S5921

Staurosporine

Name: Staurosporine
Brand: SIGMA

from Streptomyces sp., ≥95% (HPLC), film, protein kinase inhibitor

Synonym(s):

protein kinase c inhibitor, staurosporine, Antibiotic AM-2282

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About This Item

Empirical Formula (Hill Notation):

C₂₈H₂₆N₄O₃

CAS Number:

62996-74-1

Molecular Weight:

466.53

Beilstein:

1060573

MDL number:

MFCD00077402

UNSPSC Code:

12161501

PubChem Substance ID:

24899680

NACRES:

NA.77

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Product Name

Staurosporine from Streptomyces sp., Molecular Biology, ≥95% (HPLC)

grade

Molecular Biology

Quality Level

300

Assay

≥95% (HPLC)

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

CN[C@@H]1C[C@@H]2O[C@@](C)([C@@H]1OC)n3c4ccccc4c5c6CNC(=O)c6c7c8ccccc8n2c7c35

InChI

1S/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20?,26-,28+/m1/s1

InChI key

HKSZLNNOFSGOKW-ZGQXJOJZSA-N

General description

Chemical structure: indol derivative

Staurosporine is an alkaloid that is obtained from Streptomyces sp. It possesses a wide range of activities such as protein kinase C inhibitor, inhibition of tumor cell proliferation, and blockage of cell cycle progression in various cells. Staurosporine is a well-known inducer of apoptosis in various cell lines. The mechanisms of staurosporine-induced apoptosis vary among different cell lines that include, mitochondrial apoptotic pathway, Bcl-2 overexpression, and caspase-independent mechanisms. It partially reverses multi-drug resistance (MDR), sensitizing cells with MDR phenotype to cytotoxic agents. Staurosporine inhibits p-glycoprotein (Pgp) phosphorylation. However, the functional significance of Pgp phosphorylation is ill-defined.

Application

Staurosporine has been used as an apoptosis inducer in apoptosis assay in human colorectal cancer cell lines and to evaluate the caspase 3 and 7 activity in endothelial cell line. It has also been used as a positive control in apoptosis assay in human umbilical vein endothelial cells.

Biochem/physiol Actions

Potent inhibitor of phospholipid/calcium-dependent protein kinase. Inhibits the upregulation of VEGF expression in tumor cells.

Features and Benefits

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