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Merck

B6292

GF 109203X hydrochloride

≥95%

Synonym(s):

3-[1-(Dimethylaminopropyl)indol-3-yl]-4-(indol-3-yl)maleimide hydrochloride, Bisindolylmaleimide I hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C25H24N4O2 · HCl
CAS Number:
176504-36-2
Molecular Weight:
448.94
NACRES:
NA.77
PubChem Substance ID:
24891903
UNSPSC Code:
12352200
MDL number:
MFCD00236429

Product Name

GF 109203X hydrochloride, ≥95%

InChI

1S/C25H24N4O2.ClH/c1-28(2)12-7-13-29-15-19(17-9-4-6-11-21(17)29)23-22(24(30)27-25(23)31)18-14-26-20-10-5-3-8-16(18)20;/h3-6,8-11,14-15,26H,7,12-13H2,1-2H3,(H,27,30,31);1H

SMILES string

Cl.CN(C)CCCn1cc(C2=C(C(=O)NC2=O)c3c[nH]c4ccccc34)c5ccccc15

InChI key

XRAMWNCMYJHGGH-UHFFFAOYSA-N

biological source

synthetic (organic)

assay

≥95%

form

solid

solubility

methanol: 10 mg/mL, clear, orange to red

storage temp.

2-8°C

Quality Level

200

Related Categories

Application

GF 109203X hydrochloride has been used to inhibit protein kinase C in human neuroblastoma-derived kelly cells.

Biochem/physiol Actions

Inhibitor of protein kinase C; potent inhibitor of GSK-3.

General description

GF 109203X prevents collagen-triggered adenosine and three phosphate (ATP) secretion. It also inhibits collagen and α-thrombin-induced platelet aggregation. It functions as an inhibitor of glycogen synthase kinase-3 (GSK-3). GF 109203X also functions as an anti-inflammatory agent.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000272832
0000258741
0000272832
0000258741
SLCL4045

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Anti-inflammatory properties of the protein kinase C inhibitor, 3-[1-[3-(dimethylamino) propyl]-1H-indol-3-yl]-4 (1H-indol-3-yl)-1H-pyrrole-2, 5-dione monohydrochloride (GF109203X) in the PMA-mouse ear edema model
Kuchera S, et al.
Agents and Actions, 39(1), C169-C173 (1993)
Phorbol-ester mediated suppression of hASH1 synthesis: multiple ways to keep the level down
Benko E, et al.
Frontiers in Molecular Neuroscience, 4(1), 1-1 (2011)
The bisindolylmaleimide GF 109203X is a potent and selective inhibitor of protein kinase C
Toullec D1, et al.
The Journal of Biological Chemistry, 266(24), 15771-15781 (1991)
The protein kinase C inhibitors bisindolylmaleimide I (GF 109203x) and IX (Ro 31-8220) are potent inhibitors of glycogen synthase kinase-3 activity
Hers I, et al.
Febs Letters, 460(3), 433-436 (1999)
Meredith V Brown et al.
Experimental cell research, 315(1), 39-49 (2008-10-28)
p120-catenin (p120) is required for cadherin stability and is thought to have a central role in modulating cell-cell adhesion. Several lines of evidence suggest that S/T phosphorylation may regulate p120 activity, but the upstream kinases involved have not been established
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