Fluoroenesulphonamides: N-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition

After hydrofluorination of ynesulphonamides in superacid or in the presence of hydrofluoric acid/base reagents, a series of α-fluoroenamides has been synthesised and tested for the inhibition of carbonic anhydrase (CA, EC 4.2.1.1) isoforms. This study reveals a new, highly selective family of cancer...

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Autores principales: Métayer, Benoit, Angeli, Andrea, Mingot, Agnès, Jouvin, Kévin, Evano, Gwilherm, Supuran, Claudiu T., Thibaudeau, Sébastien
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Taylor & Francis 2018
Materias:
Short Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009971/
https://www.ncbi.nlm.nih.gov/pubmed/29706097
http://dx.doi.org/10.1080/14756366.2018.1461097
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author Métayer, Benoit
Angeli, Andrea
Mingot, Agnès
Jouvin, Kévin
Evano, Gwilherm
Supuran, Claudiu T.
Thibaudeau, Sébastien
author_facet Métayer, Benoit
Angeli, Andrea
Mingot, Agnès
Jouvin, Kévin
Evano, Gwilherm
Supuran, Claudiu T.
Thibaudeau, Sébastien
author_sort Métayer, Benoit
collection PubMed
description After hydrofluorination of ynesulphonamides in superacid or in the presence of hydrofluoric acid/base reagents, a series of α-fluoroenamides has been synthesised and tested for the inhibition of carbonic anhydrase (CA, EC 4.2.1.1) isoforms. This study reveals a new, highly selective family of cancer-related transmembrane human (h) CA IX/XII inhibitors. These original fluorinated ureido isosters do not inhibit the widespread cytosolic isoforms hCA I and II and selectively inhibit the transmembrane cancer-related hCA IX and XII, offering interesting new leads for future studies.
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spelling pubmed-60099712018-07-11 Fluoroenesulphonamides: N-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition Métayer, Benoit Angeli, Andrea Mingot, Agnès Jouvin, Kévin Evano, Gwilherm Supuran, Claudiu T. Thibaudeau, Sébastien J Enzyme Inhib Med Chem Short Communication After hydrofluorination of ynesulphonamides in superacid or in the presence of hydrofluoric acid/base reagents, a series of α-fluoroenamides has been synthesised and tested for the inhibition of carbonic anhydrase (CA, EC 4.2.1.1) isoforms. This study reveals a new, highly selective family of cancer-related transmembrane human (h) CA IX/XII inhibitors. These original fluorinated ureido isosters do not inhibit the widespread cytosolic isoforms hCA I and II and selectively inhibit the transmembrane cancer-related hCA IX and XII, offering interesting new leads for future studies. Taylor & Francis 2018-04-30 /pmc/articles/PMC6009971/ /pubmed/29706097 http://dx.doi.org/10.1080/14756366.2018.1461097 Text en © 2018 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group. http://creativecommons.org/licenses/by/4.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Short Communication
Métayer, Benoit
Angeli, Andrea
Mingot, Agnès
Jouvin, Kévin
Evano, Gwilherm
Supuran, Claudiu T.
Thibaudeau, Sébastien
Fluoroenesulphonamides: N-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition
title Fluoroenesulphonamides: N-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition
title_full Fluoroenesulphonamides: N-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition
title_fullStr Fluoroenesulphonamides: N-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition
title_full_unstemmed Fluoroenesulphonamides: N-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition
title_short Fluoroenesulphonamides: N-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition
title_sort fluoroenesulphonamides: n-sulphonylurea isosteres showing nanomolar selective cancer-related transmembrane human carbonic anhydrase inhibition
topic Short Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009971/
https://www.ncbi.nlm.nih.gov/pubmed/29706097
http://dx.doi.org/10.1080/14756366.2018.1461097
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