Syntheses and applications of fluorescent and biotinylated epolactaene derivatives: Epolactaene and its derivative induce disulfide formation

Syntheses and applications of fluorescent and biotinylated epolactaene derivatives are described. A hypothetical mechanism of action of epolacataene and its derivatives is proposed. Epolactaene, isolated from cultured Penicillium sp. BM 1689-P mycelium, induces neurite outgrowth and arrests the cell...

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Published in:Bioorganic & medicinal chemistry 2008-05, Vol.16 (9), p.5039-5049
Main Authors: Kuramochi, Kouji, Yukizawa, Shunsuke, Ikeda, Seiki, Sunoki, Takashi, Arai, Satoshi, Matsui, Rie, Morita, Akinori, Mizushina, Yoshiyuki, Sakaguchi, Kengo, Sugawara, Fumio, Ikekita, Masahiko, Kobayashi, Susumu
Format: Article
Language:English
Subjects:
Acetylcysteine - analogs & derivatives
Acetylcysteine - chemistry
Antibiotics
Antibiotics. Antiinfectious agents. Antiparasitic agents
Binding proteins
Biological and medical sciences
Biotin - chemistry
Biotinylation
Cell Death - drug effects
Disulfides - chemistry
Drug Screening Assays, Antitumor
Epoxides
Epoxy Compounds - chemical synthesis
Epoxy Compounds - chemistry
Epoxy Compounds - pharmacology
Fluorescence
General aspects
Humans
Medical sciences
Molecular Structure
Penicillium
Pharmacology. Drug treatments
Polyenes - chemical synthesis
Polyenes - chemistry
Polyenes - pharmacology
Proteins
Reaction mechanism
Stereoisomerism
Tumor Cells, Cultured
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Summary:Syntheses and applications of fluorescent and biotinylated epolactaene derivatives are described. A hypothetical mechanism of action of epolacataene and its derivatives is proposed. Epolactaene, isolated from cultured Penicillium sp. BM 1689-P mycelium, induces neurite outgrowth and arrests the cell cycle of the human neuroblastoma cell line, SH-SY5Y, at the G1 phase. We have found that epolactaene and its derivatives induce apoptosis in the human leukemia B-cell line, BALL-1. In this study, we prepared fluorescent and biotinylated epolactaene derivatives. We characterized the cellular location and the identification of BALL-1 proteins that reacted with these compounds. The results obtained from the reaction of epolactaene or its derivative with N-acetylcysteine methyl ester indicate that these compounds induce the disulfide formation and the α-position of the epoxylactam core is the reactive site.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2008.03.029