C9911

Sigma-Aldrich

(S)-(+)-Camptothecin

≥90% (HPLC), powder

Empirical Formula (Hill Notation):
C20H16N2O4
Número de CAS:
Peso molecular:
348.35
Beilstein/REAXYS Number:
631069
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥90% (HPLC)

form

powder

mp

260 °C (dec.) (lit.)

solubility

chloroform/methanol (4:1): 5 mg/mL

Mode of action

DNA synthesis | interferes
enzyme | inhibits

antibiotic activity spectrum

neoplastics

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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Packaging

1 g in glass bottle
100, 250 mg in glass bottle

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 also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.
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

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

hazcat

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 Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificado de Análisis

Certificado de origen

  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) and methanol (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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Contenido relacionado
Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.
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n proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during the synthesis (S) phase, which is followed by a second gap phase (G2) during which growth and preparation for cell division occurs. Together, these three stages comprise the interphase phase of the cell cycle. Interphase is followed by the mitotic (M) phase.
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