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

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.

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Kouji Kuramochi, Shunsuke Yukizawa, Seiki Ikeda, Takashi Sunoki, Satoshi Arai, Rie Matsui, Akinori Morita, Yoshiyuki Mizushina, Kengo Sakaguchi, Fumio Sugawara, Masahiko Ikekita, Susumu Kobayashi. Syntheses and applications of fluorescent and biotinylated epolactaene derivatives: Epolactaene and its derivative induce disulfide formation. Bioorganic & medicinal chemistry. 2008 May 1;16(9):5039-49

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PMID: 18375133

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