Oxime derivatives of betulonic acid and platanic acid as novel cytotoxic or antiviral agents

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F24%3A43929383" target="_blank" >RIV/60461373:22330/24:43929383 - isvavai.cz</a>
Alternative codes found
RIV/61389030:_____/24:00587983 RIV/61388963:_____/24:00587983 RIV/61989592:15310/24:73627370
Result on the web
<a href="https://pubs.rsc.org/en/content/articlelanding/2024/re/d4re00032c" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2024/re/d4re00032c</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d4re00032c" target="_blank" >10.1039/d4re00032c</a>

Result language
angličtina
Original language name
Oxime derivatives of betulonic acid and platanic acid as novel cytotoxic or antiviral agents
Original language description
Less frequently studied plant triterpenoids betulonic acid and platanic acid were selected to design, synthesize and investigate their oxime derivatives as novel and potentially effective cytotoxic and/or antiviral agents. The target compounds were subjected to cytotoxicity screening tests in several human cancer cell lines. Several of them displayed cytotoxicity against T-lymphoblastic leukemia (CCRF-CEM), breast adenocarcinoma (MCF7), malignant melanoma (G-361) and cervical cancer (HeLa) cell lines. Betulonic acid oxime (3) displayed cytotoxicity against CCRF-CEM (IC50 = 18.9 +/- 1.1 mu M; SI = 2.4) and G-361 (IC50 = 21.3 +/- 2.8 mu M; SI = 2.2) cancer cell lines. The benzyl ester of platanic acid oxime (17) displayed an anti-HIV-1 effect (EC50 = 3.2 +/- 0.43 mu M; SI > 31) and no anti-HSV-1 effect (EC50 > 100 mu M), while platanic acid oxime (15) showed lower effects, EC50 = 36 +/- 4.0 mu M (HIV-1) and EC50 = 48 +/- 6.0 mu M (HSV-1), respectively. Compound 17 showed high selectivity in antiviral effects, being effective in HIV-1 and inactive in HSV-1. A side product 18 showed antiviral activity with EC50 = 15 +/- 1.3 mu M (HIV-1) and EC50 = 12 +/- 0.21 mu M (HSV-1), while another side product 19 was cytotoxic to HeLa (IC50 = 24.5 +/- 1.8 mu M).
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
10401 - Organic chemistry

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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