Sulfonamide-phosphonate hybrids as new carbonic anhydrase inhibitors: In vitro enzymatic inhibition, molecular modeling, and ADMET prediction

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dc.authoridParham Taslimi / 0000-0002-3171-0633en_US
dc.authorscopusidParham Taslimi / 56658628800en_US
dc.authorwosidParham Taslimi / AAL-2788-2020
dc.contributor.authorZareei, Samira
dc.contributor.authorMohammadi-Khanaposhtani, Maryam
dc.contributor.authorAdib, Mehdi
dc.contributor.authorMahdavi, Mohammad
dc.contributor.authorTaslimi, Parham
dc.date.accessioned2022-10-31T07:13:35Z
dc.date.available2022-10-31T07:13:35Z
dc.date.issued2023en_US
dc.departmentİstinye Üniversitesi, Mühendislik ve Doğa Bilimleri Fakültesi, Kimya Bölümüen_US
dc.description.abstractIn the presented work, we report the synthesis of a new series of sulfonamide-phosphonate hybrids 4a-m. These newly synthesized compounds were assessed for their inhibitory effects toward two human carbonic anhydrase isoforms I and II (hCA I and II). These examined isoforms were as well inhibited by the most of prepared sulfonamide-phosphonates in comparison to standard inhibitor acetazolamide. Obtained data exhibited that compounds 4b-m with Ki values in the range of 8.11–48.08 nM were more potent than standard drug acetazolamide with Ki value of 64.52 Nm against hCA I. Moreover, all the synthesized compounds (Ki values = 7.08–64.24 nM), with the exception of compound 4b, were more potent than acetazolamide (Ki value = 75.36) against hCA II. In particular, sulfonamide-phosphonates 4l and 4j, respectively, with substituents 5?chloro-2-nitro and 2,3-dichloro emerged as the most potent hCA inhibitors. Thereafter, the molecular docking of compounds 4l and 4j at hCA I and II active sites was performed and the obtained results revealed that these compounds interacted whit the important amino acids of the active site. Finally, the predicted parameters of Lipinski's rule of five, ADME, and toxicity analysis showed that compounds 4l and 4j had good drug-likeness and acceptable physicochemical properties. Therefore, the hybridization of the sulfonamide and phosphonate moieties could be promising strategy for achieve to potent lead compounds for inhibition of hCA.en_US
dc.identifier.citationZareei, S., Mohammadi-Khanaposhtani, M., Adib, M., Mahdavi, M., & Taslimi, P. (2023). Sulfonamide-phosphonate hybrids as new carbonic anhydrase inhibitors: In vitro enzymatic inhibition, molecular modeling, and ADMET prediction. Journal of Molecular Structure, 1271 doi:10.1016/j.molstruc.2022.134114en_US
dc.identifier.doi10.1016/j.molstruc.2022.134114en_US
dc.identifier.scopus2-s2.0-85138058149en_US
dc.identifier.scopusqualityN/Aen_US
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2022.134114
dc.identifier.urihttps://hdl.handle.net/20.500.12713/3208
dc.identifier.volume1271en_US
dc.identifier.wosWOS:000888875300001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.institutionauthorTaslimi, Parham
dc.language.isoenen_US
dc.publisherElsevier B.V.en_US
dc.relation.ispartofJournal of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectCarbonic Anhydraseen_US
dc.subjectEnzyme Inhibitionen_US
dc.subjectPhosphonateen_US
dc.subjectSulfonamideen_US
dc.titleSulfonamide-phosphonate hybrids as new carbonic anhydrase inhibitors: In vitro enzymatic inhibition, molecular modeling, and ADMET predictionen_US
dc.typeArticleen_US

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