Synthesis and carbonic anhydrase I, II, IV and XII inhibitory properties of N-protected amino acid - sulfonamide conjugates

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dc.authoridKUCUKBAY, HASAN/0000-0002-7180-9486
dc.authoridSupuran, Claudiu/0000-0003-4262-0323
dc.authoridKucukbay, Fatumetuzzehra/0000-0001-7784-4138
dc.authorwosidkucukbay, fatumetuzzehra/X-5743-2019
dc.authorwosidKUCUKBAY, HASAN/A-5050-2019
dc.contributor.authorKucukbay, F. Zehra
dc.contributor.authorKucukbay, Hasan
dc.contributor.authorTanc, Muhammet
dc.contributor.authorSupuran, Claudiu T.
dc.date.accessioned2024-08-04T20:41:32Z
dc.date.available2024-08-04T20:41:32Z
dc.date.issued2016
dc.departmentİnönü Üniversitesien_US
dc.description.abstractN-protected amino acids (Gly, Ala and Phe protected with Boc and Z groups) were reacted with sulfonamide derivatives, leading to the corresponding N-protected amino acid-sulfonamide conjugates. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was assessed against four human (h) isoforms, hCA I, hCA II, hCA IV and hCA XII. Among them, hCA II, IV and XII are antiglaucoma drug targets, being involved in aqueous humor secretion within the eye. Low nanomolar inhibition was measured against all four isoforms with the 20 reported sulfonamides, but no selective inhibitory profiles, except for some CA XII-selective derivatives, were observed. hCA I, II and XII were generally better inhibited by sulfonamides incorporating longer scaffolds and Gly/Ala, whereas the best hCA IV inhibitors were homosulfanilamide derivatives, incorporating Phe moieties. The amino acid-sulfonamide conjugates show good water solubility and effective hCA II, IV and XII inhibition, and may be considered as interesting candidates for antiglaucoma studies.en_US
dc.description.sponsorshipInonu University, Turkey (BAPB); Universita degli Studi di Firenze, Italy; European Unionen_US
dc.description.sponsorshipWe thank Inonu University, Turkey (BAPB), Universita degli Studi di Firenze, Italy, and the European Union of the 7th Framework Program Dynano for financial support.en_US
dc.identifier.doi10.3109/14756366.2016.1147438
dc.identifier.endpage1483en_US
dc.identifier.issn1475-6366
dc.identifier.issn1475-6374
dc.identifier.issue6en_US
dc.identifier.pmid26899532en_US
dc.identifier.scopus2-s2.0-84959037298en_US
dc.identifier.scopusqualityQ1en_US
dc.identifier.startpage1476en_US
dc.identifier.urihttps://doi.org/10.3109/14756366.2016.1147438
dc.identifier.urihttps://hdl.handle.net/11616/97188
dc.identifier.volume31en_US
dc.identifier.wosWOS:000385270300079en_US
dc.identifier.wosqualityQ1en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherTaylor & Francis Ltden_US
dc.relation.ispartofJournal of Enzyme Inhibition and Medicinal Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectCarbonic anhydraseen_US
dc.subjectglaucomaen_US
dc.subjectinhibitoren_US
dc.subjectN-protected amino aciden_US
dc.subjectsulfonamideen_US
dc.titleSynthesis and carbonic anhydrase I, II, IV and XII inhibitory properties of N-protected amino acid - sulfonamide conjugatesen_US
dc.typeArticleen_US

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