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557520

Ro-31-8220

Name: Ro-31-8220
Brand: MM

A cell-permeable, reversible, competitive, and selective inhibitor of protein kinase C (PKC; IC₅₀ = 10 nM) over CaM kinase II (IC₅₀ = 17 µM) and protein kinase A (IC₅₀ = 900 nM).

Synonym(s):

Ro-31-8220, 3-[1-[3-(Amidinothio)propyl-1H-indol-3-yl]-3-(1-methyl-1H-indol-3-yl)maleimide, Bisindolylmaleimide IX, Methanesulfonate

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About This Item

Empirical Formula (Hill Notation):

C₂₅H₂₃N₅O₂S · xCH₄O₃S

CAS Number:

138489-18-6

Molecular Weight:

457.55 (free base basis)

UNSPSC Code:

12352200

Quality Level

100

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze
desiccated (hygroscopic)
protect from light

color

red

solubility

water: 1 mg/mL
DMSO: 100 mg/mL

shipped in

ambient

storage temp.

2-8°C

InChI

1S/C25H23N5O2S.CH4O3S/c1-29-13-17(15-7-2-4-9-19(15)29)21-22(24(32)28-23(21)31)18-14-30(11-6-12-33-25(26)27)20-10-5-3-8-16(18)20;1-5(2,3)4/h2-5,7-10,13-14H,6,11-12H2,1H3,(H3,26,27)(H,28,31,32);1H3,(H,2,3,4)

InChI key

SAWVGDJBSPLRRB-UHFFFAOYSA-N

General description

A cell-permeable, competitive, reversible, and selective inhibitor of protein kinase C (PKC; IC₅₀ = 10 nM) over CaM kinase II (IC₅₀ = 17 µM) and protein kinase A (IC₅₀ = 900 nM). Potently inhibits GSK-3 in primary adipocytes (IC₅₀ = 6.8 nM) and in GSK-3β immunoprecipitates (IC₅₀ 2.8 nM). An inhibitor of MAP kinase phosphatase-1 expression and an activator of JNK1. Inhibits the phosphorylation of Raf-1 and induces apoptosis, independent of its effects on PKC, in HL-60 cells. Also inhibits sirtuin in a NAD-competitive manner (IC₅₀ = 3.5 µM and 0.8 µM for SIRT1 and SIRT2, respectively), and induces hyperacetylation of tubulin in A549 cells.

A cell-permeable, reversible, competitive, and selective inhibitor of protein kinase C (PKC; IC₅₀ = 10 nM) over CaM kinase II (IC₅₀ = 17 µM) and protein kinase A (IC₅₀ = 900 nM). Potently inhibits GSK-3 in primary adipocytes (IC₅₀ = 6.8 nM) and in GSK-3β immunoprecipitates (IC₅₀ = 2.8 nM). An inhibitor of MAP kinase phosphatase-1 expression and an activator of JNK1. Inhibits the phosphorylation of Raf-1 and induces apoptosis, independent of its effects on PKC, in HL-60 cells. Also inhibits sirtuin in a NAD-competitive manner (IC₅₀ = 3.5 µM and 0.8 µM for SIRT1 and SIRT2, respectively), and induces hyperacetylation of tubulin in A549 cells. A 5 mM (500 µg/181 µl) solution of Ro-31-8220 (Cat. No. 557521) in H₂O is also available.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
PKC

Product competes with ATP.

Reversible: yes

Target IC₅₀: 10 nM, 17 µM, 900 nM against PKC, CaM kinase II, and protein kinase A, respectively; 6.8 nM against GSK-3 in primary adipocytes; 2.8 nM against GSK-3β immunoprecipitates)

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). DMSO stock solutions are stable for up to 4 months at -20°C.

Other Notes

Trapp, J., et al. 2006. J. Med. Chem.In press.
Powell, D.J., et al. 2003. Mol. Cell Biol.23, 7794.
Han, Z., et al. 2000. Cell Death Differ.7, 521.
Hers, I., et al. 1999. FEBS Lett.460, 433.
Beltman, J., et al. 1996. J. Biol. Chem. 271, 27018.
Keller, H.U., and Niggli, V. 1993. Biochem. Biophys. Res. Commun.194, 1111.
McKenna, J.P., and Hanson, P.J. 1993. Biochem. Pharmacol.46, 583.
Davis, P.D., et al. 1992. J. Med. Chem. 35, 994.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c