Cas No.: | 12684-33-2 |
Chemical Name: | Sibiromycin |
Synonyms: | 5H-Pyrrolo[2,1-c][1,4]benzodiazepin-5-one,7-[[4,6-dideoxy-3-C-methyl-4-(methylamino)-a-L-mannopyranosyl]oxy]-1,10,11,11a-tetrahydro-9,11-dihydroxy-8-methyl-2-(1E)-1-propen-1-yl-,(11R,11aS)-;(6R,6aS)-2-[(2S,3R,4R,5S,6S)-3,4-dihydroxy-4,6-dimethyl-5-(methylamino)oxan-2-yl]oxy-4,6-dihydroxy-3-methyl-8-[(E)-prop-1-enyl]-5,6,6a,7-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one;Sibiromycin;C24H31N3O7;Sybiromycin;7-[(4,6-Dideoxy-3-methyl-4-methylamino-α-L-mannopyranosyl)oxy]-10,11-dihydro-9,11-dihydroxy-8-methyl-2-(1-propenyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one;5H-Pyrrolo(2,1-C)(1,4)benzodiazepin-5-one, 7-((4,6-dideoxy-3-C-methyl-4-(methylamino)-alpha-L-mannopyranosyl)oxy)-1,10,11,11A-treahydro-9,11-dihydroxy-8-methyl-2-(1E)-1-propenyl-, (11R,11as)-;Q27162933 |
SMILES: | O1[C@]([H])([C@@]([H])([C@@](C([H])([H])[H])([C@]([H])([C@]1([H])C([H])([H])[H])N([H])C([H])([H])[H])O[H])O[H])OC1=C(C([H])([H])[H])C(=C2C(=C1[H])C(N1C([H])=C(/C(/[H])=C(\[H])/C([H])([H])[H])C([H])([H])[C@@]1([H])[C@]([H])(N2[H])O[H])=O)O[H] |
Formula: | C24H33N3O7 |
M.Wt: | 475.5347 |
Purity: | >98% |
Sotrage: | 2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO |
Description: | Sibiromycin is a naturally produced glycosylated pyrrolobenzodiazepines (PBDs). Sibiromycin is also a potent antitumor antibiotic that binds covalently to DNA in the minor groove at the NH2 of guanine[1][2]. |
In Vitro: | Pyrrolobenzodiazepines (PBDs) are sequence selective DNA alkylating agents with remarkable antineoplastic activity[1]. Alkylation of DNA by anthramycin, sibiromycin and tomaymycin is sequence specific with the following trend for binding preference 5′-Pu-G-Pu>5′-Py-G-Pu>5′-Pu-G-Py>5′-Py-G-Py[1]. Sibiromycin shows cytotoxicity against L1210 (leukemia), ADJ/PC6 (plasmacytoma) and CH1 (ovarian) cells with IC50s of ranging 0.000017 ~0.0029 μM[1]. |
References: | [1]. Gerratana B. Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines. Med Res Rev. 2012;32(2):254-293. [2]. Li W, et al. Biosynthesis of sibiromycin, a potent antitumor antibiotic. Appl Environ Microbiol. 2009;75(9):2869-2878. |