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S5921

Sigma-Aldrich

Staurosporine

from Streptomyces sp., ≥95% (HPLC), film, protein kinase inhibitor

Synonyma:

protein kinase c inhibitor, staurosporine, Antibiotic AM-2282

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About This Item

Empirický vzorec (Hillův zápis):
C28H26N4O3
Číslo CAS:
62996-74-1
Molekulová hmotnost:
466.53
Beilstein/REAXYS Number:
1060573
MDL number:
MFCD00077402
UNSPSC Code:
12161501
PubChem Substance ID:
24899680
NACRES:
NA.77

product name

Staurosporine from Streptomyces sp., for molecular biology, ≥95% (HPLC)

grade

for molecular biology

Quality Level

300

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

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General description

Chemical structure: indol derivative
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.

Application

Staurosporine has been used as an apoptosis inducer in apoptosis assay in human colorectal cancer cell lines and to evaluate the caspase 3 and 7 activity in endothelial cell line. It has also been used as a positive control in apoptosis assay in human umbilical vein endothelial cells.

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.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Osvědčení o analýze (COA)

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Martin Forsthuber et al.
Environmental pollution (Barking, Essex : 1987), 293, 118543-118543 (2021-11-21)
Perfluorooctane sulfonic acid (PFOS) is a ubiquitous environmental pollutant. In humans, PFOS exposure has been associated with a number of adverse health outcomes, including reduced birth weight. Whether PFOS is capable of affecting angiogenesis and thus possibly fetal development is
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
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
A Gescher
General pharmacology, 31(5), 721-728 (1998-11-11)
1. Protein kinase C (PKC) is a family of serine/threonine-directed protein kinases that are pivotal regulators of cellular growth, transformation and death. PKC has therefore been considered to be a suitable target for novel antineoplastic drugs. 2. Twenty years ago
S Ståhl et al.
Cell death & disease, 4, e454-e454 (2013-01-11)
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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