Protein kinase inhibitors - potential chemotherapeutic agents

• Autorzy: Shugar D.
• Języki publikacji: EN

Abstrakty

EN

Protein kinase inhibitors, widely exploited for elucidation of the biological functions of kinases, have more recently come under active consideration as potential chemo­therapeutic agents for tumour and other diseases. A brief overview is presented of diverse approaches to the design and development of selective protein kinase inhi­bitors, and related problems such as donor and acceptor specificities, stereochemical aspects, emerging relationships between protein, sugar and nucleoside kinases. In particular, and contrary to popular belief that ATP-competitive inhibifcrs cannot be selective because of the close homology of the ATP catalytic sites, numerous examples are presented of such inhibitors which are both potent and selective for a given kinase or class of kinases. Some of these are undergoing preclinical trials. Attention is also directed to the role of cellular and viral protein kinases in the ljfe cycle of viruses, and the potential of these enzymes, especially those encoded by, and essential for repli­cation of, a given virus as targets for antiviral chemotherapy.

Słowa kluczowe

EN

viral kinase; chemotherapeutic agent; inhibitor; protein kinase

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 1995
• Tom: 42
• Numer: 4
• Opis fizyczny: p.405-418,fig.

Twórcy

autor

Shugar D.

• Polish Academy of Sciences, A.Pawinskiego 5a, 02-106 Warsaw, Poland

Bibliografia

• 1. Hunter, T. (1995) 1001 protein kinase redux — towards 2000. Seminar. Cell Biol. 5, 367-376.
• 2. Varmus, H. & Weinberg, R.A. (1993) Genes and the Biology of Cancer. Scientific American Library, New York.
• 3. Lindberg, R.A., Quinn, A.M. & Hunter, T. (1992) Dual-specificity protein kinases: will any hydroxyl do? Trends Biochem. Sci. 17,114-119.
• 4. Kwon, Y.-G., Mendelow, M. & Lawrence, D.S. (1994) The active site substrate specificity of protein kinase C. J. Am. Chem. Soc. 269, 4839-4844.
• 5. Shugar, D. (1992) Phosphorylating enzymes involved in activation of chemotherapeutic nucleosides and nucleotides; in Molecular Aspects of Chemotherapy (Shugar, D., Rode, W. & Borowski, E., eds.) pp. 239-270, Springer- Verlag, Berlin, New York.
• 6. Dekker, L.V. & Parker, P.J. (1994) Protein kinase C — a question of specificity. Trends Biochem. Sci. 19,73-77.
• 7. Adams, V., Schieber, A. & McCabe, E.R.B. (1994) Hexokinase autophosphorylation: Identifi­cation of a new dual specificity kinase. Biochem. Med. Metabol. Biol. 53,80-86.
• 8. Shugar, D. (1994) Development of inhibitors of protein kinases CK-I and CK-II, and some related aspects, including donor and acceptor specificities, and viral protein kinases. Cell. Mol. Biol Res. 40,411^19.
• 9. Shugar, D. (1995) Protein kinases — enticing targets for antiviral agents. Int. Antiviral News 3, 4-6.
• 10. Burke, T.R., Jr. (1992) Protein-tyrosine kinase inhibitors. Drugs of the Future 17,119-131.
• 11. Broom, A.D. (1989) Rational design of enzyme inhibitors: Multisubstrateanalogue inhibitors./. Med. Chem. 32, 2-7.
• 12. Wang, S., Zaharevitz, D.W., Sharma, R., Mar- quez, V.E., Lewin, N.E., Du, L., Blumberg, P.M. & Milne, G.W.A. (1994) The discovery of novel structurally diverse protein kinase C agonists through computer 3D-database pharma­cophore search. Molecular modeling studies. /. Med. Chem. 37,4479-4489.
• 13. Matthews, H.R. (1995) Protein kinases and phosphatases that act on histidine, lysine or arginine residues in eukaryotic proteins: A possible regulator of the mitogen-activated protein kinase cascade. Pharmacol. Ther. 67, 323-350.
• 14. Baltensperger, K., Lewis, R.E., Woon, C.-W., Vissavajhala, P., Ross, A.H. & Czech, M.P. (1992) Catalysis of serine and tyrosine autophos­phorylation by the human insulin receptor. Proc. Natl. Acad. Sci. U.S.A. 89, 7885-7889.
