Synthesis, characterization and antiproliferative activity of seco analogues of brassinosteroids
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
30885649
DOI
10.1016/j.steroids.2019.03.004
PII: S0039-128X(19)30055-8
Knihovny.cz E-zdroje
- Klíčová slova
- Apoptosis, Brassinosteroids, Cyclization, Cytotoxicity, Seco analogues, Skeletal modification,
- MeSH
- apoptóza účinky léků MeSH
- brassinosteroidy chemická syntéza chemie farmakologie MeSH
- HeLa buňky MeSH
- lidé MeSH
- MFC-7 buňky MeSH
- proliferace buněk účinky léků MeSH
- protinádorové látky chemická syntéza chemie farmakologie MeSH
- screeningové testy protinádorových léčiv MeSH
- techniky syntetické chemie MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- brassinosteroidy MeSH
- protinádorové látky MeSH
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 We have discovered unpublished behaviour of 2,3-seco-2,3-dihydroxy-6-ketones leading to formation of intramolecular ketal with two new steroidal rings.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.
Citace poskytuje Crossref.org
Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain
