Design, synthesis, biological evaluation, and antioxidant and cytotoxic activity of heteroatom-substituted 1,4-naphtho- and benzoquinones

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dc.contributor.authorDeniz, Nahide Gülşah
dc.contributor.authorİbiş, Cemil
dc.contributor.authorGökmen, Zeliha
dc.contributor.authorStasevych, Maryna
dc.contributor.authorNovikov, Volodymyr
dc.contributor.authorPorokhnyavets, Olena Komarovska
dc.contributor.authorÖzyürek, Mustafa
dc.contributor.authorGüçlü, Kubilay
dc.contributor.buuauthorKarakaş, Didem
dc.contributor.buuauthorUlukaya, Engin
dc.contributor.departmentUludağ Üniversitesi/Fen-Edebiyat Fakültesi/Biyoloji Anabilim Dalı.tr_TR
dc.contributor.departmentUludağ Üniversitesi/Tıp Fakültesi/Klinik Biyokimya Anabilim Dalı.tr_TR
dc.contributor.orcid0000-0002-3781-6834tr_TR
dc.contributor.researcheridL-6682-2018tr_TR
dc.contributor.researcheridK-5792-2018tr_TR
dc.contributor.scopusid56422040600tr_TR
dc.contributor.scopusid6602927353tr_TR
dc.date.accessioned2022-06-10T12:38:56Z
dc.date.available2022-06-10T12:38:56Z
dc.date.issued2015-12
dc.description.abstractIn the present paper, we report the synthesis, characterization, and biological evaluation as antifungal, antibacterial, antioxidant, and cytotoxic/anticancer agents of N-, S-, O-substituted-1,4-naphtho- and 2,5-bis(amino-substituted)-1,4-benzoquinone derivatives. In the synthesized compounds, antimicrobial activity at low concentrations against Escherichia coli B-906, Staphylococcus aureus 209-P, and Mycobacterium luteum B-917 bacteria and Candida tennis VKM Y-70 and Aspergillus niger F-1119 fungi in comparison with controls was identified. 2-(N-Diphenylmethylpiperazin-1-yl)-3-chloro-1,4-naphthoquinone 9a was the most potent, with a minimum inhibitory concentration value of 3.9, mu g/mL against test culture M. luteum. The synthesized compounds were screened for their antioxidant capacity using the cupric-reducing antioxidant capacity (CUPRAC) method. 2,2'-[1-(2-Aminoethyl)piperazin-1-yl]-3,3'-dichloro-bis(1,4-naphthoquinone) 10 showed the highest antioxidant capacity, with a 0.455 CUPRAC-trolox equivalent antioxidant capacity (TEAC) coefficient. Other parameters of antioxidant activity (scavenging effects on OH center dot, O-2(center dot-), and H2O2) of these compounds were also determined. The cytotoxic activity of the compounds was investigated by employing the sulforhodamine B cell viability assay against A549 (lung), MCF-7 (breast), DU145 (prostate), and HT-29 (colon) cancer cell lines. Compound 10 exhibited the most powerful cytotoxic activity at a concentration of 20 mu m against all cell lines. In addition to the strongest antioxidant activity of compound 10, it also had lowest IC50 values (<3 mu m), warranting further in vivo studies due to its anticancer activity.en_US
dc.description.sponsorshipİstanbul Üniversitesi (NP-45621)tr_TR
dc.identifier.citationDeniz, N. G. vd. (2015). "Design, synthesis, biological evaluation, and antioxidant and cytotoxic activity of heteroatom-substituted 1,4-naphtho- and benzoquinones". Chemical and Pharmaceutical Bulletin, 63(12), 1029-1039.en_US
