The first total synthesis of the marine acetylenic alcohol, lembehyne B - a selective inducer of early apoptosis in leukemia cancer cells.

Abstract

The communication reports a new stereoselective method for the synthesis of a natural acetylenic alcohol, lembehyne B. The key stage of the process uses new cross-cyclomagnesiation reaction of aliphatic and oxygenated 1,2-dienes with Grignard reagents in the presence of a catalytic amount of Cp2TiCl2. A study of the cytotoxic properties of lembehyne B on tumor cell lines using flow cytometry demonstrated that this is a selective inducer of early apoptosis of the Jurkat, HL-60 and K562 cell cultures and hypodiploid (sub-G1) sub-population inducer in cell cycle studies for all cell lines used.

• Authors: Lilya U Dzhemileva, Vladimir A D'yakonov, Aleksey A Makarov, Evgeny N Andreev, Milyausha M Yunusbaeva, Usein M Dzhemilev
• Journal: Organic & biomolecular chemistry (Org Biomol Chem) Vol. 15 Issue 2 Pg. 470-476 (Jan 04 2017) ISSN: 1477-0539 [Electronic] England
• PMID: 27929178 (Publication Type: Journal Article)

Chemical References

• Alcohols
• Alkynes
• Antineoplastic Agents
• Fatty Alcohols
• acetylenic alcohol
• lembehyne B

Topics

• Alcohols (chemical synthesis, chemistry, pharmacology)
• Alkynes (chemical synthesis, chemistry, pharmacology)
• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Apoptosis (drug effects)
• Cell Cycle (drug effects)
• Cell Proliferation (drug effects)
• Cell Survival (drug effects)
• Dose-Response Relationship, Drug
• Drug Screening Assays, Antitumor
• Fatty Alcohols (chemical synthesis, chemistry, pharmacology)
• Humans
• Molecular Structure
• Structure-Activity Relationship
• Tumor Cells, Cultured