Synthesis, characterization and antiproliferative activity of seco analogues of brassinosteroids
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
30885649
DOI
10.1016/j.steroids.2019.03.004
PII: S0039-128X(19)30055-8
Knihovny.cz E-resources
- Keywords
- Apoptosis, Brassinosteroids, Cyclization, Cytotoxicity, Seco analogues, Skeletal modification,
- MeSH
- Apoptosis drug effects MeSH
- Brassinosteroids chemical synthesis chemistry pharmacology MeSH
- HeLa Cells MeSH
- Humans MeSH
- MCF-7 Cells MeSH
- Cell Proliferation drug effects MeSH
- Antineoplastic Agents chemical synthesis chemistry pharmacology MeSH
- Drug Screening Assays, Antitumor MeSH
- Chemistry Techniques, Synthetic MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Brassinosteroids MeSH
- Antineoplastic Agents 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 We have discovered unpublished behaviour of 2,3-seco-2,3-dihydroxy-6-ketones leading to formation of intramolecular ketal with two new steroidal rings.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.
References provided by Crossref.org
Synthesis and Biological Activity of Brassinosteroid Analogues with a Nitrogen-Containing Side Chain
