmara1,2
1
Funchal, Portugal
2
Faculdade de Ciências Exatas e da Engenharia da Universidade da Madeira, Campus da Penteada,
Funchal 9020-105, Portugal
In the last decade, the CQM Analytical Chemistry and Enology Lab (ACE-lab) of was a pioneer in
the application of innovative extraction methodologies for the analysis of bioactive compounds
in different food matrices. This approach was particularly successful in the analysis of dietary
polyphenols in wine, beer, coffee, tea and several fruits and vegetables. As it will be shown,
coupling modern microextraction solutions, as MEPS and SPEed, with ultrafast liquid
chromatography, has allowed us to develop “greener” methodologies, involving hundreds of
times less sample and solvents volumes without compromising the analytical performance.
Nevertheless, there are always challenges to overcome, particularly when complex matrices or
compounds with very different chemicals properties are being simultaneously analysed.
Acknowledgments: The author acknowledges the Portuguese Foundation for Science and Technology (FCT)
through the CQM Pluriannual base funding (Project UID/QUI/00674/2013) and MS Portuguese Networks
(RNEM/2015) and the fellowship SFRH/BPD/66177/2009 given to JAMP.
29
[O-12]
Ultra-high Performance Liquid Chromatography method development for determination
of oxidative stress biomarkers caused by hyperhomocysteinemia
Liliana da Silva Rodriguesa, José S. Câmaraa,b and Helena Caldeira Araújoa,c
a
Funchal, Portugal
b
Faculdade de Ciências Exatas e da Engenharia, Universidade da Madeira, Campus da Penteada, 9020-105
Funchal, Portugal
c
Projeto Medicina, Faculdade de Ciências da Vida, Universidade da Madeira, Campus da Penteada, 9020105 Funchal, Portugal
Thiol compounds such as homocysteine (Hcy), glutathione (GSH) and cysteine (Cys), are involved
in relevant physiological processes including elimination of toxins, homeostasis and redox
signalling, transport and metabolic storage, protein functionality, as well as, gene expression,
proliferation, differentiation and cell death. Several studies have shown that maladjustment of
these functions is the basis of many human pathologies.
The goal of the present work was to optimize an Ultra-high Performance Liquid
Chromatography (UHPLC) method for simultaneous detection and quantification of thiols in
biological fluids.
For this purpose, an ACQUITY UPLC H-Class System with fluorescence detection equipped with an
HSS T3 column was used. Preliminary experiences to optimize chromatographic separation of
standard compounds involved testing of various mobile phase compositions, pHs, reduction of
compounds and detection conditions. Optimum separation was achieved with a mobile phase
consting of Milli-Q water acidified with 0.1% formic acid and acetonitrile 95:5 (v/v). An isocratic
program with a flow-rate of 0.200 μL/min was used. As the analyzed compounds, do not emit
fluorescence it was necessary to previously label them with a florescent molecule. Derivatization
was performed with 7-fluorobenzo-2-oxa-1,3-diazole-4-sulfonic acid ammonium salt (SBD-F)
after reduction of disulphide bonds with tributylphosphine.
A good resolution was obtained for the three standard compounds, with GSH, Cys and Hcy
eluting at 0.656±0.006, 2.182±0.001 and 3.015±0.001 min. Inter-day precision for GSH, Cys and
Hcy retention times were 0.89, 0.026 and 0.033% and for areas were 0.87, 7.66 and 1.33%,
respectively. Linearity was tested in a range of concentrations from 100 to 1000 μM with good
correlation coefficients.
Acknowledgments: The Portuguese Fundação para a Ciência e a Tecnologia (FCT) is acknowledged for funding
through pluriannual base funding of CQM (Pest UID/QUI/00674/2013). We acknowledge Catarina Silva for her
support in UPLC usage.
