(S)-(+)-Camptothecin

CHF 35.00
In stock
AG-CN2-0463-M05050 mgCHF 35.00
AG-CN2-0463-M250250 mgCHF 125.00
More Information
Product Details
Synonyms CPT; NSC 94600
Product Type Chemical
Properties
Formula C20H16N2O4
MW 348.4
Merck Index 14: 1735
CAS 7689-03-4
RTECS UQ0492000
Source/Host Chemicals Isolated from Camptotheca acuminata.
Purity Chemicals >98% (HPLC)
Appearance White solid.
Solubility Soluble in DMSO, DMF or MeOH. Insoluble in water
Identity Determined by NMR/IR.
InChi Key VSJKWCGYPAHWDS-FQEVSTJZSA-N
Shipping and Handling
Shipping AMBIENT
Short Term Storage +20°C
Long Term Storage +4°C
Handling Advice Protect from moisture.
Use/Stability Stable for at least 2 years after receipt when stored at +4°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Potent anticancer compound.
  • Cell permeable potent DNA topoisomerase I (Topo I) complex inhibitor.
  • Potent apoptosis inducer.
  • Binds reversibly to the DNA topoisomerase I complex, inhibiting the reassociation of DNA after cleavage by topoisomerase I and traps the enzyme in a covalent linkage with DNA. The enzyme complex is ubiquinated and destroyed by the 26S proteasome, consequently depleting cellular topoisomerase I.
  • Prevents DNA re-ligation and therefore causes DNA damage which results in apoptosis.
  • Inhibits mitochondrial topoisomerase I (mtTop1).
  • Blocks the cell cycle at low dose and induces apoptosis in a large number of normal and tumor cell lines by cell cycle-dependent and cell cycle-independent processes.
  • Antiprotozoal and antimalarial compound.
  • Inhibitor of HIV replication and of other viruses.
  • Suppresses nitric oxide (NO) biosynthesis.
  • Shown to suppress TNF-α-induced expression of the inflammasome and cyclooxygenase 2 (COX-2).
Product References
  1. Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from camptotheca acuminate: M.E. Wall, et al.; JACS 88, 3888 (1966)
  2. Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I: Y.H. Hsiang, et al.; J. Biol. Chem. 260, 14873 (1985)
  3. On the mechanism of topoisomerase I inhibition by camptothecin: evidence for binding to an enzyme-DNA complex: R.P. Hertzberg, et al.; Biochem. 28, 4629 (1989)
  4. Arrest of replication forks by drug-stabilized topoisomerase I-DNA cleavable complexes as a mechanism of cell killing by camptothecin: Y.H. Hsiang, et al.; Cancer Res. 49, 5077 (1989)
  5. Irreversible trapping of the DNA-topoisomerase I covalent complex. Affinity labeling of the camptothecin binding site: R.P. Hertzberg, et al.; J. Biol. Chem. 265, 19287 (1990)
  6. Apoptosis induced by Actinomycin D, Camptothecin or Aphidicolin can occur in all phases of the cell cycle: J.M. Glynn, et al.; Biochem. Soc. Trans. 20, 84S (1992)
  7. Camptothecin inhibits Tat-mediated transactivation of type 1 human immunodeficiency virus: C.J. Li, et al.; J. Biol. Chem. 269, 7051 (1994)
  8. Molecular and cytotoxic effects of camptothecin, a topoisomerase I inhibitor, on trypanosomes and Leishmania: A.L. Bodley & T.A. Shapiro; PNAS 92, 3726 (1995)
  9. Human mitochondrial topoisomerase I: H. Zhang, et al.; PNAS 98, 10608 (2001)
  10. Camptothecin suppresses nitric oxide biosynthesis in RAW 264.7 macrophages: W.F. Chiou, et al.; Life Sci. 69, 625 (2001)
  11. Camptothecin induced mitochondrial dysfunction leading to programmed cell death in unicellular hemoflagellate Leishmania donovani: N. Sen, et al.; Cell Death Differ. 11, 924 (2004)
  12. Camptothecin and its analogues: a review on their chemotherapeutic potential: D. Sriram, et al.; Nat. Prod. Res. 19, 393 (2005) (Review)
  13. Review camptothecin: current perspectives: Q.Y. Li, et al.; Curr. Med. Chem. 13, 2021 (2006) (Review)
  14. The effects of camptothecin on RNA polymerase II transcription: roles of DNA topoisomerase I: G. Capranico, et al.; Biochimie 89, 482 (2007)
  15. Camptothecin promotes the production of nitric oxide that triggers subsequent S-nitrosoproteome-mediated signaling cascades in endothelial cells: B. Huang, et al.; Vascul. Pharmacol. (Epub ahead of print) 1537 (2015)
  16. Freezing Responses in DMSO‐Based Cryopreservation of Human iPS Cells: Aggregates vs. Single Cells: R. Li, et al.; Tissue Eng. Part C Methods, ahead of print (2018)
© 2017 Adipogen Life Sciences. Pictures: © 2012 Martin Oeggerli. All Rights Reserved.