Chymase inhibitors and their therapeutic potential

Drugs of the Future

Volumn 27, Issue 8, 2002, Pages 765-770

  Akahoshi, Fumihiko ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 FLUORO 2,4 DINITROBENZENE; 2 [5 AMINO 2 (4 FLUOROPHENYL) 1,6 DIHYDRO 6 OXO 1 PYRIMIDINYL] N [1 [(5 METHOXYCARBONYL 2 BENZOXAZOLYL)CARBONYL] 2 PHENYLETHYL]ACETAMIDE; ANGIOTENSIN; CANDESARTAN HEXETIL; CHYMASE; CHYMASE INHIBITOR; CHYMOSTATIN; CYPROHEPTADINE; HISTAMINE; HYDANTOIN DERIVATIVE; IMMUNOGLOBULIN E; INTERLEUKIN 1BETA; ISOCOUMARIN DERIVATIVE; N [1 BENZYL 2,3 DIOXO 6 (2 PYRIDYLOXY)HEXYL] 2 (5 FORMYLAMINO 1,6 DIHYDRO 6 OXO 2 PHENYL 1 PYRIMIDINYL)ACETAMIDE; PREDNISOLONE; QUINAZOLINE 2,4 DIONE DERIVATIVE; SACCHARIN; SERINE PROTEINASE INHIBITOR; STEM CELL FACTOR; SUN C8257; TRANSFORMING GROWTH FACTOR BETA1; UNCLASSIFIED DRUG; Y 40018; Y 40079;

ADHESION; ANGIOGENESIS; ATOPIC DERMATITIS; CORONARY ARTERY BYPASS GRAFT; CORONARY ARTERY OBSTRUCTION; HISTAMINE RELEASE; HUMAN; MAST CELL; NONHUMAN; PRURITUS; RESTENOSIS; REVIEW; SKIN ALLERGY; TRANSLUMINAL CORONARY ANGIOPLASTY;

EID: 0036707280     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.2002.027.08.688468     Document Type: Review

References (56)

