Pyrrolo and pyrrolopyrimidine sulfonamides act as cytotoxic agents in hypoxia via inhibition of transmembrane carbonic anhydrases
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Date
2/15/2020
Journal Title
Journal ISSN
Volume Title
Type
Article
Publisher
Elsevier Masson SAS
Series Info
European Journal of Medicinal Chemistry;Volume 188, 15 February 2020, Article number 112021
Scientific Journal Rankings
Abstract
A series of novel sulfonamide derivatives bearing pyrrole and pyrrolopyrimidine scaffolds were synthesized and screened as carbonic anhydrase inhibitors. The inhibition activity of the synthesized compounds was evaluated against the cytosolic human carbonic anhydrase isoforms I and II and the transmembranal isoforms IX and XII. Several candidates showed potent inhibitory activity against IX and XII isoforms. Furthermore, ex vivo screening of cytotoxic selectivity and activity of the most potent derivatives were carried out against normal cells (WI38) and cervical cancer cell line (HeLa) under normal and hypoxic conditions using acetazolamide as reference drug. Compound 11b potency was nearly three folds higher in hypoxic than normoxic condition whereas that of compound 11f was nearly four folds higher in hypoxic vs. normoxic HeLa cells. All the screened derivatives exhibited less potency on normal cells (WI38). Molecular docking was carried out to discover the possible binding mode of compounds within the active site of isoform CA IX. © 2019 Elsevier Masson SAS
Description
scopus
Keywords
Sulfonamide, Pyrrolopyrimidine, Cytotoxic, Carbonic anhydrase inhibitor
Citation
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