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

Product Name

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

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

biological source

Streptomyces sp.

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

Quality Level

300

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Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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.

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.

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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A single coxsackievirus B2 capsid residue controls cytolysis and apoptosis in rhabdomyosarcoma cells.

Maria Gullberg et al.

Journal of virology, 84(12), 5868-5879 (2010-04-09)

Coxsackievirus B2 (CVB2), one of six human pathogens of the group B coxsackieviruses within the enterovirus genus of Picornaviridae, causes a wide spectrum of human diseases ranging from mild upper respiratory illnesses to myocarditis and meningitis. The CVB2 prototype strain

Reduced oxygen tension attenuates differentiation capacity of human mesenchymal stem cells and prolongs their lifespan.

Christine Fehrer et al.

Aging cell, 6(6), 745-757 (2007-10-11)

Mesenchymal stem cells (MSC) are capable of differentiating into bone, fat, cartilage, tendon and other organ progenitor cells. Despite the abundance of MSC within the organism, little is known about their in vivo properties or about their corresponding in vivo

Molecular mechanism of staurosporine-induced apoptosis in osteoblasts.

H J Chae et al.

Pharmacological research, 42(4), 373-381 (2000-09-16)

Staurosporine, a microbial alkaloid, is a strong inhibitor of protein kinases. We induced apoptosis in murine osteoblast MC3T3E-1 cells by exposure to the staurosporine. Staurosporine transiently increased the phosphotransferase activity of c-Jun N-terminal kinase-1 (JNK1), which in turn may activate

A BioDesign Approach to Obtain High Yields of Biosimilars by Anti-apoptotic Cell Engineering: a Case Study to Increase the Production Yield of Anti-TNF Alpha Producing Recombinant CHO Cells.

Sultan Gulce Iz et al.

Applied biochemistry and biotechnology, 184(1), 303-322 (2017-07-08)

Recent developments in medical biotechnology have facilitated to enhance the production of monoclonal antibodies (mAbs) and recombinant proteins in mammalian cells. Human mAbs for clinical applications have focused on three areas, particularly cancer, immunological disorders, and infectious diseases. Tumor necrosis

Staurosporine induces apoptosis of melanoma by both caspase-dependent and -independent apoptotic pathways.

Xu Dong Zhang et al.

Molecular cancer therapeutics, 3(2), 187-197 (2004-02-27)

Staurosporine has long been used in vitro as an initiator of apoptosis in many different cell types, but the mechanism involved remains poorly understood. In the present study, we have examined the apoptosis-inducing potential of staurosporine in cultured melanoma cell

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