C9911

(S)-(+)-Camptothecin

≥90% (HPLC), powder, DNA topoisomerase I inhibitor

• Synonym(s): (S)-4-Ethyl-4-hydroxy-1H-pyrano-[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• Empirical Formula (Hill Notation): C₂₀H₁₆N₂O₄
• CAS Number: 7689-03-4
• Molecular Weight: 348.35
• Beilstein: 631069
• MDL number: MFCD00081076
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278352
• NACRES: NA.77

Properties

• product name: (S)-(+)-Camptothecin, ≥90% (HPLC), powder
• Assay: ≥90% (HPLC)
• form: powder
• mp: 260 °C (dec.) (lit.)
• solubility: chloroform/methanol (4:1): 5 mg/mL
• antibiotic activity spectrum: neoplastics
• Mode of action: DNA synthesis | interferes; enzyme | inhibits
• storage temp.: 2-8°C
• SMILES string: CC[C@@]1(O)C(=O)OCC2=C1C=C3N(Cc4cc5ccccc5nc34)C2=O
• InChI: 1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1
• InChI key: VSJKWCGYPAHWDS-FQEVSTJZSA-N
• Gene Information: human ... TOP1(7150) ; mouse ... Prkca(18750) ; rat ... Sstr2(54305)

Description

Biochem/physiol Actions

(S)-(+)-Camptothecin binds irreversibly 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, thus depleting cellular topoisomerase I. Blocks the cell cycle in S-phase at low does and induces apoptosis in a large number of normal and tumor cell lines by cell cycle-dependent and cell cycle-independent processes.

Features and Benefits

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Other Notes

20S isomer

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H301,H340
• Precautionary Statements: P202 - P264 - P280 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral - Muta. 1B
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves