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Merck

C9911

(S)-(+)-camptothécine

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

Synonyme(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

Formule empirique (notation de Hill) :
C20H16N2O4
Numéro CAS:
Poids moléculaire :
348.35
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Beilstein/REAXYS Number:
631069

Nom du produit

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

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

SMILES string

CC[C@@]1(O)C(=O)OCC2=C1C=C3N(Cc4cc5ccccc5nc34)C2=O

InChI key

VSJKWCGYPAHWDS-FQEVSTJZSA-N

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

Quality Level

Gene Information

human ... TOP1(7150)
mouse ... Prkca(18750)
rat ... Sstr2(54305)

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Biochem/physiol Actions

La (S)-(+)-camptothécine se lie de manière irréversible au complexe ADN-topoisomérase I, inhibant la réassociation de l'ADN après clivage par la topoisomérase I et piégeant l'enzyme dans une liaison covalente avec l'ADN. Le complexe enzymatique est ubiquiné et détruit par le protéasome 26S, ce qui épuise la topoisomérase I cellulaire. Bloque le cycle cellulaire en phase S à faible dose et induit l'apoptose dans un grand nombre de lignées cellulaires normales et tumorales par des processus dépendants et indépendants du cycle cellulaire.

Features and Benefits

Ce composé fait partie de notre sélection de produits pour la recherche sur l′apoptose. Cliquez ici pour découvrir d′autres produits sélectionnés en lien avec l′apoptose. Pour en savoir plus sur les petites molécules bioactives destinées à d′autres domaines de la recherche, rendez-vous sur sigma.com/discover-bsm.

Other Notes

Isomère 20S

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral - Muta. 1B

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3.  What is Product C9911, (S)-(+)-Camptothecin, soluble in?

    This product is soluble in DMSO (10 mg/mL). At higher concentrations, heating is required for the product to dissolve completely (approximately 10 minutes at 95°C), but some precipitation occurs upon cooling to room temperature. It is also soluble in 1 N NaOH (50 mg/mL).

  4. What is the solution stability of Product C9911, (S)-(+)-Camptothecin?

    Stock solutions of camptothecin in DMSO can be stored at -20°C for up to 3 months.

  5. What is the extinction coefficient of Product C9911, (S)-(+)-Camptothecin?

    The millimolar extinction coefficients (EmM) at various wavelengths are 37.3 (220 nm); 29.2 (254 nm); 4.9 (290 nm); 19.9 (370 nm).

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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