PMID: 11906288Mar 22, 2002Paper

Carbonic anhydrase inhibitors. A general approach for the preparation of water-soluble sulfonamides incorporating polyamino-polycarboxylate tails and of their metal complexes possessing long-lasting, topical intraocular pressure-lowering properties

Journal of Medicinal Chemistry
Andrea ScozzafavaClaudiu T Supuran

Abstract

Reaction of polyamino-polycarboxylic acids or their dianhydrides with aromatic/heterocyclic sulfonamides possessing a free amino/imino/hydrazino/hydroxy group afforded mono- and bis-sulfonamides containing polyamino-polycarboxylic acid moieties in their molecule. The acids/anhydrides used in synthesis included IDA, NTA, EDDA, EDTA and EDTA dianhydride, DTPA and DTPA dianhydride, EGTA and EGTA dianhydride, and EDDHA, among others. All the newly prepared derivatives showed strong affinity toward isozymes I, II, and IV of carbonic anhydrase (CA). Metal complexes of the new compounds have also been prepared. Metal ions used in such preparations included di- and trivalent main-group and transition cations, such as Zn(II), Cu(II), Al(III), etc. Some of the new sulfonamides/disulfonamides obtained in this way, as well as their metal complexes, behaved as nanomolar CA inhibitors against isozymes II and IV, being slightly less effective in inhibiting isozyme I. Some of these sulfonamides as well as their metal complexes strongly lowered intraocular pressure (IOP) when applied topically, directly into the normotensive/glaucomatous rabbit eye, as 1-2% water solutions/suspensions. The good water solubility of these sulfonamide CA inhibitor...Continue Reading

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Citations

Jun 23, 2010·Expert Opinion on Drug Delivery·Gladys E Granero, Marcela R Longhi
Oct 27, 2016·Expert Opinion on Drug Discovery·Claudiu T Supuran
Jun 2, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Daniela De VitaClaudiu T Supuran
Sep 28, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Grazia LuisiPaolo Tortorella
Sep 30, 2017·Bioinformatics·Lewis H MervinAndreas Bender
Dec 13, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Andrea AngeliClaudiu T Supuran
Jan 13, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Aikaterini PeperidouClaudiu T Supuran
Dec 25, 2002·Medicinal Research Reviews·Claudiu T SupuranAngela Casini
Apr 4, 2012·Journal of Enzyme Inhibition and Medicinal Chemistry·Claudiu T Supuran
Jul 14, 2012·Expert Opinion on Therapeutic Patents·Mayank Aggarwal, Robert McKenna
Oct 28, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Stanislav KalininMikhail Krasavin
Oct 28, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Melissa D'AscenzioClaudiu T Supuran
Oct 25, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Halise Inci GulClaudiu T Supuran
Oct 27, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Suleyman AkocakClaudiu T Supuran
Sep 30, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Claudiu T Supuran
Dec 2, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Claudiu T Supuran
May 1, 2013·Expert Opinion on Therapeutic Patents·Emanuela MasiniClaudiu T Supuran
Mar 27, 2015·BioMed Research International·Melissa A PinardRobert McKenna
Oct 25, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Halise Inci GulClaudiu T Supuran
Oct 3, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·P V Sri RamyaAhmed Kamal
Nov 4, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Daniela VulloClaudiu T Supuran
Dec 23, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ylenia CauMaurizio Botta
Sep 25, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Andrea AngeliClaudiu T Supuran
Jun 24, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Murat BozdagClaudiu T Supuran
Dec 5, 2019·Environmental Science and Pollution Research International·Anand Giri, Deepak Pant
Dec 8, 2011·Journal of Enzyme Inhibition and Medicinal Chemistry·Ramazan DemirdağClaudiu T Supuran
Jun 16, 2012·Expert Opinion on Therapeutic Patents·Fabrizio CartaClaudiu T Supuran
Aug 31, 2016·Expert Opinion on Therapeutic Patents·Claudiu T Supuran
May 1, 2013·Expert Opinion on Drug Discovery·Giuseppina De SimoneClaudiu T Supuran
Jul 29, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Morteza AbdoliClaudiu T Supuran
Nov 2, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Erol LicsandruClaudiu T Supuran
Mar 25, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Marco BragagniClaudiu T Supuran
Mar 22, 2018·Metabolites·Claudiu T Supuran
Oct 27, 2004·Journal of Enzyme Inhibition and Medicinal Chemistry·Silvia PastorekovaClaudiu T Supuran
Jul 7, 2020·Acta Crystallographica. Section D, Structural Biology·Shengyang JinYong Gui Gao
Jan 3, 2008·Nature Reviews. Drug Discovery·Claudiu T Supuran

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