208925

(S)-(+)-Camptothecin

from Camptotheca acuminata, ≥95% (HPLC), solid, DNA topoisomerase I inhibitor, Calbiochem

• Synonym(s): Camptothecin, Camptotheca acuminata, 4-Ethyl-4-hydroxy-1H-pyrano[3ʹ,4ʹ:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)dione
• Empirical Formula (Hill Notation): C₂₀H₁₆N₂O₄
• CAS Number: 7689-03-4
• Molecular Weight: 348.35
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00081076
• Assay: ≥95% (HPLC)
• Form: solid
• Storage condition: OK to freeze

Properties

• Product Name: Camptothecin, Camptotheca acuminata, A cell-permeable DNA topoisomerase I inhibitor.
• Quality Segment: 100
• description: Merck USA index - 14, 1735
• assay: ≥95% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: pale yellow
• solubility: DMSO: 10 mg/mL, methanol: 40 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: N21Cc3c(nc5c(c3)cccc5)C2=CC4=C(COC(=O)[C@]4(O)CC)C1=O
• InChI: 1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1
• InChI key: VSJKWCGYPAHWDS-FQEVSTJZSA-N

Description

General description

A cell-permeable DNA topoisomerase I inhibitor. Exhibits anti-leukemic and antitumor properties. Induces apoptosis in HL-60 cells and mouse thymocytes. Arrests cells at the G₂/M phase.

A cell-permeable, reversible DNA topoisomerase I inhibitor that binds to and stabilizes the topoisomerase-DNA covalent complex. Possesses antileukemic and antitumor properties. Inhibits Tat-mediated transactivation of HIV-1. Cytostatic for non-tumorigenic cells but cytotoxic for tumorigenic cells. Induces apoptosis of HL-60 cells and mouse thymocytes.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
DNA topoisomerase 1

Product does not compete with ATP.

Reversible: no

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 months at -20°C.

Stock solutions made with methanol will remain cloudy.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.

Jones, C.B., et al. 1997. Cancer Chemother. Pharmacol.40, 475.
Staron, K., et al. 1994. Carcinogenesis 15, 2953.
Tanizawa, A., et al. 1994. J. Natl. Cancer Inst. 86, 836.
Gorczyca, W., et al. 1993. Toxicol. Lett.67, 249.
Onishi, Y., et al. 1993. Biochim. Biophys. Acta1175, 147.
Pantazis, P., et al. 1993. Int. J. Cancer53, 863.
Morham, S.G., and Shuman, S. 1992. J. Biol. Chem.267, 15984.
Hertzberg, R.P., et al. 1990. Biochem. J.28, 4629.
Hertzberg, R.P., et al. 1990. J. Biol. Chem.265, 19287.
Hsiang, Y.H., et al. 1985. J. Biol. Chem.260, 14873.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Toxic & Carcinogenic / Teratogenic (G)

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Codes: H301,H340
• Precautionary Statements: P202 - P264 - P270 - P280 - P301 + P310 - P405
• Hazard Classifications: Acute Tox. 3 Oral - Muta. 1B
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable