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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†.
J Enzyme Inhib Med Chem. 2019 Dec; 34(1):773-782.JE

Abstract

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.

Authors+Show Affiliations

a Laboratoire de Chimie, physique Université du 8 Mai 1945 , Guelma , Algérie. b CNRS, Laboratoire de Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique, SPCMIB , Toulouse , France. c Université de Toulouse, UPS, Laboratoire de Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique, SPCMIB , Toulouse , France.b CNRS, Laboratoire de Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique, SPCMIB , Toulouse , France. c Université de Toulouse, UPS, Laboratoire de Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique, SPCMIB , Toulouse , France.d Institut de Chimie de Toulouse (FR 2599) , Toulouse , France.d Institut de Chimie de Toulouse (FR 2599) , Toulouse , France.e Institut des Biomolécules Max Mousseron, ENSCM, Université de Montpellier , Montpellier , France.f Neurofarba Department , Section of Pharmaceutical and Nutriceutical Sciences, Università degli Studi di Firenze , Florence , Italy.f Neurofarba Department , Section of Pharmaceutical and Nutriceutical Sciences, Università degli Studi di Firenze , Florence , Italy.b CNRS, Laboratoire de Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique, SPCMIB , Toulouse , France. c Université de Toulouse, UPS, Laboratoire de Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique, SPCMIB , Toulouse , France.a Laboratoire de Chimie, physique Université du 8 Mai 1945 , Guelma , Algérie.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30843736

Citation

Aimene, Yassine, et al. "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†." Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 34, no. 1, 2019, pp. 773-782.
Aimene Y, Eychenne R, Mallet-Ladeira S, et al. 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†. J Enzyme Inhib Med Chem. 2019;34(1):773-782.
Aimene, Y., Eychenne, R., Mallet-Ladeira, S., Saffon, N., Winum, J. Y., Nocentini, A., Supuran, C. T., Benoist, E., & Seridi, A. (2019). 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†. Journal of Enzyme Inhibition and Medicinal Chemistry, 34(1), 773-782. https://doi.org/10.1080/14756366.2019.1585835
Aimene Y, et al. 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†. J Enzyme Inhib Med Chem. 2019;34(1):773-782. PubMed PMID: 30843736.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 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†. AU - Aimene,Yassine, AU - Eychenne,Romain, AU - Mallet-Ladeira,Sonia, AU - Saffon,Nathalie, AU - Winum,Jean-Yves, AU - Nocentini,Alessio, AU - Supuran,Claudiu T, AU - Benoist,Eric, AU - Seridi,Achour, PY - 2019/3/8/entrez PY - 2019/3/8/pubmed PY - 2019/5/8/medline KW - Click chemistry KW - DFT calculations KW - carbonic anhydrase inhibitors KW - crystal structures KW - rhenium(I) complexes SP - 773 EP - 782 JF - Journal of enzyme inhibition and medicinal chemistry JO - J Enzyme Inhib Med Chem VL - 34 IS - 1 N2 - 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. SN - 1475-6374 UR - https://www.unboundmedicine.com/medline/citation/30843736/Novel_Re_I__tricarbonyl_coordination_compounds_based_on_2_pyridyl_123_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†_ L2 - http://www.tandfonline.com/doi/full/10.1080/14756366.2019.1585835 DB - PRIME DP - Unbound Medicine ER -