30
[O-21]
A concise history of Kurdish Jewish mtDNA lineages through
the assemblage of HVS-I, -II and -III gene sequences
Catarina J. Cruz[a], Sara C. Gomes[a], Alexandra Rosa[a] and António Brehm[a,b]
[a]
LGH – Laboratório de Genética Humana, Universidade da Madeira, Campus da Penteada, 9020-105
Funchal, Portugal
[b]
Portugal
The Kurdish people, originating from the Middle East, is composed of 36 million people
scattered across four different countries: Turkey, Iran, Iraq and Syria. Despite their diverse ethnic
origins, language and culture are closely related to the Persian population (corresponding to
present-day Iran). In this study, the genetic profile of the maternal lineage of Kurdish Jews was
investigated through the analysis of the control region of mitochondrial DNA (mtDNA), and then
compared with other populations from Europe, Africa and Middle East, as well as other Jewish
populations. We identified a high genetic diversity with the prevalence of mitochondrial
haplogroups H, J1 and N1, all common in the Middle East. The search for a possible genetic
relationship between this population of Kurdish Jews and other relevant populations specified
in the literature, pointed to a closer relationship to populations from Bulgaria, Iran and
Azerbaijan and with the Jews in the same region than with other peoples from the Middle East.
The present results suggest that the Kurdish Jewish people, while subject of dispute by other
populations, remained relatively isolated from the influences of the surrounding populations.
31
[O-5]
Brewer’s spent grain as a source of ferulic acid
Pedro Ideia and Paula C. Castilho
Funchal, Portugal
The food industry produces a large amount of by-products every year, which are still treated as
waste since they don't have direct applications.
The brewing industry, in particular, is associated with the production of several residues,
including brewer's spent grain (BSG). In Madeira Island only the BSG production exceeds 2,000
tons/year, produced at a rate of 20 kg per 100 L of beer.
This work was carried out to study the use of BSG as starting material for extraction of ferulic acid
(FA), a hydroxycinnamic acid with several bioactive properties and applications.
Alkaline hydrolysis is one of the techniques that enable the extraction of compounds such as FA
from lignocellulosic materials. It was studied in BSG samples submitted to pre-treatment with
dilute acid, which proved to be efficient in the extraction of FA from BSG.
The extraction in autoclave was efficient in the extraction of FA [0.28% (w/w)] and a
simplification of the procedure which followed the alkaline hydrolysis reaction increased the
yield of extraction in about 84%. The optimal conditions for alkaline hydrolysis in auto
pressurized tubes occurred at 120 °C for 1.5 hours in a ratio of 20 mL/g and NaOH (1.5%).
The extracted FA purification process by adsorption on a synthetic resin resulted in adsorption
percentages of 90.8% and desorption around 68.7%.
Acknowledgments: The authors are thankful to Empresa de Cervejas da Madeira for providing fresh BSG. Thanks are
also due to FCT for CQM Strategic Project UID/QUI/00674/2013; this work used equipment from Portuguese
National Mass Spectrometry Network (Contract RNEMREDE/1508/REM/2005) in the framework of the National
Programme for Scientific Re-equipment, with funds from POCI 2010 (FEDER).
32
[O-10]
Antifungal activity of Helichrysum devium extracts
Sandra Agrela1, Paula C. Castilho1 and Irene C. Camacho2
1
Funchal, Portugal
2
Portugal
Natural products from plants have great potential as source of novel fungicide for controlling
pathogenic fungi.
Banana anthracnose is caused by Colletotrichum spp. a fungal pathogen that affects a high
variety of plants in the tropics and sub-tropics. Among the pathogens of the Colletotrichum
genus, there is a specialization for certain groups of hosts. Colletotrichum musae (Berk. & Curtis)
Arx. is responsible for causing anthracnose, the most important postharvest disease of banana.
The fungus attacks mainly fruits, but the infection process can occur during flowering and fruit
development.
The present study aimed to assess the in vivo and in vitro effects of 3 solvent extracts of
Helichrysum devium in three different concentrations (1%, 1,5% e 2%,) and their efficiency in
controlling anthracnose caused by C. musae on banana fruits.
