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

Abstract

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 alpha-position of the epoxylactam core is the reactive site.

• Authors: Kouji Kuramochi, Shunsuke Yukizawa, Seiki Ikeda, Takashi Sunoki, Satoshi Arai, Rie Matsui, Akinori Morita, Yoshiyuki Mizushina, Kengo Sakaguchi, Fumio Sugawara, Masahiko Ikekita, Susumu Kobayashi
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 16 Issue 9 Pg. 5039-49 (May 01 2008) ISSN: 1464-3391 [Electronic] England
• PMID: 18375133 (Publication Type: Journal Article)

Chemical References

• Disulfides
• Epoxy Compounds
• Polyenes
• epolactaene
• Biotin
• Acetylcysteine

Topics

• Acetylcysteine (analogs & derivatives, chemistry)
• Biotin (chemistry)
• Biotinylation
• Cell Death (drug effects)
• Disulfides (chemistry)
• Drug Screening Assays, Antitumor
• Epoxy Compounds (chemical synthesis, chemistry, pharmacology)
• Fluorescence
• Humans
• Molecular Structure
• Polyenes (chemical synthesis, chemistry, pharmacology)
• Stereoisomerism
• Tumor Cells, Cultured