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US 4,675,187 AGranted
BBM-1675, a new antibiotic complex
AssigneeBristol-Myers Company
InventorsMasataka Konishi, Kyoichiro Saitoh, Hiroaki Ohkuma, Hiroshi Kawaguchi
Life of this patent
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Abstract
A novel antibiotic complex designated herein as BBM-1675 complex is produced by fermentation of certain novel strains of Actinomadura verrucosospora. The complex may be separated into two major components, BBM-1675 A.sub.1 and A.sub.2, and four minor components, BBM-1675 A.sub.3, A.sub.4, B.sub.1 and B.sub.2, and such components exhibit antimicrobial activity and also antitumor activity in certain mouse tumor systems.
Claims4
The antitumor antibiotic BBM-1675 A.sub.3 which:
- (a) is soluble in chloroform, ethyl acetate, acetone, ethanol and methanol, slightly soluble in benzene and water, and insoluble in n-hexane and carbon tetrachloride;
- (b) gives a positive reaction with ferric chloride, Ehrlich and Tollen's reagents and a negative reaction in Sakaguchi, ninhydrin and anthrone tests;
- (c) exhibits an infrared absorption spectrum (KBr) substantially as shown in FIG. 3;
- (d) when dissolved in CDCl.sub.3 exhibits a proton magnetic resonance spectrum substantially as shown in FIG. 7;
- (e) has a melting point in the range of about 125.degree.-127.degree. C.;
- (f) has an optical rotation of [.alpha]sub.D.sup.27 =-161.degree. (c 0.5, CHCl.sub.3);
- (g) has an approximate elemental composition of 54.55% carbon, 6.46% hydrogen, 3.73% nitrogen, 7.49% sulfur and 27.77% (by difference) oxygen;
- (h) exhibits in silica gel thin layer chromatography an Rf value of 0.72 with the solvent system CHCl.sub.3 -CH.sub.3 OH (5:1 v/v) and exhibits in reverse phase silica gel thin layer chromatography an Rf value of 0.28 with the solvent system CH.sub.3 CN-H.sub.2 O (75:25 v/v);
- (i) exhibits the following ultraviolet absorption maxima when dissolved in methanol, 0.01N HCl-CH.sub.3 OH and 0.01N NaOH-CH.sub.3 OH
- ______________________________________ UV .lambda..sub.max nm (E.sup.1% .sub.1cm) 253 (286) in methanol 282 (158) 320 (122) UV .lambda..sub.max nm (E.sup.1% .sub.1cm) 253 (287) in 0.01N HCl--CH.sub.3 OH 282 (160) 320 (126) UV .lambda..sub.max nm (E.sup.1% .sub.1cm) 252 (280) in 0.01N NaOH--CH.sub.3 OH 283 (162) 318 (120);
- ______________________________________
- (j) exhibits a high performance liquid chromatography retention time of 8.0 minutes with a C.sub.18 reversed phase silica gel column and the solvent system CH.sub.3 CN-CH.sub.3 OH-0.1M CH.sub.3 COONH.sub.4 (5:2:3 v/v);
- (k) is effective in inhibiting the growth of various bacteria and fungi;
- (l) induces prophage in lysogenic bacteria;
- and
- (m) is effective in inhibiting the growth of P-388 leukemia in mice.
13 more elements
The antitumor antibiotic BBM-1675 A.sub.4 which:
- (a) is soluble in chloroform, ethyl acetate, acetone, ethanol and methanol, slightly soluble in benzene and water, and insoluble in n-hexane and carbon tetrachloride;
- (b) gives a positive reaction with ferric chloride, Ehrlich and Tollen's reagents and a negative reaction in Sakaguchi, ninhydrin and anthrone tests;
- (c) exhibits an infrared absorption spectrum (KBr) substantially as shown in FIG. 4;
- (d) when dissolved in CDCl.sub.3 exhibits a proton magnetic resonance spectrum substantially as shown in FIG. 8;
- (e) has a melting point in the range of about 123.degree.-126.degree. C.;
- (f) has an optical rotation of [.alpha]sub.D.sup.27 -176.degree. (c 0.5, CHCl.sub.3);
- (g) has an approximate elemental composition of 54.65% carbon, 6.29% hydrogen, 3.51% nitrogen, 8.07% sulfur and 27.48% (by difference) oxygen;
- (h) exhibits in silica gel thin layer chromatography an Rf value of 0.71 with the solvent system CHCl.sub.3 -CH.sub.3 OH (5:1 v/v) and exhibits in reverse phase silica gel thin layer chromatography an Rf value of 0.78 with the solvent system CH.sub.3 CN-H.sub.2 O (75:25 v/v);
- (i) exhibits the following ultraviolet absorption maxima when dissolved in methanol, 0.01N HCl-CH.sub.3 OH and 0.01N NaOH-CH.sub.3 OH
- ______________________________________ UV .lambda..sub.max nm (E.sup.1% .sub.1 cm):
- 253 (257) in methanol 282 (153) 320 (117) UV .lambda..sub.max nm (E.sup.1% .sub.1 cm):
- 253 (258) in 0.01N HCl--CH.sub.3 OH 282 (155) 320 (118) UV .lambda..sub.max nm (E.sup.1% .sub.1 cm):
- 252 (266) in 0.01N NaOH--CH.sub.3 OH 283 (160) 318 (118);
- ______________________________________
- (j) exhibits a high performance liquid chromatography retention time of 5.1 minutes with a C.sub.18 reversed phase silica gel column and the solvent system CH.sub.3 CN-CH.sub.3 OH-0.1M CH.sub.3 COONH.sub.4 (5:2:3 v/v);
- (k) is effective in inhibiting the growth of various bacteria and fungi;
- (l) induces prophage in lysogenic bacteria;
- and
- (m) is effective in inhibiting the growth of P-388 leukemia in mice.
16 more elements
Dependencies are inferred from the claim text.