• 15. Pinna, L.A., Meggio, F. & Sarno, S. (1995) Casein kinase-2 and cell signaling; in Biochemistry of Cell Membranes (Papa, S. & Tager, J.M., eds.) pp. 15- -27, Birkhauser Verlag, Basel.
• 16. Pinna, L.A. (1990) Casein kinase-2; an eminence grise in cellular regulation? Biochim. Biophys. Acta 1054, 267-284.
• 17. Tuazon, P.T. & Traugh, J.A. (1991) Casein kinases I and II—multi-potential serine protein kinases: structure, function and regulation. Adv. Sec. Messenger Phosphoryl. Res. 23,123-164.
• 18. Zandomeni, R., Zandomeni, M.C., Shugar, D. & Weinmann, R. (1986) Casein kinase type II is involved in the inhibition by 5,6-dichloro- -1-p-D-ribofuranosylbenzimidazole of specific RNA polymerase II transcription. J. Biol. Chem. 26,3414-3419.
• 19. Horikoshi, M., Nakanishi, Y., Hirashima, Y., Ohtsuki, M. Kobayashi, T. & Notari, S. (1987) Phosphorylation of S-II, a eukaryotic transcrip­tion factor, by casein kinase II. Chem. Pharm. Bull. (Japan) 35,4181-4187.
• 20. Meggio, F., Shugar, D. & Pinna, L.A. (1990) Ribofuranosylbenzimidazole derivatives as inhibitors of casein kinase-2 and casein kinase-1. Eur. J. Biochem. 187,89-94.
• 21. Dobrowolska, G., Muszynska, G. & Shugar, D. (1991) Benzimidazole nucleoside analogues as inhibitors of plant (maize seedling) casein kinases. Biochim. Biophys. Acta 1080, 221-226.
• 22. Szyszka, A., Grankowski, N., Felczak, K. & Shugar, D. (1995) Halogenated benzimidazoles and benzotriazoles as selective inhibitors of protein kinases CK-I and CK-II from Sac- charomyces cerevisiae and other sources. Biochem. Biophys. Res. Commun. 208,418-424.
• 23. Hidaka, H., Watanabe, M. & Kobayashi, R. (1991) Properties and use of H-series of com­pounds as protein kinase inhibitors. Methods Enzymol. 201,328-339.
• 24. Egyhazi, E., Ossoinak, A., Tayip, U., Kazi- mierczuk, Z. & Shugar, D. (1982) Specific inhi­bition of hnRNA synthesis by 5,6-dichloro- -l-p-D-ribofuranosylbenzimidazole. Require­ment of a free 3'-hydroxyl group, but not 2'- or 5'-hydroxyls. Biochim. Biophys. Acta 697, 213-220.
• 25. Vesely, J., Havlicek, L., Strnad, M., Blow, J.J., Donella-Deana, A., Pinna, L., Letham, D.S., Kato, J.-y., Detivaud, L., Leclerc, S. & Meijer, L. (1994) Inhibition of cyclin-dependent kinases by purine analogues. Eur.}. Biochem. 224, 771-786.
• 26. Hirschmann, R., Smith, A.B. Ill & Sprengeler, PA. (1995) Some interactions of macromo- lecules with low molecular weight ligands. Recent advances in peptidomimetic research; in New Perspectives in Drug Design (Dean, P.M., Jolles, G. & Newton, C.G., eds.) pp. 1-14, Academic Press, New York.
• 27. Ruegg, U.T. & Burgess, G.M. (1989) Stauros- porine, K-252 and UCN-01: potent but non­specific inhibitors of protein kinases. Trends Biochem. Sci. 10,218-220.
• 28. Nakanishi, S., Yamada, K., Iwahashi, K., Kuroda, K. & Kase, H. (1990) KT5926, a potent and selective inhibitor of myosin light chain kinase. Mol. Pharmacol. 37, 482-488.
• 29. Meggio, F., Donella-Deana, A., Ruzzene, M., Brunati, A.M., Cesaro, L., Guerra, B., Meyer, T., Mett, H., Fabbro, D., Furet, P., Dobrowolska, G. & Pinna, L.A. (1995) Different susceptibility of protein kinases to staurosporine inhibition. Kinetic studies and molecular bases for the resistance of protein kinase CK2 (casein kinase-2). Eur. ]. Biochem. in press.
• 30. Basu, A. (1993) The potential of protein kinase C as a target for anticancer treatment. Pharmcol. Ther. 59, 257-280.
• 31. Davis, P.D., Hallam, T.J., Harris, W., Hill, C.H., Lawson, G., Nixon, J.S., Smith, J.L., Vesey, D.R. & Wilkinson, S.E. (1994) Bisindolylmaleimide inhibitors of protein kinase C. Further conformational restriction of a tertiary amine side chain. Bioorg. Medicinal Chem. Lett. 4, 1303-1308.
• 32. Gschwendt, M„ Kittstein, W., Kielbassa, K. & Marks, F. (1995) PKC 8 accepts GTP for auto- phosphorylation. Biochem. Biophys. Res. Com- mun. 206, 614-620.
