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G2911

Sigma-Aldrich

GF 109203X

synthetic, ≥90% (HPLC)

Synonym(s):

3-(N-[Dimethylamino]propyl-3-indolyl)-4-(3-indolyl)maleimide, 3-[1-[3-(Dimethylamino)propyl]1H-indol-3-yl]-4-(1Hindol-3-yl)1H-pyrrole-2,5dione, Bisindolylmaleimide I

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About This Item

Empirical Formula (Hill Notation):
C25H24N4O2
CAS Number:
133052-90-1
Molecular Weight:
412.48
MDL number:
MFCD00236428
UNSPSC Code:
12352202
PubChem Substance ID:
329799908
NACRES:
NA.77

biological source

synthetic

Quality Level

100

Assay

≥90% (HPLC)

solubility

DMSO: soluble (~1 mg/ml)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C25H24N4O2/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)

InChI key

QMGUOJYZJKLOLH-UHFFFAOYSA-N

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Application

GF 109203X has been used as a protein kinase C inhibitor in HUVECs (human umbilical vein endothelial cells), angiotensinogen gene knockout (AGT KO) mice, and in granulosa cell cultures of female rats.

Biochem/physiol Actions

A potent and selective competitive inhibitor of protein kinase C (PKC) and of glycogen synthase kinase-3 (GSK-3). Inhibits parathyroid hormone-induced Ca2+ resorption from isolated bone tissue, Staurosporine, another protein kinase inhibitor, actually enhanced Ca2+ resorption elicited by a number of agents, but GF109203X counteracted that enhancement.
A potent and selective competitive inhibitor of protein kinase C (PKC) and of glycogen synthase kinase-3 (GSK-3). In certain cells, inhibition of PKC leads to an increase in autophagy. For PKC inhibition, typically used at a concentration of 0.1-10 μM.

Quantity

For PKC inhibition, typically used at a concentration of 0.1-10 μM.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H350

Hazard Classifications

Carc. 1B

Supplementary Hazards

EUH019

Storage Class Code

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

WGK

WGK 3

Certificates of Analysis (COA)

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H2O2 Treatment of HUVECs Facilitates PKC Mediated Thr495 Phosphorylation on eNOS when Pre-treated with High Glucose Levels.
Guterbaum TJ, et al.
Journal of Metabolic Syndrome, 4(189), 2167-0943 (2015)
K Iizuka et al.
British journal of pharmacology, 128(4), 925-933 (1999-11-11)
1 G protein-mediated Ca2+ sensitization of airway smooth muscle contraction was investigated with respect to the relative importance of Rho-associated coiled coil forming protein kinase (ROCK) and protein kinase C (PKC). We examined the effects of Y-27632, a ROCK inhibitor
Src is required for mechanical stretch-induced cardiomyocyte hypertrophy through angiotensin II type 1 receptor-dependent beta-arrestin2 pathways.
Wang S, et al.
PloS one, 9(4), e92926-e92926 (2014)
Follicle-stimulating hormone (FSH) stimulates phosphorylation and activation of protein kinase B (PKB/Akt) and serum and glucocorticoid-induced kinase (Sgk): evidence for A kinase-independent signaling by FSH in granulosa cells.
Gonzalez-Robayna IJ, et al.
Molecular Endocrinology, 14(8), 1283-1300 (2000)
Yun Zhu et al.
Environmental toxicology and pharmacology, 48, 197-202 (2016-11-07)
Studies have shown that corticotrophin-releasing hormone (CRH) and relaxin are associated with early delivery. Our lab previously has shown the mycotoxin zeranol increases placental CRH expression. The mycotoxin is used in the farming industry to promote cattle growth, and some
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