(S)-(+)-Camptothecin

Article No AG-CN2-0463-M050
Product Type Chemicals & Biochemicals
Research Area Cell Death
Format Powder
Size 50 mg

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Specifications

CAS No 7689-03-4
MW 348.4
Country Availability DK, EE, FI, IS, LT, LV, NO, SE
Data Sheet Link https://www.adipogen.com/productmanagement/resource/download/type/sheet/id/11664
Description (S)-(+)-Camptothecin
Supplier Adipogen Life Sciences
Notes 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).
Molecular Formula C20H16N2O4
Alias Names CPT; NSC 94600
Purity >98% (HPLC)
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) | Camptothecin induced mitochondrial dysfunction leading to programmed cell death in unicellular hemoflagellate Leishmania donovani: N. Sen, et al.; Cell Death Differ. 11, 924 (2004) | Camptothecin and its analogues: a review on their chemotherapeutic potential: D. Sriram, et al.; Nat. Prod. Res. 19, 393 (2005) (Review) | Review camptothecin: current perspectives: Q.Y. Li, et al.; Curr. Med. Chem. 13, 2021 (2006) (Review) | The effects of camptothecin on RNA polymerase II transcription: roles of DNA topoisomerase I: G. Capranico, et al.; Biochimie 89, 482 (2007) | 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)
Solubility Soluble in DMSO, DMF or MeOH. Insoluble in water
Source / Host plant
Storage +4°C
Technical Specifications 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).
Product Page Updated 2019-01-09T14:34:57.552Z

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