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Mannich bases of 1,2,4-triazole-3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies
dc.creator | Milošev, Milorad Z. | |
dc.creator | Jakovljević, Katarina | |
dc.creator | Joksović, Milan D. | |
dc.creator | Stanojković, Tatjana | |
dc.creator | Matić, Ivana Z. | |
dc.creator | Perović, Milka | |
dc.creator | Tešić, Vesna | |
dc.creator | Kanazir, Selma | |
dc.creator | Mladenović, Milan | |
dc.creator | Rodić, Marko | |
dc.creator | Leovac, Vukadin M. | |
dc.creator | Trifunović, Snežana S. | |
dc.creator | Marković, Violeta | |
dc.date.accessioned | 2019-07-10T12:23:17Z | |
dc.date.available | 2017-11-21 | |
dc.date.issued | 2017 | |
dc.identifier.issn | 1747-0277 | |
dc.identifier.uri | https://cherry.chem.bg.ac.rs/handle/123456789/3221 | |
dc.description.abstract | A series of 18 novel N-Mannich bases derived from 5-adamantyl-1,2,4-triazole-3-th ione was synthesized and characterized using NMR spectroscopy and X-ray diffraction technique. All derivatives were evaluated for their anticancer potential against four human cancer cell lines. Several tested compounds exerted good cytotoxic activities on K562 and HL-60 cell lines, along with pronounced selectivity, showing lower cytotoxicity against normal fibroblasts MRC-5 compared to cancer cells. The effects of compounds 5b,5e, and 5j on the cell cycle were investigated by flow cytometric analysis. It was found that these compounds cause the accumulation of cells in the subG1 and G1 phases of the cell cycle and induce caspase-dependent apoptosis, while the anti-angiogenic effects of 5b, 5e, and 5j have been confirmed in EA. hy926 cells using a tube formation assay. Further, the interaction of Bax protein with compound 5b was investigated by means of molecular modeling, applying the combined molecular docking/molecular dynamics approach. | |
dc.publisher | Wiley, Hoboken | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172016/RS// | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/175011/RS// | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Integrated and Interdisciplinary Research (IIR or III)/43004/RS// | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/173056/RS// | |
dc.rights | embargoedAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc/4.0/ | |
dc.source | Chemical Biology and Drug Design | |
dc.subject | adamantane | |
dc.subject | anticancer activity | |
dc.subject | Mannich bases | |
dc.subject | molecular modeling | |
dc.subject | triazoles | |
dc.title | Mannich bases of 1,2,4-triazole-3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies | |
dc.type | article | |
dc.rights.license | BY-NC | |
dcterms.abstract | Родић, Марко; Станојковић, Татјана; Милошев, Милорад З. ; Перовић, Милка; Јоксовић, Милан Д.; Марковић, Виолета; Јаковљевић, Катарина; Тешић, Весна; Каназир, Селма; Младеновић, Милан; Леовац, Вукадин М. ; Трифуновић, Снежана С.; Матић, Ивана З. ; | |
dc.citation.volume | 89 | |
dc.citation.issue | 6 | |
dc.citation.spage | 943 | |
dc.citation.epage | 952 | |
dc.identifier.wos | 000405100700012 | |
dc.identifier.doi | 10.1111/cbdd.12920 | |
dc.citation.rank | M23 | |
dc.description.other | This is the peer-reviewed version of the following article: Milošev, M. Z.; Jakovljević, K.; Joksović, M. D.; Stanojković, T.; Matić, I. Z.; Perović, M.; Tešić, V.; Kanazir, S.; Mladenović, M.; Rodić, M. V.; et al. Mannich Bases of 1,2,4-Triazole3-Thione Containing Adamantane Moiety: Synthesis, Preliminary Anticancer Evaluation, and Molecular Modeling Studies. Chemical Biology and Drug Design 2017, 89 (6), 943–952. [https://doi.org/10.1111/cbdd.12920] | |
dc.description.other | Supplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3222] | |
dc.type.version | acceptedVersion | |
dc.identifier.scopus | 2-s2.0-85019213707 | |
dc.identifier.fulltext | https://cherry.chem.bg.ac.rs/bitstream/id/7990/10.1111@cbdd.12920.pdf |