557520
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).
别名:
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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关于此项目
经验公式（希尔记法）:
C25H23N5O2S · xCH4O3S
化学文摘社编号:
分子量:
457.55 (free base basis)
MDL number:
UNSPSC Code:
12352202
NACRES:
NA.77
Assay:
≥95% (HPLC)
Form:
solid
Storage condition:
OK to freeze, desiccated (hygroscopic), protect from light
Quality Segment
assay
≥95% (HPLC)
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze, desiccated (hygroscopic), protect from light
color
red
solubility
DMSO: 100 mg/mL, water: 1 mg/mL
shipped in
ambient
storage temp.
2-8°C
SMILES string
[S](=O)(=O)(O)C.S(CCC[n]1c2c(c(c1)C3=C(C(=O)NC3=O)c4c5c([n](c4)C)cccc5)cccc2)\C(=N\[H])\N
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
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)
Preparation Note
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.
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
Disclaimer
Toxicity: Standard Handling (A)
存储类别
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable