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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)
Kristin Klarström Engström et al.
Scientific reports, 9(1), 2296-2296 (2019-02-21)
To prevent the onset of urosepsis and reduce mortality, a better understanding of how uropathogenic Escherichia coli (UPEC) manages to infiltrate the bloodstream through the kidneys is needed. The present study elucidates if human renal interstitial fibroblasts are part of
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