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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

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

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

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

8032-32-4 + 75-09-2

CAS No.

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Certificates of Analysis (COA)

Lot/Batch Number
0000069151
118K4090
058K4041
028K4066
127K4014

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Articles

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Protein-based drug transporters are expressed in Sf9 cells. Understanding the specific mechanisms of tumor cell transporters is an essential aspect of chemotherapeutic drug design.

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Radiation therapy is frequently used to treat non-small cell lung cancers (NSCLCs). We have previously shown that a combination of ionizing radiation (IR) and the staurosporine analog PKC 412, but not Ro 31-8220, increases cell death in NSCLC cells. To
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Global Trade Item Number

SKUGTIN
S4400-.1MG04061836926083
S4400-.5MG04061836926229
S4400-1MG04061836926304