p38 Mitogen-activated protein kinase inhibitors-mechanisms and therapeutic potentials

Pharmacology and Therapeutics

Volumn 82, Issue 2-3, 1999, Pages 389-397

  Lee, John C ^a   Kassis, Shouki ^a   Kumar, Sanjay ^a   Badger, Alison ^a   Adams, Jerry L ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Cytokine signaling; Inflammatory disease; Inhibitors; Mechanism of action; p38 MAP kinase; Pyridinylimidazole

Indexed keywords

4 (4 FLUOROPHENYL) 2 (4 METHYLSULFINYLPHENYL) 5 (4 PYRIDYL)IMIDAZOLE; ADENOSINE TRIPHOSPHATE; CYTOKINE; IMIDAZOLE DERIVATIVE; MITOGEN ACTIVATED PROTEIN KINASE; MITOGEN ACTIVATED PROTEIN KINASE INHIBITOR; PYRIDINYLIMIDAZOLE DERIVATIVE; SYNAPTOPHYSIN; UNCLASSIFIED DRUG;

ANIMAL MODEL; ARTHRITIS; ARTHROPATHY; BINDING SITE; CONFERENCE PAPER; DRUG MECHANISM; DRUG SELECTIVITY; ENZYME SUBSTRATE; HEART MUSCLE INJURY; INFLAMMATION; INFLAMMATORY DISEASE; NONHUMAN; PRIORITY JOURNAL; PROTEIN FAMILY; SEPTIC SHOCK; SIGNAL TRANSDUCTION; SITE DIRECTED MUTAGENESIS; X RAY CRYSTALLOGRAPHY;

CHEMOKINES; ENZYME INHIBITORS; FORECASTING; IMIDAZOLES; INFLAMMATION; MITOGEN-ACTIVATED PROTEIN KINASE KINASES; MITOGENS; MOLECULAR STRUCTURE; PROTEIN BINDING; PYRIDINES; PYRIDINIUM COMPOUNDS; SEQUENCE HOMOLOGY, AMINO ACID;

EID: 0033030207     PISSN: 01637258     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0163-7258(99)00008-X     Document Type: Conference Paper

References (67)