The extracts were obtained by macerating 500 g Helichrysum devium in 5L n-hexane for 24h,
followed by 5L acetone and 5L ethanol. The filtrates were concentrated by removing the solvent
under reduced pressure at 40 °C using a rotary evaporator. The isolate of C. musae was obtained
from anthracnose lesions typical of infected bananas and cultivated in agar.
In the in vivo study, healthy unripe bananas were washed with sodium hypochlorite, 70 %. After
drying, a small wound was inflicted and a portion of the fungus and extracts were placed there.
Fungal growth was monitored for 10 days at room temperature.
The in vitro study was conducted using impregnated paper disks with the different extracts. Petri
dishes containing agar medium were inoculated with the fungus and three disks per plate were
arranged. Ten days after inoculation, the inhibition diameter was measured.
In both assays, hexane extract caused inhibition only at the highest concentration, while
acetone and ethanol inhibited the growth of C. musae in dose dependent way.
Acknowledgments: Thanks are due to Portuguese Foundation for Science and Technology (FCT) through the CQM
Pluriannual base funding (Project UID/QUI/00674/2013)
33
[O-4]
Preparation of a new family of poly(alkylidenamine)s
dendrimers with different functional groups
Dina Maciel,1 María de los Ángeles Múñoz-Fernández,2 Helena Tomás1 and João Rodrigues1
1
2
Laboratorio de Inmunobiologia Molecular, Hospital General Universitario Gregorio Marañón, Madrid,
Spain
Dendrimers are highly branched, well-defined molecules, three-dimensional, synthetic
nanostructures commonly used for biomedical applications[1]. Among these characteristics,
dendrimers present excellent physiological stability, and can be conjugated or encapsulated
with drugs. The combination of metals with dendrimers provides metallodendrimers, which are
being use in a broad range of applications, due to their excellent properties[1,2].
Polyamidoamine (PAMAM) and polypropyleneimine (PPI)-based dendrimers are the most
extensively studied dendrimers for drug delivery[3]. Our purpose is to develop a new family of
metallodendrimers based on poly(alkylidenamine)s[4] with different terminal groups including
anionic groups, with improved solubility in biological media. The efficacy of these
metallodendrimers will be studied against cancer and infection diseases, such HIV infection.
In this project, will be presented the preliminary results on the preparation and characterization,
by NMR, IR and MS, of this poly(alkylidenamine)-based dendrimers having, at each generation,
nitrile, amine, sulfonate and carboxylate terminal groups. The nitrile and amine terminal groups
on the surface of dendrimers will serve to grow the dendrimer generation and will act as
bridging groups for complexation of metallodrugs.
References:
[1] Viñas, C.; Teixidor, F.; Núñez, R. Inorg. Chim. Acta. 2014, 409, 12.
[2] Smith, G.S.; Therrien, B. Dalton Trans. 2011, 40, 10793.
[3] Kesharwani, P.; Iyer, A.K., Drug Delivery Today, 2015, 20, 536.
[4] a) Jardim, M.G.; Rissanen, K.; Rodrigues, J. Eur. J. Inorg. Chem. 2010, 1729. b) Rodrigues J.; Jardim M. J.; Gouveia
M.; Tomás H.; Rissanen K., New J. Chem. 2011, 35, 1938. c) García-Gallego, S.; Cangiotti, M.; Fiorani, L.; Fattori, A.;
Muñoz-Fernández, M.A.; Gomez, R.; Ottaviani, M.F.; de la Mata, F.J., Dalton Trans. 2013, 42, 5874.
Government funds through the CQM Strategic Project UID/QUI/00674/2013, the NMR Network – (PTNMR-2015) and
the Ph. D. Grant SFRH/BD/102123/2014 (D.M). The support of the international network CYTED 214RT0482 in the
domain of the HIV infection is highly appreciated. We also acknowledge the continuous support of our work by
Hotel Vidamar Resorts Madeira.
