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557520

Sigma-Aldrich

Ro-31-8220

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).

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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
Empirical Formula (Hill Notation):
C25H23N5O2S · xCH4O3S
CAS Number:
Molecular Weight:
457.55 (free base basis)

Quality Level

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

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This Item
557514557525557508
vibrant-m

557520

Ro-31-8220

vibrant-m

557514

Ro-31-8425

vibrant-m

557525

Ro-32-0432

vibrant-m

557508

Ro-31-7549, Monohydrate

assay

≥95% (HPLC)

assay

≥94% (HPLC)

assay

≥98% (HPLC)

assay

≥93% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage condition

OK to freeze, protect from light, desiccated (hygroscopic)

storage condition

OK to freeze, protect from light

storage condition

OK to freeze, protect from light

storage condition

OK to freeze, protect from light

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

Not applicable


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Anne Bessard et al.
Hepatology (Baltimore, Md.), 44(1), 152-163 (2006-06-27)
We show that MLCK (myosin light chain kinase) plays a key role in cell cycle progression of hepatocytes: either chemical inhibitor ML7 or RNA interference led to blockade of cyclin D1 expression and DNA replication, providing evidence that MLCK regulated
Virginie Menez et al.
Frontiers in oncology, 13, 1229312-1229312 (2023-10-27)
We previously identified VRK3 as a specific vulnerability in DMG-H3K27M cells in a synthetic lethality screen targeting the whole kinome. The aim of the present study was to elucidate the mechanisms by which VRK3 depletion impact DMG-H3K27M cell fitness. Gene

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