Synthesis, characterization and antiproliferative activity of seco analogues of brassinosteroids

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F19%3A00504856" target="_blank" >RIV/61389030:_____/19:00504856 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388963:_____/19:00504856 RIV/61989592:15310/19:73598526

Výsledek na webu

<a href="http://doi.org/10.1016/j.steroids.2019.03.004" target="_blank" >http://doi.org/10.1016/j.steroids.2019.03.004</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.steroids.2019.03.004" target="_blank" >10.1016/j.steroids.2019.03.004</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis, characterization and antiproliferative activity of seco analogues of brassinosteroids

Popis výsledku v původním jazyce

Synthesis and structure–activity relationship analysis of a two groups of 2,3-seco analogues of brassinosteroids (BRs) were performed to examine their antiproliferative activities. Two steroid skeletons were chosen for the preparation of seco analogues – cholestane and stigmastane. The synthetic strategy consists of multistep reactions and detailed analysis of compounds prepared. We have discovered unpublished behaviour of 2,3-seco-2,3-dihydroxy-6-ketones leading to formation of intramolecular ketal with two new steroidal rings. Their reaction intermediates were also characterized in some cases. All compounds prepared were fully characterized with NMR and MS techniques. Most of compounds were tested for in vitro cytotoxicity on three cancer cell lines (CEM, MCF7, and HeLa) and normal human fibroblasts (BJ). It was discovered that some seco analogues caused apoptosis in cancer cells. The most promising seco derivative 28 proved to have high therapeutic index.

Název v anglickém jazyce

Synthesis, characterization and antiproliferative activity of seco analogues of brassinosteroids

Popis výsledku anglicky

Synthesis and structure–activity relationship analysis of a two groups of 2,3-seco analogues of brassinosteroids (BRs) were performed to examine their antiproliferative activities. Two steroid skeletons were chosen for the preparation of seco analogues – cholestane and stigmastane. The synthetic strategy consists of multistep reactions and detailed analysis of compounds prepared. We have discovered unpublished behaviour of 2,3-seco-2,3-dihydroxy-6-ketones leading to formation of intramolecular ketal with two new steroidal rings. Their reaction intermediates were also characterized in some cases. All compounds prepared were fully characterized with NMR and MS techniques. Most of compounds were tested for in vitro cytotoxicity on three cancer cell lines (CEM, MCF7, and HeLa) and normal human fibroblasts (BJ). It was discovered that some seco analogues caused apoptosis in cancer cells. The most promising seco derivative 28 proved to have high therapeutic index.

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

2019

Kód důvěrnosti údajů

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

Název periodika

Steroids

ISSN

0039-128X

e-ISSN

—

Svazek periodika

146

Číslo periodika v rámci svazku

JUN

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

13

Strana od-do

1-13

Kód UT WoS článku

000467508700001

EID výsledku v databázi Scopus

2-s2.0-85062949132