1. Adams J.L., Boehm J.C., Kassis S., Gorycki P.D., Webb E.F., Hall R., Sorenson M., Lee J.C., Ayrton A., Griswold D.E., Gallagher T.F. Pyrimidinylimidazole inhibitors of CSBP/p38 kinase demonstrating decreased inhibition for hepatic cytochrome P450 enzymes. Bioorg. Med. Chem. Lett. 8:1998;3111-3116.
2. Badger A.M., Bradbeer J.N., Votta B., Lee J.C., Adams J.L., Griswold D.E. Pharmacological profile of SB 203580, a selective inhibitor of CSBP/p38 kinase, in animal models of arthritis, bone resorption, endotoxin shock and immune function. J. Pharmacol. Exp. Ther. 279:1996;1453-1461.
3. Badger A.M., Cook M.N., Lark M.W., Newman-Tarr T.M., Swift B.A., Nelson A.H., Barone F.C., Kumar S. SB 203580 inhibits p38 mitogen-activated protein kinase, nitric oxide production, and inducible nitric oxide synthase in bovine cartilage-derived chondrocytes. J. Immunol. 161:1998;467-473.
4. Ben-Levy R., Hooper S., Wilson R., Paterson H.F., Marshall C.J. Nuclear export of the stress-activated protein kinase p38 mediated its substrate MAPKAP kinase-2. Curr. Biol. 8:1998;1049-1057.
5. Boehm J.C., Smietana J.M., Sorenson M.E., Garigipati R.S., Gallagher T.F., Sheldrake P.L., Bradbeer J., Badger A.M., Laydon J.T., Lee J.C., Hillegass L.M., Griswold D.E., Breton J.J., Chabotfletcher M.C., Adams J.L. 1-Substituted 4-aryl-5-pyridinylimidazoles - a new class of cytokine suppressive drugs with low 5-lipoxygenase and cyclooxygenase inhibitory potency. J. Med. Chem. 39:1996;3929-3937.
6. c-src tyrosine kinase reactions. Biochemistry. 34:1995;16419-16423.
7. Cobb M.H., Goldsmith E.J. How MAP kinases are regulated. J. Biol. Chem. 270:1995;14843-14846.
8. Cook P.F., Neville M.E. Jr., Vrana K.E., Hartl F.T., Roskoski R. Jr. Adenosine cyclic 3′-5′-monophosphate dependent protein kinase. kinetic mechanism for the bovine skeletal muscle catalytic subunit Biochemistry. 21:1982;5794-5799.
9. Cuenda A., Rouse J., Doza Y.N., Meier R., Cohen P., Gallagher T.F., Young P.R., Lee J.C. SB 203580 is a specific inhibitor of a MAP kinase homologue which is stimulated by cellular stresses and interleukin-1. FEBS Lett. 364:1995;229-233.
10. Cuenda A., Cohen P., Bu'ee-Scherrer V., Goedert M. Activation of stress-activated protein kinase-3 (SAPK3) by cytokines and other cellular stresses is mediated by SAPKK3 (MKK6), comparison of the specificities of SAPK3 and SAPK2 (RK/p38). EMBO J. 16:1997;295-305.
11. Deak M., Clifton A.D., Lucocq J.M., Alessi D.R. Mitogen- and stress-activated protein kinase-1 (MSK1) is directly activated by MAPK and SAPK2/p38, and may mediate activation of CREB. EMBO J. 17:1998;4426-4441.
12. de Laszlo S.E., Visco D., Agarwal L., Chang L., Chin J., Croft G., Forsyth A., Fletcher D., Frantz B., Hacker C., Hanlon W., Harper C., Kostura M., Li B., Luell S., MacCoss M., Mantlo N., O'Neill E.A., Orevillo C., Pang M., Parsons J., Rolando A., Sahly Y., Sidler K., Widmer W.R., O'Keefe S.J. Pyrroles and other heterocyles as inhibitor of p38 kinase. Bioorg. Med. Chem. Lett. 8:1998;2689-2694.
13. Derijard B., Hib I.M., Wu I.-H., Barrett T., Su B., Deng T., Karin M., Davis R.J. JNK1. a protein kinase stimulated by UV light and H-Ras that binds and phosphorylates the c-jun activation domain Cell. 76:1994;1025-1037.
14. Derijard B., Raingeaud J., Barrett T., Wu I.H., Han J., Ulevitch R.J., Davis R.J. Independent human MAP kinase signal transduction pathways defined by MEK and MKK isoforms. Science. 267:1995;682-685.
15. Enslen H., Raingeaud J., Davis R.J. Selective activation of p38 mitogen-activated protein (MAP) kinase isoforms by the MAP kinase kinases MKK3 and MKK6. J. Biol. Chem. 273:1998;1741-1748.
16. Eyers P.A., Craxton M., Morrice N., Cohen P., Goedert M. Conversion of SB 203580-insensitive MAP kinase family members to drug-sensitive forms by a single amino-acid substitution. Chem. Biol. 5:1998;321-328.