1. Schechter, N.M. Chymotrypsin-like proteases of human skin mast cells. In: Mast Cell Proteases in Immunology and Biology. Clinical Allergy and Immunology. Caughey, G.H. (Ed). Marcel Dekker: New York 1995, 47-69.
2. Redington, A.E., Polosa, R., Walls, A.F., Howarth, P.H., Holgate, S.T. Role of mast cells and basophils in asthma. In: Human Basophils and Mast Cells: Clinical Aspects, Chemical Immunology. Marone, G. (Ed). Karger AG: Basel 1995, 22-59.
3. Kovanen, P.T. Mast cells in human fatty streaks and atheromas: Implications forintimal lipid accumulation. Curr Opin Lipidol 1996, 7: 281-6.
4. Okunishi, H., Miyazaki, M., Toda, N. Evidence for a putatively new angiotensin II-generating enzyme in the vascular wall. J Hypertens 1984, 2: 277-84.
5. Urata, H., Kinoshita, A., Misono, K.S., Bumpus, F.M., Husain, A. Identification of a highly specific chymase as the major angiotensin II-forming enzyme in the human heart. J Biol Chem 1990, 265: 22348-57.
6. Miyazaki, M., Takai, S. Local angiotensin II-generating system in vascular tissues: The roles of chymase. Hypertens Res 2001, 24: 189-93.
7. Takai, S., Shiota, N., Kobayashi, S., Matsumura, E., Miyazaki, M. Induction of chymase that forms angiotensin II in the monkey atherosclerotic aorta. FEBS Lett 1997, 412: 86-90.
8. Shiota, N., Fukamizu, A., Takai, S., Okunishi, H., Murakami, K., Miyazaki, M. Activation of angiotensin II-forming chymase in the cardiomyopathic hamster heart. J Hypertens 1997, 15: 431-40.
9. Ihara, M., Urata, H., Kinoshita, A. et al. Increased chymase-dependent angiotensin II formation in human atherosclerotic aorta. Hypertension 1999, 33: 1399-405.
10. Kokkonen, J.O., Saarinen, J., Kovanen, P.T. Angiotensin II formation in the human heart: An ACE or non-ACE-mediated pathway? Ann Med 1998, 30 (Suppl. 1): 9-13.
11. Liao, Y., Husain, A. The chymase-angiotensin system in humans: Biochemistry, molecular biology and potential role in cardiovascular diseases. Can J Cardiol 1995, 11 (Suppl. F): 13F-19F.
12. Wypij, D.M., Nichols, J.S., Novak, P.J., Stacy, D.L., Berman, J., Wiseman, J.S. Role of mast cell chymase in the extracellular processing of big-endothelin-1 to endothelin-1 in the perfused rat lung. Biochem Pharmacol 1992, 43: 845-53.
13. Takai, S., Shiota, N., Jin, D., Miyazaki, M. Chymase processes big-endothelin-2 to endothelin-2-(1-31) that induces contractile responses in the isolated monkey trachea. Eur J Pharmacol 1998, 358: 229-33.
14. Lindstedt, K.A., Wang, Y., Shiota, N. et al. Activation of paracrine TGF-β1 signaling upon stimulation and degranulation of rat serosal mast cells: A novel function for chymase. FASEB J 2001, 15: 1377-88.
15. Kato, Y., Kido, H., Fukusen, N., Katunuma, N. Peptide boronic acids, substrate analogs, inhibit chymase and histamine release from rat mast cells. J Biochem 1988, 103: 820-2.
16. Shaoheng, H., Walls, A.F. Human mast cell chymase induces the accumulation of neutrophils, eosinophils and other inflammatory cells in vivo. Br J Pharmacol 1998, 125: 1491-500.
17. Mizutani, H., Schechter, N., Lazarus, G., Black, R.A., Kupper, T.S. Rapid and specific conversion of precursor interleukin 1beta (IL-1β) to an active IL-1 species by human mast cell chymase. J Exp Med 1997, 174: 821-5.
18. Brattsand, M., Egelrud, T. Purification and characterization of interleukin 1β from human plantar stratum corneum. Evidence of interleukin 1β processing in vivo not involving interleukin 1beta convertase. Cytokine 1998, 10: 506-13.
19. Longley, B.J., Tyrrell, L., Ma, Y. et al. Chymase cleavage of stem cell factor yields a bioactive, soluble product. Proc Natl Acad Sci USA 1997, 94: 9017-21.
