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Discovery of 2,4-thiazolidinedione-tethered coumarins as novel selective inhibitors for carbonic anhydrase IX and XII isoforms.

ABSTRACT: Different 2,4-thiazolidinedione-tethered coumarins 5a-b, 10a-n and 11a-d were synthesised and evaluated for their inhibitory action against the cancer-associated hCAs IX and XII, as well as the physiologically dominant hCAs I and II to explore their selectivity. Un-substituted phenyl-bearing coumarins 10a, 10 h, and 2-thienyl/furyl-bearing coumarins 11a-c exhibited the best hCA IX (KIs between 0.48 and 0.93 µM) and hCA XII (KIs between 0.44 and 1.1 µM) inhibitory actions. Interestingly, none of the coumarins had any inhibitory effect on the off-target hCA I and II isoforms. The sub-micromolar compounds from the biochemical assay, coumarins 10a, 10 h and 11a-c, were assessed in an in vitro antiproliferative assay, and then the most potent antiproliferative agent 11a was tested to explore its impact on the cell cycle phases and apoptosis in MCF-7 breast cancer cells to provide more insights into the anticancer activity of these compounds.

SUBMITTER: Eldehna WM 

PROVIDER: S-EPMC8745369 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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Discovery of 2,4-thiazolidinedione-tethered coumarins as novel selective inhibitors for carbonic anhydrase IX and XII isoforms.

Eldehna Wagdy M WM   Taghour Mohammed S MS   Al-Warhi Tarfah T   Nocentini Alessio A   Elbadawi Mostafa M MM   Mahdy Hazem A HA   Abdelrahman Mohamed A MA   Alotaibi Ohoud J OJ   Aljaeed Nada N   Elimam Diaaeldin M DM   Afarinkia Kamyar K   Abdel-Aziz Hatem A HA   Supuran Claudiu T CT  

Journal of enzyme inhibition and medicinal chemistry 20221201 1

Different 2,4-thiazolidinedione-tethered coumarins <b>5a-b</b>, <b>10a-n</b> and <b>11a-d</b> were synthesised and evaluated for their inhibitory action against the cancer-associated <i>h</i>CAs IX and XII, as well as the physiologically dominant <i>h</i>CAs I and II to explore their selectivity. Un-substituted phenyl-bearing coumarins <b>10a</b>, <b>10 h</b>, and 2-thienyl/furyl-bearing coumarins <b>11a-c</b> exhibited the best <i>h</i>CA IX (K<sub>I</sub>s between 0.48 and 0.93 µM) and <i>h</i  ...[more]

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