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Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines
dc.creator | Živković, Marijana | |
dc.creator | Matić, Ivana Z. | |
dc.creator | Rodić, Marko V. | |
dc.creator | Novaković, Irena | |
dc.creator | Sladić, Dušan | |
dc.creator | Krstić, Natalija | |
dc.date.accessioned | 2019-01-30T17:51:56Z | |
dc.date.available | 2019-01-30T17:51:56Z | |
dc.date.issued | 2016 | |
dc.identifier.issn | 2046-2069 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/2028 | |
dc.description.abstract | A series of new steroidal mono- and bis(thiosemicarbazones) (2a-e and 3a-e) and corresponding mono- and bis(1,3,4-thiadiazolines) (4a-e and 5a-e) was synthesized, characterized and evaluated for their anticancer activity. Detailed NMR analysis of the mono-and bis(thiosemicarbazones) revealed the presence of two stereoisomers (Z and E) with different configurations in the hydrazone moiety at the C-3 position, where the substituents on the C(3)]=N double bond in the main isomers adopted the E configuration. The configurations at C-3 and C-17 in thiadiazolines 4a-e and 5a-e were deduced by detailed NMR analysis as well as by the examination of Dreiding molecular models and X-ray analysis of 3-thiadiazoline 4a, which confirmed the structure and absolute configuration at C-3. The synthesized compounds were tested against six cancer cell lines (HeLa, K562, MDA-MB-361, MDA-MB-453, LS174 and A549), the normal human cell line MRC-5 and peripheral blood mononuclear cells (PBMC) isolated from healthy donors. The best activity was exhibited by 3-thiosemicarbazones 2a, 2b, 2c and 2e and 3,17-bis(thiadiazolines) 5a and 5d. Examination of the mechanisms of cytotoxicity on cervical adenocarcinoma HeLa cells revealed the pro-apoptotic action of these compounds, which triggered both extrinsic and intrinsic apoptotic pathways. These compounds also showed the ability to decrease angiogenesis in vitro. In addition, 3,17-bis(thiadiazolines) 5a and 5d showed high selectivity in anticancer activity against all the examined malignant cell lines. Compound 5a displayed prominent anticancer potential. The tested compounds showed poor antimicrobial activity. | en |
dc.publisher | Royal Soc Chemistry, Cambridge | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172055/RS// | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/175011/RS// | |
dc.rights | openAccess | |
dc.rights.uri | https://creativecommons.org/licenses/by-nc/4.0/ | |
dc.source | RSC Advances | |
dc.title | Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines | en |
dc.type | article | |
dc.rights.license | BY-NC | |
dcterms.abstract | Живковић, Маријана; Крстић, Наталија; Матиц, Ивана З; Новаковић, Ирена; Родић, Марко В.; Сладиц, Дусан М; | |
dc.citation.volume | 6 | |
dc.citation.issue | 41 | |
dc.citation.spage | 34312 | |
dc.citation.epage | 34333 | |
dc.citation.other | 6(41): 34312-34333 | |
dc.citation.rank | M21 | |
dc.identifier.doi | 10.1039/c6ra01516f | |
dc.identifier.fulltext | https://cer.ihtm.bg.ac.rs//bitstream/id/8458/2026.pdf | |
dc.identifier.scopus | 2-s2.0-84964664175 | |
dc.identifier.wos | 000374049700028 | |
dc.type.version | publishedVersion |