20. de Paulis, A., Minopoli, G., Piaz, F.D., Pucci, P., Russo, T., Marone, G. Novel autocrine and paracrine loops of the stem cell factor/chymase network. Int Arch Allergy Immunol 1999, 118: 422-5.
21. Mao, X.Q., Shirakawa, T., Yoshikawa, T. et al. Association between genetic variants of mast-cell chymase and eczema. Lancet 1996, 348: 581-3.
22. Kawashima, T., Noguchi, E., Arinami, T., Kobayashi, K., Otsuka, F., Hamaguchi, H. No evidence for an association between a variant of the mast cell chymase gene and atopic dermatitis based on case-control and haplotype-relative-risk analyses. Hum Hered 1998, 48: 271-4.
23. Tanaka, K., Sugiura, H., Uehara, M., Sato, H., Hashimoto-Tamaoki, T., Furuyama, J. Association between mast cell chymase genotype and atopic eczema: Comparison between patients with atopic eczema alone and those with atopic eczema and atopic respiratory disease. J Clin Exp Allergy 1999, 29: 800-3.
24. Umezawa, H., Aoyagi, T., Morishima, H., Kunimoto, S., Matsuzaki, M. Chymostatin, a new chymotrypsin inhibitor produced by actinomycetes. J Antibiot 1970, 23: 425-7.
25. Eda, M., Ashimori, A., Akahoshi, F. et al. Peptidyl human heart chymase inhibitors. 1. Synthesis and inhibitory activity of difluoromethylene ketone derivatives bearing P' binding subsites. Bioorg Med Chem Lett 1998, 8: 913-8.
26. 3 site. Bioorg Med Chem Lett 1998, 8: 919-24.
27. Powers, J.C., Tanaka, T., Harper, J.W. et al. Mammalian chymotrypsin-like enzymes. Comparative reactivities of rat mast cell proteases, human and dog skin chymases, and human cathepsin G with peptide 4-nitroanilide substrates and with peptide chloromethyl ketone and sulfonyl fluoride inhibitors. Biochemistry 1985, 24: 2048-58.
28. Burzycki, T.A., Hoover, K.W., Thomsen, D.L. III, Sneddon, S.F., Rauch, A.L., Hoover, D.J. IBC Conference on Developmental Therapy for Hypertension: Beyond ACE Inhibitors and Calcium Antagonists (Philadelphia, Jan 25) 1993.
29. Bastos, M., Maeji, N.J., Abeles, R.H. Inhibitors of human heart chymase based on a peptide library. Proc Natl Acad Sci USA 1995, 92: 6738-42.
30. Oleksyszyn, J., Powers, J.C. Irreversible inhibition of serine proteases by peptide derivatives of (α-aminoalkyl)phosphonate diphenyl esters. Biochemistry 1991, 30: 485-93.
31. Hayashi, Y., Iijima, K., Katada, J., Kiso, Y. Structure-activity relationship studies of chloromethyl ketone derivatives for selective human chymase inhibitors. Bioorg Med Chem Lett 2000, 10: 199-201.
32. Zimmerman, M., Morman, H., Mulvey, D., Jones, H., Frankshun, R., Ashe, B.M. Inhibition of elastase and other serine proteases by heterocyclic acylating agents. J Biol Chem 1980, 255: 9848-51.
33. Harper, J.W., Powers, J.C. Reaction of serine proteases with substituted 3-alkoxy-4-chloroisocoumarins and 3-alkoxy-7-amino-4-chloroisocoumarins: new reactive mechanism-based inhibitors. Biochemistry 1985, 24: 7200-13.
34. Niwata, S., Fukami, H., Sumida, M. et al. Substituted 3-(phenylsulfonyl)-1-phenylimidazolidine-2,4-dione derivatives as novel nonpeptide inhibitors of human heart chymase. J Med Chem 1997, 40: 2156-63.
35. Fukami, H., Imajo, S., Ito, A. et al. Substituted 3-phenylsul-fonylquinazoline-2,4-dione derivatives as novel nonpeptide inhibitors of human heart chymase. Drug Des Discov 2000, 17: 69-84.
36. Iijima, K., Katada, J., Yasuda, E., Uno, I., Hayashi, Y. N-[2,2-Dimethyl-3-(N-(4-cyanobenzoyl)amino)nonanoyl]-L-phenylala-nine ethyl ester as a stable ester-type inhibitor of chymotrypsin-like serine proteases: Structural requirements for potent inhibition of α-chymotrypsin. J Med Chem 1999, 42: 312-23.
37. Iijima, K., Katada, J., Hayashi, Y. Symmetrical anhydride-type serine protease inhibitors: Structure-activity relationship studies of human chymase inhibitors. Bioorg Med Chem Lett 1999, 9: 4138.
