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dc.creatorJakovljević, Katarina
dc.creatorJoksovic, Milan D.
dc.creatorMatić, Ivana Z.
dc.creatorPetrovic, Nina
dc.creatorStanojković, Tatjana
dc.creatorSladić, Dušan
dc.creatorVujčić, Miroslava
dc.creatorJanović, Barbara
dc.creatorJoksovic, Ljubinka
dc.creatorTrifunović, Snežana
dc.creatorMarkovic, Violeta
dc.date.accessioned2019-10-11T22:04:58Z
dc.date.available2019-08-23
dc.date.issued2018
dc.identifier.issn2040-2503
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/2379
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/3136
dc.description.abstractHybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.en
dc.publisherRoyal Soc Chemistry, Cambridge
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172016/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172055/RS//
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/175011/RS//
dc.rightsembargoedAccess
dc.sourceMedchemcomm
dc.titleNovel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studiesen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractЈановић, Барбара; Матиц, Ивана З.; Петровиц, Нина; Сладић, Душан; Вујчић, Мирослава; Јаковљевиц, Катарина; Станојковиц, Татјана; Јоксовиц, Милан Д.; Марковиц, Виолета; Трифуновић, Снежана; Јоксовиц, Љубинка;
dc.citation.volume9
dc.citation.issue10
dc.citation.spage1679
dc.citation.epage1697
dc.citation.other9(10): 1679-1697
dc.citation.rankM22
dc.description.otherThis is the peer-reviewed version of the following article: Jakovljević, K.; Joksović, M. D.; Matić, I. Z.; Petrović, N.; Stanojković, T.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Trifunović, S.; et al. Novel 1,3,4-Thiadiazole-Chalcone Hybrids Containing Catechol Moiety: Synthesis, Antioxidant Activity, Cytotoxicity and DNA Interaction Studies. MedChemComm 2018, 9 (10), 1679–1697. [https://doi.org/10.1039/c8md00316e]
dc.description.other[http://cer.ihtm.bg.ac.rs/handle/123456789/2379]
dc.identifier.pmid30429973
dc.identifier.doi10.1039/c8md00316e
dc.identifier.rcubConv_4010
dc.identifier.fulltexthttp://cer.ihtm.bg.ac.rs/bitstream/id/14134/jakovljevic2018.pdf
dc.identifier.scopus2-s2.0-85055283028
dc.identifier.wos000448343300009
dc.type.versionacceptedVersion


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