G2911

Bisindolylmaleimide I

Name: Bisindolylmaleimide I
Brand: SIGMA

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

UNSPSC Code:

12352202

PubChem Substance ID:

329799908

NACRES:

NA.77

MDL number:

MFCD00236428

Product Name

GF 109203X, synthetic, ≥90% (HPLC)

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

biological source

synthetic

assay

≥90% (HPLC)

solubility

DMSO: soluble (~1 mg/ml)

storage temp.

2-8°C

Quality Level

100

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Bioactive Small Molecule Inhibitors

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.

Preparation Note

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

pictograms

GHS08

signalword

Danger

hcodes

H350

pcodes

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Carc. 1B

supp_hazards

EUH019

Storage Class

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

wgk

WGK 3

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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)

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)

Assessing placental corticotrophin-releasing hormone disruption by hexestrol in a cell model.

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

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)

Human renal fibroblasts are strong immunomobilizers during a urinary tract infection mediated by uropathogenic Escherichia coli.

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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