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Staurosporine

Staurosporine structure

CAS No:
62996-74-1
Formula:
C28H26N4O3
Chemical 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,10R,11R,13R)-;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,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 AM 2282;Staurosporine;Staurosporin;AM-2282;Alkaloid AM-2282 from Streptomyces;(+)-Staurosporine;Antibiotic 230;CGP 39360;109189-95-9
Categories:
Pharmaceutical Intermediates > Antineoplastics

Description

Staurosporine is a potent and non-selective inhibitor of protein kinases with IC50s of 6 nM, 15 nM, 2 nM, and 3 nM for PKC, PKA, c-Fgr, and Phosphorylase kinase respectively.

An indolocarbazole that is a potent PROTEIN KINASE C inhibitor which enhances cAMP-mediated responses in human neuroblastoma cells. (Biochem Biophys Res Commun 1995;214(3):1114-20)

Staurosporine Basic Attributes

Molecular Weight：

466.53

Exact Mass：

466.53

EC Number：

613-127-7

NSC Number：

374128

DSSTox ID：

DTXSID6041131

HScode：

29419090

Characteristics

PSA：

69.45000

XLogP3：

5.07370

Appearance：

off-white powder

Density：

1.6±0.1 g/cm3

Melting Point：

270°C

Boiling Point：

677.5ºC at 760 mmHg

Flash Point：

363.6±31.5 °C

Refractive Index：

1.810

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.

Storage Conditions：

2-8°C

Specific rotation：

D25 +35.0° (c = 1 in methanol); D22 +56.1° (c = 0.14 in methanol)

Safety Information

Hazard category：

Transport codes：

UN 2811 6.1 / PGII

wgk germany：

hazard class code：

40-45-36/37/38-46

safety instructions：

36/37-53-36-26-45

RTECS Number：

KD5084000

Marks：

Xn,T,Xi

Precautionary statement(s)：

P201-P280-P308 + P313

Hazard Statements：

H340-H350

GHS Classification：

|Danger|H228 (14.29%): Flammable solid [Danger Flammable solids]|P201, P202, P210, P240, P241, P260, P262, P264, P270, P273, P280, P281, P301+P310, P301+P312, P302+P350, P308+P313, P310, P314, P321, P322, P330, P361, P363, P370+P378, P391, P405, and P501|Aggregated GHS information provided by 7 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

MeSH Entry Terms：

8,12-Epoxy-1H,8H-2,7b,12a-triazadibenzo(a,g)cyclonona(cde)trinden-1-one, 2,3,9,10,11,12-hexahydro-9-methoxy-8-methyl-10-(methylamino)-, (8alpha,9beta,10beta,12alpha)-(+)-

Staurosporine Use and Manufacturing

Methods of Manufacturing

General procedure: A mixture of 2a (50 mg, 0.11 mmol), 4 (59 mg, 0.17 mmol), K2CO3 (46 mg, 0.33 mmol), and KI (55 mg, 0.33 mmol) in DMF (0.4 mL) was stirred at 80 C for 5 hr. To this mixture was added 4 (60 mg), K2CO3 (45 mg, 0.32 mmol), and KI (55 mg, 0.33 mmol) in DMF (0.2 mL) and the mixture was stirred at 80 C for 12 hr. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by preparative HPLC. The desired fraction was neutralized with sat. NaHCO3 aq. and half of the solvent was evaporated and extracted with EtOAc. The organic layer was separated, washed with water and brine dried over MgSO4 and concentrated in vacuo to give 5a (60 mg, 0.082 mmol, 75 %) as a pale yellow amorphous solid.Under the protection of argon, in 100 ml two port in the reaction bottle, add 2.33 g cross spore alkali (5.0 mmol) for 50 ml tetrahydrofuran is dissolved, add 2 ml triethylamine, 0 C adding 1.3 g of di-T-butyl dicarbonate (6.0 mmol), 0 C reaction 30 min, water to terminate the reaction, methylene chloride extraction, anhydrous sodium sulfate concentrated after drying, silica gel column chromatography separation, dichloromethane: methanol (v/v 30:1) elute and get the 3' -N- Tert butoxycarbonyl cross spore alkali 2.18 g, yield 76%.

Uses

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

Computed Properties

Molecular Weight:466.5
XLogP3:3.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:466.20049070
Monoisotopic Mass:466.20049070
Topological Polar Surface Area:69.4
Heavy Atom Count:35
Complexity:901
Undefined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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