Camptothecin


CAS No. : 7689-03-4

Camptothecin,7689-03-4
Product Details
For research use only. Not Intended for Therapeutic Use!
Cat No:I000061
Synonyms:(S)-4-ethyl-4-hydroxy-1H-pyrano[3/',4/':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
Molecular Formula:C₂₀H₁₆N₂O₄
Molecular Weight:348.4
Target:Topoisomerase
IC50:50 nM(in MDA-MB-231 cell line)
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Source:Camptotheca acuminata (plant)
Impurity Profile:RRT1.32 Impurity: Not more than 0.7%
Cat No:I000061
Cas No:7689-03-4
Product-Name:Camptothecin
MDL No:MFCD00081076
InChI: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
InChIKey:VSJKWCGYPAHWDS-FQEVSTJZSA-N
SMILES:CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O

Camptothecin (CPT) is a potent DNA enzyme topoisomerase I (topo I) inhibitor with an IC50 and IC70 of 50 nM and 0.225 μM for breast cancer cell line MDA-MB-231.
IC50 Value: 50 nM(in MDA-MB-231 cell line)
Target: topoisomerase
Camptothecin (CPT) has recently been undergoing phase I clinical trials. In 3D fluorescence spectra, Camptothecin presented 3 fluorescence peaks with excitation wavelengths lambdaex of 215, 255 and 365 nm, separately. Camptothecin shows high activity against various tumor cells. Camptothecin was originally isolated from the stem wood of the Camptotheca acuminata tree and was shown to exhibit antileukemic/antitumour activity, and reversibly inhibit Mitochondrial Topo I (nuclear Topo I (topoisomerase I)) by binding to and stabilizing the topoisomerase-DNA covalent complex. Advancing replication forks are believed to interact with these complexes leading to double strand breaks, which is thought to be responsible for much of the cytotoxicity; other research has shown that some of the antitumor activity could be derived from the inhibition of NOS2 (iNOS or inducible nitric oxide synthase) which generates nitric oxide, an important regulator of angiogenesis and other biochemical pathways. The discovery of Camptothecin spurred the development of many derivatives with superior activity and solubility, including Irinotecan (sc-202186) and Topotecan (sc-204919). Although most noted for its anticancer activity, Camptothecin and derivatives have shown other pertinent biochemical actions, including: antiprotozoal, antimalarial, inhibition of HIV, upregulation of p53, and induction of apoptosis. This product also exhibits intense blue fluorescence when exposed to UV light, which could be useful in optical experiments.


[1]. Peter Platzer, Theresia Thalhammer, Gerhard Hamilton, et al. Metabolism of camptothecin, a potent topoisomerase I inhibitor, in the isolated perfused rat liver. Cancer Chemotherapy and Pharmacology.2000, 45(1):50-54
[2]. Tanizawa A, Kohn KW, Kohlhagen G et al. Differential stabilization of eukaryotic DNA topoisomerase I cleavable complexes by camptothecin derivatives. Biochemistry. 1995 May 30;34(21):7200-6.
[3]. Slichenmyer WJ, Rowinsky EK, Donehower RC, Kaufmann SH. The current status of camptothecin analogues as antitumor agents. J Natl Cancer Inst. 1993 Feb 17;85(4):271-91.
[4]. Hertzberg RP, Busby RW, Caranfa MJ et al. Irreversible trapping of the DNA-topoisomerase I covalent complex. Affinity labeling of the camptothecin binding site. J Biol Chem. 1990 Nov 5;265(31):19287-95.
[5]. Hsiang YH, Hertzberg R, Hecht S, Liu LF. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J Biol Chem. 1985 Nov 25;260(27):14873-8.

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