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(+)-Camptothecin

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(+)-Camptothecin Basic information
(+)-Camptothecin Chemical Properties
  • Melting point:260 °C (dec.)(lit.)
  • alpha D25 +31.3° (in chloroform-methanol, 8:2)
  • Boiling point:482.73°C (rough estimate)
  • Density 1.3112 (rough estimate)
  • refractive index 1.5700 (estimate)
  • storage temp. 2-8°C
  • solubility chloroform/methanol (4:1): 4 mg/mL
  • pkapKa 10.83 (Uncertain)
  • form solid
  • color yellow
  • Water Solubility insoluble
  • Merck 14,1735
  • BRN 631069
  • InChIKeyVSJKWCGYPAHWDS-FQEVSTJZSA-N
  • CAS DataBase Reference7689-03-4(CAS DataBase Reference)
Safety Information
  • Hazard Codes T,Xi,Xn
  • Risk Statements 36/37/38-25-20/21/22
  • Safety Statements 45-36/37/39-26-36
  • RIDADR UN 1544 6.1/PG 3
  • WGK Germany 3
  • RTECS UQ0492000
  • Hazard Note Irritant
  • HazardClass 6.1
  • PackingGroup 
  • HS Code 29399990
MSDS
(+)-Camptothecin Usage And Synthesis
  • Chemical Propertieslight yellow crystal powde
  • UsesAntitumor alkaloid. Binds irreversible 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. A cytotoxic antitumor agent
  • Usesantineoplastic
  • UsesAntitumor agent;Topoisomerase I inhibitor
  • Uses10-hydroxycamptothecine precursor, topoisomerase inhibitor, binds irreversibly to DNA-topoisomerase I complex
  • DefinitionChEBI: A pyranoindolizinoquinoline that is pyrano[3',4':6,7]indolizino[1,2-b]quinoline which is substituted by oxo groups at positions 3 and 14, and by an ethyl group and a hydroxy group at position 4 (the S enantiomer).
  • Biological ActivityCytotoxic plant alkaloid with antitumor properties; prototypic DNA topoisomerase I inhibitor.
  • Anticancer ResearchCamptothecin (CPT) is a monoterpene indole alkaloid which is isolatedfrom the Chinese plant, Camptotheca acuminata (Nyssaceae) (Wall et al. 1966).CPT is used in cancer treatment since it is a potent inhibitor of DNA topoisomeraseI, which leads to DNA damage and the apoptosis in cancer cells. Studies have shownthat CPT itself is not suitable for clinical application since it has low water solubilityand certain side effects; therefore, water-soluble CPT derivatives such as topotecan and irinotecan were synthesized and have been successfully used for thetreatment of ovarian, lung, and colorectal cancers, and CPT has been approved by theFood and Drug Administration (FDA) of the USA. Currently, topotecan and irinotecanare all synthesized from natural camptothecin which is mainly extracted fromCamptotheca acuminata (Beegum et al. 2007). Subsequently, CPT was also recognizedand extracted from other plant species such as Ervatamia heyneana (Gunasekeraet al. 1979), Melliodendron megacarpum (Arisawa et al. 1981), Nothapodytes foetida(Govindachari and Viswanathan 1972), and Ophiorrhiza species (Beegum et al.2007). However, the extraction of CPT from plants is limited because of low yields(about 1 mg/g dry weight) and scanty natural resources (Lopez-Meyer et al. 1994),and scientists have used biotechnological ways especially cell culture methods forthe production of CPT and its derivatives (Kai et al. 2015).
  • Anticancer ResearchCPT is extracted from Camptotheca acuminata, also called Chinese ornamentaltree. Irinotecan and topotecan are semisynthetic derivatives of camptothecin, whichcan be used for the therapy of colorectal and ovarian and small cell lung carcinoma,respectively (Shoeb 2006). Camptothecin is a potent antitumor agent that targetstopoisomerase I (Desai et al. 2008). The synthetic derivatives of camptothecin[20-(S)-9-nitrocamptothecin and 20-(S)-camptothecin] have the antitumor effects inbreast, prostate, and melanoma cancers. CPT-11 is a new derivative that showsantitumor effects against metastatic colorectal cancer (Hosseini and Ghorbani2015). It selectively inhibits topoisomerase I which is involved in cleavage andreassembly of DNA (Balunas and Kinghorn 2005). Camptothecin inhibits thesynthesis of nucleic acid in L-120 cells and HeLa cells (Desai et al. 2008).
  • Anticancer ResearchIt has low watersolubility and sideeffects. Thus, usedfor clinical purposes.The chemicalmodification of itsderivatives (e.g.,topotecan andirinotecan) iscurrently used inchemotherapy.
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