119139-23-0

Basic information

• Product Name: 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione
• Synonyms: RO 31-6233;3,4-BIS(3-INDOLYL)MALEIMIDE;2,3-BIS(1H-INDOL-3-YL)MALEIMIDE;BISINDOLYLMALEIMIDE IV;ARCYRIARUBIN A;BISINDOLYMALEIMIDE IV;3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione;3,4-BIS(3-INDOLYL)MALEIMIDE (ARCYRIARUBIN A), 95+%
• CAS NO: 119139-23-0
• Molecular Formula: C₂₀H₁₃N₃O₂
• Molecular Weight: 327.34
• Mol File: 119139-23-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 161 °C
• Boiling Point: 690.133 °C at 760 mmHg
• Flash Point: 371.179 °C
• Appearance: dark red/solid
• Density: 1.486 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.829
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• PKA: 8.44±0.60(Predicted)
• CAS DataBase Reference: 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione(119139-23-0)
• EPA Substance Registry System: 3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione(119139-23-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 119139-23-0(Hazardous Substances Data)

Usage

General Description

A potent, cell permeable, and selective inhibitor of protein kinase C (IC50 = 87 nM). Inhibits protein kinase A at much higher concentrations (IC50 = 2.7 μM).

Biological Activity

bisindolylmaleimide iv is a protein kinase c (pkc) inhibitor.the enzyme family protein kinase c2 (pkc) occupies a central role in the transduction of signals from a variety of mediators across the cell membrane.3 receptor occupation by a number of hormones, cytokines, neurotransmitters, and growth factors results in activation of pkc via activation of phospholipase c through either a g protein mechanism or a tyrosine kinase mechanism. pkc then propagates the signal by phosphorylation of proteins on serine or threonine, with atp as cosubstrate, resulting in modification of the properties of these proteins. thus pkc appears to regulate mechanisms of cell proliferation, secretion, and gene expression.

Biochem/physiol Actions

Target IC50: 87 nM against protein kinase C

in vitro

bisindolylmaleimide iv was identified as a cell permeable inhibitor of protein kinase c (pkc) with ic50 values from 0.10 to 0.55 μm. bisindolylmaleimide iv was designed to be more discriminative than its parent compound staurosporine, the non-selective pkc inhibitor. in addition, bisindolylmaleimide iv also found to be able to inhibit protein kinase a with ic50 values ranging from 2 to 11.8 μm [1, 2].

in vivo

animal study found that, in neonatal rats, high glucose levels could induce the hypertrophy of cardiomyocytes. ro-31-8220, a analog of bisindolylmaleimide viii, was able to reverse the effect of high glucose on the cardiac myocytes, which might be through pkc/nf-κb/c-fos pathway [3].

IC 50

from 0.10 to 0.55 μm

references

[1] davis, p. d.,hill, c.h.,lawton, g., et al. inhibitors of protein kinase c. 1.1 2,3-bisarylmaleimides. journal of medicinal chemistry 35, 177-184 (1992).[2] toullec, d. ,pianetti, p.,coste, h., et al. the bisindolylmaleimide gf 109203x is a potent and selective inhibitor of protein kinase c. the journal of biological chemisty 266(24), 15771-15781 (1991).[3] zhang, w. b. et al. reverse effect of protein kinase c inhibitor ro-31-8220 on the hypertrophy of cardiomyocytes of neonatal rats induced by high glucose levels. chinese journal of pathophysiology. 2009-08.

InChI:InChI=1/C20H13N3O2/c24-19-11-14(17-9-12-5-1-3-7-15(12)21-17)20(25)23(19)18-10-13-6-2-4-8-16(13)22-18/h1-11,21-22H

