Title: Tallysomycin
CAS Registry Number: 67995-68-0
Additional Names: Talisomycin
Manufacturers' Codes: BU-2231
Literature References: Antitumor antibiotic complex and third generation analog of bleomycins, q.v., produced by Streptoalloteichus hindustanus E 465-94. Prodn, isoln, properties of the major components, tallysomycins A and B: H. Kawaguchi et al., BE 845513; eidem, US 4051237 (both 1977 to Bristol-Myers); eidem, J. Antibiot. 30, 779 (1977). Structure of A and B, based on originally proposed bleomycin structure: M. Konishi et al., ibid. 789; cf. bleomycin for revised structure. Antitumor activity: H. Imanishi et al., ibid. 31, 667 (1978). Radioimmunoassay: A. Broughton et al., Cancer Treat. Rep. 63, 1829 (1979). Pharmacokinetics: J. E. Strong et al., ibid. 1821. 13C-NMR spectra of tallysomycin and its zinc complex: F. T. Greenaway et al., Org. Magn. Reson. 13, 270 (1980). Biosynthetic derivs: T. Miyaki et al., J. Antibiot. 34, 658, 665 (1981). Relative pulmonary toxicity: A. Broughton et al., Cancer Treat. Rep. 64, 659 (1980). Review: S. T. Crooke et al., Recent Results Cancer Res. 76, 83-90 (1981).
Derivative Type: Tallysomycin A
CAS Registry Number: 65057-90-1
CAS Name: N1-[4-Amino-6-[[3-[(4-aminobutyl)amino]propyl]amino]-6-oxohexyl]-13-[(4-amino-4,6-dideoxy-a-L-talopyranosyl)oxy]-19-demethyl-12-hydroxybleomycinamide
Manufacturers' Codes: BU-2231A
Molecular Formula: C68H110N22O27S2
Molecular Weight: 1731.86
Percent Composition: C 47.16%, H 6.40%, N 17.79%, O 24.94%, S 3.70%
Literature References: The term "talisomycin" has also been used to refer to tallysomycin A.
Properties: White amorphous solid. No definite mp; gradually dec >210°. Sol in water, methanol, DMF; slightly sol in ethanol. Practically insol in other organic solvents. [a]D23 -21° (c = 0.5 in water). uv max (water): 290 nm (E1%1cm 67). LD50 s.c. in mice: 28 mg/kg (US 4051237).
Optical Rotation: [a]D23 -21° (c = 0.5 in water)
Absorption maximum: uv max (water): 290 nm (E1%1cm 67)
Toxicity data: LD50 s.c. in mice: 28 mg/kg (US 4051237)
Derivative Type: Tallysomycin B
CAS Registry Number: 65057-91-2
CAS Name: N1-[3-[(4-Aminobutyl)amino]propyl]-13-[(4-amino-4,6-dideoxy-a-L-talopyranosyl)oxy]-19-demethyl-12-hydroxybleomycinamide
Additional Names: talisomycin B
Manufacturers' Codes: BU-2231B
Molecular Formula: C62H98N20O26S2
Molecular Weight: 1603.69
Percent Composition: C 46.43%, H 6.16%, N 17.47%, O 25.94%, S 4.00%
Properties: Mp, soly similar to tallysomycin A. [a]D23 -19° (c = 0.5 in water). uv max (water): 289.5 (E1%1cm 77). LD50 s.c. in mice: >50 mg/kg (US 4051237).
Optical Rotation: [a]D23 -19° (c = 0.5 in water)
Absorption maximum: uv max (water): 289.5 (E1%1cm 77)
Toxicity data: LD50 s.c. in mice: >50 mg/kg (US 4051237)
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