(+)-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-on, (9 alpha,10 beta, 11 beta, 13 alpha)-

Bezeichnung:(+)-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-on, (9 alpha,10 beta, 11 beta, 13 alpha)-

CAS-Nr62996-74-1

Englisch Name:STAUROSPORINE

CBNumberCB2486697

SummenformelC28H26N4O3

Molgewicht466.54

MOL-Datei62996-74-1.mol

Synonyma

(+)-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-on, (9 alpha,10 beta, 11 beta, 13 alpha)-

(+)-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-on, (9 alpha,10 beta, 11 beta, 13 alpha)- physikalisch-chemischer Eigenschaften

Schmelzpunkt	270°C
alpha	D25 +35.0° (c = 1 in methanol); D22 +56.1° (c = 0.14 in methanol)
Siedepunkt	677.5±55.0 °C(Predicted)
Dichte	1.56±0.1 g/cm3(Predicted)
RTECS-Nr.	KD5084000
storage temp.	2-8°C
Löslichkeit	DMSO: soluble
Aggregatzustand	White to pale yellow solid
pka	14.25±0.70(Predicted)
Farbe	Off white to pale yellow
Wasserlöslichkeit	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
Stabilität	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 Datenbank	62996-74-1

Sicherheit

Kennzeichnung gefährlicher	Xn,T,Xi
R-Sätze:	40-45-36/37/38-46
S-Sätze:	36/37-53-36-26-45
RIDADR	UN 2811 6.1 / PGII
WGK Germany	2
F	8-10
HazardClass	3
HS Code	29419090

Gefahreninformationscode (GHS)

STAUROSPORINE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R40:Verdacht auf krebserzeugende Wirkung.
R45:Kann Krebs erzeugen.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
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.
Chemische Eigenschaften
Light Yellow Solid
Occurrence
A complex alkaloid. staurosporine has been isolated from a strain of Streptomyces.
Verwenden
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.
Verwenden
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.
Allgemeine Beschreibung
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.
Biologische Aktivität
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
Lager
+4°C
Einzelnachweise
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 Upstream-Materialien And Downstream Produkte

(+)-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-on, (9 alpha,10 beta, 11 beta, 13 alpha)- Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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