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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

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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Qi Weng et al.
Cancer chemotherapy and pharmacology, 84(3), 527-537 (2019-04-29)
Recent researches are attempting to verify that the 3D cell models can provide a gap bridge between in vitro and in vivo for anticancer drug evaluations. The aim of this study was to continue the development of novel in vitro
H-S Chen et al.
European review for medical and pharmacological sciences, 23(15), 6621-6628 (2019-08-06)
MicroRNAs (miRNAs) are a conserved class of endogenous and short non-coding RNAs that post-transcriptionally regulate the expression of genes involved in diverse cellular processes. MiR-28-5p has been reported to be associated with several cancers, including human glioma. However, the roles
Dinh Trung Nguyen et al.
Polymers, 11(5) (2019-05-10)
Herein, a new process to manufacture multicore micelles nanoparticles reinforced with co-assembly via hydrophobic interaction and electrostatic interaction under the help of ultrasonication was developed. The precise co-assembly between negative/hydrophobic drug and positive charged amphiphilic copolymer based pluronic platform allows
Pinakin Pandya et al.
Cellular signalling, 62, 109340-109340 (2019-06-09)
Protein kinase C (PKC)-interacting cousin of thioredoxin (PICOT; also termed glutaredoxin 3 (Glrx3)) is a ubiquitously expressed protein that possesses an N-terminal monothiol thioredoxin (Trx) domain and two C-terminal tandem copies of a monothiol Glrx domain. It has an overall
Gudrun Meinhardt et al.
Scientific reports, 6, 28127-28127 (2016-06-18)
The maternal uterine environment is likely critical for human placental morphogenesis and development of its different trophoblast subtypes. However, factors controlling growth and differentiation of these cells during early gestation remain poorly elucidated. Herein, we provide evidence that the ligand
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