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BioViotica
Rebeccamycin
110
CHF
CHF 110.00
In stock
BVT-0139-C250250 µgCHF 110.00
BVT-0139-M0011 mgCHF 325.00
| Product Details | |
|---|---|
| Synonyms | NSC 359079; BRN 4732638 |
| Product Type | Chemical |
| Properties | |
| Formula |
C27H21Cl2N3O7 |
| MW | 570.4 |
| CAS | 93908-02-2 |
| Source/Host Chemicals | Isolated from Streptomyces sp. |
| Purity Chemicals | ≥98% (HPLC) |
| Appearance | Yellow solid. |
| Solubility | Soluble in DMSO. |
| Identity | Determined by 1H-NMR. |
| Declaration | Manufactured by BioViotica. |
| InChi Key | QEHOIJJIZXRMAN-UMHCKEELSA-N |
| Smiles | COC1C(O)C(O)C(OC1CO)N1C2=C3NC4=C(C=CC=C4Cl)C3=C3C(=O)NC(=O)C3=C2C2=C1C(Cl)=CC=C2 |
| Shipping and Handling | |
| Shipping | BLUE ICE |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Handling Advice | Protect from light when in solution. |
| Use/Stability |
Stable for at least 1 year after receipt when stored at -20°C. Stock solutions are stable for at least 3 months when stored at -20°C. After reconstitution, prepare aliquots and store at -20°C. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- Antibiotic. Structurally similar to staurosporine.
- Selective activity against several cancer cell lines.
- DNA intercalator, resulting in catalytic inhibition of topoisomerases I.
- Shows significant antitumor properties in vitro (IC50 = 480 nM against mouse B16 melanoma cells and IC50 = 500 nM against P388 leukemia cells).
- Does not show any inhibitory activity against protein kinases.
Product References
- Production and biological activity of rebeccamycin, a novel antitumor agent: J.A. Bush, et al.; J. Antibiot. (Tokyo) 40, 668 (1987)
- Induction of mammalian DNA topoisomerase I mediated DNA cleavage by antitumor indolocarbazole derivatives: Y. Yamashita, at al.; Biochemisty 31, 12069 (1992)
- DNA cleavage by topoisomerase I in the presence of indolocarbazole derivatives of rebeccamycin: C. Bailly, et al.; Biochemistry 36, 3917 (1997)
- Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group: F. Anizon, et al.; J. Med. Chem. 40, 3456 (1997)
- Calories from carbohydrates: energetic contribution of the carbohydrate moiety of rebeccamycin to DNA binding and the effect of its orientation on topoisomerase I inhibition: C. Bailly, et al.; Chem. Biol. 6, 277 (1999)
- Discovery of Antitumor Indolocarbazoles: Rebeccamycin, NSC 655649, and Fluoroindolocarbazoles: B.H. Long, et al.; Curr. Med. Chem. 2, 255 (2002)
- Rebeccamycin derivatives as dual DNA-damaging agents and potent checkpoint kinase 1 inhibitor: C. Marminon, et al.; Mol Pharmacol 74, 1620-1629 (2008)
- Phase II and pharmacokinetic trial of rebeccamycin analog in advanced biliary cancers: A. Dowlati, et al.; Cancer Chemother Pharmacol 65, 73-78 (2009)
- New progress of researches in carbazole compounds: F. Zhang, et al.; Chinese J. Org. Chem. 30, 783 (2010)
- Checkpoint Kinase 1 activation enhances intestinal epithelial barrier function via regulation of claudin-5 expression: A. Watari, et al.; PLoS One 11, e0145631/1 (2016)
- Rebeccamycin attenuates TNF-a-induced intestinal epithelial barrier dysfunction by inhibiting myosin light chain kinase production: A. Watari, et al.; Cell. Physiol. Biochem. 41, 1924 (2017)
- The antitumor antibiotic rebeccamycin-challenges and advanced approaches in production processes: K. Pommerehne, et al.; Appl. Microbiol. Biotechnol. 103, 3627 (2019)
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