8827. Streptonigrin

Nomenclature

CAS number: 3930-19-6
5-Amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-2-pyridinecarboxylic acid; 5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpicolinic acid; bruneomycin; NSC-45383.
C25H22N4O8; mol wt 506.46.
C 59.29%, H 4.38%, N 11.06%, O 25.27%.

Description and references

Antitumor antibiotic produced by Streptomyces flocculus: Rao, Cullen, Antibiot. Annu. 1959-1960, 950. Structure: Rao et al., J. Am. Chem. Soc. 85, 2532 (1963). Crystal and molecular structure: Y. Y. H. Chiu, W. N. Lipscomb, ibid. 97, 2525 (1975). Identity with bruneomycin: Brazhnikova et al., Antibiotiki 13, 99 (1968), C.A. 68, 89890q (1968). Synthetic studies: Kametani et al., C.A. 76, 14272w (1972); 79, 31817g (1973). Total synthesis: F. Z. Basha et al., J. Am. Chem. Soc. 102, 3962 (1980); A. S. Kende et al., ibid. 103, 1271 (1981); S. M. Weinreb et al., ibid. 104, 536 (1982). Biosynthesis: S. J. Gould, D. E. Cane, ibid. 343. Reviews: N. S. Mizuno in Antibiotics vol. 5, pt. 2, F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 372-384; S. J. Gould, S. M. Weinreb, Fortschr. Chem. Org. Naturst. 41, 77-111 (1982). Review of genotoxicity: A. D. Bolzán, M. S. Bianchi, Mutat. Res. 488, 25-37 (2001).

Chemical structure

Properties

Coffee-brown to almost black rectangular plates from acetone or dioxane, dec 275°; brown needles, mp 262-263° (Brazhnikova). uv max (methanol): 248, 375-380 nm (ε 38400, 17400). Weak acid. pKa 6.2-6.4 (1:1 aq dioxane). Sol in dioxane, pyridine, dimethylformamide, aq sodium bicarbonate with decompn; slightly sol in water, lower alcohols, ethyl acetate, chloroform.

Caution

Potential symptoms of overexposure include severe and prolonged bone marrow depression (Bolzán, Bianchi).