C9911
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C9911
Sigma
(S)-(+)-Camptothecin
~95% (HPLC), powder
| CAS Number: | 7689-03-4 |
| Linear Formula: | C20H16N2O4 |
| Molecular Weight: | 348.35 |
| Beilstein Registry Number: | 631069 |
| MDL number: | MFCD00081076 |
| PubChem Substance ID: | 24278352 |
Description
| Frequently Asked Questions | Live Chat and Frequently Asked Questions are available for this Product. |
| Other Notes | 20S isomer |
| Biochem/physiol Actions | (S)-(+)-Camptothecin binds irreversibly to the DNA-topoisomerase I complex, inhibiting the reassociation of DNA after cleavage by topoisomerase I and traps the enzyme in a covalent linkage with DNA. The enzyme complex is ubiquinated and destroyed by the 26S proteasome, thus depleting cellular topoisomerase I. Blocks the cell cycle in S-phase at low does and induces apoptosis in a large number of normal and tumor cell lines by cell cycle-dependent and cell cycle-independent processes. |
Properties
| assay | ~95% (HPLC) |
| form | powder |
| color | yellow |
| mp | 260 °C (dec.)(lit.) |
| solubility | chloroform/methanol (4:1): 4 mg/mL |
| Gene Information | human ... TOP1(7150) |
| rat ... Sstr2(54305) | |
| mouse ... Prkca(18750) | |
| storage temp. | 2-8°C |
Safety
| Personal Protective Equipment | Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges |
| Hazard Codes | T |
| Risk Statements | 25 |
| Safety Statements | 45 |
| RIDADR | UN1544 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | UQ0492000 |
References
| reference | Fan, Y., et al., Molecular modeling studies of the DNA-topoisomerase I ternary cleavable complex with camptothecin. J. Med. Chem. 41, 2216-2226, (1998) Abstract |
| Pommier, Y., et al., Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzyme. Biochim. Biophys. Acta 1400, 83-105, (1998) Abstract | |
| Desai, S. D., et al., Ubiquitin-dependent destruction of topoisomerase I is stimulated by the antitumor drug camptothecin. J. Biol. Chem. 272, 24159-24164, (1997) Abstract | |
| Beidler, D.R., and Cheng, Y.C., Camptothecin induction of a time- and concentration-dependent decrease of topoisomerase I and its implication in camptothecin activity. Mol. Pharmacol. 47, 907-914, (1994) | |
| Borovitskaya, A.E., and D-Arpa, P., Replication-dependent and -independent camptothecin cytotoxicity of seven human colon tumor cell lines. Oncol. Res. 10, 271-276, (1998) Abstract | |
| Morris. E.J., and Geller, H.M., Induction of neuronal apoptosis by camptothecin, an inhibitor of DNA topoisomerase-I: evidence for cell cycle-independent toxicity. J. Cell Biol. 134, 757-770, (1996) Abstract | |
| Kaufmann, S. H., Cell death induced by topoisomerase-targeted drugs: more questions than answers. Biochim. Biophys. Acta 1400, 195-211, (1998) Abstract | |
| Merck | Merck 13,1743 |
| FT-IR 2 (3), 4267:D / Structure Index 1, 462:C:1 |
