Novel 1,2,4-triazole-maleamic acid derivatives: synthesis and evaluation as anticancer agents with carbonic anhydrase inhibitory activity

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dc.authoridTaslimi, Parham/0000-0002-3171-0633
dc.authoridSahin, Onur/0000-0003-3765-3235
dc.authoridBAS TOPCU, KUBRA SENA/0000-0003-3161-1042
dc.contributor.authorTapera, Michael
dc.contributor.authorKekecmuhammed, Huseyin
dc.contributor.authorTuzun, Burak
dc.contributor.authorDastan, Sevgi Durna
dc.contributor.authorCelik, Muhammed Safa
dc.contributor.authorTaslimi, Parham
dc.contributor.authorDastan, Taner
dc.date.accessioned2025-03-23T19:39:19Z
dc.date.available2025-03-23T19:39:19Z
dc.date.issued2024
dc.departmentSinop Üniversitesi
dc.description.abstractHybrid compounds with 1,2,4-triazole ring and a hydrazone moiety were designed and synthesized by amine acylation of uncommon triaminogunidine derivatives using maleic anhydride. Synthesized compounds were characterized by various spectral techniques, including FTIR, 1H NMR, 13C NMR, and HRMS. Furthermore, the proposed structure of TM-2 was resolved by single-crystal X-ray analysis. The compounds were evaluated for their anticancer activity in vitro against the colon cancer cell line HCT116 and the ovarian cancer cell line A2780. Among them, some compounds, TM-3, TM-4, and TM-14, exhibited remarkable antiproliferative activity in the cell line A2780, with IC50 values of 6.11, 5.15, and 5.93 mu M, respectively. Further investigation revealed that these compounds could inhibit cancerous cell growth by inducing an increase in caspase-3 activity. In addition, antioxidant capabilities, interaction with plasmid pBR322 DNA, and inhibitory effects against two physiologically and pharmacologically relevant human carbonic anhydrase (hCA) isoforms, namely hCA I and hCA II, of the synthesized compounds were also assessed. Finally, computational studies, such as DFT calculation, molecular docking, and in silico predictions of ADME/T analysis, were conducted to gain an understanding of the specific reactive sites of the compounds, the binding modes in the active sites, and the pharmacokinetic parameters of the newly synthesized hybrid compounds, which were calculated to establish their drug-likeness properties.
dc.description.sponsorshipErciyes University's Research Foundation; Scientific Research Project Fund of Sivas Cumhuriyet University (CUBAP) [RGD-020]
dc.description.sponsorshipThe authors express a debt of gratitude to Erciyes University's Research Foundation (Grant No. FYL-2021-11122) . This work was also supported by the Scientific Research Project Fund of Sivas Cumhuriyet University (CUBAP) under the project number RGD-020. The authors acknowledge TUBITAK ULAKBIM for allowing access to their facilities for numerical calculations in this paper.
dc.identifier.doi10.1016/j.molstruc.2024.138680
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85194278195
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2024.138680
dc.identifier.urihttps://hdl.handle.net/11486/6317
dc.identifier.volume1313
dc.identifier.wosWOS:001247041400001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectTriazole
dc.subjectHydrazole
dc.subjectSynthesis
dc.subjectCytotoxic activity
dc.subjectEnzyme inhibition
dc.subjectComputational studies
dc.titleNovel 1,2,4-triazole-maleamic acid derivatives: synthesis and evaluation as anticancer agents with carbonic anhydrase inhibitory activity
dc.typeArticle

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