The expertise in synthetic organic chemistry, especially nitrogen-based heterocycles and carbohydrates, acquired by members of the group “Heterocycles for Societal Challenges” (HSC) have been applied to the design, preparation and characterization of a wide range of novel molecules, mainly tailored to meet the societal needs in terms of new drug candidates or materials.
The group maintains intense collaborative activities reflecting that current research is developed at the interface of organic chemistry with areas such as biology and medicine, physics, materials science and nanotechnology.
- HSC Group Leader: Fernanda Proença
New drug candidates:
The search for new drug candidates reflects the requirements of a society where life expectancy is increasing, reinforcing the need to find solutions for age-related and chronic diseases. Part of the group members has been involved in the synthesis of a broad range of heterocyclic compounds, sugar derivatives and macrocycles either through metal-catalysed reactions or by new synthetic methods, including asymmetric synthesis. Most of the molecules are selected on the basis of in silico screening or molecular docking studies on the relevant targets. The biological activity of the new compounds is tested through external collaborations, in particular as anticancer (Dep.Biologia, ICVS-3Bs, IBMC) and/or antiangiogenics (IPBragança, IPATIMUP and FMUP), antipsychotics (Fac.Farmácia-USCompostela) and antimicrobials (Univ. Fernando Pessoa – Porto, Fac. Farmácia-UP), including the search for new and improved antiturbercular agents (ICVS-3Bs). Studies on the encapsulation of new fluorescent anticancer compounds in nanoliposomes has been developed for drug delivery in collaboration with CFUM.
The quality of our lives is also profoundly influenced by the development of new technological solutions. The access to new molecules provides the basis for the discovery of new materials with improved/specific properties. Part of the group members is dedicated to the design and preparation of new heterocycles for nonlinear optical, photochromic, catalytic and sensor applications, including the synthesis of heterocyclic pi-conjugated systems for organic light-emitting diodes (OLEDs), optical chemosensors, imaging probes or for dye-sensitized solar cell (DSSCs). The optical and electronic properties of the novel heterocyclic systems are evaluated in solution and in solid matrixes through national and international collaborations. In particular as nonlinear optical (CF-UM, Bordeaux Univ-France), photochromic (CQ-UTAD, Barcelona University- Spain), OLEDs (Curtin University-Australia, Bologna University – Italy, University of Coimbra), chemosensor (Polytechnic University of Valencia-Spain) and DSSCs materials (Faculty of Engineering, University of Porto).Carbon nanotubes (CNT) present extraordinary mechanical, thermal and electrical properties and are powerful candidates for diverse industrial applications, depending on the capacity to promote efficient interactions with different substrates. This relies on the appropriate chemical functionalization of the CNT surface and members of the research group developed expertise in this area and in the use of functionalized CNT as precursors of graphene nanoribbons. The research proceeds namely for the modulation of induced pluripotent stem cells differentiation and for composite or sensor applications.
Recent HSC Publications:
- Synthesis and evaluation of the chromo-fluorogenic recognition ability of imidazoquinoline derivatives toward ions
Mar\'in-Hern\'andez, C.; Santos-Figueroa, L.E.; El Sayed, S.; Pardo, T.; Raposo, M.M.M.; Batista, R.M.F.; Costa, S.P.G.; Sancen\'on, F.; Mart\'inez-M\'a\~nez, R.
Dyes and Pigments, 2015
- Magnetoliposomes based on manganese ferrite nanoparticles as nanocarriers for antitumor drugs
Rodrigues, A.R.O.; Ramos, J.M.F.; Gomes, I.T.; Almeida, B.G.; Ara\'ujo, J.P.; Queiroz, M.J.R.P.; Coutinho, P.J.G.; Castanheira, E.M.S.
RSC Advances, 2016
- Total facial selectivity of a d-erythrosyl aromatic imine in [4π + 2π] cycloadditions; Synthesis of 2-alkylpolyol 1,2,3,4-tetrahydroquinolines
Ferreira, J.; Duarte, V.C.M.; Noro, J.; Gil Fortes, A.; Alves, M.J.
Organic and Biomolecular Chemistry, 2016
- Dehydrodipeptide Hydrogelators Containing Naproxen N-Capped Tryptophan: Self-Assembly, Hydrogel Characterization, and Evaluation as Potential Drug Nanocarriers
Vila?a, H.; Hortel\~ao, A.C.L.; Castanheira, E.M.S.; Queiroz, M.-J.R.P.; Hilliou, L.; Hamley, I.W.; Martins, J.A.; Ferreira, P.M.T.
- Chemical composition, antioxidant activity and bioaccessibility studies in phenolic extracts of two Hericium wild edible species
Heleno, S.A.; Barros, L.; Martins, A.; Queiroz, M.J.R.P.; Morales, P.; Fern\'andez-Ruiz, V.; Ferreira, I.C.F.R.
LWT - Food Science and Technology, 2015
- Fast (hetero)aryl-benzothiazolium ethenes photoswitches activated by visible-light at room temperature
Coelho, P.J.; Castro, M.C.R.; Raposo, M.M.M.
