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Merck

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:
62996-74-1
Molecular Weight:
466.53
UNSPSC Code:
12161501
PubChem Substance ID:
24899680
NACRES:
NA.77
Beilstein/REAXYS Number:
1060573
MDL number:
MFCD00077402
Assay:
≥95% (HPLC)
Quality level:
300

Key Documents

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Product Name

Staurosporine from Streptomyces sp., Molecular Biology, ≥95% (HPLC)

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

grade

Molecular Biology

assay

≥95% (HPLC)

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

2-8°C

Quality Level

300

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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

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.

Class I Designated Chemical Substances

prtr

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

S5921-BULK: + S5921-1MG:4548174007297 + S5921-.1MG-PW: + S5921-.1MG:4548174007273 + S5921-1MG-PW: + S5921-VAR: + S5921-.5MG-PW: + S5921-.5MG:4548174007280

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Certificates of Analysis (COA)

Lot/Batch Number
089M4136V
058M4061V
14190611
069M4147V
14190307

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Subhasish Saha et al.
Molecules (Basel, Switzerland), 25(17) (2020-08-23)
Heterocytous cyanobacteria are among the most prolific sources of bioactive secondary metabolites, including anabaenopeptins (APTs). A terrestrial filamentous Brasilonema sp. CT11 collected in Costa Rica bamboo forest as a black mat, was studied using a multidisciplinary approach: genome mining and
S L Taylor et al.
Molecular human reproduction, 10(11), 825-834 (2004-10-07)
In this study we extended earlier work to determine whether sperm respond to somatic cell apoptotic stimuli and whether apoptotic phenotypes are significant indicators of human sperm quality. We evaluated ejaculated sperm from fertile donors and subfertile patients following purification
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
V Borgdorff et al.
Oncogene, 33(19), 2531-2539 (2013-06-04)
The microphthalmia-associated transcription factor (MITF) is indispensable for the viability of melanocytic cells, is an oncogene in melanoma and has a cell type-specific expression pattern. As the modulation of MITF activity by direct chemical targeting remains a challenge, we assessed
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
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