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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:
138489-18-6
Molecular Weight:
553.65
MDL number:
MFCD03788207
UNSPSC Code:
12352200
PubChem Substance ID:
329824000
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

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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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