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S4400

Staurosporine

Name: Staurosporine
Brand: SIGMA

from Streptomyces sp., ≥98% (HPLC), film, protein kinase inhibitor

Synonym(s):

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

UNSPSC Code:

12161501

PubChem Substance ID:

57654618

NACRES:

NA.77

Beilstein/REAXYS Number:

1060573

MDL number:

MFCD00077402

Assay:

≥98% (HPLC)

Form:

film

Quality level:

300

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Properties

Product Name

Staurosporine from Streptomyces sp., ≥98% (HPLC), film

biological source

Streptomyces sp.

Quality Level

300

assay

≥98% (HPLC)

form

film

mp

288-291 °C

solubility

DMSO: soluble, H₂O: insoluble, ethanol: soluble, methanol: soluble

antibiotic activity spectrum

neoplastics

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

Description

General description

Chemical structure: indol derivative

Staurosporinefrom Streptomyces sp. is an alkaloid that induces apoptosis in a rangeof cell lines. It facilitates the inhibition of tumor cell proliferation, PKCinhibition, and blockage of cell cycle progression in various cells. Themechanisms followed by staurosporine-induced apoptosis differ among differentcell lines that include, mitochondrial apoptotic pathway, Bcl-2 overexpession,and caspase-independent mechanisms. It partially reverses multi-drug resistance (MDR), sensitizing cellswith MDR phenotype to cytotoxic agents. Staurosporine inhibits p-glycoprotein(Pgp) phosphorylation. However, the functional significance of Pgpphosphorylation is ill-defined.

Application

Staurosporine from Streptomyces sp. was used to induce cell death in human mesenchymal stem cells and to induce cell death by PKC inhibition in hamster lung fibroblast line CCL-39.

Biochem/physiol Actions

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

Staurosporine from Streptomyces sp. yields clear, colorless to faint yellow solution in methanol at 2 mg/ml.

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.

This compound is featured on the CDKs and InsR pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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pictograms

GHS08

signalword

Danger

hcodes

H340,H350,H361d,H413

pcodes

P202 - P273 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Aquatic Chronic 4 - Carc. 1B - Muta. 1B - Repr. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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