17. Frantz B., Klatt T., Pang M., Parsons J., Rolando A., Williams H., Tocci M.J., O'Keefe S.J., O'Neill E.A. The activation state of p38 mitogen-activated protein kinase determines the efficiency of ATP competition of pyridinylimidazole inhibitor binding. Biochemistry. 37:1998;13846-13853.
18. Freshney N.W., Rawlinson L., Guesdon F., Jones E., Cowley S., Hsuan J., Saklatvala J. Interleukin-l activates a novel protein kinase cascade that results in the phosphorylation of Hsp27. Cell. 78:1994;1039-1049.
19. Fukunaga R., Hunter T. MNK1. a new MAP kinase-activated protein kinase, isolated by a novel expression screening method for identifying protein kinase substrates EMBO J. 16:1997;1921-1933.
20. Gallagher T.F., Seibel G.L., Kassis S., Laydon J.T., Lee J.C., Lee D., Boehm J.C., Bender P.E., Erhard K.F., Krog A.J., Hofmann G.A., Adams J.L. Regulation of stress-induced cytokine production by pyridinylimidazoles. inhibition of CSBP kinase Bioorg. Med. Chem. 5:1997;49-64.
21. Gille H., Sharrocks A.D., Shaw P. Phosphorylation of transcription factor p62TCF by MAP kinase stimulates ternary complex formation at c-fos promoter. Nature. 358:1992;414-417.
22. Goedert M., Cuenda A., Craxton M., Jakes R., Cohen P. Activation of the novel stress-activated protein kinase SAPK4 by cytokines and cellular stresses is mediated by SKK3 (MKK6) - comparison of its substrate specificity with that of other SAP kinases. EMBO J. 16:1997;3563-3571.
23. Gum R.J., McLaughlin M.M., Kumar S., Wang Z.L., Bower M.J., Lee J.C., Adams J.L., Livi G.P., Goldsmith E.J., Young P.R. Acquisition of sensitivity of stress-activated protein kinases to the p38 inhibitor, SB 203580, by alteration of one or more amino acids within the ATP binding pocket. J. Biol. Chem. 273:1998;15605-15610.
24. Han J., Lee J.-D., Bibb S.L., Ulevitch R.J. A MAP kinase targeted by endotoxin and in mammalian cells. Science. 265:1994;808-811.
25. Han J., Lee J.-D., Jiang Y., Li Z., Feng L., Ulevitch R.J. Characterization of the structure and function of a novel MAP kinase kinase (MKK6). J. Biol. Chem. 271:1996;2886-2891.
26. Han J., Jiang Y., Li Z., Kravchenko V.V., Ulevitch R.J. Activation of the transcription factor MEF2C by the MAP kinase p38 in inflammation. Nature. 386:1997;296-299.
27. Hanks S., Quinn A.M. Protein kinase catalytic domain sequence database. identification of conserved features of primary structure and classification of family members Methods Enzymol. 200:1991;38-62.
28. Hanson G.J. Inhibitors of p38 kinase. Expert Opin. Ther. Patents. 7:1997;729-733.
29. Henry J.R., Rupert K.C., Dodd J.H., Turchi I.J., Wadsworth S.A., Cavender D.E., Fahmy B., Olini G.C., Davis J.E., Pellegrino-Gensey J.L., Schafer P.H., Siekierka J.J. 6-Amino-2-(4-fluorophenyl)-4-methoxy-3-(4-pyridyl)-1H-pyrrolo[2,3-b]pyridine (RWJ 68354). a potent and selective p38 kinase inhibitor J. Med. Chem. 41:1998;4196-4198.
30. Jackson J.R., Bolognese B., Hillegass L., Kassis S., Adams J., Griswold D.E., Winkler J.D. Pharmacological effects of SB 220025, a selective inhibitor of p38 mitogen-activated protein kinase, in angiogenesis and chronic inflammatory disease models. J. Pharmacol. Exp. Ther. 284:1998;687-692.
31. Jiang Y., Gra H., Zhao M., New L.G., Gu J., Feng L.L., Dipadova F., Ulevitch R.J., Han J.H. Characterization of the structure and function of the fourth member of p38 group of mitogen-activated protein kinases. J. Biol. Chem. 272:1997;30122-30128.
32. Kracht M., Shiroo M., Marshall C.J., Hsuan J.J., Saklatvala J. Interleukin-1 activates a novel protein kinase that phosphorylates the epidermal-growth-factor receptor peptide T669. Biochem. J. 302:1994;897-905.
