Camptothecin CAS: 7689-03-4
MF: C20H16N2O4
MW: 348.4
A reversible Mitochondrial Topo I inhibitor shown to exhibit antitumor activity.

Camptothecin (CAS 7689-03-4)

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Synonyme: (S)-(+)-Camptothecin
Application: A reversible Mitochondrial Topo I inhibitor shown to exhibit antitumor activity
Numéro CAS: 7689-03-4
Pureté: ≥98%
Masse Moléculaire: 348.4
Formule Moléculaire: C20H16N2O4
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Camptothecin was originally isolated from the stem wood of the Camptotheca acuminata tree and was shown to exhibit antileukemic/antitumor 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.


Références

1. Hertzberg, R.P., et al. 1990. J. Biol. Chem. 265: 19287-19295. PMID: 2172250
2. Slichenmyer, W.J., et al. 1993. J. Natl. Cancer Inst. 85: 271-291. PMID: 8381186
3. Tanizawa, A., et al. 1995. Biochemistry. 34: 7200-7206. PMID: 7766631
4. Ljungman, M., et al. 1996. Carcinogenesis. 17: 31-35. PMID: 8565133
5. Suzuki, A., et al. 1996. Exp. Cell Res. 227: 154-159. PMID: 8806462
6. Shimizu, T., et al. 1997. Leukemia. 11: 1238-1244. PMID: 9264376
7. Pommier, Y., et al. 1998. Biochim. Biophys. Acta. 1400: 83-105. PMID: 9748515
8. Chiou, W.F., et al. 2001. Life Sci. 69: 625-635. PMID: 11476184
9. Sriram, D., et al. 2005. Nat. Prod. Res. 19: 393-412. PMID: 15938148

État Physique :
Solid
Solubilité :
Soluble in chloroform/methanol (4:1) (4 mg/ml), DMSO (10 mg/ml), methanol (40 mg/ml), 0.1N sodium hydroxide (50 mg/ml), and acetic acid. Insoluble in water.
STOCKAGE :
Store at -20° C
Point de fusion :
260° C (dec.)
Indice de Réfraction :
n20D 1.75
IC50 :
DNA enzyme topoisomerase I (topo I): IC50 = 0.68 µM
Pour la Recherche Uniquement. Non conforme pour le Diagnostic ou pour une Utilisation Thérapeutique.
WGK Allemagne :
3
RTECS :
UQ0492000
PubChem CID :
24360
Index Merck :
14: 1735
Numéro MDL :
MFCD00081076
Registre Beilstein :
631069
SMILES :
CC[[email protected]@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O

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Camptothecin  Références bibliographiques

Consultez les publications faisant référence à l' utilisation de Camptothecin. Cliquez sur le lien pour afficher lentrée PubMed .

Citations 1 à 10 sur un total de 15

PMID: # 30514321  Tan, SN. et al. 2018. BMC Mol. Biol. 19: 15.

PMID: # 30213795  Funato, K.|Hayashi, T.|Echizen, K.|Negishi, L.|Shimizu, N.|Koyama-Nasu, R.|Nasu-Nishimura, Y.|Morishita, Y.|Tabar, V.|Todo, T.|Ino, Y.|Mukasa, A.|Saito, N.|Akiyama, T.| et al. 2018. EMBO Rep. 19:

PMID: # 29031818  Khageh Hosseini, S. et al. 2017. Biochem. Pharmacol. 146: 53-62.

PMID: # 27852435  Lopez-Mosqueda, J. et al. 2016. Elife. 5:

PMID: # 26703711  Claus, C. et al. 2015. Viruses. 7: 6108-26.

PMID: # 25525250  Funato, K. et al. 2014. Science. 346: 1529-33.

PMID: # 22851130  Gillies, AT. et al. 2012. Molecular bioSystems. 8: 2901-8.

PMID: # 17965250  Legrand, M. et al. 2007. Eukaryotic Cell. 6: 2194-2205.

PMID: # 17515603  Seiler, JA. et al. 2007. Mol. Cell. Biol. 27: 5806-5818.

PMID: # 17030995  Malavazi, I. et al. 2006. Eukaryotic Cell. 5: 1688-1704.

Citations 1 à 10 sur un total de 15
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