Effect of modification of betulinic acid at the C3-carbon atom of homolupane triterpenoids on the antiproliferative activity in vitro

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F22%3A00562286" target="_blank" >RIV/61389030:_____/22:00562286 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15310/22:73616106
Result on the web
<a href="https://doi.org/10.1016/j.jsbmb.2022.106161" target="_blank" >https://doi.org/10.1016/j.jsbmb.2022.106161</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.jsbmb.2022.106161" target="_blank" >10.1016/j.jsbmb.2022.106161</a>

Result language
angličtina
Original language name
Effect of modification of betulinic acid at the C3-carbon atom of homolupane triterpenoids on the antiproliferative activity in vitro
Original language description
In search of new cytotoxic derivatives based on the lupane scaffold, methyl betulonate and methyl 20,29-dihydrobetulonate were conjugated with Reformatsky reagents to provide homolupanes extended at the C3-carbon atom. Further transformations of the functional groups afforded a series of derivatives with 2-hydroxyethyl and allyl alcohol moieties. Their varying antiproliferative activity in vitro was then investigated in four cancer cell lines and in normal human BJ fibroblasts. In cervical carcinoma HeLa cells, derivatives 5, 6 and 17 were the most promising with lower micromolar IC50s and no toxicity to fibroblasts, thus showing a high therapeutic index. In addition, induction of apoptosis was found in HeLa cells after 24 h treatment with compounds 5, 6, 13 and 29. This newly synthesized series is more interesting than the published lupane and homolupane triterpenes and saponins, due to their nontoxicity towards healthy human cells and stronger cytotoxicity to various cancer cell lines. This approach increases their potential as anticancer agents.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
30107 - Medicinal chemistry

Project
<a href="/en/project/GA20-25308S" target="_blank" >GA20-25308S: Modulation of cyclin-dependent kinases for targeted treatment of tumors with molecularly defined deregulation G1/S phase of cell cycle</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2022
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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