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C9911

(S)-(+)-Camptothecin

Name: (<I>S</I>)-(+)-Camptothecin
Brand: SIGMA

≥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

NACRES:

NA.77

PubChem Substance ID:

24278352

UNSPSC Code:

12352200

MDL number:

MFCD00081076

Beilstein/REAXYS Number:

631069

Assay:

≥90% (HPLC)

Form:

powder

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Properties

Product Name

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

Quality Segment

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)

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

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

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pictograms

GHS06,GHS08

signalword

Danger

hcodes

H301,H340

pcodes

P202 - P264 - P280 - P301 + P310 - P405 - P501

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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