S5921

Sigma-Aldrich

Staurosporine from Streptomyces sp.

for molecular biology, ≥95% (HPLC)

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

Quality Level

grade

for molecular biology

assay

≥95% (HPLC)

Mode of action

enzyme | inhibits

antibiotic activity spectrum

fungi

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.

Analysis Note

Tested for inhibition of interleukin 2 production in Jurkat cells.

Pictograms

Health hazard

Signal Word

Danger

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

  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?

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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...
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...
Karolien De Bosscher et al.
Cellular and molecular life sciences : CMLS, 71(1), 143-163 (2013-06-21)
Glucocorticoids (GCs) block inflammation via interference of the liganded glucocorticoid receptor (GR) with the activity of pro-inflammatory transcription factors NF-κB and AP-1, a mechanism known as transrepression. This mechanism is believed to involve the activity of GR monomers. Here, we...
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...
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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