Synthesis and biological evaluation of histamine Schiff bases as carbonic anhydrase I, II, IV, VII, and IX activators

Journal of Enzyme Inhibition and Medicinal Chemistry
Suleyman AkocakClaudiu T Supuran

Abstract

A series of 20 histamine Schiff base was synthesised by reaction of histamine, a well known carbonic anhydrase (CA, E.C 4.2.2.1.) activator pharmacophore, with substituted aldehydes. The obtained histamine Schiff bases were assayed as activators of five selected human (h) CA isozymes, the cytosolic hCA I, hCA II, and hCA VII, the membrane-anchored hCA IV and transmembrane hCA IX. Some of these compounds showed efficient activity (in the nanomolar range) against the cytosolic isoform hCA VII, which is a key CA enzyme involved in brain metabolism. Moderate activity was observed against hCA I and hCA IV (in the nanomolar to low micromolar range). The structure-activity relationship for activation of these isoforms with the new histamine Schiff bases is discussed in detail based on the nature of the aliphatic, aromatic, or heterocyclic moiety present in the aldehyde fragment of the molecule, which may participate in diverse interactions with amino acid residues at the entrance of the active site, where activators bind, and which is the most variable part among the different CA isoforms.

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Feb 6, 2013·Journal of Enzyme Inhibition and Medicinal Chemistry·Claudiu T Supuran
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May 1, 2013·Expert Opinion on Therapeutic Patents·Emanuela MasiniClaudiu T Supuran
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Apr 29, 2014·Journal of Enzyme Inhibition and Medicinal Chemistry·Clemente Capasso, Claudiu T Supuran
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Dec 2, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Claudiu T Supuran
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Nov 2, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Erol LicsandruClaudiu T Supuran
Mar 7, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Halise Inci GulClaudiu T Supuran

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Citations

Dec 14, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Adriano MollicaClaudiu T Supuran
Dec 29, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sonia Del PreteClemente Capasso
Dec 13, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Andrea AngeliClaudiu T Supuran
Dec 28, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Andrea AngeliClaudiu T Supuran
May 12, 2018·Journal of Enzyme Inhibition and Medicinal Chemistry·Azzurra StefanucciClaudiu T Supuran
Feb 27, 2018·Future Medicinal Chemistry·Claudiu T Supuran
Apr 28, 2020·Journal of Enzyme Inhibition and Medicinal Chemistry·Niccolò ChiaramonteMaria Novella Romanelli
Jun 25, 2020·Journal of Enzyme Inhibition and Medicinal Chemistry·Alessio NocentiniClaudiu T Supuran
Oct 18, 2019·Journal of Enzyme Inhibition and Medicinal Chemistry·Manuel A LlanosLuciana Gavernet
Feb 9, 2019·Journal of Enzyme Inhibition and Medicinal Chemistry·Marouan RamiSaïd Yous
Sep 19, 2019·Journal of Enzyme Inhibition and Medicinal Chemistry·Suleyman Akocak, Claudiu T Supuran
Mar 29, 2020·Journal of Enzyme Inhibition and Medicinal Chemistry·Andrea AngeliClaudiu T Supuran
Jun 27, 2019·Journal of Enzyme Inhibition and Medicinal Chemistry·Suleyman AkocakClaudiu T Supuran

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