STAUROSPORINE Property

Melting point:

270°C

alpha 

D25 +35.0° (c = 1 in methanol); D22 +56.1° (c = 0.14 in methanol)

Boiling point:

677.5±55.0 °C(Predicted)

Density 

1.56±0.1 g/cm3(Predicted)

RTECS 

KD5084000

storage temp. 

2-8°C

solubility 

DMSO: soluble

form 

White to pale yellow solid

pka

14.25±0.70(Predicted)

color 

Off white to pale yellow

Water Solubility 

Soluble in DMSO or ethanol.Soluble in dimethyl sulfoxide , dimethyl formamide, ethyl acetate, hot acetone and ethanol. Slightly soluble in chloroform and methanol. Insoluble in water.

BRN 

1060573

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 4 months.

InChIKey

HKSZLNNOFSGOKW-WIFUGMKFSA-N

CAS DataBase Reference

62996-74-1

Safety

Hazard Codes 

Xn,T,Xi

Risk Statements 

40-45-36/37/38-46

Safety Statements 

36/37-53-36-26-45

RIDADR 

UN 2811 6.1 / PGII

WGK Germany 

2

F 

8-10

HazardClass 

3

HS Code 

29419090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

STAUROSPORINE Chemical Properties,Usage,Production

Description

Staurosporine (Stsp) is potent inhibitor of protein kinase C (PKC) from rat brain, exhibiting an IC₅₀ value of 2.7 nM. It inhibits rat recombinant PKC-α approximately 100- and 1,000-fold better than PKC-δ and PKC-ζ, respectively. However, Stsp is non-selective in that it also inhibits the activity of a variety of other protein kinases, not only PKC isoforms. The biological effects of Stsp include cytotoxicity, relaxation of smooth muscle, and regulation of eNOS gene expression.

Chemical Properties

Light Yellow Solid

Occurrence

A complex alkaloid. staurosporine has been isolated from a strain of Streptomyces.

Uses

Staurosporine is an unusual indolocarbazole alkaloid produced by a range of actinomycete species. It is a potent antitumour active, inducing apoptosis in a variety of cell lines. Staurosporine is a potent inhibitor of many kinases including protein kinase C, tyrosine kinase, CDK2/cyclin A and CDK4/cyclin D. At submicromolar concentrations, staurosporine inhibits both IKKalpha and IKKbeta.

Uses

Staurosporine is a protein Kinase C inhibitor that induces apoptosis in many cell types.

Definition

ChEBI: Staurosporine is an indolocarbazole alkaloid and an organic heterooctacyclic compound. It has a role as an EC 2.7.11.13 (protein kinase C) inhibitor, a geroprotector, a bacterial metabolite and an apoptosis inducer. It is a conjugate base of a staurosporinium.

General Description

A potent, cell-permeable, reversible, ATP-competitive and broad spectrum inhibitor of protein kinases. Inhibits CaM kinase (IC₅₀ = 20 nM), myosin light chain kinase (IC₅₀ = 1.3 nM), protein kinase A (IC₅₀ = 7 nM), protein kinase C (IC₅₀ = 0.7 nM), and protein kinase G (IC₅₀ = 8.5 nM). Also inhibits platelet aggregation induced by collagen or ADP but has no effect on thrombin-induced platelet aggregation. Induces apoptosis in human malignant glioma cell lines. Arrests normal cells at the G₁ checkpoint.

Biological Activity

Broad spectrum protein kinase inhibitor. Enzymes inhibited include protein kinase C (IC 50 = 3 nM), protein kinase A (IC 50 = 7 nM), p 60v-src tyrosine protein kinase (IC 50 = 6 nM) and CaM kinase II (IC 50 = 20 nM). Also available as part of the Mixed Kinase Inhibitor Tocriset™ .

Biochem/physiol Actions

Reversible: yes

storage

+4°C

References

1) Omura et al. (1977) A new alkaloid AM-2282 of Streptomyces origin taxonomy, fermentation, isolation and preliminary characterization; J. Antibiot., 30 275 2) Ruegg and Burgess (1989) Staurosporine, K-252 and UCN-01: potent but nonspecific inhibitors of protein kinases; Trends in Pharmacological Science 10 218