34
[O-6]
Generation 0 and 1 of new PAMAM dendrimers with different terminal groups.
Synthesis and characterization
Nádia Nunes, João Rodrigues and Helena Tomás
Dendrimers with different terminal groups or conjugated with a variety of ligands at their
periphery could have therapeutic, and/or diagnostic applications.[1]
The goal of this work was, to synthesize and characterize, different PAMAM dendrimers based:
G0/G1-CO2tBu and G0/G1-OH for further functionalization with nitrile groups. The applied
synthetic strategy was to increase the length of the lateral chains of the core (generations 0 and
1) by incorporating tert-butyl ester and hydroxyl functional groups at the periphery of each
dendrimer. The obtained hydroxyl moieties can be the precursors for the synthesis of the G0(CN)8 and G1-(CN)16 dendrimers, respectively. These polynitrile compounds exhibit a biomedical
importance since it can be the core ligands for the preparation of another family of dendrimers,
such as, the ruthenium metallodendrimers that are promising alternatives to the clinically used
platinum antitumor metallodrugs. [1, 2]
The preparation of these dendrimers was achieved by adapting the reported methodology of N.
Jayaraman et al.[3,4] (amine  ester  alcohol) and their characterization was performed by 1H
and 13C-NMR, FTIR and MS structural techniques.
Regarding the achieved results, the first functionalized PAMAM dendrimers, G0-(CO2tBu)8 and
G1-(CO2tBu)16, were obtained with good yields of 95% (4.5 g) and 83% (6.0 g) from 1.6 g of G0PAMAM and 3.0 g of G1, respectively. 3.6 g of the G0-(CO2tBu)8 was used to obtain 2.0 g of G0(OH)8 with a good yield of 90%. The synthesis reaction of G1-(OH)16 is ongoing.
References:
[1] J. Rodrigues, M.G. Jardim, J. Figueira, M. Gouveia, H. Tomás, K. Rissanen, New J. Chem. 2011, 35, 1938-1943; [2] B.
A. Aderibigbe, J. Inorg. Organomet. Polym. 2015, 25, 339-353; [3] T. R. Krishna, N. Jayaraman, J. Org. Chem., 2003, 68,
9694-9704; [4] G. Jayamurugan, N. Jayaraman, Tetrahedron, 2006, 62, 9582-9588.
Acknowledgments: The Portuguese Fundação para a Ciência e a Tecnologia (FCT) is acknowledged for funding
through the NMR and MS Portuguese Networks (PTNMR-2015, RNEM-2015) and the pluriannual base funding of
CQM (PEst UID/QUI/00674/2013) and the NMR Network – (PTNMR-2015). We acknowledge the continuous support
of our work by Vidamar Resorts Madeira.
35
[O-17]
Simultaneous quantification of carotenoids and tocopherols in tomato by LLUSAE/UHPLC
using PDA and FLR detection
José A. Figueiraa, Priscilla Porto-Figueiraa and José S. Câmaraa,b
a
Funchal, Portugal
b
Faculdade de Ciências Exactas e da Engenharia, Universidade da Madeira, Campus da Penteada, 9020105 Funchal, Portugal
Tomato (Lycopersicon esculentum L.) is one of the main constituents of the Mediterranean diet.
Its consumption has been proposed to reduce the risk of cardiovascular diseases and certain
types of cancer. It is therefore one of the most popular and extensively consumed vegetable
crop worldwide. To gain insights on the potential of Lycopersicon esculentum L. as bioactive
food, an analytical methodology based on ultrasound assisted liquid extraction (LLUSAE) was
developed to determine the levels of the lipophilic antioxidants, namely tocopherols (e.g. αtocopherol, δ-tocopherol) and carotenoids (e.g. lycopene and β-carotene).
