Deniz, Nahide Gülşahİbiş, CemilGökmen, ZelihaStasevych, MarynaNovikov, VolodymyrPorokhnyavets, Olena KomarovskaÖzyürek, MustafaGüçlü, Kubilay2022-06-102022-06-102015-12Deniz, 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), 1029-1039.0009-2363https://doi.org/10.1248/cpb.c15-00607https://www.jstage.jst.go.jp/article/cpb/63/12/63_c15-00607/_articlehttp://hdl.handle.net/11452/27047In 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.eninfo:eu-repo/semantics/closedAccessAntimicrobial activityAntioxidant activityCupric-reducing antioxidant capacity methodCytotoxicityQuinoneReactive oxygen species-scavenging activityRadical radical scavenging activityNaphthoquinone derivativesAntifungal activitySpectral propertiesAnticancer agentsMechanismsInhibitorsQsarPharmacology & pharmacyChemistryAnti-bacterial agentsAntifungal agentsAntineoplastic agentsAntioxidantsAspergillus nigerBenzoquinonesCandidaCell line, tumorCell survivalDose-responser relationship drugDrug designDrug screening assays, antitumorEscherichia coliHumansMicrobial sensitivity testsMolecular structureMycobacteriumNaphthoquinonesStaphylococcus aureusStructure-activity relationshipArticle0003656949000072-s2.0-8495546121310291039631226633024Chemistry, medicinalChemistry, multidisciplinaryPharmacology & pharmacyCytotoxicity; Naphthoquinones; Quinones2 (1 ethylsulfanyl) 3 (1 n diphenylmethylpiperazin 1 yl) 1,4 naphthoquinone2 (n diphenylmethylpiperazin 1 yl) 3 chloro 1,4 naphthoquinone2 [1 piperonylpiperazin 1 yl] 3 chloro 1,4 naphthoquinone2 [4 (2 aminoethyl)morpholin 1 yl] 3 chloro 1,4 naphthoquinone2(n diphenylmethylpiperazin 1 yl) 3 benzylsulfanyl 1,4 naphthoquinone2,2' [1 (2 aminoethyl)piperazin 1 yl] 3,3' dichloro bis(1,4 naphthoquinone2,3 bis(benzylsulfanyl) 1,4 naphthoquinon2,5 bis[1 piperonylpiperazin 1 yl] 3,6 dichloro 1,4 benzoquinone2,5 bis[4 (2 aminoethyl)morpholin 1 yl] 3,6 dichloro 1,4 benzoquinoneAntiinfective agentAntioxidantBenzoquinone derivativeCytotoxic agentHydrogen peroxideNaphthalene derivativeNystatinReactive oxygen metaboliteSulforhodamine BSuperoxideUnclassified drugVancomycinAntifungal agentAntiinfective agentAntineoplastic agentAntioxidantBenzoquinone derivativeNaphthoquinoneAntibacterial activityAntifungal activityAntineoplastic activityAntioxidant activityArticleAspergillus nigerBacterium cultureCancer cell lineCandidaCandida tenuisCarbon nuclear magnetic resonanceCell viability assayConcentration responseControlled studyCytotoxicity assayDilutionDrug designDrug synthesisEscherichia coliFourier transform infrared photoacoustic spectroscopyFourier transformationHumanHuman cellIC50In vivo studyMass spectrometryMCF 7 cell lineMinimum inhibitory concentrationMycobacteriumMycobacterium luteumNonhumanProton nuclear magnetic resonanceStaphylococcus aureusStructure activity relationUltraviolet spectroscopyCell survivalChemical structureChemistryDose responseDrug designDrug effectsDrug screeningMicrobial sensitivity testSynthesisTumor cell line