ChemicalBook CAS DataBase List 62996-74-1

62996-74-1

Name	STAUROSPORINE
CAS	62996-74-1
EINECS(EC#)	999-999-2
Molecular Formula	C28H26N4O3
MDL Number	MFCD00077402
Molecular Weight	466.53
MOL File	62996-74-1.mol

Synonyms

STSP AM-2282 CGP 39360 Staurosporin Stauroporine STAUROSPORINE Antibiotic 230 AM 2282, M 193 ANTIBIOTIC M 193 Staurosporine,98% ANTIBIOTIC AM-2282 STAUROSPORINE, 99+%. Staurosporineinsolution Staurosporine(CGP 41251) Staurosporine,AM-2282,STS STAUROSPORINE READY-MADE SOLUTION Staurosporine, Antibiotic AM-2282 STAUROSPORINE, STREPTOMYCES SPECIES STAUROSPORINE FROM STREPTOMYCES SP. InSolution Staurosporine, Streptomyces sp STAUROSPORINE, STREPTOMYCES STAUROSPOREUS STAUROSPORINE FROM STREPTOMYCES SP., PGE WITH 250 UG STAUROSPORINE FROM STREPTOMYCES SP MOLECULAR BIOLOGY REAGENT 98+% yT5720idec Monophosphorothioate, Rp-IsoMer, TriethylaMMoniuM SaltuM Saltnoic acid salt 2,3,10,11,12,13-HEXAHYDRO-10R-METHOXY-9S-METHYL-11R-METHYLAMINO-9S,13R-EPOXY-1H,9H-DIINDOLO[1,2,3-GH:3',2',1'-LM]PYRROLO[3,4-J][1,7]BENZODIAZONIN-1 ONE 9,13-Epoxy-1H,9H-diindolo1,2,3-gh:3,2,1-lmpyrrolo3,4-j1,7benzodiazonin-1-one, 2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-, (9S,10R,11R,13R)- (9S,10R,11R,13R)-2,3,10,11,12,13-Hexahydro-10-methoxy-9-methyl-11-(methylamino)-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one (9S,10α,11α,13β)-2,3,10,11,12,13-Hexahydro-10-methoxy-9-methyl-11-(methylamino)-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one [9S,10α,11α,13β,(+)]-2,3,10,11,12,13-Hexahydro-10-methoxy-9-methyl-11-(methylamino)-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one [9S-(9α,10β,11β,13α)]-2,3,10,11,12,13-Hexahydro-10-methoxy-9-methyl-11-(methylamino)-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one [9S-(9A,10B,11B,13A)]-2,3,10,11,12,13-HEXAHYDRO-10-METHOXY-9-METHYL-11-(METHYLAMINO)-9,13-EPOXY-1H,9H-DIINDOLO[1,2,3-GH:3',2',1'-1M]PYRROLO[3,4-J][1,7]BENZODIAZONIN-1-ONE 9,13-Epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one, 2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-, [9S-(9α,10β,11β,13α)]- [9S-(9alpha,10beta,11beta,13alpha)]-2,3,10,11,12,13-Hexahydro-10-methoxy-9-methyl-11-(methylamino)-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-1m]pyrrolo[3,4-j][1,7]benzodiazonin-1-one

Chemical Properties

Appearance	Light Yellow Solid
Occurrence	A complex alkaloid. staurosporine has been isolated from a strain of Streptomyces.
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
SMILES	CN[C@@H]1C[C@@H]2O[C@@](C)([C@@H]1OC)n3c4ccccc4c5c6CNC(=O)c6c7c8ccccc8n2c7c35
CAS DataBase Reference	62996-74-1

Safety Data

Symbol(GHS)	GHS08
Signal word	Warning
Hazard statements	H361d-H413
Precautionary statements	P201-P202-P273-P280-P308+P313-P405
Hazard Codes	Xn,T,Xi
Risk Statements	40-45-36/37/38-46 less more
Safety Statements	36/37-53-36-26-45 less more
RIDADR	UN 2811 6.1 / PGII
WGK Germany	2
F	8-10
HazardClass	3
HS Code	29419090
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Aquatic Chronic 4 Carc. 1B Muta. 1B Repr. 2

Hazard Information

Chemical Properties

Light Yellow Solid

Uses

A protein Kinase C inhibitor that induces apoptosis in many cell types

Uses

Staurosporine is an unusual indolocarbazole alkaloid produced by a range of actinomycete species. It is a potent antitumor 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 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.

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™ .

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.

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.

Biochem/physiol Actions

Reversible: yes

storage

Store at -20°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

Spectrum Detail

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