| Identification | Back Directory | [Name]
3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione | [CAS]
119139-23-0 | [Synonyms]
RO 31-6233
ARCYRIARUBIN A
BISINDOLYMALEIMIDE IV
3,4-Di(1H-indol-3-yl)
BISINDOLYLMALEIMIDE IV
3,4-BIS(3-INDOLYL)MALEIMIDE
2,3-BIS(1H-INDOL-3-YL)MALEIMIDE
BisindolylMaleiMide IV [Ro 31-6233]
3,4-Di(3-indolyl)-1H-pyrrole-2,5-dione
3,4-Bis(1H-indol-3-yl)pyrrole-2,5-dione
Bisindolylmaleimide IV (Arcyriarubin A)
3,4-Di-1H-indol-3-yl-1H-pyrrole-2,5-dione
3,4-Bis(1H-indol-3-yl)-1H-pyrrole-2,5-dione
1H-Pyrrole-2,5-dione, 3,4-di-1H-indol-3-yl-
3,4-BIS(3-INDOLYL)MALEIMIDE (ARCYRIARUBIN A).
3,4-BIS(3-INDOLYL)MALEIMIDE (ARCYRIARUBIN A), 95+%
Bisindolylmaleimide IV - CAS 119139-23-0 - Calbiochem
3-(1H-Indole-3-yl)-4-(1H-indole-3-yl)-1H-pyrrole-2,5-dione
bisindolylmaleimide iv:2,3-bis(1h-indol-3-yl)maleimide: 3,4-di-1h-indol-3-yl-1h-pyrrole-2,5-dione | [Molecular Formula]
C20H13N3O2 | [MDL Number]
MFCD00236432 | [MOL File]
119139-23-0.mol | [Molecular Weight]
327.34 |
| Chemical Properties | Back Directory | [Melting point ]
161 °C | [Boiling point ]
690.1±55.0 °C(Predicted) | [density ]
1.486±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
DMSO: soluble
| [form ]
solid
| [pka]
8.44±0.60(Predicted) | [color ]
dark red
| [biological source]
synthetic (organic) | [InChI]
1S/C20H13N3O2/c24-19-17(13-9-21-15-7-3-1-5-11(13)15)18(20(25)23-19)14-10-22-16-8-4-2-6-12(14)16/h1-10,21-22H,(H,23,24,25) | [InChIKey]
DQYBRTASHMYDJG-UHFFFAOYSA-N | [SMILES]
O=C1NC(=O)C(c2c[nH]c3ccccc23)=C1c4c[nH]c5ccccc45 |
| Hazard Information | Back Directory | [Definition]
ChEBI: 3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione is a member of indoles and a member of maleimides. | [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 | [Synthesis]
A. Chemical Examples; Example 1; 3,4-Di-(1H-indol-3-yl)pyrrole-2,5-dione (Compound 1); Potassium tert-butanolate (0.976 g, 8.7 mmol) was added to a stirred (1H-indol-3-yl)acetamide (0.5 g, 2.8 mmol) and methyl 3-indolylglyoxylate (0.650 g, 3.15 mmol) in a suspension of anhydrous tetrahydrofuran (15 mL) and the temperature was maintained at -10 °C. After 15 minutes of reaction, the resulting dark red solution was slowly warmed to 20 °C over 3.5 hours. Subsequently, concentrated hydrochloric acid (2 mL) was added under cooling conditions and stirred overnight to dissolve the orange-red precipitate in ethyl acetate. The organic phase was washed sequentially with water and brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give bisindolylmaleimide IV (0.780 g, 80.2% yield) in red crystalline form with a melting point of 234 °C. 1H-NMR (DMSO-d6, δ/ ppm): 11.6 (br s, 1H), 10.95 (br s, 1H), 7.68 (s, 1H) , 7.38 (d, 1H), 6.98 (t, 1H), 6.8 (d, 1H), 6.6 (t, 1H). | [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. |
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