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Merck
CN

85660

Staurosporine from Streptomyces sp.

≥95.0% (HPLC)

Synonym(s):

Antibiotic AM-2282

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About This Item

Empirical Formula (Hill Notation):
C28H26N4O3
CAS Number:
62996-74-1
Molecular Weight:
466.53
UNSPSC Code:
12161501
Beilstein/REAXYS Number:
1060573
MDL number:
MFCD00077402

Key Documents

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assay

≥95.0% (HPLC)

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

CN[C@@H]1C[C@@H]2O[C@@](C)([C@@H]1OC)n3c4ccccc4c5c6CNC(=O)c6c7c8ccccc8n2c7c35

InChI

1S/C28H26N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20?,26-,28+/m1/s1

InChI key

HKSZLNNOFSGOKW-ZGQXJOJZSA-N

General description

Chemical structure: indol derivative

Biochem/physiol Actions

Potent inhibitor of phospholipid/calcium-dependent protein kinase. Inhibits the upregulation of VEGF expression in tumor cells.

Other Notes

A potent inhibitor of phospholipid / calcium dependent protein kinase; Inhibits the respiratory burst and induces exocytosis in human neutrophils

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Aquatic Chronic 4 - Carc. 1B - Muta. 1B - Repr. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Use and specificity of staurosporine, UCN-01, and calphostin C as protein kinase inhibitors.
T Tamaoki
Methods in enzymology, 201, 340-347 (1991-01-01)
B Dewald et al.
The Biochemical journal, 264(3), 879-884 (1989-12-15)
The protein kinase C inhibitor staurosporine influenced in different ways the functions of human neutrophils. Staurosporine prevented the enhanced protein phosphorylation in phorbol ester- and N-formylmethyionyl-leucylphenylalanine (fMLP)-stimulated cells, and was a powerful inhibitor of the respiratory burst induced by phorbol
T Tamaoki et al.
Biochemical and biophysical research communications, 135(2), 397-402 (1986-03-13)
Staurosporine, microbial alkaloid which has been known to have antifungal activity was found to inhibit markedly phospholipid/Ca++dependent protein kinase (protein kinase C) from rat brain, with an IC50 value of 2.7 nM. However, it had little effect on the binding

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