113963-68-1

Basic information

• Product Name: Bisindolylmaleimide V
• Synonyms: 1-Methyl-3,4-bis(indol-3-yl)maleimide, Ro 31-6045;1-Methyl 3,4-bis(1H-indole-3-yl)-3-pyrroline-2,5-dione;1-Methyl-3-(1H-indole-3-yl)-4-(1H-indole-3-yl)-1H-pyrrole-2,5-dione;1-Methyl-3,4-bis(1H-indole-3-yl)-3-pyrroline-2,5-dione;3,4-Bis(1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione;3,4-Bis(1H-indole-3-yl)-1-methyl-3-pyrroline-2,5-dione;BisindolylMaleiMide V [Ro 31-6045];bisindolylmaleimide v:1-methyl-3,4-bis(3-indolyl)maleimide
• CAS NO: 113963-68-1
• Molecular Formula: C₂₁H₁₅N₃O₂
• Molecular Weight: 341.37
• EINECS: 604-604-1
• Mol File: 113963-68-1.mol
• Article Data: 30

Chemical Properties

• Melting Point: >260 °C
• Boiling Point: 655.691 °C at 760 mmHg
• Flash Point: 350.349 °C
• Appearance: /solid
• Density: 1.451 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.794
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• PKA: 15.89±0.30(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: Bisindolylmaleimide V(CAS DataBase Reference)
• NIST Chemistry Reference: Bisindolylmaleimide V(113963-68-1)
• EPA Substance Registry System: Bisindolylmaleimide V(113963-68-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 113963-68-1(Hazardous Substances Data)

Usage

Description

Bisindolylmaleimide V, also known as Ro 31-6045, is a bis indolylmaleimide derivative that serves as a potent inhibitor of the mitogen-stimulated protein kinase p70 (S6K). It acts independently of its upstream activator mTOR and does not inhibit PKC at concentrations below 100 μM. This characteristic makes it a suitable negative control for bisindolylmaleimide PKC inhibitors, such as GF 109203X and other structurally related inhibitors.

Uses

Used in Pharmaceutical Research:
Bisindolylmaleimide V is used as a research tool for studying the role of protein kinase p70 (S6K) in various cellular processes. Its ability to inhibit S6K independently of mTOR makes it valuable in understanding the complex interactions between these proteins and their impact on cell signaling.
Used in Drug Development:
Bisindolylmaleimide V is used as a lead compound in the development of new drugs targeting protein kinase p70 (S6K). Its specificity and potency in inhibiting S6K without affecting PKC make it a promising candidate for the treatment of diseases where S6K plays a significant role, such as cancer and other proliferative disorders.
Used in Cell Signaling Studies:
Bisindolylmaleimide V is used as a reagent in cell signaling research to investigate the role of S6K in mitogen-stimulated pathways. By inhibiting S6K, researchers can gain insights into the downstream effects on cellular processes and identify potential therapeutic targets for various diseases.
Used in Cancer Research:
Bisindolylmaleimide V is used as an inhibitor in cancer research to study the role of S6K in tumor growth and progression. Its ability to inhibit S6K without affecting PKC allows researchers to explore the specific contributions of S6K to cancer development and identify potential therapeutic strategies for cancer treatment.
Used in Drug Screening:
Bisindolylmaleimide V is used as a reference compound in drug screening assays to identify novel inhibitors of protein kinase p70 (S6K). Its specificity and potency make it an ideal control for assessing the activity of new compounds targeting S6K in various disease models.

References

1) Marmy-Conus?et al.?(2002),?Ro 31-6045, the inactive analogue of the protein kinase C inhibitor Ro 31-8220, blocks in vivo activation of p70(s6k)/p85(s6k): implications for the analysis of S6K signalling; FEBS Lett.,?519?135 2) Harmon?et al.?(1997),?Bisindolylmaleimide protein-kinase C inhibitors delay in the decline in DNA synthesis in mouse hair follicle organ cultures; Skin Pharmacol.,?10?71 3) Toullec?et al.?(1991),?The bisindolylmaleimide GF 109203X is a potent and selective inhibitor of protein kinase C; J. Biol. Chem.,?266?15771 4) Davis?et al. (1992),?Inhibitors of protein kinase C. 1. 2,3-Bisarylmaleimides; J. Med. Chem.,?35?177

InChI:InChI=1/C21H15N3O2/c1-24-20(25)18(14-10-22-16-8-4-2-6-12(14)16)19(21(24)26)15-11-23-17-9-5-3-7-13(15)17/h2-11,22-23H,1H3

