In pursuit of cytotoxic triterpenoids. Functionalization of lupane, taraxastane, friedelane, and baccharane derivatives via oxidation with selenium reagents

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dc.contributor.authorKuczyńska, Kinga
dc.contributor.authorCmoch, Piotr
dc.contributor.authorRárová, Lucie
dc.contributor.authorJaźwiński, Jarosław
dc.contributor.authorKorda, Anna
dc.contributor.authorMorzycki, Jacek W.
dc.contributor.authorKvasnicová, Marie
dc.contributor.authorGwardiak, Katarzyna
dc.contributor.authorKarczewski, Romuald
dc.contributor.authorYaghoobi Anzabi, Mohadese
dc.contributor.authorLuboradzki, Roman
dc.contributor.authorStrnad, Miroslav
dc.contributor.authorPakulski, Zbigniew
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciences
dc.contributor.organizationLaboratory of Growth Regulators, Faculty of Science, Palacký University, Czech Republic
dc.contributor.organizationInstitute of Experimental Botany, Czech Academy of Sciences, Czech Republic
dc.contributor.organizationDepartment of Organic Chemistry, Faculty of Chemistry, University of Bialystok
dc.contributor.organizationDepartment of Experimental Biology, Faculty of Science, Palacký University, Czech Republic
dc.contributor.organizationInstitute of Physical Chemistry, Polish Academy of Sciences
dc.date.accessioned2025-06-03T13:36:32Z
dc.date.available2025-06-03T13:36:32Z
dc.date.issued2025
dc.description.abstractA series of triterpenoids of the lupane, taraxastane, friedelane and baccharane type were oxidized using selenium dioxide (SeO2) and benzeneseleninic anhydride (BSA) under various conditions. Depending on the reaction conditions, different reaction pathways were observed, including dehydrogenation, allylic oxidation, and 1,2-diketone formation. In this way, derivatives functionalized in the triterpene core (especially in rings A, D, and E), difficult to obtain by other methods, can be easily prepared. In some cases, rarely observed α-phenylseleno-ketones were isolated. An unexpected reaction involving the cleavage of the carbon-carbon double bond was observed in the presence of stoichiometric amounts of osmium tetroxide. Further transformations of selected intermediates facilitated the synthesis of new, functionally enriched derivatives. The key reaction pathways were investigated using density functional theory (DFT), focusing on bond length variations and transition states, revealing energetically favored pathways and critical transition structures, including covalent and noncovalent interactions. Solvent and isomerization equilibrium effects were proposed to explain the experimentally observed discrepancies. Cytotoxic activity of selected derivatives was investigated. Derivatives 4 and 38 showed strongest cytotoxicity in cancer cells and fibroblasts (IC50 2.6–26.4 μM); some compounds were selective for G-361 or HeLa cells. These results suggest that they may find application in pharmaceuticals.en
dc.description.sponsorshipNational Science Centre, Poland 2016/21/B/ST5/02141; Grant Agency of the Czech Republic 23-05474S.
dc.identifier.citationEuropean Journal of Medicinal Chemistry, 295, 2025, 117770 // https://doi.org/10.1016/j.ejmech.2025.117770
dc.identifier.doi10.1016/j.ejmech.2025.117770
dc.identifier.issn0223-5234
dc.identifier.issn1768-3254
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/25945
dc.language.isoen
dc.publisherElsevier
dc.rightsUznanie autorstwa 4.0 Międzynarodoween
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.sourceEuropean Journal of Medicinal Chemistry
dc.subjectoxidation of triterpenoidsen
dc.subjectSeO2 oxidationen
dc.subjectBSA oxidationen
dc.subjectα-phenylseleno-ketoneen
dc.subjectDFT calculationsen
dc.subjectcytotoxic activityen
dc.subjectcytotoxicity of O-Mesylatesen
dc.titleIn pursuit of cytotoxic triterpenoids. Functionalization of lupane, taraxastane, friedelane, and baccharane derivatives via oxidation with selenium reagentsen
dc.typearticle
dc.type.versionpublishedVersion
person.identifier.orcidKuczyńska, Kinga [0000-0002-7526-177X]
person.identifier.orcidCmoch, Piotr [0000-0002-8413-9290]
person.identifier.orcidJaźwiński, Jarosław [0000-0003-2346-5815]
person.identifier.orcidGwardiak, Katarzyna [0000-0001-8566-5869]
person.identifier.orcidKarczewski, Romuald [0000-0002-4633-0430]
person.identifier.orcidPakulski, Zbigniew [0000-0002-8085-0050]
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