Some key parameters influencing the chromatography analysis were taken into account, namely
the nature stationary phase of column (HSS T3 1.8μm, BEH C18 1.7μm, Cortecs C18 1.6μm), the
detector system (PDA and FLR), nature of solvent system, elution gradient and mobile phase
flow rate. The ultra-high performance liquid chromatographic using photodiode array and
fluorescence detection (UHPLC-PDA/FLR), allows the identification and quantification of the
target lipophilic antioxidants. UHPLC-PDA and -FLR is fast, simple and revealed a high sensitivity
for the target compounds.
The results showed the potentiality of the proposed methodology, with LODs and LOQs lower
than the reported in literature using similar detectors. Good recoveries (> 95%), precision (< 10%
intra- and inter-day) and negligible matrix effect, were observed. Finally, the methodology was
applied for the determination of the carotenoid and tocopherol content in tomato from gordal
variety during maturation (full mature green, breaker and ripe stages) and in different parts (skin,
seeds, locular cavity and pericarp) of the tomato ripe fruit.
Acknowledgements: The authors acknowledge the Portuguese Foundation for Science and Technology (FCT)
through the CQM Strategic Plan (UID/QUI/00674/2013), MS Portuguese Networks (RNEM), and the FEDER
(Transnational Cooperation MAC 2007-2013 Program) through AVC-MaC-CV (MAC/3/M251) Project for the financial
support.
36
[O-11]
Electroactive properties and biological applications of electrospun PVDF polymer
Xiang Yao, Ana Olival, Pedro Pires and Helena Tomás
In this project the electrospinning technique has been used to prepare PVDF (polyvinylidene
fluoride) and PVDF/PLGA [poly(lactic-co-glycolic acid)] blended polymeric scaffolds for tissue
engineering. The main objective is the preparation of electroactuated devices for cell
stimulation.
Crystal phase changes and morphology of the PVDF fibre mesh surface were characterized by
attenuated total reflectance Fourier transform infrared (FTIR/ATR) spectroscopy and scanning
electron micrograph (SEM). Several devices were prepared from assemblies of PVDF fibre
meshes and conductive ink electrodes, with different geometries. The devices’ electrical
impedance was measured as a function of frequency. Finally, the in vitro biocompatibility of the
PVDF fibre meshes was tested.
The results revealed that electrospinning parameters had significant effects on crystal phase
content and structure. As it was expected, the electrical impedance of PVDF decreased with the
increase of β crystal phase content, as required for the electrostrictive behaviour of the PVDF
fibres. The results also illustrated that the impedance of PVDF fibre mesh assemblies changed
with varying shape, thickness, the geometric alignment of the fibres and the distance between
conductive ink electrodes. In vitro cytocompatibility tests of PVDF scaffolds shown that the
NIH3T3 cells cultured on scaffolds were alive which meant PVDF biocompatibility was
acceptable for biomedical applications.
The use of PVDF polymer fibres for electromechanical stimulation of living cells will be tried and
its effects on the biological activity of specific tissue cells (bone, muscle, nervous) will be studied.
The potential use of electroactive polymers, conductor or semiconductor polymers for sensor
applications will be looked upon, taking as long time objective the design of micro-nano-bio
systems devices and application.
Acknowledgments:This research project was executed in the framework of the Nanochemistry and Nanomaterials
Master Degree and was supported by Fundação para a Ciência e a Tecnologia (FCT) with Portuguese Government
funds through the CQM Strategic Project UID/QUI/00674/2013.