Upstream product

• 3005-27-4 3,4-dibromo-1-methyl-2,5-dihydropyrrole-2,5-dione 
• 7553-56-2 iodine 
• 120-72-9 indole 
• 10185-29-2 3-(1H-indole-3-yl)pyrrolidine-2,5-dione 
• 221905-22-2 3-(1H-3-indolyl)-2,5-dihydro-1H-2,5-pyrroledione 
• 1477-49-2 3-indolylglyoxylic acid 
• 342416-19-7 1-(2,4-dimethoxybenzyl)-3,4-bis-(1H-indol-3-yl)pyrrole-2,5-dione 
• 1193-54-0 3,4-dichloromaleimide 
• 115684-57-6 2,3-bis(1H-indol-3-yl)maleic anhydride 
• 1122-10-7 2,3-dibromomaleimide 
• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 879-37-8 3-indolylacetamide 
• 18372-22-0 2-(3-indolyl)oxoacetic acid methyl ester 
• 91026-01-6 2,3-bis(1H-indol-3-yl)-N-benzylmaleimide 

Downstream Products

• 113963-68-1 bisindolylmaleimide V 
• 1239173-47-7 2,3-bis(N-(4-bromobenzyl)-3'-indolyl)-N-(4'-bromobenzyl)maleimide 
• 1187080-89-2 C₄₁H₃₁N₃O₂ 
• 133233-25-7 3,4-bis(1-methyl-3-indolyl)-1-methyl-pyrrole-2,5-dione 
• 133053-46-0 3-(1H-indol-3-yl)-1-methyl-4-(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione 
• 118458-54-1 arcyriaflavin A 

Relevant articles and documents

An indole-based conjugated microporous polymer: A new and stable lithium storage anode with high capacity and long life induced by cation-π interactions and a N-rich aromatic structure

An indole-based conjugated microporous polymer, poly(bisindolylmaleimide) (PBIM), with superior electrochemical performance as an anode material for LIBs has been obtained by FeCl3-promoted oxidative coupling polymerization. Benefiting from reversible cation-π interactions and a unique aromatic structure containing N heteroatoms, the prepared PBIM anode shows high capacity (1172 mA h g-1, 50 mA g-1), outstanding cycle life (1000 cycles), and remarkable rate performance (214 mA h g-1, 2.5C).

Palladium-Catalyzed Tandem Regioselective Oxidative Coupling from Indoles and Maleimides: One-Pot Synthesis of Indolopyrrolocarbazoles and Related Indolylmaleimides

An efficient Pd(II)-catalyzed approach for the direct synthesis of indolo[3,2-a]pyrrolo[3,4-c]carbazole-6,8-diones has been developed from both free and protected (NH) indoles and maleimides via a regioselective tandem oxidative coupling reaction. The yie

Synthesis and properties of novel heat-resistant fluorescent conjugated polymers with bisindolylmaleimide

Conjugated polymers with bisindolylmaleimide (BIM) backbone are obtained by the condensation polymerization of methyl and octanyl N-substituted BIMs with 4,4'-difluoro-diphenylsulfone and 4,4'-difluoro-diphenylketone. The structures of polymers are confirmed by FTIR and NMR spectroscopy. The polymers exhibit both high glass transition temperatures (Tg > 175 °C) and high decomposition temperatures (T5 > 395 °C). Meanwhile, The UV–vis absorption and fluorescence spectra of the polymers are similar to the corresponding substituted BIMs. The quantum chemistry calculations indicate that the first excited states of polymers are mostly contributed by BIM structures.

Diarylmaleic anhydrides: unusual organic luminescence, multi-stimuli response and photochromism

Diarylmaleic anhydride derivatives containing benzene (BPMA), thiophene (BTMA) and indole (BIMA) exhibit diverse and distinct fluorescence: aggregation-caused quenching (ACQ) of red emission of BIMA, blue aggregation-induced emission (AIE) of BPMA, and green dual-state emission (DSE) of BTMA in both solution and the solid state. Theoretical calculation and crystal structure analysis indicate that intramolecular and intermolecular interactions are responsible for their different emission behavior. A series of DSE-active molecules with full-color emission could be developed for the first time, through modification of the structures of BPMA and BIMA. Interestingly, BTMA and BPMA display multi-stimuli-responsive luminescence with a high-contrast (Δλem > 100 nm) and an unusual photochromic phenomenon in dichloromethane, which were utilized to construct rewritable data storage and mimic molecular logic operation (4-to-2 encoder and 1?:?2 demultiplexer), respectively.