STAUROSPORINE

STAUROSPORINE Basic information
Product Name:STAUROSPORINE
Synonyms: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)]-;InSolution Staurosporine, Streptomyces sp;Staurosporineinsolution;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)-;Staurosporine, Antibiotic AM-2282;(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;Antibiotic 230;CGP 39360
CAS:62996-74-1
MF:C28H26N4O3
MW:466.54
EINECS:613-127-7
Product Categories:Inhibitor;All Inhibitors;Signalling;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Protein Kinase Inhibitors and Activators;Protein Kinase;API;antibiotic
Mol File:62996-74-1.mol
STAUROSPORINE Structure
STAUROSPORINE Chemical Properties
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
pka14.25±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.
InChIKeyHKSZLNNOFSGOKW-WIFUGMKFSA-N
CAS DataBase Reference62996-74-1
Safety Information
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
8-10
HazardClass 3
HS Code 29419090
MSDS Information
ProviderLanguage
SigmaAldrich English
STAUROSPORINE Usage And Synthesis
DescriptionStaurosporine (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 PropertiesLight Yellow Solid
OccurrenceA complex alkaloid. staurosporine has been isolated from a strain of Streptomyces.
UsesStaurosporine 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.
UsesStaurosporine is a protein Kinase C inhibitor that induces apoptosis in many cell types.
DefinitionChEBI: 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 DescriptionA 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 ActivityBroad 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 ActionsReversible: yes
storage+4°C
References1) 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
Succinylcholine Chloride Diphenhydramine Hydrochloride Methimazole Staurosporine, Streptomyces sp. in Solution STAUROSPORINE READY MADE INSTA-Blot, Apoptotic Jurkat Cells, Staurosporine-Treated INSTA-Blot, Apoptotic HeLa Cells, Staurosporine-Treated INSTA-BLOT(TM), APOPTOTIC HL-60 CELLS, STAUROSPORINE-TREATED { STAUROSPORINE--N/H STAUROSPORINE AGLYCONE Staurosporine, Streptomyces sp. INSTA-Blot, Apoptotic HL-60 Cells, Staurosporine-Treated JURKAT AND STAUROSPORINE LYSATE (8H),JURKAT AND STAUROSPORINE LYSATE (4H) INSTA-BLOT(TM), APOPTOTIC HELA CELLS, STAUROSPORINE-TREATED 1,2,3,4-Tetrahydro Staurosporine ent-Staurosporine INSTA-BLOT(TM), APOPTOTIC JURKAT CELLS, STAUROSPORINE-TREATED STAUROSPORINE,STAUROSPORINE, STREPTOMYCES SPECIES,STAUROSPORINE, STREPTOMYCES STAUROSPOREUS

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