A class of sulfonamide carbonic anhydrase inhibitors with neuropathic pain modulating effects

Bioorganic & Medicinal Chemistry
Fabrizio CartaClaudiu T Supuran

Abstract

A series of benzene sulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitors which incorporate lipophilic 4-alkoxy- and 4-aryloxy moieties, together with several derivatives of ethoxzolamide and sulfanilamide are reported. These derivatives were investigated as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) of which multiple isoforms are known, and some appear to be involved in pain. These sulfonamides showed modest inhibition against the cytosolic isoform CA I, but were generally effective, low nanomolar CA II, VII, IX and XII inhibitors. X-ray crystallographic data for the adduct of several such sulfonamides with CA II allowed us to rationalize the good inhibition data. In a mice model of neuropathic pain induced by oxaliplatin, one of the strong CA II/VII inhibitors reported here induced a long lasting pain relieving effect, a fact never observed earlier. This is the first report of rationally designed sulfonamide CA inhibitors with pain effective modulating effects.

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Citations

Dec 2, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Claudiu T Supuran
Aug 20, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Erhan BaşarMuharrem Kaya
Jul 3, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Parham TaslimiClaudiu T Supuran
Nov 27, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Lorenzo Di Cesare MannelliClaudiu T Supuran
Feb 24, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·F Zehra KüçükbayClaudiu T Supuran
Feb 16, 2016·Expert Opinion on Drug Metabolism & Toxicology·Claudiu T Supuran
May 28, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Jorge R A DiazGerardo E Camí
May 24, 2016·Expert Review of Neurotherapeutics·Claudiu T Supuran
Oct 27, 2016·Expert Opinion on Drug Discovery·Claudiu T Supuran
Mar 21, 2017·Bioorganic & Medicinal Chemistry·Menshawy A MohamedClaudiu T Supuran
Nov 2, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Erol LicsandruClaudiu T Supuran
Jul 29, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Morteza AbdoliClaudiu T Supuran
Jul 22, 2016·International Journal of Molecular Sciences·Carrie L LomelinoRobert McKenna
Sep 30, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Claudiu T Supuran
Jan 13, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Aikaterini PeperidouClaudiu T Supuran
Dec 23, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ylenia CauMaurizio Botta
Mar 27, 2018·Journal of Enzyme Inhibition and Medicinal Chemistry·Silvia BuaClaudiu T Supuran
Sep 25, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Andrea AngeliClaudiu T Supuran
Dec 23, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Simona Maria MontiClaudiu T Supuran
Dec 28, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Andrea AngeliClaudiu T Supuran
Sep 4, 2018·Expert Opinion on Therapeutic Patents·Claudiu T Supuran
Sep 16, 2018·Expert Opinion on Therapeutic Patents·Claudiu T Supuran
Nov 15, 2018·Expert Opinion on Investigational Drugs·Claudiu T Supuran
Feb 3, 2018·Journal of Enzyme Inhibition and Medicinal Chemistry·Claudiu T Supuran
Oct 27, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Suleyman AkocakClaudiu T Supuran
Apr 21, 2019·International Journal of Molecular Sciences·Laura MicheliLorenzo Di Cesare Mannelli
Aug 23, 2019·Expert Opinion on Drug Discovery·Alessio Nocentini, Claudiu T Supuran
Feb 27, 2018·Future Medicinal Chemistry·Claudiu T Supuran
Mar 17, 2020·Expert Opinion on Drug Metabolism & Toxicology·Claudiu T Supuran
Jul 5, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Emanuela BerrinoFabrizio Carta
Apr 5, 2020·International Journal of Molecular Sciences·Jyoti Singh Tomar, Jun Shen
Jun 23, 2018·Current Medicinal Chemistry·Murat BozdagFabrizio Carta
Aug 12, 2020·Journal of Enzyme Inhibition and Medicinal Chemistry·Claudiu T Supuran
Mar 27, 2020·Frontiers in Pharmacology·Andrea BediniSanti Spampinato
Oct 18, 2020·Metabolites·Andrea AngeliClaudiu T Supuran
Sep 2, 2019·Bioorganic Chemistry·Y Kalisha ValiClaudiu T Supuran

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