MilliporeSigma
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S5921

Sigma-Aldrich

Staurosporine from Streptomyces sp.

for molecular biology, ≥95% (HPLC)

All Photos(1)
Synonym(s):
staurosporine, Antibiotic AM-2282, protein kinase c inhibitor
Empirical Formula (Hill Notation):
C28H26N4O3
CAS Number:
62996-74-1
Molecular Weight:
466.53
Beilstein:
1060573
MDL number:
MFCD00077402
PubChem Substance ID:
24899680
NACRES:
NA.77

Quality Level

300

grade

for molecular biology

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

Application

Staurosporine from Streptomyces sp. was used to induce cell death in MDCK, 293T, Vero, HeLa, and Swiss Webster primary macrophage cells.5 It was used to study the effect of caspase activation on human sperm quality.6

Packaging

0.1, 0.5, 1 mg in serum bottle

Biochem/physiol Actions

Partially reverses MDR, sensitizing cells with MDR phenotype to cytotoxic agents. Inhibits Pgp phosphorylation. However, functional significance of Pgp phosphorylation is ill defined.
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.

Pictograms

Health hazard
GHS08

Signal Word

Danger

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More documents

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Quotes and Ordering

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What concentration of Staurosporin is used for the release of microparticles from apoptotic cells?

    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.

  6. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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
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
Osman A B S M Gani et al.
Natural product reports, 27(4), 489-498 (2010-03-26)
The isolation in 1977 of the microbial alkaloid staurosporine inaugurated research into several distinct series of related natural and synthetic compounds. This has especially included research into applications as anticancer drugs, beginning with the observation of low nanomolar inhibition of
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