Upstream product

• 3005-27-4 3,4-dibromo-1-methyl-2,5-dihydropyrrole-2,5-dione 
• 13884-15-6 (Indol-1-yl)magnesium iodide 
• 1207184-82-4 2,3-bis(1-tosyl-indol-3-yl)-N-methylmaleimide 
• 120-72-9 indole 
• 221905-17-5 2,5-dihydro-1-methyl-3-(indol-3-yl)-pyrrole-2,5-dione 
• 930-88-1 N-methylmaleimide 
• 1123-61-1 3,4-dichloro-1-methyl-pyrrole-2,5-dione 
• 925-90-6 ethylmagnesium bromide 
• 879-37-8 3-indolylacetamide 
• 18372-22-0 2-(3-indolyl)oxoacetic acid methyl ester 
• 119139-23-0 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione 
• 74-88-4 methyl iodide 
• 96-54-8 N-Methylpyrrole 
• 238734-42-4 C₃₁H₃₁N₃O₆ 

Downstream Products

• 119139-23-0 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione 
• 1370029-80-3 C₃₇H₃₇N₅O₅ 
• 1370029-69-8 C₃₂H₂₉N₅O₃ 
• 192050-59-2 Ruboxistaurin mesylate 
• 170277-76-6 (9S)-6,7,10,11-tetrahydro-9-[(triphenylmethoxy)methyl]-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]-oxadiazacyclohexadecine-18,20(19H)-dione 
• 170277-75-5 (9S)-6,7,10,11-tetrahydro-9-[(triphenylmethoxy)methyl]-5,21:12,17-dimetheno-9H-dibenzo[e,k]furo[3,4-h][1,4,13]-oxadiazacyclohexadecine-18,20-dione 
• 102622-95-7 AT2433-B2 
• 849950-07-8 2,5-dihydro-3-[1-(tert-butyloxycarbonyl)-1H-indol-3-yl]-4-[1-(4-O-benzoyl-3-N,N-dibenozylamino-2,3,6-trideoxy-β-L-lyxo-hexosyl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione 
• 849950-09-0 6-methyl-12-(4-O-benzoyl-3-N,N-dibenzoylamino-2,3,6-trideoxy-β-L-lyxo-hexosyl)-6,7,12,13-tetrahydroindolo[2,3-α]pyrrolo[3,4-c]carbazole-5,7-dione 
• 849950-08-9 2,5-dihydro-3-[1H-indol-3-yl]-4-[1-(4-O-benzoyl-3-N,N-dibenzoylamino-2,3,6-trideoxy-β-L-lyxo-hexosyl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione 

Relevant articles and documents

Synthesis and cytotoxic activities of a series of novel N -methyl-bisindolylmaleimide amide derivatives

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Friedel-Crafts alkylation on indolocarbazoles catalyzed by two dimethylallyltryptophan synthases from Aspergillus

Prenylated indolocarbazoles have been reported neither from natural sources, nor by chemical synthetic approaches. In this Letter, we report a regiospecific prenylation of indolocarbazoles at the para-position of the indole N-atom by two recombinant enzymes from the dimethylallyltryptophan synthase (DMATS) superfamily, that is, 5-DMATS from Aspergillus clavatus and FgaPT2 from Aspergillus fumigatus.

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Synthesis and Characterization of the Selective, Reversible PKCβ Inhibitor (9 S)-9-[(Dimethylamino)methyl]-6,7,10,11-tetrahydro-9 H,18 H-5,21:12,17-dimethenodibenzo[ e,k]pyrrolo[3,4- h][1,4,13]oxadiazacyclohexadecine-18,20(19 H)-dione, Ruboxistaurin (LY333531)

The demonstrated role of PKCβ in mediating amphetamine-stimulated dopamine efflux, which regulates amphetamine-induced dopamine transporter trafficking and activity, has promoted the research use of the selective, reversible PKCβ inhibitor (9S)-9-[(dimethylamino)methyl]-6,7,10,11-tetrahydro-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione, ruboxistaurin. Despite the interest in development of ruboxistaurin as the mesylate monohydrate (Arxxant) for the treatment of diabetic retinopathy, macular edema, and nephoropathy, several crucial details in physicochemical characterization were erroneous or missing. This report describes the synthesis and full characterization of ruboxistaurin free base (as a monohydrate), including X-ray crystallography to confirm the absolute configuration, and of the mesylate salt, isolated as a hydrate containing 1.5 mol of water per mole.

3. 4 - b (3 - indole) - 2, 5 - dione -3 - pyrroline imine compound and its preparation method and application

The invention discloses a 3,4-bi(3-indole)-2,5-dione-3-pyrrolineimine compound, a preparation method of the compound and application of the compound in an anti-cancer drug. The key points of the technical scheme are that the 3,4-bi(3-indole)-2,5-dione-3-pyrrolineimine compound is prepared by taking an aldehyde compound R-CHO and 1-amino-3,4-bi(3-indole)-3-pyrroline-2,5-dione with the structural formula which is as shown in the specification as raw materials; and the general structural formula of the compound is as shown in the specification. The invention also discloses a method for preparing the 3,4-bi(3-indole)-2,5-dione-3-pyrrolineimine compound and application of the compound in the anti-cancer drug. According to the preparation method disclosed by the invention, the raw materials are low in price and readily available, the operation is simple, and the prepared 3,4-bi(3-indole)-2,5-dione-3-pyrrolineimine compound has high biological activity and has good application prospects in the preparation of anti-cancer drug compounds.