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Synthesis of different thio-scaffolds bearing sulfonamide with subnanomolar carbonic anhydrase II and IX inhibitory properties and X-ray investigations for their inhibitory mechanism.
Bioorg Chem. 2018 12; 81:642-648.BC

Abstract

Several new molecules with different thio-scaffolds were designed, synthesised, and evaluated biologically as inhibitors of Carbonic Anhydrases (CAIs). The structure-activity relationship analysis identified thioether derivatives, here reported, as a potent and selective CAIs against hCA II and hCA IX. High resolution X-ray structure of inhibitor bound hCA II revealed extensive interactions with the hydrophobic pocket of active site and provided molecular insight into the binding properties of these new inhibitors.

Authors+Show Affiliations

Department of University of Florence, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino (Florence), Italy.Department of University of Florence, Department of Chemistry "Ugo Schiff", Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy.Department of University of Florence, Department of Chemistry "Ugo Schiff", Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy.Department of University of Florence, Department of Chemistry "Ugo Schiff", Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy.Department of University of Florence, Department of Chemistry "Ugo Schiff", Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy.Department of University of Florence, Department of Chemistry "Ugo Schiff", Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy.Department of University of Florence, NEUROFARBA Dept., Sezione di Scienze Farmaceutiche, Via Ugo Schiff 6, 50019 Sesto Fiorentino (Florence), Italy. Electronic address: claudiu.supuran@unifi.it.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30253337

Citation

Angeli, Andrea, et al. "Synthesis of Different Thio-scaffolds Bearing Sulfonamide With Subnanomolar Carbonic Anhydrase II and IX Inhibitory Properties and X-ray Investigations for Their Inhibitory Mechanism." Bioorganic Chemistry, vol. 81, 2018, pp. 642-648.
Angeli A, Tanini D, Capperucci A, et al. Synthesis of different thio-scaffolds bearing sulfonamide with subnanomolar carbonic anhydrase II and IX inhibitory properties and X-ray investigations for their inhibitory mechanism. Bioorg Chem. 2018;81:642-648.
Angeli, A., Tanini, D., Capperucci, A., Malevolti, G., Turco, F., Ferraroni, M., & Supuran, C. T. (2018). Synthesis of different thio-scaffolds bearing sulfonamide with subnanomolar carbonic anhydrase II and IX inhibitory properties and X-ray investigations for their inhibitory mechanism. Bioorganic Chemistry, 81, 642-648. https://doi.org/10.1016/j.bioorg.2018.09.028
Angeli A, et al. Synthesis of Different Thio-scaffolds Bearing Sulfonamide With Subnanomolar Carbonic Anhydrase II and IX Inhibitory Properties and X-ray Investigations for Their Inhibitory Mechanism. Bioorg Chem. 2018;81:642-648. PubMed PMID: 30253337.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of different thio-scaffolds bearing sulfonamide with subnanomolar carbonic anhydrase II and IX inhibitory properties and X-ray investigations for their inhibitory mechanism. AU - Angeli,Andrea, AU - Tanini,Damiano, AU - Capperucci,Antonella, AU - Malevolti,Gianni, AU - Turco,Francesca, AU - Ferraroni,Marta, AU - Supuran,Claudiu T, Y1 - 2018/09/20/ PY - 2018/08/02/received PY - 2018/09/07/revised PY - 2018/09/18/accepted PY - 2018/9/27/pubmed PY - 2019/4/16/medline PY - 2018/9/26/entrez KW - Carbonic anhydrase KW - Inhibitor KW - Metalloenzymes KW - Sulfur SP - 642 EP - 648 JF - Bioorganic chemistry JO - Bioorg. Chem. VL - 81 N2 - Several new molecules with different thio-scaffolds were designed, synthesised, and evaluated biologically as inhibitors of Carbonic Anhydrases (CAIs). The structure-activity relationship analysis identified thioether derivatives, here reported, as a potent and selective CAIs against hCA II and hCA IX. High resolution X-ray structure of inhibitor bound hCA II revealed extensive interactions with the hydrophobic pocket of active site and provided molecular insight into the binding properties of these new inhibitors. SN - 1090-2120 UR - https://www.unboundmedicine.com/medline/citation/30253337/Synthesis_of_different_thio_scaffolds_bearing_sulfonamide_with_subnanomolar_carbonic_anhydrase_II_and_IX_inhibitory_properties_and_X_ray_investigations_for_their_inhibitory_mechanism_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0045-2068(18)30811-3 DB - PRIME DP - Unbound Medicine ER -