38. Aoyama, Y., Uenaka, M., Konoike, T. at al. Synthesis and structure-activity relationships of a new class of 1-oxacephem-based human chymase inhibitors. Bioorg Med Chem Lett 2000, 10: 2397-401.
39. Aoyama, Y., Uenaka, M., Konoike, T. at al. 1-Oxacephem-based human chymase inhibitors: Discovery of stable inhibitors in human plasma. Bioorg Med Chem Lett 2000, 10: 2403-6.
40. Aoyama, Y., Uenaka, M., Konoike, T. Hayasaki-Kajiwara, Y., Naya, N., Nakajima, M. Inhibition of serine proteases: Activity of 1,3-diazetidine-2,4-diones. Bioorg Med Chem Lett 2001, 11: 1691-4.
41. Aoyama, Y., Uenaka, M., Kii, M. at al. Design, synthesis and pharmacological evaluation of 3-benzylazetidine-2-one-based human chymase inhibitors. Bioorg Med Chem 2001, 9: 3065-75.
42. Aoyama, Y., Konoike, T., Kanda, A., Naya, N., Nakajima, M. Total synthesis of human chymase inhibitor methyllinderone and structure-activity relationships of its derivatives. Bioorg Med Chem Lett 2001, 11: 1695-7.
43. Akahoshi, F., Ashimori, A., Yoshimura, T. et al. Non-peptidic inhibitors of human chymase. Synthesis, structure-activity relationships, and pharmacokinetic profiles of a series of 5-amino-6-oxo-1,6-dihydropyrimidine-containing trifluoromethyl ketones. Bioorg Med Chem 2001, 9: 301-15.
44. Akahoshi, F., Ashimori, A., Sakashita, H. et al. Synthesis, structure-activity relationships, and pharmacokinetic profiles of nonpeptidic α-keto heterocycles as novel inhibitors of human chymase. J Med Chem 2001, 44: 1286-96.
45. Akahoshi, F., Ashimori, A., Sakashita, H. et al. Synthesis, structure-activity relationships, and pharmacokinetic profiles of nonpeptidic difluoromethylene ketones as novel inhibitors of human chymase. J Med Chem 2001, 44: 1297-304.
46. Takai, S., Jin, D., Nishimoto, M. et al. Oral administration of a specific chymase inhibitor, NK3201, inhibits vascular proliferation in grafted vein. Life Sci 2001, 69: 1725-32.
47. Takai, S., Yuda, A., Jin, D. et al. Inhibition of chymase reduces vascular proliferation in dog grafted veins. FEBS Lett 2000, 467: 141-4.
48. Nishimoto, M., Takai, S., Kim, S. et al. Significance of chymase-dependent angiotensin II-forming pathway in the development of vascular proliferation. Circulation 2001, 104: 1274-9.
49. Yao, Y.L., Ishihara, T., Takai, S., Miyazaki, M., Mita, S. Association between the expression of mast cell chymase and intraperitoneal adhesion formation in mice. J Surg Res 2000, 92: 40-4.
50. Okamoto, Y., Takai, S., Miyazaki, M. Chymase inhibitor suppresses adhesion formation in a hamster experimental model. Eur J Pharmacol 2002, 435: 265-7.
51. Muramatsu, M., Katada, J., Hayashi, I., Majima, M. Chymase as a proangiogenic factor. A possible involvement of chymase-angiotensin-dependent pathway in the hamster sponge angiogenesis model. J Biol Chem 2000, 275: 5545-52.
52. Muramatsu, M., Katada, J., Hattori, M., Hayashi, I., Majima, M. Chymase mediates mast cell-induced angiogenesis in hamster sponge granulomas. Eur J Pharmacol 2000, 402: 181-91.
53. Hagermark, O., Rajka, G., Bergvist, U. Experimental itch in human skin elicited by rat mast cell chymase. Acta Derm Venereol 1972, 52: 125-8.
54. Imada, T., Komorita, N., Kobayashi, F. et al. Therapeutic potential of specific chymase inhibitors in atopic dermatitis. 56th Annu Meet Am Acad Allergy, Asthma Immunol (March 3-8, San Diego, California) 2000, Abst S792.
55. Yoshikawa, T., Imada, T., Nakakubo, H., Nakamura, N., Naito, K. Rat mast cell protease-1 enhances immunoglobulin E production by mouse B cells stimulated with interleukin-4. Immunology 2001, 104: 333-40.
56. Tomimori, Y., Muto, T., Fukami, H. et al. Mast cell chymaseregulates dermal mast cell number in mice. Biochem Biophys Res Commun 2002, 290:1478-82.