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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Synonym (S)-(+)-Camptothecin
Anwendungen A reversible Mitochondrial Topo I inhibitor shown to exhibit antitumor activity
CAS Nummer: 7689-03-4
Reinheit: ≥98%
Molekulargewicht: 348.4
Summenformel: C20H16N2O4
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
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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.


Literaturhinweise

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

Aggregatzustand :
Solid
Löslichkeit :
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.
LAGERUNG: :
Store at -20° C
Schmelztemperatur :
260° C (dec.)
Brechungsindex :
n20D 1.75
IC50 :
DNA enzyme topoisomerase I (topo I): IC50 = 0.68 µM
Ausschließlich für Forschungszwecke. Nicht Geeignet für Verwendung in Diagnostik oder Therapie.
Deutsche WGK :
3
RTECS :
UQ0492000
PubChem CID :
24360
Merck Index :
14: 1735
MDL-Nummer :
MFCD00081076
Beilstein-Registernummer :
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  Publikationen

Lesen Sie wie andere Anwender Camptothecin eingesetzt haben. Klicken Sie auf den jeweiligen Eintrag um den entsprechenden PubMed-Abstract abzurufen .

Produktreferenz 1 bis 10 von 15 insgesamt

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.

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