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208925

Sigma-Aldrich

(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

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About This Item

Empirical Formula (Hill Notation):
C20H16N2O4
CAS Number:
7689-03-4
Molecular Weight:
348.35
MDL number:
MFCD00081076
UNSPSC Code:
12352200
NACRES:
NA.77

product name

Camptothecin, Camptotheca acuminata, A cell-permeable DNA topoisomerase I inhibitor.

Quality Level

100

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

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

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

Warning

Toxicity: Toxic & Carcinogenic / Teratogenic (G)

Preparation Note

Stock solutions made with methanol will remain cloudy.

Reconstitution

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

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

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H301,H340

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Frederick A Partridge et al.
Molecules (Basel, Switzerland), 26(20) (2021-10-24)
Mosquito-borne viruses including dengue, Zika, and Chikungunya viruses, and parasites such as malaria and Onchocerca volvulus endanger health and economic security around the globe, and emerging mosquito-borne pathogens have pandemic potential. However, the rapid spread of insecticide resistance threatens our
Wade R Gutierrez et al.
JCI insight (2022-10-14)
The DNA methyltransferase inhibitor decitabine has classically been used to reactivate silenced genes and as a pre-treatment for anti-cancer therapies. In a new variation of this idea, this study explores the concept of adding low-dose decitabine following administration of chemotherapy
Md Akram Hossain et al.
Frontiers in cell and developmental biology, 9, 738502-738502 (2021-11-20)
The maintenance of genome integrity and fidelity is vital for the proper function and survival of all organisms. Recent studies have revealed that APE2 is required to activate an ATR-Chk1 DNA damage response (DDR) pathway in response to oxidative stress
Elisabetta Rubini et al.
Molecules (Basel, Switzerland), 26(23) (2021-12-11)
The β-isomer of hexachlorocyclohexane (β-HCH) is a globally widespread pollutant that embodies all the physicochemical characteristics of organochlorine pesticides, constituting an environmental risk factor for a wide range of noncommunicable diseases. Previous in vitro studies from our group disclosed the
Jianming Wang et al.
Cell reports, 34(7), 108759-108759 (2021-02-18)
As transcription and replication use DNA as substrate, conflicts between transcription and replication can occur, leading to genome instability with direct consequences for human health. To determine how the two processes are coordinated throughout S phase, we characterize both processes
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