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R136

Sigma-Aldrich

Ro 31-8220 methanesulfonate salt

solid

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Synonym(s):
2-{1-[3-(Amidinothio)propyl]-1H-indol-3-yl}-3-(1-methylindol-3-yl)maleimide methanesulfonate salt, Bisindoylmaleimidine IX
Linear Formula:
C25H23N5O2S · CH3SO3H
CAS Number:
Molecular Weight:
553.65
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

solid

color

orange to red

solubility

H2O: 7.3 mg/mL

storage temp.

2-8°C

SMILES string

CS(O)(=O)=O.Cn1cc(C2=C(C(=O)NC2=O)c3cn(CCCSC(N)=N)c4ccccc34)c5ccccc15

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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557520557514557508
Ro 31-8220 methanesulfonate salt solid

R136

Ro 31-8220 methanesulfonate salt

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).

557520

Ro-31-8220

Ro-31-8425 A potent, cell-permeable, reversible, ATP-competitive, and selective protein kinase C inhibitor (IC₅₀ = 15 nM for rat brain PKC).

557514

Ro-31-8425

Ro-31-7549, Monohydrate A cell permeable, reversible, selective protein kinase C (PKC) inhibitor (IC₅₀ = 158 nM for rat brain PKC) that acts at the ATP binding site of PKC.

557508

Ro-31-7549, Monohydrate

form

solid

form

solid

form

solid

form

solid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

H2O: 7.3 mg/mL

solubility

water: 1 mg/mL, DMSO: 100 mg/mL

solubility

DMSO: 10 mg/mL

solubility

DMSO: 5 mg/mL

color

orange to red

color

red

color

red to orange-red

color

red to red-orange

biological source

synthetic (organic)

biological source

-

biological source

-

biological source

-

General description

Ro 31-8220 is a bisindolylmaleimide derivative of staurosporine. Ro 31-8220 blocks MAP kinase phosphatase-1 (MKP-1) expression, induces c-Jun expression and stimulates Jun N-terminal Kinase (JNK1). It has immunosuppressive properties.

Biochem/physiol Actions

Inhibitor of GRK-5 (G protein-coupled receptor kinase); PKC (protein kinase C); MAPKAP kinase 1β and p70 S6 kinase.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the GRKs, GSK-3, MAPKAPs and PKC pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Caution

Photosensitive

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Ro 31-8220, A Novel Protein Kinase C Inhibitor, Inhibits Early And Late T Cell Activation Events1
Geiselhart L, et al.
Transplantation, 61(11), 1637-1642 (1996)
D R Alessi
FEBS letters, 402(2-3), 121-123 (1997-02-03)
The protein kinase C (PKC) inhibitors Ro 318220 and GF 109203X have been used in over 350 published studies to investigate the physiological roles of PKC. Here we demonstrate that these inhibitors are not selective for PKC isoforms as was
J Beltman et al.
The Journal of biological chemistry, 271(43), 27018-27024 (1996-10-25)
The role of protein kinase C (PKC) in inflammation, mitogenesis, and differentiation has been deduced in part through the use of a variety of PKC inhibitors. Two widely used inhibitors are the structurally related compounds GF109203X and Ro-31-8220, both of
The selective protein kinase C inhibitor, Ro-31-8220, inhibits mitogen-activated protein kinase phosphatase-1 (MKP-1) expression, induces c-Jun expression, and activates Jun N-terminal kinase
Beltman J, et al.
The Journal of Biological Chemistry, 271(43), 27018-27024 (1996)
Inhibition of PTH desensitization by inhibition of the G protein-coupled receptor kinase-5 enzyme with Ro 32-0432.
Moore, J.B., et al.
Faseb Journal, 12, A741-A741 (1998)

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