Rebeccamycin An indolocarbazole topoisomerase inhibitor

Rebeccamycin (CAS 93908-02-2)

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Application: An indolocarbazole topoisomerase inhibitor
CAS Number: 93908-02-2
Purity: ≥98%
Molecular Weight: 570.4
Molecular Formula: C27H21Cl2N3O7
* Refer to Certificate of Analysis for lot specific data (including water content).
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Rebeccamycin is an indolocarbazole small molecule antibiotic, functional as an inhibitor of Topo I (DNA topoisomerase I). It is suggested that Rebeccamycin and the other related indolocarbazoles intercalate into DNA and prevent topoisomerase activity from a position on the backbone. The stereochemistry of the pendant sugar on Rebeccamycin is demonstrated to be crucial for the specificity of this DNA interaction. The glycosyl moiety is also shown to be essential for the translocation of Rebeccamycin from the lipid membrane into the vital structures of the cell.


References

1. Bush, J.A., et al. 1987. J. Antibiot. 40: 668-678. PMID: 3112080
2. Bailly, C., et al. 1997. Biochemistry. 36: 3917-3929. PMID: 9092822
3. Anizon, F., et al. 1997. J. Med. Chem. 40: 3456-3465. PMID: 9341921
4. Anizon, F., et al. 1998. Bioorg. Med. Chem. 6: 1597-1604. PMID: 9801830
5. Bailly, C., et al. 1999. Chem. Biol. 6: 277-286. PMID: 10322124
6. Goossens, J.F., et al. 2000. Eur. J. Pharmacol. 389: 141-146. PMID: 10688977
7. Long, B.H., et al. 2002. Curr Med Chem Anticancer Agents. 2: 255-266. PMID: 12678746
8. Woo, M.H., et al. 2002. J. Biol. Chem. 277: 3813-3822. PMID: 11733535

Physical State :
Solid
Derived From :
Lechevalieria sp.
Solubility :
Soluble in DMSO (≥3 mg/ml), THF, and methanol (≤0.2 mg/ml).
Storage :
Store at -20° C
Density :
1.88 g/cm3 (Predicted)
Refractive Index :
n20D 1.84 (Predicted)
IC50 :
L1210: IC50 = 100 nM (mouse); K562: IC50 = 200 nM (human); A549: IC50 = 300 nM (human); B16 melanoma cells: IC50 = 480 nM (mouse); P388 leukemia cells: IC50 = 500 nM
pK Values :
pKa: 9.31 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
73110
MDL Number :
MFCD01718312
Beilstein Registry :
4732638
SMILES :
CO[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)N2C3=C(C=CC=C3Cl)C4=C5C(=C6C7=C(C(=CC=C7)Cl)NC6=C42)C(=O)NC5=O)CO

Download SDS (MSDS)

Certificate of Analysis

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