dc.identifier.endpage1039tr_TR
dc.identifier.issn0009-2363
dc.identifier.issue12tr_TR
dc.identifier.pubmed26633024tr_TR
dc.identifier.scopus2-s2.0-84955461213tr_TR
dc.identifier.startpage1029tr_TR
dc.identifier.urihttps://doi.org/10.1248/cpb.c15-00607
dc.identifier.urihttps://www.jstage.jst.go.jp/article/cpb/63/12/63_c15-00607/_article
dc.identifier.urihttp://hdl.handle.net/11452/27047
dc.identifier.volume63tr_TR
dc.identifier.wos000365694900007tr_TR
dc.indexed.pubmedPubMeden_US
dc.indexed.scopusScopusen_US
dc.indexed.wosSCIEen_US
dc.language.isoenen_US
dc.publisherPharmaceutical Soc Japanen_US
dc.relation.collaborationYurt içitr_TR
dc.relation.collaborationYurt dışıtr_TR
dc.relation.journalChemical and Pharmaceutical Bulletinen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergitr_TR
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectAntimicrobial activityen_US
dc.subjectAntioxidant activityen_US
dc.subjectCupric-reducing antioxidant capacity methoden_US
dc.subjectCytotoxicityen_US
dc.subjectQuinoneen_US
dc.subjectReactive oxygen species-scavenging activityen_US
dc.subjectRadical radical scavenging activityen_US
dc.subjectNaphthoquinone derivativesen_US
dc.subjectAntifungal activityen_US
dc.subjectSpectral propertiesen_US
dc.subjectAnticancer agentsen_US
dc.subjectMechanismsen_US
dc.subjectInhibitorsen_US
dc.subjectQsaren_US
dc.subjectPharmacology & pharmacyen_US
dc.subjectChemistryen_US
dc.subject.emtree2 (1 ethylsulfanyl) 3 (1 n diphenylmethylpiperazin 1 yl) 1,4 naphthoquinoneen_US
dc.subject.emtree2 (n diphenylmethylpiperazin 1 yl) 3 chloro 1,4 naphthoquinoneen_US
dc.subject.emtree2 [1 piperonylpiperazin 1 yl] 3 chloro 1,4 naphthoquinoneen_US
dc.subject.emtree2 [4 (2 aminoethyl)morpholin 1 yl] 3 chloro 1,4 naphthoquinoneen_US
dc.subject.emtree2(n diphenylmethylpiperazin 1 yl) 3 benzylsulfanyl 1,4 naphthoquinoneen_US
dc.subject.emtree2,2' [1 (2 aminoethyl)piperazin 1 yl] 3,3' dichloro bis(1,4 naphthoquinoneen_US
dc.subject.emtree2,3 bis(benzylsulfanyl) 1,4 naphthoquinonen_US
dc.subject.emtree2,5 bis[1 piperonylpiperazin 1 yl] 3,6 dichloro 1,4 benzoquinoneen_US
dc.subject.emtree2,5 bis[4 (2 aminoethyl)morpholin 1 yl] 3,6 dichloro 1,4 benzoquinoneen_US
dc.subject.emtreeAntiinfective agenten_US
dc.subject.emtreeAntioxidanten_US
dc.subject.emtreeBenzoquinone derivativeen_US
dc.subject.emtreeCytotoxic agenten_US
dc.subject.emtreeHydrogen peroxideen_US
dc.subject.emtreeNaphthalene derivativeen_US
dc.subject.emtreeNystatinen_US
dc.subject.emtreeReactive oxygen metaboliteen_US
dc.subject.emtreeSulforhodamine Ben_US
dc.subject.emtreeSuperoxideen_US
dc.subject.emtreeUnclassified drugen_US
dc.subject.emtreeVancomycinen_US
dc.subject.emtreeAntifungal agenten_US
dc.subject.emtreeAntiinfective agenten_US
dc.subject.emtreeAntineoplastic agenten_US
dc.subject.emtreeAntioxidanten_US
dc.subject.emtreeBenzoquinone derivativeen_US
dc.subject.emtreeNaphthoquinoneen_US
dc.subject.emtreeAntibacterial activityen_US
