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Merck
CN

R136

Ro 31-8220 methanesulfonate salt

solid

Synonym(s):

2-{1-[3-(Amidinothio)propyl]-1H-indol-3-yl}-3-(1-methylindol-3-yl)maleimide methanesulfonate salt, Bisindoylmaleimidine IX

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About This Item

Linear Formula:
C25H23N5O2S · CH3SO3H
CAS Number:
138489-18-6
Molecular Weight:
553.65
NACRES:
NA.77
PubChem Substance ID:
329824000
UNSPSC Code:
12352200
MDL number:
MFCD03788207

Key Documents

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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)

SMILES string

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

InChI key

SAWVGDJBSPLRRB-UHFFFAOYSA-N

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

solid

color

orange to red

solubility

H2O: 7.3 mg/mL

storage temp.

2-8°C

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.

Disclaimer

Photosensitive

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCP0157
SLCN5293
SLCM9461
SLCF4538
SLCC3838

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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)
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
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
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)
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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