MEDICINAL ORGANIC CHEMISTRY GROUP

Bahls, B.; Aljnadi, I.M.; Emídio, R.; Mendes, E.; Paulo, A. G-Quadruplexes in c-MYC Promoter as Targets for Cancer Therapy. Biomedicines 2023, 11, 969, doi:10.3390/biomedicines11030969.

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Barcherini, V.; Loureiro, J.B.; Sena, A.; Madeira, C.; Leandro, P.; Saraiva, L.; Antunes, A.M.M.; Santos, M.M.M. Metabolism-Guided Optimization of Tryptophanol-Derived Isoindolinone P53 Activators. Pharmaceuticals (Basel) 2023, 16, 146, doi:10.3390/ph16020146.

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Ferreira, R.; Pacheco, P. A. F.; Santos, M.M.M. Reativação Da P53 Usando Pequenas Moléculas Para Terapia Anticancerígena. Química 2023, 47, 30. https://b-quimica.spq.pt/files/files/BSPQ/74.pdf.

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Pinho, J.O.; Matias, M.; Marques, V.; Eleutério, C.; Fernandes, C.; Gano, L.; Amaral, J.D.; Mendes, E.; Perry, M.J.; Moreira, J.N.; Storm, G.; Francisco, A. P.; Rodrigues, C. M. P.; Gaspar, M. M.  Preclinical Validation of a New Hybrid Molecule Loaded in Liposomes for Melanoma Management. Biomed. Pharmacother. 2023, 157, 114021, doi:10.1016/j.biopha.2022.114021.

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Espadinha, M.; Lopes, E.A.; Marques, V.; Amaral, J.D.; dos Santos, D.J.V.A.; Mori, M.; Daniele, S.; Piccarducci, R.; Zappelli, E.; Martini, C.; Rodrigues, C.M.; Santos, M. M. M. Discovery of MDM2-P53 and MDM4-P53 Protein-Protein Interactions Small Molecule Dual Inhibitors. Eur. J. Med. Chem. 2022, 241, 114637, doi:10.1016/j.ejmech.2022.114637.

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Pais, J.P.; Policarpo, M.; Pires, D.; Francisco, A.P.; Madureira, A.M.; Testa, B.; Anes, E.; Constantino, L. Fluoroquinolone Derivatives in the Treatment of Mycobacterium Tuberculosis Infection. Pharmaceuticals (Basel) 2022, 15, 1213, doi:10.3390/ph15101213.

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Pais, J.P.; Magalhães, M.; Antoniuk, O.; Barbosa, I.; Freire, R.; Pires, D.; Valente, E.; Testa, B.; Anes, E.; Constantino, L. Benzoic Acid Derivatives as Prodrugs for the Treatment of Tuberculosis. Pharmaceuticals (Basel) 2022, 15, 1118, doi:10.3390/ph15091118.

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Mendes, E.; Bahls, B.; Aljnadi, I.M.; Paulo, A. Indoloquinolines as Scaffolds for the Design of Potent G-Quadruplex Ligands. Bioorg. Med. Chem. Lett. 2022, 72, 128862, doi:10.1016/j.bmcl.2022.128862.

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Lopes, E.A.; Mestre, R.; Fontinha, D.; Legac, J.; Pei, J.V.; Sanches-Vaz, M.; Mori, M.; Lehane, A.M.; Rosenthal, P.J.; Prudêncio, M.; Santos, M. M. M. Discovery of Spirooxadiazoline Oxindoles with Dual-Stage Antimalarial Activity. Eur. J. Med. Chem. 2022, 236, 114324, doi:10.1016/j.ejmech.2022.114324.

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Pacheco, P.A.F.; Santos, M.M.M. Recent Progress in the Development of Indole-Based Compounds Active against Malaria, Trypanosomiasis and Leishmaniasis. Molecules 2022, 27, 319, doi:10.3390/molecules27010319.

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Mendes, E.; Aljnadi, I.M.; Bahls, B.; Victor, B.L.; Paulo, A. Major Achievements in the Design of Quadruplex-Interactive Small Molecules. Pharmaceuticals (Basel) 2022, 15, 300, doi:10.3390/ph15030300.

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Loureiro, J.B.; Ribeiro, R.; Nazareth, N.; Ferreira, T.; Lopes, E.A.; Gama, A.; Machuqueiro, M.; Alves, M.G.; Marabini, L.; Oliveira, P.A.; Santos, M.M.M. Mutant P53 Reactivator SLMP53-2 Hinders Ultraviolet B Radiation-Induced Skin Carcinogenesis. Pharmacol. Res. 2022, 175, 106026, doi:10.1016/j.phrs.2021.106026.

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Mendes, R.M.; Francisco, A.P.; Carvalho, F.A.; Dardouri, M.; Costa, B.; Bettencourt, A.F.; Costa, J.; Gonçalves, L.; Costa, F.; Ribeiro, I.A.C. Fighting S. Aureus Catheter-Related Infections with Sophorolipids: Electing an Antiadhesive Strategy or a Release One? Colloids Surf. B Biointerfaces 2021, 208, 112057, doi:10.1016/j.colsurfb.2021.112057.

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Granada, M.; Mendes, E.; Perry, M.J.; Penetra, M.J.; Gaspar, M.M.; Pinho, J.O.; Serra, S.; António, C.T.; Francisco, A.P. Sulfur Analogues of Tyrosine in the Development of Triazene Hybrid Compounds: A New Strategy against Melanoma. ACS Med. Chem. Lett. 2021, 12, 1669–1677, doi:10.1021/acsmedchemlett.1c00252.

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Pinto, L.M.A.; Adeoye, O.; Thomasi, S.S.; Francisco, A.P.; Cabral-Marques, H. A Single-Step Multicomponent Synthesis of a Quinoline Derivative and the Characterization of Its Cyclodextrin Inclusion Complex. J. Mol. Struct. 2021, 1237, 130391, doi:10.1016/j.molstruc.2021.130391.

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Cadoni, E.; Magalhães, P.R.; Emídio, R.M.; Mendes, E.; Vítor, J.; Carvalho, J.; Cruz, C.; Victor, B.L.; Paulo, A. New (Iso)Quinolinyl-Pyridine-2,6-Dicarboxamide G-Quadruplex Stabilizers. A Structure-Activity Relationship Study. Pharmaceuticals (Basel) 2021, 14, 669, doi:10.3390/ph14070669.

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Valente, E.; Testa, B.; Constantino, L. Activation of Benzoate Model Prodrugs by Mycobacteria. Comparison with Mammalian Plasma and Liver Hydrolysis. Eur. J. Pharm. Sci. 2021, 162, 105831, doi:10.1016/j.ejps.2021.105831.

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Espadinha, M.; Barcherini, V.; Gonçalves, L.M.; Molins, E.; Antunes, A.M.M.; Santos, M.M.M. Tryptophanol-Derived Oxazolopyrrolidone Lactams as Potential Anticancer Agents against Gastric Adenocarcinoma. Pharmaceuticals (Basel) 2021, 14, 208, doi:10.3390/ph14030208.

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Raposo, L.R.; Silva, A.; Silva, D.; Roma-Rodrigues, C.; Espadinha, M.; Baptista, P.V.; Santos, M.M.M.; Fernandes, A.R. Exploiting the Antiproliferative Potential of Spiropyrazoline Oxindoles in a Human Ovarian Cancer Cell Line. Bioorg. Med. Chem. 2021, 30, 115880, doi:10.1016/j.bmc.2020.115880.

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Barcherini, V.; Almeida, J.; Lopes, E.A.; Wang, M.; Magalhães e Silva, D.; Mori, M.; Wang, S.; Saraiva, L.; Santos, M.M.M. Potency and Selectivity Optimization of Tryptophanol‐derived Oxazoloisoindolinones: Novel P53 Activators in Human Colorectal Cancer. ChemMedChem 2021, 16, 250–258, doi:10.1002/cmdc.202000522.

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Lopes, E.A.; Santos, M.M.M.; Mori, M. Pharmacological Treatment of Malaria. In Topics in Medicinal Chemistry; Topics in medicinal chemistry; Springer International Publishing: Cham, 2021; pp. 219–240 doi.org/10.1007/7355_2021_125.

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Pinto, L.M.A.; Adeoye, O.; Thomasi, S.S.; Francisco, A.P.; Carvalheiro, M.C.; Cabral-Marques, H. Preparation and Characterization of a Synthetic Curcumin Analog Inclusion Complex and Preliminary Evaluation of in Vitro Antileishmanial Activity. Int. J. Pharm. 2020, 589, 119764, doi:10.1016/j.ijpharm.2020.119764.

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Ghosh, R.; Vitor, J.B.; Mendes, E.; Paulo, A.; Acharya, P.C. Stereoselective Synthesis of Spirooxindole Derivatives Using One-Pot Multicomponent Cycloaddition Reaction and Evaluation of Their Antiproliferative Efficacy. ACS Omega 2020, 5, 27332–27343, doi:10.1021/acsomega.0c03675.

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Ramos, H.; Calheiros, J.; Almeida, J.; Barcherini, V.; Santos, S.; Carvalho, A.T.P.; Santos, M.M.M.; Saraiva, L. SLMP53-1 Inhibits Tumor Cell Growth through Regulation of Glucose Metabolism and Angiogenesis in a P53-Dependent Manner. Int. J. Mol. Sci. 2020, 21, 596, doi:10.3390/ijms21020596.

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Adeoye, O.; Bártolo, I.; Conceição, J.; da Silva, A.B.; Duarte, N.; Francisco, A.P.; Taveira, N.; Cabral-Marques, H. Pyromellitic Dianhydride Crosslinked Soluble Cyclodextrin Polymers: Synthesis, Lopinavir Release from Sub-Micron Sized Particles and Anti-HIV-1 Activity. Int. J. Pharm. 2020, 583, 119356, doi:10.1016/j.ijpharm.2020.119356.

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Espadinha, M.; Viejo, L.; Lopes, R.M.R.M.; Herrera-Arozamena, C.; Molins, E.; dos Santos, D.J.V.A.; Gonçalves, L.; Rodríguez-Franco, M.I.; Ríos, C. de L.; Santos, M.M.M. Identification of Tetracyclic Lactams as NMDA Receptor Antagonists with Potential Application in Neurological Disorders. Eur. J. Med. Chem. 2020, 194, 112242, doi:10.1016/j.ejmech.2020.112242.

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Zwergel, C.; Fioravanti, R.; Stazi, G.; Sarno, F.; Battistelli, C.; Romanelli, A.; Nebbioso, A.; Mendes, E.; Paulo, A.; Strippoli, R.; Tripodi, M.; Pechalrieu, D.; Arimondo, P. B.; De Luca, T.; Del Bufalo, D.; Trisciuoglio, D.; Altucci, L.; Valente, S.; Mai, A. Novel Quinoline Compounds Active in Cancer Cells through Coupled DNA Methyltransferase Inhibition and Degradation. Cancers (Basel) 2020, 12, 447, doi:10.3390/cancers12020447.

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Gomes, A.S.; Ramos, H.; Gomes, S.; Loureiro, J.B.; Soares, J.; Barcherini, V.; Monti, P.; Fronza, G.; Oliveira, C.; Domingues, L.; Bastos, M.; Dourado, D. F. A. R.; Carvalho, A. L.; Romão, M. J.; Pinheiro, B.; Marcelo, F.; Carvalho, A.; Santos, M. M. M.; Saraiva, L.  SLMP53-1 Interacts with Wild-Type and Mutant P53 DNA-Binding Domain and Reactivates Multiple Hotspot Mutations. Biochim. Biophys. Acta Gen. Subj. 2020, 1864, 129440, doi:10.1016/j.bbagen.2019.129440.

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Lopes, E.A.; Santos, M.M.M. Synthesis of Spirooxindoles by Multicomponent Reactions. Synthetic Approaches to Nonaromatic Nitrogen Heterocycles 2020, 225–247, doi.org/10.1002/9781119708841.ch9.

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Espadinha, M.; Conway, S.J.; Santos, M.M.M. PPIs as Therapeutic Targets for Anticancer Drug Discovery: The Case Study of MDM2 and BET Bromodomain Inhibitors. In Small Molecule Drug Discovery; Elsevier, 2020; pp. 267–288. doi.org/10.1016/B978-0-12-818349-6.00010-8.

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Lopes, E.A.; Gomes, S.; Saraiva, L.; Santos, M.M.M. Small Molecules Targeting Mutant P53: A Promising Approach for Cancer Treatment. Curr. Med. Chem. 2020, 26, 7323–7336, doi:10.2174/0929867325666181116124308.

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Gomes, S.; Bosco, B.; Loureiro, J.B.; Ramos, H.; Raimundo, L.; Soares, J.; Nazareth, N.; Barcherini, V.; Domingues, L.; Oliveira, C.; Bisio, A.; Piazza, S.; Bauer, M. R.; Brás, J. P.; Almeida, M. I.; Gomes, C.; Reis, F.; Fersht, A. R.; Inga, A.; Santos, M. M. M.; Saraiva, L. SLMP53-2 Restores Wild-Type-like Function to Mutant P53 through Hsp70: Promising Activity in Hepatocellular Carcinoma. Cancers (Basel) 2019, 11, 1151, doi:10.3390/cancers11081151.

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Francisco, A.P.; Mendes, E.; Santos, A.R.; Perry, M.J. Anticancer Triazenes: From Bioprecursors to Hybrid Molecules. Curr. Pharm. Des. 2019, 25, 1623–1642, doi:10.2174/1381612825666190617155749.

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Amaral, J.D.; Silva, D.; Rodrigues, C.M.P.; Solá, S.; Santos, M.M.M. A Novel Small Molecule P53 Stabilizer for Brain Cell Differentiation. Front. Chem. 2019, 7, doi:10.3389/fchem.2019.00015.

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Mendes, E.; Cadoni, E.; Carneiro, F.; Afonso, M.B.; Brito, H.; Lavrado, J.; Dos Santos, D.J.V.A.; Vítor, J.B.; Neidle, S.; Rodrigues, C.M.P.; Paulo, A. Combining 1,3-Ditriazolylbenzene and Quinoline to Discover a New G-Quadruplex-Interactive Small Molecule Active against Cancer Stem-like Cells. ChemMedChem 2019, 14, 1325–1328, doi:10.1002/cmdc.201900243.

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Espadinha, M.; Lourenço, N.M.T.; Sobral, L.; Antunes, R.; Santos, M.M.M. A More Sustainable Process for Preparation of the Muscarinic Acetylcholine Antagonist Umeclidinium Bromide. ChemMedChem 2018, 13, 2053–2056, doi:10.1002/cmdc.201800387.

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Raimundo, L.; Espadinha, M.; Soares, J.; Loureiro, J.B.; Alves, M.G.; Santos, M.M.M.; Saraiva, L. Improving Anticancer Activity towards Colon Cancer Cells with a New P53‐activating Agent. Br. J. Pharmacol. 2018, 175, 3947–3962, doi:10.1111/bph.14468.

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Faustino, C.; Francisco, A.P.; Isca, V.M.S.; Duarte, N. Cytotoxic Stilbenes and Derivatives as Promising Antimitotic Leads for Cancer Therapy. Curr. Pharm. Des. 2019, 24, 4270–4311, doi:10.2174/1381612825666190111123959.

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Espadinha, M.; Barcherini, V.; Lopes, E.A.; Santos, M.M.M. An Update on MDMX and Dual MDM2/X Inhibitors. Curr. Top. Med. Chem. 2018, 18, 647–660, doi:10.2174/1568026618666180604080119.

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Duarte, A.R.; Cadoni, E.; Ressurreição, A.S.; Moreira, R.; Paulo, A. Design of Modular G‐quadruplex Ligands. ChemMedChem 2018, 13, 869–893, doi:10.1002/cmdc.201700747.

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Francisco, A.P.; Paulo, A. Oncogene Expression Modulation in Cancer Cell Lines by DNA G-Quadruplex-Interactive Small Molecules. Curr. Med. Chem. 2017, 24, 4873–4904, doi:10.2174/0929867323666160829145055.

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Ribeiro, C.J.A.; Nunes, R.C.; Amaral, J.D.; Gonçalves, L.M.; Rodrigues, C.M.P.; Moreira, R.; Santos, M.M.M. Spirotriazoline Oxindoles: A Novel Chemical Scaffold with in Vitro Anticancer Properties. Eur. J. Med. Chem. 2017, 140, 494–509, doi:10.1016/j.ejmech.2017.09.037.

 

Sousa, A.; Santos, F.; Gaspar, M.M.; Calado, S.; Pereira, J.D.; Mendes, E.; Francisco, A.P.; Perry, M.J. The Selective Cytotoxicity of New Triazene Compounds to Human Melanoma Cells. Bioorg. Med. Chem. 2017, 25, 3900–3910, doi:10.1016/j.bmc.2017.04.049.

 

Nunes, R.C.; Ribeiro, C.J.A.; Monteiro, Â.; Rodrigues, C.M.P.; Amaral, J.D.; Santos, M.M.M. In Vitro Targeting of Colon Cancer Cells Using Spiropyrazoline Oxindoles. Eur. J. Med. Chem. 2017, 139, 168–179, doi:10.1016/j.ejmech.2017.07.057.

 

Soares, J.; Espadinha, M.; Raimundo, L.; Ramos, H.; Gomes, A.S.; Gomes, S.; Loureiro, J.B.; Inga, A.; Reis, F.; Gomes, C.; Santos, M. M. M. DIMP53-1: A Novel Small-Molecule Dual Inhibitor of P53-MDM2/X Interactions with Multifunctional P53-Dependent Anticancer Properties. Mol. Oncol. 2017, 11, 612–627, doi:10.1002/1878-0261.12051.

 

Mariz, I.F.A.; Pinto, S.; Lavrado, J.; Paulo, A.; Martinho, J.M.G.; Maçôas, E.M.S. Cryptolepine and Quindoline: Understanding Their Photophysics. Phys. Chem. Chem. Phys. 2017, 19, 10255–10263, doi:10.1039/c7cp00455a.

 

Espadinha, M.; Dourado, J.; Lajarin-Cuesta, R.; Herrera-Arozamena, C.; Gonçalves, L.M.D.; Rodríguez-Franco, M.I.; de los Rios, C.; Santos, M.M.M. Optimization of Bicyclic Lactam Derivatives as NMDA Receptor Antagonists. ChemMedChem 2017, 12, 537–545, doi:10.1002/cmdc.201700037.