Camptothecin A reversible Mitochondrial Topo I inhibitor shown to exhibit antitumor activity

Camptothecin (CAS 7689-03-4)

Camptothecin | CAS 7689-03-4 is rated 5.0 out of 5 by 2.
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Synonym: (S)-(+)-Camptothecin
Application: A reversible Mitochondrial Topo I inhibitor shown to exhibit antitumor activity
CAS Number: 7689-03-4
Purity: ≥98%
Molecular Weight: 348.4
Molecular Formula: C20H16N2O4
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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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.


References

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

Physical State :
Solid
Solubility :
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.
Storage :
Store at -20° C
Melting Point :
260° C (dec.)
Refractive Index :
n20D 1.75
IC50 :
DNA enzyme topoisomerase I (topo I): IC50 = 0.68 µM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
UQ0492000
PubChem CID :
24360
Merck Index :
14: 1735
MDL Number :
MFCD00081076
Beilstein Registry :
631069
SMILES :
CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O

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Camptothecin  Product Citations

See how others have used Camptothecin. Click on the entry to view the PubMed entry .

Citations 1 to 10 of 12 total

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

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

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

PMID: # 16199871  Rao, VA. et al. 2005. Mol. Cell. Biol. 25: 8925-8937.

PMID: # 16055725  Saleh-Gohari, N. et al. 2005. Mol. Cell. Biol. 25: 7158-7169.

PMID: # 12058036  Han, BH. et al. 2002. J. Biol. Chem. 277: 30128-30136.

Citations 1 to 10 of 12 total

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. The compound, sc-200871, is provided as a light yellow crystalline powder. If you have any further questions or concerns, please feel free to contact our Technical Service department by calling 800-457-3801 option 2, emailing scbt@scbt.com, or using the Live Chat function on our website.
Answered by: Tech Service 8
Date published: 2017-01-18

What is the solubility of this product?

Asked by: hawkeye11
Thank you for your question. The solubility is as follows: Hot Acetic acid: 20 mg/ml Acetic acid at room temperature: 2 mg/ml DMSO: 10 mg/ml Methanol: 40 mg/ml Please contact Technical Service if you have further questions about this chemical.
Answered by: Tech Service 9
Date published: 2016-12-15
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Rated 5 out of 5 by from great It was easy to induce apoptosis by using this drug for a short time.
Date published: 2016-11-01
Rated 5 out of 5 by from Seiler Seiler, et. al. (PubMed ID 17515603) was able to show that DNA replication in HT29 cells was successfully and quickly inhibited after a short dose of camptothecin. It was also noted that it took several hours for recovery post removal of the drug. -SCBT Publication Review
Date published: 2015-04-12
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