Synthesis and evaluation of cytotoxic and Na+/K+-ATP-ase inhibitory activity of selected 5α-oleandrigenin derivatives
Language English Country France Media print-electronic
Document type Journal Article
PubMed
31325787
DOI
10.1016/j.ejmech.2019.07.028
PII: S0223-5234(19)30647-6
Knihovny.cz E-resources
- Keywords
- ATP-ase inhibition, Cardenolides, Cytotoxicity, Furan transformation, Partial synthesis,
- MeSH
- Cell Line MeSH
- Antineoplastic Agents, Phytogenic chemical synthesis chemistry pharmacology MeSH
- Enzyme Inhibitors chemical synthesis chemistry pharmacology MeSH
- Cardenolides chemical synthesis chemistry pharmacology MeSH
- Humans MeSH
- Molecular Conformation MeSH
- Nerium chemistry MeSH
- Cell Proliferation drug effects MeSH
- Drug Screening Assays, Antitumor MeSH
- Sodium-Potassium-Exchanging ATPase antagonists & inhibitors metabolism MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Antineoplastic Agents, Phytogenic MeSH
- Enzyme Inhibitors MeSH
- Cardenolides MeSH
- oleandrigenin MeSH Browser
- Sodium-Potassium-Exchanging ATPase MeSH
Oleandrin, the major biologically active constituent of shrub Nerium oleander preparations of which have been used in traditional Mediterranean and Asian medicine, attracts a great deal of attention due to its pronounced anticancer activity. The synthesis of oleandrigenin model, 16β-hydroxy-3β-methoxy-5α-card-20(22)-enolide 16-acetate, from androstenolone acetate through 17β-(3-furyl)-intermediates has been developed. Several related 17β-(butenolidyl)- and 17β-(furyl)-androstane derivatives were synthesized and tested for in vitro cytotoxic and Na+/K+-ATP-ase inhibitory activities. Comparison of Na+/K+-ATP-ase inhibitory and cytotoxic activity underlines complex nature of the relationship.
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