dc.subject.emtreeAntifungal activityen_US
dc.subject.emtreeAntineoplastic activityen_US
dc.subject.emtreeAntioxidant activityen_US
dc.subject.emtreeArticleen_US
dc.subject.emtreeAspergillus nigeren_US
dc.subject.emtreeBacterium cultureen_US
dc.subject.emtreeCancer cell lineen_US
dc.subject.emtreeCandidaen_US
dc.subject.emtreeCandida tenuisen_US
dc.subject.emtreeCarbon nuclear magnetic resonanceen_US
dc.subject.emtreeCell viability assayen_US
dc.subject.emtreeConcentration responseen_US
dc.subject.emtreeControlled studyen_US
dc.subject.emtreeCytotoxicity assayen_US
dc.subject.emtreeDilutionen_US
dc.subject.emtreeDrug designen_US
dc.subject.emtreeDrug synthesisen_US
dc.subject.emtreeEscherichia colien_US
dc.subject.emtreeFourier transform infrared photoacoustic spectroscopyen_US
dc.subject.emtreeFourier transformationen_US
dc.subject.emtreeHumanen_US
dc.subject.emtreeHuman cellen_US
dc.subject.emtreeIC50en_US
dc.subject.emtreeIn vivo studyen_US
dc.subject.emtreeMass spectrometryen_US
dc.subject.emtreeMCF 7 cell lineen_US
dc.subject.emtreeMinimum inhibitory concentrationen_US
dc.subject.emtreeMycobacteriumen_US
dc.subject.emtreeMycobacterium luteumen_US
dc.subject.emtreeNonhumanen_US
dc.subject.emtreeProton nuclear magnetic resonanceen_US
dc.subject.emtreeStaphylococcus aureusen_US
dc.subject.emtreeStructure activity relationen_US
dc.subject.emtreeUltraviolet spectroscopyen_US
dc.subject.emtreeCell survivalen_US
dc.subject.emtreeChemical structureen_US
dc.subject.emtreeChemistryen_US
dc.subject.emtreeDose responseen_US
dc.subject.emtreeDrug designen_US
dc.subject.emtreeDrug effectsen_US
dc.subject.emtreeDrug screeningen_US
dc.subject.emtreeMicrobial sensitivity testen_US
dc.subject.emtreeSynthesisen_US
dc.subject.emtreeTumor cell lineen_US
dc.subject.meshAnti-bacterial agentsen_US
dc.subject.meshAntifungal agentsen_US
dc.subject.meshAntineoplastic agentsen_US
dc.subject.meshAntioxidantsen_US
dc.subject.meshAspergillus nigeren_US
dc.subject.meshBenzoquinonesen_US
dc.subject.meshCandidaen_US
dc.subject.meshCell line, tumoren_US
dc.subject.meshCell survivalen_US
dc.subject.meshDose-responser relationship drugen_US
dc.subject.meshDrug designen_US
dc.subject.meshDrug screening assays, antitumoren_US
dc.subject.meshEscherichia colien_US
dc.subject.meshHumansen_US
dc.subject.meshMicrobial sensitivity testsen_US
dc.subject.meshMolecular structureen_US
dc.subject.meshMycobacteriumen_US
dc.subject.meshNaphthoquinonesen_US
dc.subject.meshStaphylococcus aureusen_US
dc.subject.meshStructure-activity relationshipen_US
dc.subject.scopusCytotoxicity; Naphthoquinones; Quinonesen_US
dc.subject.wosChemistry, medicinalen_US
dc.subject.wosChemistry, multidisciplinaryen_US
dc.subject.wosPharmacology & pharmacyen_US
dc.titleDesign, synthesis, biological evaluation, and antioxidant and cytotoxic activity of heteroatom-substituted 1,4-naphtho- and benzoquinonesen_US
dc.typeArticle
dc.wos.quartileQ4en_US
dc.wos.quartileQ3 (Chemistry, multidisciplinary)en_US

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