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Merck

203290

Bisindolylmaleimide I

≥95% (HPLC), protein kinase C inhibitor , solid

Synonyme(s) :

Bisindolylmaleimide I, 2-[1-(3-Dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleimide, Gö 6850, GF 109203X

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A propos de cet article

Formule empirique (notation de Hill) :
C25H24N4O2
Numéro CAS:
133052-90-1
Poids moléculaire :
412.48
UNSPSC Code:
12352111
NACRES:
NA.77
MDL number:
MFCD00236428

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Nom du produit

Bisindolylmaleimide I, A highly selective, cell-permeable, and reversible protein kinase C (PKC) inhibitor (IC50 = 10 nM) that is structurally similar to staurosporine.

SMILES string

N1C(=O)C(=C(C1=O)c4c5c([nH]c4)cccc5)c2c3c([n](c2)CCCN(C)C)cccc3

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

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

deep orange

solubility

DMSO: 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

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Cet article
203291203293361553
Bisindolylmaleimide I A highly selective, cell-permeable, and reversible protein kinase C (PKC) inhibitor (IC50 = 10 nM) that is structurally similar to staurosporine.

Sigma-Aldrich

203290

Bisindolylmaleimide I

Bisindolylmaleimide I, Hydrochloride An enhanced water-soluble form of Bisindolylmaleimide I.

Sigma-Aldrich

203291

Bisindolylmaleimide I, Hydrochloride

Bisindolylmaleimide I InSolution, ≥95%, protein kinase C (PKC) inhibitor

Sigma-Aldrich

203293

Bisindolylmaleimide I

GSK-3β Inhibitor XI The GSK-3β Inhibitor XI, also referenced under CAS 626604-39-5, controls the biological activity of GSK-3β. This small molecule/inhibitor is primarily used for Phosphorylation & Dephosphorylation applications.

Sigma-Aldrich

361553

GSK-3β Inhibitor XI

form

solid

form

solid

form

liquid

form

solid

assay

≥95% (HPLC)

assay

≥95% (HPLC)

assay

≥95% (HPLC)

assay

≥95% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

solubility

DMSO: 10 mg/mL

solubility

water: 10 mg/mL, DMSO: 20 mg/mL

solubility

-

solubility

DMSO: 5 mg/mL

Biochem/physiol Actions

Cell permeable: yes
Primary Target
PKC
Product competes with ATP.
Reversible: yes
Target IC50: 10 nM against protein kinase C (PKC); 360 nM, 170 nM against GSK-3 in primary adipocyte lysates and in GSK-3β immunoprecipitates, respectively

Disclaimer

Toxicity: Standard Handling (A)

General description

A highly selective cell-permeable protein kinase C (PKC) inhibitor (IC50 = 10 nM) that is structurally similar to staurosporine. Acts as a competitive inhibitor for the ATP-binding site of PKC. Shows high selectivity for PKCα, βI, βII, γ, δ, and ε isozymes. May inhibit protein kinase A at a much higher concentration (IC50 = 2 µM). Also inhibits telomerase activity in quercetin, H-89, or herbimycin A treated NPC-076 cells.
A highly selective, cell-permeable, and reversible protein kinase C (PKC) inhibitor (IC50 = 10 nM) that is structurally similar to staurosporine. Acts as a competitive inhibitor for the ATP-binding site of PKC. Shows high selectivity for PKCα-, βI-, βII-, γ-, δ-, and ε- isozymes. Potently inhibits GSK-3 in primary adipocyte lysates (IC50 = 360 nM) and in GSK-3β immunoprecipitates (IC50 = 170 nM). May inhibit protein kinase A at a much higher concentration (IC50 = 2 µM). A 1 mg/ml solution of Bisindolylmaleimide I (Cat. No. 203293) in anhydrous DMSO is also available.

Other Notes

Hers, I., et al. 1999. FEBS Lett.460, 433.
Ku, W.-C., et al. 1997. Biochem. Biophys. Res. Commun. 241, 730.
Gekeler, V., et al. 1996. Br. J. Cancer 74, 897.
Kiss, Z., et al. 1995. Biochim. Biophys. Acta 1265, 93.
Toullec, D., et al. 1991. J. Biol. Chem. 266, 15771.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). DMSO stock solutions are stable for up to 4 months at -20°C.
Further dilute with aqueous buffers just prior to use.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

Certificats d'analyse (COA)

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Kirk D Haan et al.
STAR protocols, 4(4), 102744-102744 (2023-11-24)
Here, we present a protocol for live-cell immunocytochemistry to demonstrate reversible translocation of ion channels to the neuronal cell surface. We describe steps for cell preparation and isolation, experimental treatment, antibody binding prior to fixation, specific pipetting techniques, troubleshooting, and
Nicolas Chofflet et al.
Frontiers in molecular neuroscience, 17, 1371145-1371145 (2024-04-04)
The prevailing model behind synapse development and specificity is that a multitude of adhesion molecules engage in transsynaptic interactions to induce pre- and postsynaptic assembly. How these extracellular interactions translate into intracellular signal transduction for synaptic assembly remains unclear. Here
A Soledad Coria et al.
Biology of the cell, 106(1), 30-43 (2013-11-02)
Heterotrimeric GTP-binding proteins play a key role in cell trafficking regulation. Above all, specific Gβγ subunits have been shown to be a major component of a signal transduction pathway, which also involves phospholipases C (PLC), protein kinases C (PKC) and
Juliana C Corrêa-Velloso et al.
iScience, 24(10), 103139-103139 (2021-10-15)
Extracellular agonists linked to inositol-1,4,5-trisphosphate (IP3) formation elicit cytosolic Ca2+ oscillations in many cell types, but despite a common signaling pathway, distinct agonist-specific Ca2+ spike patterns are observed. Using qPCR, we show that rat hepatocytes express multiple purinergic P2Y and
Haranatha R Potteti et al.
American journal of physiology. Renal physiology, 320(3), F464-F474 (2021-01-26)
Nuclear factor erythroid 2-related factor 2 (Nrf2) and hypoxia-inducible factor-1α (HIF1α) transcription factors protect against ischemic acute kidney injury (AKI) by upregulating metabolic and cytoprotective gene expression. In this study, we tested the hypothesis that Nrf2 is required for HIF1α-mediated
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