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ProductsBack/(S)-(+)-Camptothecin [7689-03-4]
Chemical Structure
Chemical Structure
Chemical Structure

(S)-(+)-Camptothecin [7689-03-4]

Research Use Only
AG-CN2-0463
AdipoGen Life Sciences
Estimated Purity>98%
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Product group Chemicals
Molecular Weight348.4
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    (S)-(+)-Camptothecin [7689-03-4]
  • Delivery Days Customer
    10
  • ADR Class
    6.1
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Hazard Information
    Danger,Excepted quantity
  • Molecular Formula
    C20H16N2O4
  • Molecular Weight
    348.4
  • Scientific Description
    Chemical. CAS: 7689-03-4. Formula: C20H16N2O4. MW: 348.4. Isolated from Camptotheca acuminata. 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-alpha-induced expression of the inflammasome and cyclooxygenase 2 (COX-2). - 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-alpha-induced expression of the inflammasome and cyclooxygenase 2 (COX-2).
  • SMILES
    CC[C@@]1(O)C(=O)OCC2=C1C=C1N(CC3=CC4=CC=CC=C4N=C13)C2=O
  • Storage Instruction
    2°C to 8°C,RT
  • UN Number
    UN 2811
  • UNSPSC
    12352200

References

  • 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)
  • Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I: Y.H. Hsiang, et al.; J. Biol. Chem. 260, 14873 (1985)
  • 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)
  • 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)
  • 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)
  • 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)
  • Camptothecin inhibits Tat-mediated transactivation of type 1 human immunodeficiency virus: C.J. Li, et al.; J. Biol. Chem. 269, 7051 (1994)
  • Molecular and cytotoxic effects of camptothecin, a topoisomerase I inhibitor, on trypanosomes and Leishmania: A.L. Bodley & T.A. Shapiro; PNAS 92, 3726 (1995)
  • Human mitochondrial topoisomerase I: H. Zhang, et al.; PNAS 98, 10608 (2001)
  • Camptothecin suppresses nitric oxide biosynthesis in RAW 264.7 macrophages: W.F. Chiou, et al.; Life Sci. 69, 625 (2001)