37
38
Authors Index
39
40
Alexandra Rosa .......................................................... 31
Liliana da Silva Rodrigues ...................................... 30
Ana Freitas .................................................................. 26
Mara Gonçalves ......................................................... 23
Ana Olival ............................................................. 21, 37
María de los Ángeles Múñoz-Fernández .......... 34
Ana Paula Pêgo ......................................................... 27
Miguel A. R. B. Castanho ......................................... 17
António Brehm .......................................................... 31
Miguel Fernandes ..................................................... 28
Carla S. Alves .............................................................. 17
Nádia Nunes................................................................ 35
Catarina Cruz .............................................................. 26
Paula C. Castilho ................................... 24, 28, 32, 33
Catarina J. Cruz .......................................................... 31
Paula Colavita ............................................................. 18
Catarina L. Silva ......................................................... 20
Pedro Berenguer ....................................................... 22
Cláudia S. Camacho ................................................. 25
Pedro Granja ............................................................... 27
Daniela Angione ....................................................... 18
Pedro Ideia .................................................................. 32
Dina Maciel ................................................................. 34
Pedro Pires................................................................... 37
Federico Zen .............................................................. 18
Priscilla Porto-Figueira ..................................... 26, 36
Helena Caldeira Araújo ........................................... 30
Rita Castro............................................................. 21, 27
Helena Tomás .....17, 20, 21, 23, 25, 27, 34, 35, 37
Rosa Patela .................................................................. 19
Irene C. Camacho............................................... 22, 33
Sandra Agrela ............................................................. 33
Joana M. Vasconcelos ............................................. 18
Sandra Cachopo ........................................................ 19
João Rodrigues ................ 17, 21, 23, 25, 27, 34, 35
Sara C. Gomes ............................................................ 31
João Serina .................................................................. 28
Vítor Spínola ............................................................... 24
Jorge A. M. Pereira.................................................... 29
Xiang Yao ..................................................................... 37
José A. Figueira................................................... 26, 36
Yulin Li .......................................................................... 23
José S. Câmara ........................ 20, 22, 26, 29, 30, 36
41
42
Participants List
43
44
Ana Cristina Baptista de Freitas Morna
[email protected]
Ana Cristina Dias Olival
[email protected]
Carla Sofia Caseiro Miguel
[email protected]
Carla Sophia Brazão Andrade Sousa Alves
[email protected]
Catarina Grace Sousa Luís Silva
[email protected]
Catarina J. Cruz
[email protected]
Cláudia Sofia Camacho
[email protected]
Dina Maria Sousa Maciel
[email protected]
Gina Marta Ferraz Tavares
[email protected]
Gonçalo Nuno Gouveia Martins
[email protected]
Goulielmina Anyfanti
[email protected]
Helena Tomás
[email protected]
Ivo José Viveiros Martins
[email protected]
Joana Marta Candelaria Vasconcelos
[email protected]
João Luís Jesus Gonçalves
[email protected]
João Marcelo Gontardo Gaspar
[email protected]
João Rodrigues
[email protected]
Jorge A. M. Pereira
[email protected]
José Aldónio Oliveira Figueira
[email protected]
José Carlos Almeida Mesquita
[email protected]
José João Caires Serina
[email protected]
José S. Câmara
[email protected]
Joselin Maria Vieira de Aguiar
[email protected]
Liliana da Silva Rodrigues
[email protected]
Manuel Gonçalves Jardim
[email protected]
Mara Isabel Jesus Gonçalves
[email protected]
Mariangie Elisa Martinez Castillo
[email protected]
Nádia Sofia Henriques Nunes
[email protected]
Natacha Manuel Pereira Rodrigues Antunes
[email protected]
Nilsa Maria Ornelas Oliveira
[email protected]
Núria Vanessa Gouveia Fernandes
[email protected]
Paula Castilho
[email protected]
45
46
Pedro Diogo Ideia Freitas
[email protected]
Pedro Filipe Duarte Louzeiro Pires
[email protected]
Pedro Henrique Fernandes da Silva Berenguer
[email protected]
Pedro Miguel Capêlo da Silva
[email protected]
Priscilla Felicio Porto Figueira
[email protected]
Rita Maria de Castro
[email protected]
Rosa Perestrelo
[email protected]
Sandra da Conceição Rodrigues Agrela
[email protected]
Vítor Agostinho Rodrigues Spínola
[email protected]
Xiang Yao
[email protected]

3rd CQM Annual Meeting Abstract Book

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