Indole-Based Hydrazones Containing A Sulfonamide Moiety as Selective Inhibitors of Tumor-Associated Human Carbonic Anhydrase Isoforms IX and XII

Novel sulfonamidoindole-based hydrazones with a 2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamide scaffold were synthesized and tested in enzyme inhibition assays against the tumor-associated carbonic anhydrase isoforms, hCA IX and XII, and the off-targets, hCA I and II. The compounds showed se...

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Autores principales: Demir-Yazıcı, Kübra, Bua, Silvia, Akgüneş, Nurgül Mutlu, Akdemir, Atilla, Supuran, Claudiu T., Güzel-Akdemir, Özlen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6539891/
https://www.ncbi.nlm.nih.gov/pubmed/31083645
http://dx.doi.org/10.3390/ijms20092354
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author Demir-Yazıcı, Kübra
Bua, Silvia
Akgüneş, Nurgül Mutlu
Akdemir, Atilla
Supuran, Claudiu T.
Güzel-Akdemir, Özlen
author_facet Demir-Yazıcı, Kübra
Bua, Silvia
Akgüneş, Nurgül Mutlu
Akdemir, Atilla
Supuran, Claudiu T.
Güzel-Akdemir, Özlen
author_sort Demir-Yazıcı, Kübra
collection PubMed
description Novel sulfonamidoindole-based hydrazones with a 2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamide scaffold were synthesized and tested in enzyme inhibition assays against the tumor-associated carbonic anhydrase isoforms, hCA IX and XII, and the off-targets, hCA I and II. The compounds showed selectivity against hCA IX and XII over hCA I and II. Six compounds showed K(I) values lower than 10 nM against hCA IX or XII. Molecular modeling studies were performed to suggest binding interactions between the ligand and the hCA active sites.
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spelling pubmed-65398912019-06-04 Indole-Based Hydrazones Containing A Sulfonamide Moiety as Selective Inhibitors of Tumor-Associated Human Carbonic Anhydrase Isoforms IX and XII Demir-Yazıcı, Kübra Bua, Silvia Akgüneş, Nurgül Mutlu Akdemir, Atilla Supuran, Claudiu T. Güzel-Akdemir, Özlen Int J Mol Sci Article Novel sulfonamidoindole-based hydrazones with a 2-(hydrazinocarbonyl)-3-phenyl-1H-indole-5-sulfonamide scaffold were synthesized and tested in enzyme inhibition assays against the tumor-associated carbonic anhydrase isoforms, hCA IX and XII, and the off-targets, hCA I and II. The compounds showed selectivity against hCA IX and XII over hCA I and II. Six compounds showed K(I) values lower than 10 nM against hCA IX or XII. Molecular modeling studies were performed to suggest binding interactions between the ligand and the hCA active sites. MDPI 2019-05-12 /pmc/articles/PMC6539891/ /pubmed/31083645 http://dx.doi.org/10.3390/ijms20092354 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Demir-Yazıcı, Kübra
Bua, Silvia
Akgüneş, Nurgül Mutlu
Akdemir, Atilla
Supuran, Claudiu T.
Güzel-Akdemir, Özlen
Indole-Based Hydrazones Containing A Sulfonamide Moiety as Selective Inhibitors of Tumor-Associated Human Carbonic Anhydrase Isoforms IX and XII
title Indole-Based Hydrazones Containing A Sulfonamide Moiety as Selective Inhibitors of Tumor-Associated Human Carbonic Anhydrase Isoforms IX and XII
title_full Indole-Based Hydrazones Containing A Sulfonamide Moiety as Selective Inhibitors of Tumor-Associated Human Carbonic Anhydrase Isoforms IX and XII
title_fullStr Indole-Based Hydrazones Containing A Sulfonamide Moiety as Selective Inhibitors of Tumor-Associated Human Carbonic Anhydrase Isoforms IX and XII
title_full_unstemmed Indole-Based Hydrazones Containing A Sulfonamide Moiety as Selective Inhibitors of Tumor-Associated Human Carbonic Anhydrase Isoforms IX and XII
title_short Indole-Based Hydrazones Containing A Sulfonamide Moiety as Selective Inhibitors of Tumor-Associated Human Carbonic Anhydrase Isoforms IX and XII
title_sort indole-based hydrazones containing a sulfonamide moiety as selective inhibitors of tumor-associated human carbonic anhydrase isoforms ix and xii
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6539891/
https://www.ncbi.nlm.nih.gov/pubmed/31083645
http://dx.doi.org/10.3390/ijms20092354
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