Synthesis, structural investigations, DNA/BSA interactions, molecular docking studies, and anticancer activity of a new 1,4-disubstituted 1,2,3-triazole derivative

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dc.authorid0000-0002-4861-1770
dc.authorid0000-0001-5950-3436
dc.contributor.authorGöktürk, Tolga
dc.contributor.authorSakallı Çetin, Esin
dc.contributor.authorHökelek, Tuncer
dc.contributor.authorPekel, Hanife
dc.contributor.authorŞensoy, Özge
dc.contributor.authorAksu, Ebru Nur
dc.contributor.authorGüp, Ramazan
dc.date.accessioned2023-10-13T09:49:04Z
dc.date.available2023-10-13T09:49:04Z
dc.date.issued2023
dc.departmentİstanbul Medipol Üniversitesi, Sağlık Hizmetleri Meslek Yüksekokulu, Eczane Hizmetleri Ana Bilim Dalı
dc.departmentİstanbul Medipol Üniversitesi, Mühendislik ve Doğa Bilimleri Fakültesi, Bilgisayar Mühendisliği Bölümü
dc.description.abstractWe report herein a new 1,2,3-triazole derivative, namely, 4-(( 1-( 3,4-dichlorophenyl)-1H-1,2,3- triazol- 4-yl)methoxy)-2-hydroxybenzaldehyde, which was synthesized by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The structure of the compound was analyzed using Fourier transform infrared spectroscopy (FTIR), H-1 NMR, C-13 NMR, UV-vis, and elemental analyses. Moreover, X- ray crystallography studies demonstrated that the compound adapted a monoclinic crystal system with the P2(1)/c space group. The dominant interactions formed in the crystal packing were found to be hydrogen bonding and van der Waals interactions according to Hirshfeld surface (HS) analysis. The volume of the crystal voids and the percentage of free spaces in the unit cell were calculated as 152.10 A(3) and 9.80%, respectively. The evaluation of energy frameworks showed that stabilization of the compound was dominated by dispersion energy contributions. Both in vitro and in silico investigations on the DNA/bovine serum albumin (BSA) binding activity of the compound showed that the CT-DNA binding activity of the compound was mediated via intercalation and BSA binding activity was mediated via both polar and hydrophobic interactions. The anticancer activity of the compound was also tested by the 3-(4,5-dimethylthiazol2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay using human cell lines including MDA-MB-231, LNCaP, Caco-2, and HEK293. The compound exhibited more cytotoxic activity than cisplatin and etoposide on Caco-2 cancer cell lines with an IC50 value of 16.63 +/- 0.27 mu M after 48 h. Annexin V suggests the induction of cell death by apoptosis. Compound 3 significantly increased the loss of mitochondrial membrane potential (MMP) levels in Caco-2 cells, and the reactive oxygen species (ROS) assay proved that compound 3 could induce apoptosis by ROS generation.
dc.description.sponsorshipHacettepe Universityen_US
dc.identifier.citationGöktürk, T., Sakallı Çetin, E., Hökelek, T., Pekel, H., Şensoy, Ö., Aksu, E. N. ... Güp, R. (2023). Synthesis, structural investigations, DNA/BSA interactions, molecular docking studies, and anticancer activity of a new 1,4-disubstituted 1,2,3-triazole derivative. ACS Omega, 8(35), 31839-31856. https://doi.org/10.1021/acsomega.3c03355
dc.identifier.doi10.1021/acsomega.3c03355
dc.identifier.endpage31856
dc.identifier.issn2470-1343
dc.identifier.issue35
dc.identifier.pmid37692230
dc.identifier.scopus2-s2.0-85170263565
dc.identifier.scopusqualityQ1
dc.identifier.startpage31839
dc.identifier.urihttps://doi.org/10.1021/acsomega.3c03355
dc.identifier.urihttps://hdl.handle.net/20.500.12511/11583
dc.identifier.volume8
dc.identifier.wos001062295700001en_US
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.institutionauthorPekel, Hanife
dc.institutionauthorŞensoy, Özge
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.relation.ispartofACS Omegaen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.relation.tubitakinfo:eu-repo/grantAgreement/TUBITAK/SOBAG/221Z158
dc.rightsAttribution 4.0 International*
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/*
dc.subjectDNA/BSA Interactions
dc.subjectAnticancer Activity
dc.subjectMolecular Docking Studies
dc.subjectStructural Investigations
dc.titleSynthesis, structural investigations, DNA/BSA interactions, molecular docking studies, and anticancer activity of a new 1,4-disubstituted 1,2,3-triazole derivative
dc.typeArticle

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