Synthesis and cytotoxic activity of 1,2,3-triazoles derived from 2,3-seco-dihydrobetulin via a click chemistry approach

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dc.contributor.authorKuczyńska, Kinga
dc.contributor.authorBończak, Bartłomiej
dc.contributor.authorRárová, Lucie
dc.contributor.authorKvasnicová, Marie
dc.contributor.authorStrnad, Miroslav
dc.contributor.authorPakulski, Zbigniew
dc.contributor.authorCmoch, Piotr
dc.contributor.authorFiałkowski, Marcin
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciencesen
dc.contributor.organizationInstitute of Physical Chemistry, Polish Academy of Sciencesen
dc.contributor.organizationDepartment of Experimental Biology, Faculty of Science, Palacký Universityen
dc.contributor.organizationLaboratory of Growth Regulators, Institute of Experimental Botany of the Czech Academy of Sciences and Faculty of Science, Palacký Universityen
dc.date.accessioned2022-07-20T15:23:56Z
dc.date.available2022-07-20T15:23:56Z
dc.date.issued2022
dc.description.abstractIn search of new cytotoxic derivatives based on the lupane scaffold, the seco-lupane azides were coupled with a number of alkynes under the 1,3-dipolar cycloaddition (CuAAC) conditions to afford 1,2,3-triazoles. Phenylalkynes having different substituents at the para position were used as starting materials. Similarly, coupling of the seco-lupane thiocyanate with sodium azide gave 5-thiotetrazole. The cytotoxicity of thir- teen derivatives were investigated, as well as the effect of substituents in the phenyl ring on the activity of 1,2,3-triazoles. Limited activity was observed for some of these products. Most of the studied com- pounds were inactive in cancer cell lines and healthy fibroblasts. Triazole 46 exhibited cytotoxic activity against CEM and MCF-7 cancer cell lines, however, it was also toxic to normal human BJ fibroblasts. Two other derivatives – triazole 45 and tetrazole 49 – exhibited low cytotoxicity. Compound 49 showed good selectivity towards tumor cell lines compared to normal fibroblasts. This compound did not affect the growth of normal human fibroblasts and therefore has a wide therapeutic window.en
dc.description.sponsorshipNational Science Centre, Poland (grant No. 2016/21/B/ST5/02141) Czech Science Foundation No. 20-25308S.
dc.identifier.citationKuczynska, Kinga & Bonczak, Bartlomiej & Rárová, Lucie & Kvasnicová, Marie & Strnad, Miroslav & Pakulski, Zbigniew & Cmoch, Piotr & Fialkowski, Marcin. (2022). Synthesis and cytotoxic activity of 1,2,3-triazoles derived from 2,3-seco-dihydrobetulin via a click chemistry approach. Journal of Molecular Structure. 1250. 131751. https://doi.org/10.1016/j.molstruc.2021.131751en
dc.identifier.doi10.1016/j.molstruc.2021.131751
dc.identifier.issn0022-2860
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/21514
dc.language.isoen
dc.publisherElsevieren
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectlupaneen
dc.subjectbetulinen
dc.subjectclick chemistryen
dc.subjecttriazoleen
dc.subject5-Thiotetrazoleen
dc.subjectcytotoxicityen
dc.subjectSARen
dc.titleSynthesis and cytotoxic activity of 1,2,3-triazoles derived from 2,3-seco-dihydrobetulin via a click chemistry approachen
dc.typearticleen
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