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S5921
Staurosporine
from Streptomyces sp., ≥95% (HPLC), film, protein kinase inhibitor
Synonym(s):
protein kinase c inhibitor, staurosporine, Antibiotic AM-2282
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About This Item
Empirical Formula (Hill Notation):
C28H26N4O3
CAS Number:
Molecular Weight:
466.53
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77
Beilstein/REAXYS Number:
1060573
MDL number:
Assay:
≥95% (HPLC)
Pricing and availability is not currently available.
Product Name
Staurosporine from Streptomyces sp., Molecular Biology, ≥95% (HPLC)
grade
Molecular Biology
Quality Segment
assay
≥95% (HPLC)
antibiotic activity spectrum
fungi
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
Staurosporine is an alkaloid that is obtained from Streptomyces sp. It possesses a wide range of activities such as protein kinase C inhibitor, inhibition of tumor cell proliferation, and blockage of cell cycle progression in various cells. Staurosporine is a well-known inducer of apoptosis in various cell lines. The mechanisms of staurosporine-induced apoptosis vary among different cell lines that include, mitochondrial apoptotic pathway, Bcl-2 overexpression, and caspase-independent mechanisms. It partially reverses multi-drug resistance (MDR), sensitizing cells with MDR phenotype to cytotoxic agents. Staurosporine inhibits p-glycoprotein (Pgp) phosphorylation. However, the functional significance of Pgp phosphorylation is ill-defined.
Chemical structure: indol derivative
Application
Biochem/physiol Actions
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.
Analysis Note
Tested for inhibition of interleukin 2 production in Jurkat cells.
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This Item | |||
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| description Molecular Biology, ≥95% (HPLC) | description VETRANAL®, analytical standard | description Staurosporine, CAS 62996-74-, is a cell-permeable, potent, reversible, ATP-competitive inhibitor of protein kinases (IC50 = 7, 20, 1.3, 0.7, & 8.5 nM for PKA, CAMK, MLCK, PKC, & PKG, respectively). | description ≥98% (HPLC), film |
| assay ≥95% (HPLC) | assay - | assay ≥99% (HPLC) | assay ≥98% (HPLC) |
| Quality Level 300 | Quality Level 100 | Quality Level 100 | Quality Level 300 |
| storage temp. 2-8°C | storage temp. −20°C | storage temp. 2-8°C | storage temp. 2-8°C |
| grade Molecular Biology | grade analytical standard | grade - | grade - |
| mode of action enzyme | inhibits | mode of action - | mode of action - | mode of action enzyme | inhibits |
| antibiotic activity spectrum fungi | antibiotic activity spectrum - | antibiotic activity spectrum - | antibiotic activity spectrum neoplastics |
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Signal Word
Danger
Hazard Codes
Precautionary Statements
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 (personal protective equipment)
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
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What concentration of Staurosporin is used for the release of microparticles from apoptotic cells?
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Staurosporin can induce apopotosis in Jurkat cells (106/ml) at 1 ug/ml following a 1-2 hour incubation at 37°C. For the release of microparticles from apoptotic Jurkat cells, use staurosporin at 1 uM for 107 cells/ml. Please see the reference below for further details. Apoptosis 15(5):586, 2010.
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