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.
Kuramochi
Kouji
K
Department of Applied Biological Science, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Yukizawa
Shunsuke
S
Ikeda
Seiki
S
Sunoki
Takashi
T
Arai
Satoshi
S
Matsui
Rie
R
Morita
Akinori
A
Mizushina
Yoshiyuki
Y
Sakaguchi
Kengo
K
Sugawara
Fumio
F
Ikekita
Masahiko
M
Kobayashi
Susumu
S
D000111:Acetylcysteine / Q000031:analogs & derivatives / Q000737:chemistry; D001710:Biotin / Q000737:chemistry*; D019921:Biotinylation; D016923:Cell Death / Q000187:drug effects; D004220:Disulfides / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005453:Fluorescence; D006801:Humans; D015394:Molecular Structure; D011090:Polyenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
D004220:Disulfides; D004852:Epoxy Compounds; D011090:Polyenes; C095351:epolactaene; D001710:Biotin; D000111:Acetylcysteine