33. Kumar S., McLaughlin M.M., McDonnell P.C., Lee J.C., Livi G.P., Young P.R. Human mitogen-activated protein kinase CSBP1, but not CSBP2, complements a hog1 deletion in yeast. J. Biol. Chem. 270:1995;29043-29046.
34. Kumar S., McDonnell P.C., Gum R.J., Hand A.T., Lee J.C., Young P.R. Novel homologues of CSBP/p38 MAP kinase. activation, substrate specificity and sensitivity to inhibition by pyridinyl imidazoles Biochem. Biophys. Res. Commun. 235:1997;533-553.
35. Kyriakis J.M., Banerjee P., Nikolakak E., Dai I.T., Rubi E.A.E., Ahmad M.F., Avruch J., Woodgett J.R. The stress activated protein kinase subfamily of c-Jun kinases. Nature. 369:1994;156-160.
36. Lee J.C., Young P.R. Role of CSBP/p38/RK stress response kinase in LPS and cytokine signaling mechanisms. J. Leukocyte Biol. 59:1996;152-157.
37. Lee J.C., Griswold D.E., Votta B., Hamma N. Inhibition of monocyte IL-1 production by the anti-inflammatory compound, SK&F 86002. Int. J. Immunopharmacol. 10:1988;835-843.
38. Lee J.C., Rebar L., Laydon J.T. Effect of SK&F 86002 on cytokine production by human monocytes. Agents Actions. 27:1989;277-279.
39. Lee J.C., Votta B., Dalton B.J., Griswold D.E., Bender P.E., Hanna N. Inhibition of human monocyte IL-1 production by SK&F 86002. Int. J. Immunother. VI: 1-12:1990.
40. Lee J.C., Badger A.M., Griswold D.E., Dunnington D., Truneh A., Votta B., White J.R., Young P.R., Bender P.E. Bicyclic imidazoles as a novel class of cytokine biosynthesis inhibitors. Ann. NY Acad. Sci. 696:1993;149-170.
41. Lee J.C., Laydon J.T., McDonnell P.C., Gallagher T.F., Kumar S., Green D., McNulty D., Blumenthal M.J., Heys J.R., Landvatter S.W., Strickler J.E., McLaughlin M.M., Siemens I.R., Fisher S.M., Livi G.P., White J.R., Adams J.L., Young P.R. A protein kinase involved in the regulation of inflammatory cytokine biosynthesis. Nature. 372:1994;739-746.
42. Li Z.J., Jiang Y., Ulevitch R.J., Han J.H. The primary structure of p38-gamma - a new member of p38 group of MAP kinases. Biochem. Biophys. Res. Commun. 228:1996;334-340.
43. Lin A., Minden A., Martinetto H., Claret F.-X., Lange-Carter C., Mercurio F., Johnson G.L., Karin M. Identification of a dual specificity kinase that activates the Jun kinases and p38-Mpk2. Science. 268:1995;286-290.
44. LoGrasso P.V., Frantz B., Rolando A.H., O'Keefe S.J., Hermes J.D., O'Neill E.A. Kinetic mechanism for p38 MAP kinase. Biochemistry. 36:1997;10422-10427.
45. McLaughlin M.M., Kumar S., McDonnell P.C., Van Horn S., Lee J.C., Livi G.P., Young P.R. Identification of MAPKAP kinase-3, a novel substrate of CSBP/p38 MAP kinase. J. Biol. Chem. 271:1996;8488-8492.
46. Mertens S., Craxton M., Goedert M. SAP kinase-3, a new member of the family of mammalian stress-activated protein kinases. FEBS Lett. 383:1996;273-276.
47. New L., Jiang Y., Zhao M., Liu K., Zhu W., Flood L.J., Kao Y., Perry G.C.N., Han J.H. PRAK, a novel protein kinase regulated by the p38 MAP kinase. EMBO J. 17:1998;3372-3384.
48. Parker C.G., Hunt J., Diener K., Mcginley M., Soriano B., Kessler G.A., Bray J., Yao Z.B., Wang X.S., Kohno T., Lichenstein H.S. Identification of stathmin as a novel substrate for p38 delta. Biochem. Biophys. Res. Commun. 249:1998;791-796.
49. Posner I., Engel M., Levitzki A. Kinetic model of the epidermal growth factor (EGF) receptor tyrosine kinase and a possible mechanism of its activation by EGF. J. Biol. Chem. 267:1992;20638-20647.
50. Preville X., Schultz H., Knauf U., Gaestel M., Arrigo A.P. Analysis of the role of Hsp25 phosphorylation reveals the importance of the oligomerization state of this small heat shock protein in its protective function against TNFalpha- and hydrogen peroxide-induced cell death. J. Cell. Biochem. 69:1998;436-452.
