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S4400

Sigma-Aldrich

Staurosporine

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
Beilstein/REAXYS Number:
1060573
MDL number:
MFCD00077402
UNSPSC Code:
12161501
PubChem Substance ID:
57654618
NACRES:
NA.77

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

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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

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

pictograms

Health hazard
GHS08

signalword

Danger

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_germany

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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Certificates of Analysis (COA)

Lot/Batch Number
0000411503
0000411503
0000370447
0000370451
0000370453

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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
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
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
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
A Gescher
General pharmacology, 31(5), 721-728 (1998-11-11)
1. Protein kinase C (PKC) is a family of serine/threonine-directed protein kinases that are pivotal regulators of cellular growth, transformation and death. PKC has therefore been considered to be a suitable target for novel antineoplastic drugs. 2. Twenty years ago
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