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dc.creatorOpsenica, Dejan
dc.creatorPocsfalvi, G.
dc.creatorJuranić, Zorica
dc.creatorTinant, Bernard
dc.creatorDeclercq, J.-P.
dc.creatorKyle, D.E.
dc.creatorMilhous, Wilbur K.
dc.creatorŠolaja, Bogdan
dc.date.accessioned2019-01-30T17:09:14Z
dc.date.available2019-01-30T17:09:14Z
dc.date.issued2000
dc.identifier.issn0022-2623
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/21
dc.description.abstractCholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be ~2 times as active as the trans against Plasmodium falciparum D6 and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PHA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.en
dc.publisherAmerican Chemical Society (ACS)
dc.rightsrestrictedAccess
dc.sourceJournal of Medicinal Chemistry
dc.titleCholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activityen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractСолаја, Б.A.; Кyле, Д.Е.; Опсеница, Дејан; Милхоус, W.К.; Децлерцq, Ј.-П.; Поцсфалви, Г.; Јураниц, З.; Тинант, Б.;
dc.citation.volume43
dc.citation.issue17
dc.citation.spage3274
dc.citation.epage3282
dc.citation.other43(17): 3274-3282
dc.citation.rankM21
dc.identifier.pmid10966746
dc.identifier.doi10.1021/jm000952f
dc.identifier.rcubConv_4045
dc.identifier.scopus2-s2.0-0034710713
dc.identifier.wos000089023700010
dc.type.versionpublishedVersion


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