title: Chemical modification of PA-48153C, a novel immunosuppressant isolated from Streptomyces prunicolor PA-48153.
abstract: 5beta-Methoxy (20), 14-methyl (24), 14,14-dibromo-15-nor (25), 8-O-acyl (26-45), 8-O-alkyl (46), 8-O-alkoxycarbonyl (47, 48), and 8-O-carbamoyl (49) derivatives of PA-48153C, a novel immunosuppressant isolated from fermentation products of Streptomyces prunicolor PA-48153, were prepared. These compounds were found to retain the inhibitory activity on the responses of both T and B cells to mitogens. Among them, the C-8 hexanoate 28 showed potent suppressive effects on mitogen responses with less cytotoxicity to EL4 cells and was selected for in vivo evaluation.
authors.affiliation: Shionogi & Co., Ltd., Osaka, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Yasui
authors.forename: Y
authors.initials: Y
authors.lastname: Tamura
authors.forename: T
authors.initials: T
authors.lastname: Nakatani
authors.forename: I
authors.initials: I
authors.lastname: Horibe
authors.forename: K
authors.initials: K
authors.lastname: Kawada
authors.forename: K
authors.initials: K
authors.lastname: Koizumi
authors.forename: R
authors.initials: R
authors.lastname: Suzuki
authors.forename: M
authors.initials: M
authors.lastname: Ohtani
mesh_terms: D000818:Animals; D007166:Immunosuppressive Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008809:Mice, Inbred C3H; D008810:Mice, Inbred C57BL; D011753:Pyrones / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D018629:Spectrometry, Mass, Secondary Ion; D013302:Streptomyces / Q000378:metabolism*; D013602:T-Lymphocytes, Cytotoxic / Q000166:cytology / Q000187:drug effects; D014407:Tumor Cells, Cultured
chemical_list: D007166:Immunosuppressive Agents; D011753:Pyrones; C088446:pironetin