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B6292

Sigma-Aldrich

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
MDL number:
MFCD00236429
UNSPSC Code:
12352200
PubChem Substance ID:
24891903
NACRES:
NA.77

biological source

synthetic (organic)

Assay

≥95%

form

solid

solubility

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

storage temp.

2-8°C

SMILES string

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

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

InChI key

XRAMWNCMYJHGGH-UHFFFAOYSA-N

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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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 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)
D Toullec et al.
The Journal of biological chemistry, 266(24), 15771-15781 (1991-08-25)
Staurosporine is the most potent inhibitor of protein kinase C (PKC) described in the literature with a half-maximal inhibitory concentration (IC50) of 10 nM. Nevertheless, this natural product is poorly selective when assayed against other protein kinases. In order to
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