• 33. Trinks, U., Buchdunger, E., Furet, P., Kump, W., Mett, H., Meyer, T., Muller, M., Regenass, U., Rihs, G., Lydon, N. & Traxler, P. (1994) Diani- linophthalimides: Potent and selective ATP- -competitive inhibitors of the EGF-receptor protein tyrosine kinase. }. Med. Chem. 37, 1015-1027.
• 34. Buchdunger, E., Trinks, U., Mett, H., Regenass, U., Muller, M., Meyer, T., McGlynn, E., Pinna, L.A., Traxler, P. & Lydon, N.B. (1994) 4,5-Diani- linophthalimides: A protein-tyrosine kinase inhibitor with selectivity for the epidermal growth factor receptor signal transduction pathway and potent in vivo antitumour activity. Proc. Natl. Acad. Sci. U.S.A. 91, 2334-2338.
• 35. Hendricks, R.T., Sherman, D., Strulovici, B. & Broka, C.A. (1995) 2-Aryl- indolylmaleimldes — novel and potent inhibitors of PKC. Bioorg. Medicinal Chem. Lett. 5, 67-72.
• 36. Kleinschroth, J., Hartenstein, J., Rudolph, C. & Schachtele, C. (1995) Novel indolocarbazole protein kinase C inhibitors with improved biochemical and physicochemical properties. Bioorg. Medicinal Chem. Lett. 5, 55-60.
• 37. Qatsha, K.A., Rudolph, C., Marme, D., Schachtele, C. & May, A.W. (1993) Go-6976, a selective inhibitor of protein kinase C, is a potent antagonist of human immunodeficiency virus 1 induction from latent/low-level producing reservoir cells in vitro. Proc. Natl. Acad. Sci. U.S.A. 90,4674-4678.
• 38. Ward, W.H.J., Cook, P.N., Slater, A.M., Davies, D.H., Holdgate, G.A. & Green, L.R. (1994) Epidermal growth factor receptor tyrosine kinase: Investigation of catalytic mechanism, structure-based searching, and discovery of a potent inhibitor. Biochem. Pharmcol. 48,659-666.
• 39. Fry, D.W., Kraker,A.J.,McMichael,A.,Ambroso, L.A., Nelson, J.M., Leopold, W.R., Connors, R.W. & Bridges, A.J. (1994) A specific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science 265,1093-1095.
• 40. Leader, D.P. (1993) Viral protein kinases and protein phosphatases. Pharmacol. Ther. 59, 343-389.
• 41. Gao, Y. & Lenard, J. (1995) Multimerization and transcriptional activation of the phospho- protein (P) of vesicular stomatitis virus by casein kinase-II. EMBO }. 14,1240-1247.
• 42. Gupta, A.K., Das, T. & Banerjee, A.K. (1995) Casein kinase II is the P protein phospho- rylating cellular kinase associated with the ribonucleoprotein complex of purified vesicular stomatitis virus. /. Gen. Virol. 76,365-372.
• 43. Hayashi, K. (1992) Effect of protein kinase C inhibitors with different action mechanisms on Epstein-Barr virus replication. Interoirology 33, 217-224.
• 44. Yura, Y„ Yoshida, H. & Sato, M. (1993) Inhibition of herpes simplex virus replication by genistein, an inhibitor of protein-tyrosine kinase. Arch. Virol. 132,451-461.
• 45. Birnbaum, K.B., Stolarski, R. & Shugar, D. (1994) Structure and conformation of Ganciclovir, a broad spectrum antiviral agent. Biochim. Bio­phys. Acta 1200,55-63.
• 46. Lin, S. & Broyles, S.S. (1994) Vaccinia protein kinase 2: A second essential serine/threonine protein kinase encoded by vaccinia virus. Proc. Natl. Acad. Sci. U.S.A. 91, 7653-7657.
• 47. Littler, E., Stuart, A.D. & Chee, M.S. (1992) Human cytomegalovirus UL97 open reading frame encodes a protein that phosphorylates the antiviral nucleoside analogue ganciclovir. Nature 358,160-162.
• 48. Sullivan, V., Talarico, C.L., Stanat, S.C., Davis, M., Coen, D.M. & Biron, K.K. (1992) A protein kinase homologue controls phosphorylation of ganciclovir in human cytomegalovirus-infected cells. Nature 358,162-164.
• 49. Hanson, M.N., Preheim, L.C., Chou, S., Talarico, C.L., Biron, K.K. & Erice, A. (1995) Novel mutation in the UL97 gene of a clinical cytomegalovirus strain conferring resistance to Ganciclovir. Antimicrob. Agents Chemother. 39, 1204-1205.
• 50. Foulkes, J.C., Chow, M., Gorka, C., Frackelton, A.R., Jr. & Baltimore, D. (1985) Purification and characterization of a protein-tyrosine kinase encoded by the Abelsonmurine-leukemia virus. J. Biol. Chem. 260, 8070-8077.