Dyes and Pigments, 2015
- Efficient One-Pot Synthesis of Alkyl 3-[4-(Aryl or Heteroaryl)-1H-1,2,3-triazol-1-yl]thieno[3,2-b]pyridine-2-carboxylates by ‘Click’ Cu(I)-Catalyzed Azide–Alkyne Cycloaddition
Rodrigues, J.M.; Queiroz, M.-J.R.P.
Synthesis (Germany), 2016
- Bioactive properties of tabebuia impetiginosa-based phytopreparations and phytoformulations: A comparison between extracts and dietary supplements
Pires, T.C.S.P.; Dias, M.I.; Calhelha, R.C.; Carvalho, A.M.; Queiroz, M.-J.R.P.; Barros, L.; Ferreira, I.C.F.R.; McPhee, D.J.
- The contribution of phenolic acids to the anti-inflammatory activity of mushrooms: Screening in phenolic extracts, individual parent molecules and synthesized glucuronated and methylated derivatives
Taofiq, O.; Calhelha, R.C.; Heleno, S.; Barros, L.; Martins, A.; Santos-Buelga, C.; Queiroz, M.J.R.P.; Ferreira, I.C.F.R.
Food Research International, 2015
- Nutritional value, bioactive compounds and antioxidant properties of three edible mushrooms from Poland
Heleno, S.A.; Ferreira, R.C.; Antonio, A.L.; Queiroz, M.-J.R.P.; Barros, L.; Ferreira, I.C.F.R.
Food Bioscience, 2015
- Is honey able to potentiate the antioxidant and cytotoxic properties of medicinal plants consumed as infusions for hepatoprotective effects?
Pereira, C.; Barreira, J.C.M.; Calhelha, R.C.; Lopes, M.; Queiroz, M.J.R.P.; Vilas-Boas, M.; Barros, L.; Ferreira, I.C.F.R.
Food and Function, 2015
- Push-pull second harmonic generation chromophores bearing pyrrole and thiazole heterocycles functionalized with several acceptor moieties: Syntheses and characterization
Castro, M.C.R.; Belsley, M.; Raposo, M.M.M.
Dyes and Pigments, 2016
- Synthesis and characterization of novel thieno[3,2-b]thiophene based metal-free organic dyes with different heteroaromatic donor moieties as sensitizers for dye-sensitized solar cells
Fernandes, S.S.M.; Castro, M.C.R.; Mesquita, I.; Andrade, L.; Mendes, A.; Raposo, M.M.M.
Dyes and Pigments, 2017
- Chemical features of Ganoderma polysaccharides with antioxidant, antitumor and antimicrobial activities
Ferreira, I.C.F.R.; Heleno, S.A.; Reis, F.S.; Stojkovic, D.; Queiroz, M.J.R.P.; Vasconcelos, M.H.; Sokovic, M.
- Highly efficient heterogeneous catalysts for phenol oxidation: Binuclear pyrrolyl-azine metal complexes encapsulated in NaY zeolite
Ku?niarska-Biernacka, I.; Raposo, M.M.M.; Batista, R.; Parpot, P.; Biernacki, K.; Magalh\~aes, A.L.; Fonseca, A.M.; Neves, I.C.
Microporous and Mesoporous Materials, 2016
- The powerful in vitro bioactivity of Euterpe oleracea Mart. seeds and related phenolic compounds
Barros, L.; Calhelha, R.C.; Queiroz, M.J.R.P.; Santos-Buelga, C.; Santos, E.A.; Regis, W.C.B.; Ferreira, I.C.F.R.
Industrial Crops and Products, 2015
- Enhanced electrochemical sensing of polyphenols by an oxygen-mediated surface
Gusmão, R.; López-Puente, V.; Pastoriza-Santos, I.; Pérez-Juste, J.; Proenc¸a, M.F.; Bento, F.; Geraldo, D.; Paiva, M.C.; González-Romero, E.
RSC Advances, 2015
- Bioactivity of phenolic acids: Metabolites versus parent compounds: A review
Heleno, S.A.; Martins, A.; Queiroz, M.J.R.P.; Ferreira, I.C.F.R.
Food Chemistry, 2015
- Chemical characterisation and bioactive properties of Prunus avium L.: The widely studied fruits and the unexplored stems
Bastos, C.; Barros, L.; Due\~nas, M.; Calhelha, R.C.; Queiroz, M.J.R.P.; Santos-Buelga, C.; Ferreira, I.C.F.R.
Food Chemistry, 2015
- Synthesis, Fluorescence, and Two-Photon Absorption Properties of Push–Pull 5-Arylthieno[3,2-b]thiophene Derivatives
Manuela, M.; Raposo, M.; Herbivo, C.; Hugues, V.; Clermont, G.; Castro, M.C.R.; Comel, A.; Blanchard-Desce, M.
European Journal of Organic Chemistry, 2016