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
• 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

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.[1] Themechanisms followed by staurosporine-induced apoptosis differ among differentcell lines that include, mitochondrial apoptotic pathway, Bcl-2 overexpession,and caspase-independent mechanisms.[2] 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[3] and to induce cell death by PKC inhibition in hamster lung fibroblast line CCL-39.[4]

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 featured on the CDKs and InsR pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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.

Safety Information

• 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
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges