Molecular structure of Rebeccamycin, CAS Number: 93908-02-2
Rebeccamycin (CAS 93908-02-2)
Application:
Rebeccamycin is an indolocarbazole topoisomerase inhibitor
CAS Number:
93908-02-2
Purity:
≥95%
Molecular Weight:
570.4
Molecular Formula:
C27H21Cl2N3O7
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
Rebeccamycin is a compound that functions as a DNA-binding agent, targeting the minor groove of DNA. It has the ability to inhibit the activity of topoisomerase I and II enzymes. Rebeccamycin interferes with the unwinding of DNA strands and prevents the resealing of DNA breaks, ultimately leading to the accumulation of DNA damage. Rebeccamycin induces apoptosis in cancer cells by disrupting the normal functioning of the cell cycle and promoting cell death. Its mechanism of action involves the stabilization of DNA-topoisomerase complexes, leading to the formation of DNA double-strand breaks and subsequent cell death. In experimental applications, rebeccamycin is utilized to study the molecular mechanisms of DNA damage and repair.
Rebeccamycin (CAS 93908-02-2) References
- Calories from carbohydrates: energetic contribution of the carbohydrate moiety of rebeccamycin to DNA binding and the effect of its orientation on topoisomerase I inhibition. | Bailly, C., et al. 1999. Chem Biol. 6: 277-86. PMID: 10322124
- Cellular uptake and interaction with purified membranes of rebeccamycin derivatives. | Goossens, JF., et al. 2000. Eur J Pharmacol. 389: 141-6. PMID: 10688977
- Recent developments of rebeccamycin analogues as topoisomerase I inhibitors and antitumor agents. | Prudhomme, M. 2000. Curr Med Chem. 7: 1189-212. PMID: 11032967
- Active site mutations in DNA topoisomerase I distinguish the cytotoxic activities of camptothecin and the indolocarbazole, rebeccamycin. | Woo, MH., et al. 2002. J Biol Chem. 277: 3813-22. PMID: 11733535
- Discovery of antitumor indolocarbazoles: rebeccamycin, NSC 655649, and fluoroindolocarbazoles. | Long, BH., et al. 2002. Curr Med Chem Anticancer Agents. 2: 255-66. PMID: 12678746
- A Rebeccamycin Analog Provides Plasmid-Encoded Niche Defense. | Van Arnam, EB., et al. 2015. J Am Chem Soc. 137: 14272-4. PMID: 26535611
- Rebeccamycin Attenuates TNF-α-Induced Intestinal Epithelial Barrier Dysfunction by Inhibiting Myosin Light Chain Kinase Production. | Watari, A., et al. 2017. Cell Physiol Biochem. 41: 1924-1934. PMID: 28391269
- Production and biological activity of rebeccamycin, a novel antitumor agent. | Bush, JA., et al. 1987. J Antibiot (Tokyo). 40: 668-78. PMID: 3112080
- Transcriptomics and Proteomics Characterizing the Anticancer Mechanisms of Natural Rebeccamycin Analog Loonamycin in Breast Cancer Cells. | Sun, X., et al. 2022. Molecules. 27: PMID: 36296549
- Molecular Dynamics and Multi-Spectroscopic of the Interaction Behavior between Bladder Cancer Cells and Calf Thymus DNA with Rebeccamycin: Apoptosis through the Down Regulation of PI3K/AKT Signaling Pathway. | Malek-Esfandiari, Z., et al. 2023. J Fluoresc.. PMID: 36787038
- DNA cleavage by topoisomerase I in the presence of indolocarbazole derivatives of rebeccamycin. | Bailly, C., et al. 1997. Biochemistry. 36: 3917-29. PMID: 9092822
- 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. | Anizon, F., et al. 1997. J Med Chem. 40: 3456-65. PMID: 9341921
- Syntheses, biochemical and biological evaluation of staurosporine analogues from the microbial metabolite rebeccamycin. | Anizon, F., et al. 1998. Bioorg Med Chem. 6: 1597-604. PMID: 9801830
Inhibitor of:
Purα, and Topo I.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Rebeccamycin, 250 µg | sc-202309 | 250 µg | $153.00 | |||
Rebeccamycin, 1 mg | sc-202309A | 1 mg | $306.00 |