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| | 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 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 | | 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 |
| | STAUROSPORINE Usage And Synthesis |
| 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 |
| | STAUROSPORINE Preparation Products And Raw materials |
| Raw materials | 9,13-Epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one, 2-[(3,4-dimethoxyphenyl)methyl]-2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-, [9S-(9α,10β,11β,13α)]- (9CI)-->9,13-Epoxy-1H,11H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonine-1,11-dione, 2-[(3,4-dimethoxyphenyl)methyl]-2,3,9,10,12,13-hexahydro-10-methoxy-9-methyl-, 11-(O-methyloxime), [9S-(9α,10β,11Z,13α)]- (9CI) |
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