51. Raingeaud J., Gupta S., Rogers J.S., Dickens M., Han J., Ulevitch R.J., Davis R.J. Pro-inflammatory cytokines and environmental stress cause p38 mitogen-activated protein kinase activation by dual phosphorylation on tyrosine and threonine. J. Biol. Chem. 270:1995;7420-7426.
52. Raingeaud J., Whitmarsh A.J., Barrett T., Derijard B., Davis R.J. MKK3- and MKK6-regulated gene expression is mediated by the p38 mitogen-activated protein kinase signal transduction pathway. Mol. Cell. Biol. 16:1996;1247-1255.
53. Rouse J., Cohen P., Trigon S., Morange M., Alonso-Llamazares A., Zamanillo D., Hunt T., Nebreda A.R. Identification of a novel protein kinase cascade stimulated by chemical stress and heat shock which activates MAP kinase-activated protein MAPKAP kinase-2 and induces phosphorylation of the small heat shock proteins. Cell. 78:1994;1027-1037.
54. Sanchez I., Hughes R.T., Mayer B.J., Yee K., Woodgett J.R., Avruch J., Kyriakis J.M., Zon L.I. Role of SAPK/ERK kinase-1 in the stress-activated pathway regulating transcription factor c-jun. Nature. 372:1994;794-798.
55. Stein B., Yang M.X., Young D.B., Janknecht R., Hunter T., Murray B.W., Barbosa M.S. p38-2, a novel mitogen-activated protein kinase with distinct properties. J. Biol. Chem. 272:1997;19509-19517.
56. Tong L., Pav S., White D.H., Rogers S., Crane K.M., Cywin C.L., Brown M.L., Pargellis C.A. A highly specific inhibitor of human p38 HAP kinase binds in the ATP pocket. Nature Struct. Biol. 4:1997;311-316.
57. Votta B.J., Bertolini D.R. Cytokine suppressive antiinflammatory compounds inhibit bone resorption in vitro. Bone. 15:1994;533-538.
58. Wang X., Flynn A., Waskiewicz A.J., Webb B.L., Vries R.C., Baines I.A., Cooper J.A., Proud C. The phosphorylation of eukaryotic initiation factor eIF4E in response to phorbol esters, cell stresses, and cytokines is mediated by distinct MAP kinase pathways. J. Biol. Chem. 273:1998;9373-9377.
59. Wang X.Z., Ron D. Stress-induced phosphorylation and activation of the transcription factor CHOP (GADDl53) by p38 HAP kinase. Science. 272:1996;1347-1349.
60. Wang Z., Harkins P.C., Ulevitch R.J., Han J., Cobb M.H., Goldsmith E.J. The structure of mitogen activated protein kinase p38 at 2.1 Å resolution. Proc. Natl. Acad. Sci. 94:1997;2327-2332.
61. Wang Z.L., Canagarajah B.J., Boehm J.C., Kassis S., Cobb M.H., Young P.R., Abdel-Meguid S., Adams J.L., Goldsmith E.J. Structural basis of inhibitor selectivity in MAP kinases. Structure. 6:1998;1117-1128.
62. Waskiewicz A.J., Flynn A., Proud C.G., Cooper J.A. Mitogen-activated protein kinases activate the serine/threonine kinases MNK1 and MNK2. EMBO J. 16:1997;1909-1920.
63. Wen W., Meinkoth J.L., Tsien R.Y., Taylor S.S. Identification of a signal for rapid export of proteins from the nucleus. Cell. 82:1995;463-473.
64. Wilson K.P., Fitzgibbon M.J., Caron P.N., Griffith J.P., Chen W.Y., McCaffrey P.G., Chambers S.P., Su M.S.S. Crystal structure of p38 mitogen-activated protein kinase. J. Biol. Chem. 271:1996;27696-27700.
65. Wilson K.P., McCaffrey P.G., Hsiao K., Pazhanisamy S., Galullo V., Bemis G.W., Fitzgibbon M.J., Caron P.R., Murcko H.A., Su M.S.S. The structural basis for the specificity of pyridinylimidazole inhibitors of p38 MAP kinase. Chem. Biol. 4:1997;423-431.
66. Young P.R., McDonnell P., Dunnington D., Hand A., Laydon J., Lee J.C. Bicyclic imidazoles inhibit IL-1 and TNF production at the protein level. Agents Actions. 39:1993;C67-C69.
67. Young P.R., McLaughlin M.M., Kumar S., Kassis S., Doyle M.L., McNulty D., Gallagher T.F., Fisher S., McDonnell P.C., Carr S.A., Huddleston M.J., Seibel G., Porter T.G., Livi G.P., Adams J.L., Lee J.C. Pyridinyl imidazole inhibitors of p38 MAP kinase bind in the ATP site. J. Biol. Chem. 272:1997;12116-12121.