| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| Other Sizes |
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| Targets |
PKC (IC50 = 0.1-0.5 μM); HCMV (IC50 = 0.2 μM)
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|---|---|
| ln Vitro |
Arcyriarubin A, also known as bisindolylmaleimide IV, inhibits PKC with an IC50 of 0.55 μM in 10% DMSO and 0.1 μM in 1% DMSO [1].
The design and synthesis of a series of novel inhibitors of protein kinase C (PKC) is described. These 2,3-bisarylmaleimides were derived from the structural lead provided by the indolocarbazoles, staurosporine and K252a. Optimum activity required the imide NH, both carbonyl groups, and the olefinic bond of the maleimide ring. 2,3-Bisindolylmaleimides were the most active, and the potency of these was improved by a chloro substituent at the 5-position of one indole ring (compound 28, IC50 0.11 microM). In a series of (phenylindolyl)maleimides, nitro compound 74 was most active (IC50 0.67 microM). Naphthalene 19 and benzothiophene 21 showed greater than 100-fold selectivity for inhibition of PKC over the closely related cAMP-dependent protein kinase (PKA) [1]. |
| References | |
| Additional Infomation |
3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione is a member of indoles and a member of maleimides.
Bisindolylmaleimide IV has been reported in Arcyria cinerea, Arcyria denudata, and other organisms with data available. In our search for new, safer anti-HCMV agents, we discovered that the natural product Arcyriaflavin A (la) was a potent inhibitor of HCMV replication in cell culture. A series of analogues (symmetrical indolocarbazoles) was synthesised to investigate structure activity relationships in this series against a range of herpes viruses (HCMV, VZV, HSV1, and 2). This identified a number of novel, selective and potent inhibitors of HCMV, 12,13-dihydro-2,10-difluoro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazol e-5,7-(6H)-dione (1d) being the best example (IC50=40 nM, therapeutic index > 1450). Compounds described in this series were generally poor inhibitors of protein kinase C betaII, and no correlation was found between the ability to inhibit HCMV and the enzyme PKC.[2] |
| Molecular Formula |
C20H13N3O2
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|---|---|
| Molecular Weight |
327.336124181747
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| Exact Mass |
327.1
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| Elemental Analysis |
C, 73.38; H, 4.00; N, 12.84; O, 9.78
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| CAS # |
119139-23-0
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| PubChem CID |
2399
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| Appearance |
Orange to red solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
690.1±55.0 °C at 760 mmHg
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| Flash Point |
371.2±31.5 °C
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| Vapour Pressure |
0.0±2.2 mmHg at 25°C
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| Index of Refraction |
1.811
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| LogP |
3.21
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
25
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| Complexity |
576
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C1C(C2=CNC3C=CC=CC2=3)=C(C(N1)=O)C1=CNC2C=CC=CC1=2
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| InChi Key |
DQYBRTASHMYDJG-UHFFFAOYSA-N
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| InChi Code |
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)
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| Chemical Name |
3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione
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| Synonyms |
bisindolylmaleimide iv; 119139-23-0; 3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-dione; Bisindolylmaleimide; Arcyriarubin A; 3,4-Bis(3-indolyl)maleimide; 3,4-bis(1H-indol-3-yl)pyrrole-2,5-dione; 1H-Pyrrole-2,5-dione, 3,4-di-1H-indol-3-yl-;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~125 mg/mL (~381.87 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.35 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0549 mL | 15.2746 mL | 30.5493 mL | |
| 5 mM | 0.6110 mL | 3.0549 mL | 6.1099 mL | |
| 10 mM | 0.3055 mL | 1.5275 mL | 3.0549 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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