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

Kód výsledku v 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>

Nalezeny alternativní kódy

RIV/61389030:_____/24:00587983 RIV/61388963:_____/24:00587983 RIV/61989592:15310/24:73627370

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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 &gt; 31) and no anti-HSV-1 effect (EC50 &gt; 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).

Název v anglickém jazyce

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

Popis výsledku anglicky

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 &gt; 31) and no anti-HSV-1 effect (EC50 &gt; 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).

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Reaction Chemistry &amp; Engineering

ISSN

2058-9883

e-ISSN

—

Svazek periodika

9

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

9

Strana od-do

1087-1095

Kód UT WoS článku

001167274800001

EID výsledku v databázi Scopus

2-s2.0-85186486570