New lupane bidesmosides exhibiting strong cytotoxic activities in vitro

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F20%3A00531674" target="_blank" >RIV/61389030:_____/20:00531674 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61989592:15310/20:73604682

Výsledek na webu

<a href="http://doi.org/10.1016/j.bioorg.2020.103868" target="_blank" >http://doi.org/10.1016/j.bioorg.2020.103868</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.bioorg.2020.103868" target="_blank" >10.1016/j.bioorg.2020.103868</a>

Jazyk výsledku

angličtina

Název v původním jazyce

New lupane bidesmosides exhibiting strong cytotoxic activities in vitro

Popis výsledku v původním jazyce

Triterpene bidesmosides are considered as highly cytotoxic saponins, usually less toxic against normal cells than monodesmosides, and less haemolytic. Biological activity of the betulin-type bidesmosides, rarely found in Nature, and seldom prepared due to serious synthetic problems, is poorly recognized. We report herein a protocol for the preparation of disubstituted lupane saponins (betulin bidesmosides) by treatment of their benzoates with potassium carbonate in dichloromethane / methanol solution. Cytotoxicity of all compounds was tested in vitro for a series of cancer cell lines, as well as normal human skin BJ fibroblasts. Presence of L-rhamnose moiety is crucial for cytotoxicity of betulin bidesmosides. On the other hand, L-arabinose fragment connected to lupane C-3 carbon atom significantly decreases activity. Presented results clearly show that betulin bidesmosides have significant clinical potential as anticancer agents.

Název v anglickém jazyce

New lupane bidesmosides exhibiting strong cytotoxic activities in vitro

Popis výsledku anglicky

Triterpene bidesmosides are considered as highly cytotoxic saponins, usually less toxic against normal cells than monodesmosides, and less haemolytic. Biological activity of the betulin-type bidesmosides, rarely found in Nature, and seldom prepared due to serious synthetic problems, is poorly recognized. We report herein a protocol for the preparation of disubstituted lupane saponins (betulin bidesmosides) by treatment of their benzoates with potassium carbonate in dichloromethane / methanol solution. Cytotoxicity of all compounds was tested in vitro for a series of cancer cell lines, as well as normal human skin BJ fibroblasts. Presence of L-rhamnose moiety is crucial for cytotoxicity of betulin bidesmosides. On the other hand, L-arabinose fragment connected to lupane C-3 carbon atom significantly decreases activity. Presented results clearly show that betulin bidesmosides have significant clinical potential as anticancer agents.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

30107 - Medicinal chemistry

Projekt

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

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

Bioorganic Chemistry

ISSN

0045-2068

e-ISSN

—

Svazek periodika

100

Číslo periodika v rámci svazku

JUL

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

5

Strana od-do

103868

Kód UT WoS článku

000540962100003

EID výsledku v databázi Scopus

2-s2.0-85084209643