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S4400

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

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Sigma-Aldrich

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Staurosporine from Streptomyces sp.

Staurosporine solution from Streptomyces sp. Ready Made Solution, 1 mM in DMSO (100 μg/214 μL)

Sigma-Aldrich

S6942

Staurosporine solution from Streptomyces sp.

Thiostrepton from Streptomyces azureus ≥90% (HPLC)

Sigma-Aldrich

T8902

Thiostrepton from Streptomyces azureus

assay

≥98% (HPLC)

assay

≥95% (HPLC)

assay

>98% (HPLC)

assay

≥90% (HPLC)

form

film

form

-

form

-

form

-

Quality Level

300

Quality Level

300

Quality Level

300

Quality Level

200

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

solubility

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

solubility

-

solubility

-

solubility

acetic acid: soluble 25 mg/mL, clear to hazy, yellow to brownish-yellow

biological source

Streptomyces sp.

biological source

-

biological source

-

biological source

-

Application

Staurosporine from Streptomyces sp. was used to induce cell death in human mesenchymal stem cells[1] and to induce cell death by PKC inhibition in hamster lung fibroblast line CCL-39.[2]

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.[3] Themechanisms followed by staurosporine-induced apoptosis differ among differentcell lines that include, mitochondrial apoptotic pathway, Bcl-2 overexpession,and caspase-independent mechanisms.[4] 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

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

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
0000467777
0000467776
0000467774
0000467743
0000467767

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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
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
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
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
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
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