Synthesis and carbonic anhydrase inhibition of tetrabromo chalcone derivatives

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dc.authoridGULCIN, Ilhami -- 0000-0001-5993-1668; , deryanur -- 0000-0002-9115-136X;
dc.contributor.authorKoçyiğit, Ümit Muhammet
dc.contributor.authorBudak, Yakup
dc.contributor.authorEligüzel, Fikret
dc.contributor.authorTaslimi, Parham
dc.contributor.authorKılıç, Deryanur
dc.contributor.authorGülçin, İlhami
dc.contributor.authorCeylan, Mustafa
dc.date.accessioned13.07.201910:50:10
dc.date.accessioned2019-07-29T19:26:32Z
dc.date.available13.07.201910:50:10
dc.date.available2019-07-29T19:26:32Z
dc.date.issued2017
dc.departmentFen-Edebiyat Fakültesi
dc.description.abstractIn the present study, human carbonic anhydrase (hCA) enzyme was purified and characterized from fresh blood human red cells by Sepharose-4B-l-tyrosine-sulfanilamide affinity gel chromatography. Secondly, a series of new tetrabromo chalcone derivatives containing 4,7-methanoisoindol-1,3-dione (2a-i) were synthesized from the addition of Br-2 to related chalcone derivatives (1a-i). The structures of the new molecules (2a-i) were confirmed by means of H-1 NMR, C-13 NMR and elemental analysis. Finally, the inhibitory effects of 2a-i on CA activities were investigated using the esterase method under in vitro conditions. The compounds 2a-i exhibited excellent inhibitory effects, in the low nanomolar range, with K-i values in the range of 11.30-21.22nM against hCA I and in the range of 8.21-12.86nM against hCA II. Our findings suggest that the new compounds 2a-i have superior inhibitory effect over acetazolamide (AZA), which is used as clinical CA inhibitor, with obtained K-i values of 34.50 and 28.93nM against the hCA I and II isozymes, respectively. In addition to the inhibition assays, molecular modeling approaches were implemented for prediction of the binding affinities of compounds 2a and 2c, which had the highest inhibition effects, against the hCA I and II isozymes.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [111T990]; Gaziosmanpasa University Scientific Research Projects Commission [BAP2011/62]
dc.description.sponsorshipThe authors are indebted to the Scientific and Technological Research Council of Turkey (TUBITAK Project No: 111T990) and Gaziosmanpasa University Scientific Research Projects Commission (Project No: BAP2011/62) for their financial support.
dc.identifier.doi10.1002/ardp.201700198
dc.identifier.issn0365-6233
dc.identifier.issn1521-4184
dc.identifier.issue12en_US
dc.identifier.pmid29134667
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1002/ardp.201700198
dc.identifier.urihttps://hdl.handle.net/20.500.12451/5630
dc.identifier.volume350en_US
dc.identifier.wosWOS:000416834000003
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofARCHIV DER PHARMAZIE
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/embargoedAccess
dc.subjectCarbonic Anhydrase
dc.subjectChalcone
dc.subjectEnzyme Inhibition
dc.subjectMolecular Docking Simulations
dc.subjectMolecular Modeling
dc.titleSynthesis and carbonic anhydrase inhibition of tetrabromo chalcone derivatives
dc.typeArticle

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