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208925

(S)-(+)-Camptothecin

Name: (S)-(+)-Camptothecin
Brand: MM

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

Synonyme(s) :

Camptothecin, Camptotheca acuminata, 4-Ethyl-4-hydroxy-1H-pyrano[3ʹ,4ʹ:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)dione

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A propos de cet article

Formule empirique (notation de Hill) :

C₂₀H₁₆N₂O₄

Numéro CAS:

7689-03-4

Poids moléculaire :

348.35

UNSPSC Code:

12352200

NACRES:

NA.77

MDL number:

MFCD00081076

Assay:

≥95% (HPLC)

Form:

solid

Storage condition:

OK to freeze

Service technique

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Propriétés

Nom du produit

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)

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pictograms

GHS06,GHS08

signalword

Danger

hcodes

H301,H340

pcodes

P202 - P264 - P270 - P280 - P301 + P310 - P405

Hazard Classifications

Acute Tox. 3 Oral - Muta. 1B

Classe de stockage

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