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C9911

Sigma-Aldrich

(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

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About This Item

Empirical Formula (Hill Notation):
C20H16N2O4
CAS Number:
7689-03-4
Molecular Weight:
348.35
Beilstein/REAXYS Number:
631069
MDL number:
MFCD00081076
UNSPSC Code:
12352200
PubChem Substance ID:
24278352
NACRES:
NA.77

product name

(S)-(+)-Camptothecin, ≥90% (HPLC), powder

Quality Level

200

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)

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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

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Other Notes

20S isomer

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H301,H340

Hazard Classifications

Acute Tox. 3 Oral - Muta. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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