12684-33-2
12684-33-2 structure
- Name: Sibiromycin
- Chemical Name: (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
- CAS Number: 12684-33-2
- Molecular Formula: C24H31N3O7
- Molecular Weight: 473.51900
- Catalog: Signaling Pathways Cell Cycle/DNA Damage DNA Alkylator/Crosslinker
- Create Date: 2016-07-25 10:35:08
- Modify Date: 2026-07-16 18:49:32
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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].
| Name | (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 |
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| Synonyms |
Sybiromycin
(7S,8R)-13-{[(2S,3R,4R,5S,6S)-3,4-dihydroxy-4,6-dimethyl-5-(methylamino)oxan-2-yl]oxy}-8,11-dihydroxy-12-methyl-5-[(1E)-prop-1-en-1-yl]-3,9-diazatricyclo[8.4.0.03,]tetradeca-1,4,11,13-tetraen-2-one 5H-Pyrrolo[2,1-c][1,4]benzodiazin-5-one, 7-[[4,6-dideoxy-3-C-methyl-4-(methylamino)-α-L-mannopyranosyl]oxy]-1,10,11,11a-tetrahydro-9,11-dihydroxy-8-methyl-2-(1E)-1-propen-1-yl-, (11R,11aS) 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]benzodiazin-5-one 5H-Pyrrolo(2,1-C)(1,4)benzodiazin-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) C24H31N3O7 |
| 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]. |
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| Related Catalog | |
| 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 |
| Density | 1.41g/cm3 |
|---|---|
| Boiling Point | 755.7ºC at 760 mmHg |
| Molecular Formula | C24H31N3O7 |
| Molecular Weight | 473.51900 |
| Flash Point | 410.8ºC |
| Exact Mass | 473.21600 |
| PSA | 145.44000 |
| LogP | 1.99250 |
| Vapour Pressure | 5.32E-24mmHg at 25°C |
| Index of Refraction | 1.662 |
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