Chemical modification of PA-48153C, a novel immunosuppressant isolated from Streptomyces prunicolor PA-48153

• Published in: Journal of antibiotics Vol. 49; no. 2; p. 173
• Main Authors: Yasui, K, Tamura, Y, Nakatani, T, Horibe, I, Kawada, K, Koizumi, K, Suzuki, R, Ohtani, M
• Format: Journal Article
• Language: English
• Published: Japan 1996
• Subjects: Animals; Immunosuppressive Agents - chemistry; Immunosuppressive Agents - isolation & purification; Immunosuppressive Agents - metabolism; Magnetic Resonance Spectroscopy; Mice; Mice, Inbred C3H; Mice, Inbred C57BL; Pyrones - chemistry; Pyrones - isolation & purification; Pyrones - metabolism; Spectrometry, Mass, Secondary Ion; Streptomyces - metabolism; T-Lymphocytes, Cytotoxic - cytology; T-Lymphocytes, Cytotoxic - drug effects; Tumor Cells, Cultured
• ISSN: 0021-8820
• DOI: 10.7164/antibiotics.49.173

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.