Novel Re(I) tricarbonyl coordination compounds based on 2-pyridyl-1,2,3-triazole derivatives bearing a 4-amino-substituted benzenesulfonamide arm: synthesis, crystal structure, computational studies and inhibitory activity against carbonic anhydrase I, II, and IX isoforms†
| Autor: | Sonia Mallet-Ladeira, Nathalie Saffon, Claudiu T. Supuran, Romain Eychenne, Eric Benoist, Yassine Aimene, Jean-Yves Winum, Achour Seridi, Alessio Nocentini |
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| Přispěvatelé: | Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique (SPCMIB), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Structure Fédérative Toulousaine en Chimie Moléculaire (SFTCM), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Laboratorio di Chimica Bioinorganica (LCBI), Università degli Studi di Firenze = University of Florence (UniFI), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Università degli Studi di Firenze = University of Florence [Firenze] (UNIFI) |
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Gene isoform
Models Molecular carbonic anhydrase inhibitors 1 2 3-Triazole Denticity Carbonic Anhydrase I Stereochemistry Crystal structure Crystallography X-Ray 01 natural sciences Carbonic Anhydrase II rhenium(i) complexes dft calculations Coordination complex chemistry.chemical_compound Structure-Activity Relationship crystal structures Antigens Neoplasm Drug Discovery Humans [CHIM]Chemical Sciences Carbonic Anhydrase IX Density Functional Theory ComputingMilieux_MISCELLANEOUS Pharmacology chemistry.chemical_classification Carbon Monoxide Sulfonamides Dose-Response Relationship Drug Molecular Structure 010405 organic chemistry Chemistry lcsh:RM1-950 General Medicine Triazoles 0104 chemical sciences 3. Good health Isoenzymes 010404 medicinal & biomolecular chemistry Rhenium lcsh:Therapeutics. Pharmacology click chemistry Click chemistry Pharmacophore Research Paper |
| Zdroj: | Journal of Enzyme Inhibition and Medicinal Chemistry Journal of Enzyme Inhibition and Medicinal Chemistry, 2019, 34 (1), pp.773-782. ⟨10.1080/14756366.2019.1585835⟩ Journal of Enzyme Inhibition and Medicinal Chemistry, Informa Healthcare, 2019, 34 (1), pp.773-782. ⟨10.1080/14756366.2019.1585835⟩ Journal of Enzyme Inhibition and Medicinal Chemistry, Vol 34, Iss 1, Pp 773-782 (2019) |
| ISSN: | 1475-6366 1475-6374 |
| DOI: | 10.1080/14756366.2019.1585835⟩ |
| Popis: | In this work, two bidentate 2-pyridyl-1,2,3-triazole ligands (3a and 3b) containing a 4-substituted benzenesulfonamide pharmacophore prepared by classical click chemistry procedures, as well as their corresponding rhenium complexes, 4a and 4b of general formula [ReCl(CO)3(L)] (L = 3a or 3b) were prepared and fully characterised by spectroscopic methods (IR, NMR, MS, UV-Vis), elemental analysis, X-ray diffraction, and theoretical studies using DFT and TD-DFT methods. In particular, we showed that, in the solid state, the pyridine and the triazole rings of 3b adopted an uncommon cis configuration which stems from intermolecular hydrogen bonds. Preliminary assays demonstrated a promising nanomolar inhibitory activity against carbonic anhydrase isoform IX for both ligands and complexes with a strong affinity Ki of 2.8 nM for ligand 3a. More interestingly, complex 4b exhibited a pronounced selectivity against hCA IX over the off-targets hCA I and hCA II which makes this compound a promising potential anticancer drug candidate. |
| Databáze: | OpenAIRE |
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