S4400

Staurosporine

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

• Synonym(s): Staurosporine, Antibiotic AM-2282
• Empirical Formula (Hill Notation): C₂₈H₂₆N₄O₃
• CAS Number: 62996-74-1
• Molecular Weight: 466.53
• Beilstein: 1060573
• MDL number: MFCD00077402
• UNSPSC Code: 12161501
• PubChem Substance ID: 57654618
• NACRES: NA.77

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

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.

Safety Information

• Pictograms: GHS08
• Signal Word: Danger
• Hazard Statements: H340,H350,H361d,H413
• Precautionary Statements: P202 - P273 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Aquatic Chronic 4 - Carc. 1B - Muta. 1B - Repr. 2
• Storage Class Code: 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves