125313-65-7

Basic information

• Product Name: RO-31-7549
• Synonyms: BISINDOLYLMALEIMIDE VIII ACETATE;2-[1-3(AMINOPROPYL)INDOL-3-YL]-3(1-METHYL-1H-INDOL-3-YL)MALEIMIDE, ACETATE;RO-31-7549;RO 31-7549 ACETATE SALT;BIDINDOLYLMALEIMIDE VIII, ACETETE;1H-Pyrrole-2,5-dione, 3-(1-(3-aminopropyl)-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)-;3-(1-(3-Aminopropyl)-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione;Bisindolylmaleimide VIII
• CAS NO: 125313-65-7
• Molecular Formula: C26H26N4O4
• Molecular Weight: 458.51
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Protein Kinase Inhibitors and Activators
• Mol File: 125313-65-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 693 °C at 760 mmHg
• Flash Point: 372.9 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 4.7E-19mmHg at 25°C
• Refractive Index: 1.712
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• CAS DataBase Reference: RO-31-7549(CAS DataBase Reference)
• NIST Chemistry Reference: RO-31-7549(125313-65-7)
• EPA Substance Registry System: RO-31-7549(125313-65-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 125313-65-7(Hazardous Substances Data)

Usage

Uses

It is a potent inhibitor of protein kinase C (PKC) activity.

General Description

A cell permeable, reversible, selective protein kinase C (PKC) inhibitor (IC50 = 158 nM for rat brain PKC) that acts at the ATP binding site of PKC. Does not inhibit the tyrosine phosphorylation or the activation of phospholipase Cγ1. Exhibits some degree of PKC isozyme specificity (IC50 = 53 nM for PKCα, 195 nM for PKCβI, 163 nM for PKCβII, 213 nM for PKCγ, and 175 nM for PKCε). Inhibits carbachol-evoked noradrenaline release (IC50 = 600 nM).

Biochem/physiol Actions

Cell permeable: yes

InChI:InChI=1/C24H22N4O2/c1-27-13-17(15-7-2-4-9-19(15)27)21-22(24(30)26-23(21)29)18-14-28(12-6-11-25)20-10-5-3-8-16(18)20/h2-5,7-10,13-14H,6,11-12,25H2,1H3,(H,26,29,30)

Upstream product

• 125314-97-8 3-<1-(3-acetoxypropyl)-3-indolyl>-4-(1-methyl-3-indolyl)-2,5-furandione 
• 125313-60-2 3-[1-(3-hydroxy-propyl)-1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione 
• 125314-98-9 N-(3-acetoxypropyl)-indole 
• 120-72-9 indole 

Relevant articles and documents

Methods and materials for identifying agents which modulate bone remodeling and agents identified thereby

The invention discloses compositions, compounds, apparatuses and methods of using them to study bone mineralization and identify agents that regulate bone mineralization. Methods of using bone mineralization gene profiles and signatures for compound screening and research are also disclosed. Reagents for modulating bone mineralization are provided for both therapeutic and research usage.

Inhibitors of Protein Kinase C. 2. Substituted Bisindolylmaleimides with Improved Potency and Selectivity

A hypothetical mode of inhibition of protein kinase C (PKC) by the natural product staurosporine has been used as a basis for the design of substituted bisindolylmaleimides with improved potency over the parent compound.Structure-activity relationships were consistent with the interaction of a cationic group in the inhibitor with a carboxylate group in the enzyme, and the most potent compound had a Ki of 3 nM.The inhibitors were competitive with ATP but inhibited cAMP-dependent protein kinase (PKA) only at much higher concentrations despite the extensive sequence homology between ATP-binding regions of PKA and PKC.There compounds were evaluated further and found to inhibit a human allogeneic mixed lymphocyte reaction pointing to the potential utility of PKC inhibitors in immunosuppressive therapy.One of these compounds was orally absorbed in the rat and represents an attractive lead in the development of PKC inhibitors as drugs.