518 shared publications
Department of chemistry and QOPNA; University of Aveiro; Campus of Santiago Aveiro Portugal
196 shared publications
University of Porto
106 shared publications
ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
97 shared publications
UCIBIO-REQUIMTE, Laboratório de Toxicologia, Departamento de Ciências Biológicas, Faculdade de Farmácia, Universidade do Porto, 4050-313 Porto, Portugal
84 shared publications
ICBAS-Instituto de Ciências Biomédicas Abel Salazar, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
(1974 - 2019)
Antimicrobial resistance is one of the most pressing health issues of our days. The marine environment has proven to be a very rich source of diverse natural products with broad-spectra of biologically activities being a very helpful resource in the search for novel antimicrobial compounds. These structurally distinct molecules are revealing promising biological activities against a very large number of drug-resistant pathogenic bacteria and fungi, catching marine natural products attention in the discovery of new antimicrobial agents. Inspired by antimicrobial lichen xanthones  and fungi-derived alkaloids, two series of marine natural products mimics were prepared. The synthesized compounds were evaluated for their antimicrobial activity. Both series produced interesting compounds active against E. faecalis (ATCC 29212 and 29213) and S. aureus (ATCC 29213) with some synthetic alkaloids being active against a MRSA strain. Some revealed a potent fungistatic and fungicidal activity against dermatophytes clinical strains (T. rubrum, M. canis, and E. floccosum). These results highlight the potential of marine natural products as a source of new antimicrobial agents to revert resistance.
 D. I. S. P. Resende, P. Pereira-Terra, Â. S. Inácio, P. M. Costa, E. Pinto, E. Sousa, M. M. M. Pinto. Lichen Xanthones as Models for New Antifungal Agents. Molecules 2018, 23, 2617; doi:10.3390/molecules23102617
Acknowledgments: This work was partially supported through national funds provided by FCT/MCTES—Foundation for Science and Technology from the Ministry of Science, Technology, and Higher Education (PIDDAC) and the European Regional Development Fund (ERDF) through the COMPETE—Programa Operacional Factores de Competitividade (POFC) programme, under the Strategic Funding UID/Multi/04423/2013, the projects POCI-01-0145-FEDER-028736 and POCI-01-0145-FEDER-016790 (PTDC/MAR-BIO/4694/2014; 3599-PPCDT) in the framework of the programme PT2020, as well as by the project INNOVMAR—Innovation and Sustainability in the Management and Exploitation of Marine Resources (reference NORTE-01-0145-FEDER-000035, within Research Line NOVELMAR), supported by North Portugal Regional Operational Programme (NORTE 2020), under the PORTUGAL 2020 Partnership Agreement, through the European Regional Development Fund (ERDF). Solida Long thanks Erasmus Mundus Action 2 (LOTUS+, LP15DF0205) for full PhD scholarship. Diana I. S. P. Resende also acknowledge for her grant (NOVELMAR/BPD_2/2016-019) and Patrícia Pereira-Terra for her grant (NOVELMAR/BPD/2017/012).
Several biological activities from nearly 150 marine-derived sulfated steroids have been reported with both pharmacological (antimicrobial, antitumor, cardiovascular and/ or anti-inflammatory activities) and environmental (antifouling activity) applications . Sulfation is used in Nature to avoid toxicity and therefore marine-inspired sulfated steroids could be an interesting strategy for drug discovery. The sulfated aminosterol squalamine, isolated from the internal organs of the dogfish shark, is in phase III of clinical trials as anti-angiogenic drug , which evidences the potential of sulfated steroids.
Sulfation of small molecules using sulfur trioxide-amine complexes entails several advantages, such as persulfation, low degradation, and feasibility in the work-up . Moreover, these complexes appear to be suitable for sulfation of alcohol groups present in steroids . In this direction, sulfation of four sterols was achieved using triethylamine-sulfur trioxide adduct in dimethylacetamide under heating, with yields ranging from 3% to 93%. Purification involved insolubilization with diethyl ether followed by several methods to obtain the sulfated derivatives free of inorganic impurities, including dialysis and/ or chromatographic processes. Structure elucidation of these new compounds was established by infrared (IR), nuclear magnetic resonance (NMR) and high resolution mass spectrometry (HRMS). Biological activities will be further studied.
This work was supported through national funds provided by FCT/MCTES - Foundation for Science and Technology from the Ministry of Science, Technology and Higher Education (PIDDAC) and European Regional Development Fund (ERDF) through the COMPETE Programa Operacional Factores de Competitividade (POFC) programme, under the projects PTDC/MAR-BIO/4694/2014 (reference POCI-01-0145-FEDER-016790; Project 3599–PPCDT), PTDC/AAGTEC/0739/2014 (reference POCI-01-0145-FEDER-016793; Project 9471-RIDTI) and POCI-01-0145-FEDER-028736 in the framework of the programme PT2020. Carvalhal F also acknowledges FCT for the grant PTDC/AAG- TEC/0739/2014-018.
 Carvalhal, F., M. Correia-da-Silva, M.E. Sousa, M. Pinto, and A. Kijjoa, Journal of Molecular Endocrinology, 2018, 61(2) 211-231.
 NCT02727881 (https://clinicaltrials.gov/ct2/show/NCT02727881, October 15, 2018)
 Correia-da-Silva, M., E. Sousa, and M.M. Pinto, Medicinal Research Reviews, 2014, 34(2) 223-79.
 Al-Horani, R.A., and U.R. Desai, Chemical Sulfation of Small Molecules - Advances and Challenges.Tetrahedron, 2010, 66(16), 2907-2918
Over several years, xanthone derivatives have been the core of several studies, essentially due their wide range of biological and pharmacological activities . Recently, chiral derivatives of xanthones (CDXs) have come to arouse great interest considering enantioselectivity studies associated with biological activities [2,3] as well as selectors for chiral stationary phases (CSPs) in liquid chromatography (LC) [4,5].
From the perspective of Medicinal Chemistry, some CDXs synthetized by our group revealed interesting biological activities [2,3]. Besides the potential as new drugs, CDXs afford promising LC enantioresolution results .
In a continuation of our study, new enantiomerically pure CDXs were synthetized for biological activity evaluation as well as selectors for new CSPs, confirming that CDXs have important applications not only in the field of Medicinal Chemistry but also for analytical applications.
This research was partially supported by the Strategic Funding UID/Multi/04423/2013 and UID/QUI/00062/2013 through national funds provided by FCT and ERDF, in the framework of PT2020, by projects PTDC/MAR-BIO/4694/2014 (reference POCI-01-0145-FEDER-016790; Project 3599-PPCDT), and project No. POCI-01-0145-FEDER-028736, co-financed by COMPETE 2020, Portugal 2020 and the European Union through the ERDF, and by FCT through national funds, as well as by the Portuguese NMR Network, and CHIRALXANT-CESPU-2018.
 Shagufta, A.I. Eur. J. Med. Chem., 2016, 116, 267-280.
 Fernandes, C. et al. Bioorg. Med. Chem. 2014, 22, 1049-1062.
 Fernandes, C. et al. Pharmaceuticals, 2017, 10, 50, doi:10.3390/ph10020050.
 Phyo, Y.Z. et al. Molecules, 2018, 23, 142, doi:10.3390/molecules23010142.
 Carraro, M.L. et al. Chirality, 2017, 1–10
 Fernandes, C. et al. Chirality, 2017, 29(8),430-442.