Mechanism and Inhibition of Cytochrome P-450 Aromatase

Journal of Medicinal Chemistry

Volumn 33, Issue 11, 1990, Pages 2933-2942

  Cole, Philip A ^a   Robinson, Cecil H ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 CHLORO 5 (4 CHLOROPHENYL) 5H INDENO[1,2 D]PYRIMIDINE; AMINOGLUTETHIMIDE; ANDROSTANE DERIVATIVE; ANDROSTENEDIONE; AROMATASE; CYTOCHROME P450; ECONAZOLE; ESTRANE DERIVATIVE; ESTROGEN; FADROZOLE; KETOCONAZOLE;

ARTICLE; BREAST CANCER; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME MECHANISM; NONHUMAN; PRIORITY JOURNAL;

AFFINITY LABELS; AROMATASE; BINDING, COMPETITIVE; HUMAN; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; SUPPORT, U.S. GOV'T, P.H.S.;

EID: 0025187459     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00173a001     Document Type: Article

References (123)

1. Brodie, A. M. H. Biochem. Pharmacol. 1985, 34, 3213.
2. Santen, R. J.; Misbin, R. I. Pharmacotherapy 1981, 1, 95.
3. Van Wauwe, J. P.; Janssen, P. A. J. J. Med. Chem. 1989, 32, 2231.
4. Johnston, J. O.; Metcalf, B. W. In Approaches to Cancer Chemotherapy, Prasad, S. S., Ed.; Academic Press: New York, 1984; p 307.
5. Webster, N. J. G.; Green, S.; Tasset, D.; Ponglikitmongkol, M.; Chambon, P. EMBO J. 1989, 8, 1441.
6. Green, S.; Chambon, P. Nature 1987, 325, 75.
7. Walter, P.; Green, S.; Greene, G.; Krust, A.; Bomert, J. M.; Jeltsch, J. M.; Staub, A.; Jensen, E.; Scrace, G.; Waterfield, M.; Chambon, P. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7889.
8. Personal communication from the ICI Pharmaceuticals group
9. Kolata, G. Science 1985, 229, 1378.
10. Sligar, S. G.; Murray, R. I. In Cytochrome P-450: Structure, Mechanism, and Biochemistry, Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1986; p 429.
11. Poulos, T. L. In Cytochrome P-450: Structure, Mechanism, and Biochemistry, Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1986; p 505.
12. Waxman, D. J. In Cytochrome P-450: Structure, Mechanism, and Biochemistry, Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1986; p 525.
13. McMurry, T. J.; Groves, J. T. In Cytochrome P-450: Structure, Mechanism, and Biochemistry, Ortiz de Montellano, P. R., Ed.; Plenum Press: New York, 1986; p 1.
14. Nelson, D. R.; Strobel, H. W. Biochemistry 1989, 28, 656.
15. Nebert, D. W.; Gonzalez, F. J. Annu. Rev. Biochem. 1987, 56, 945.
16. White, R. E.; Coon, M. J. Annu. Rev. Biochem. 1980, 49, 315.
17. Thompson, E. A.; Siiteri, P. K. J. Biol. Chem. 1974, 249, 5364.
18. Siiteri, P. K.; Thompson, E. A. J. Steroid Biochem. 1975, 6, 317.
19. Meyer, A. S. Biochim. Biophys. Acta 1955, 17, 441.
20. Meyer, A. S. Experientia 1955, 11, 99.
21. Caspi, E.; Arunachalam, T.; Nelson, P. A. J. Am. Chem. Soc. 1986, 108, 1847.
22. Osawa, Y.; Shibata, K.; Rohrer, D.; Weeks, C.; Duax, W. L. J. Am. Chem. Soc. 1975, 97, 4400.
23. Arigoni, D.; Battaglia, R.; Akhtar, M.; Smith, T. J. Chem. Soc., Chem. Commun. 1975, 185.
24. Miyairi, S.; Fishman, J. J. Biol. Chem. 1985, 260, 320.
25. Akhtar, M.; Calder, M. R.; Corina, D. L.; Wright, J. N. Biochem. J. 1982, 201, 569.
26. Beusen, D. D.; Carrell, H. L.; Covey, D. F. Biochemistry 1987, 26, 7833.
27. Brodie, H. J.; Kripalani, K. J.; Possanza, G. J. Am. Chem. Soc. 1969, 91, 1241.
28. Fishman, J.; Guzik, H. J. Am. Chem. Soc. 1969, 91, 2805.
29. Fishman, J.; Guzik, H.; Dixon, D. Biochemistry 1969, 8, 4304.
30. Fronckowiak, M. D.; Osawa, Y. The Endocrine Society Meeting, New Orleans, June 8107–11, 1988 (Abstract 430).
31. Cole, P. A.; Robinson, C. H. Biochem. J. 1990, 268, 553.
32. Corbin, C. J.; Graham-Lorence, S.; McPhaul, M.; Mason, J. I.; Mendelson, C. R.; Simpson, E. R. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 8948.
33. Means, G. D.; Mahendroo, M. S.; Corbin, C. J.; Mathis, J. M.; Powell, F. E.; Mendelson, C. R.; Simpson, E. R. J. Biol. Chem. 1989, 264, 19385.
34. Hosoda, H.; Fishman, J. J. Am. Chem. Soc. 1974, 96, 7325.
35. Goto, J.; Fishman, J. Science (Washington, D.C.) 1977,195, 80.
36. Fishman, J.; Raju, M. S. J. Biol. Chem. 1981,256, 4472.
37. Hahn, E. F.; Fishman, J. J. Biol. Chem. 1984,259,1689.
38. Caspi, E.; Wicha, J.; Arunachalam, T.; Nelson, P.; Spiteller, G. J. Am. Chem. Soc. 1984, 106, 7282.
39. Morand, P.; Williamson, D. G.; Layne, D. S.; LompaKrzymien, L.; Salvador, J. Biochemistry 1975, 14, 635.
40. Mastalerz, H.; Morand, P. J. Chem. Soc., Perkin Trans. 1 1982, 2611.
41. Covey, D. F.; Hood, W. R.; Beusen, D. D.; Carrell, H. L. Biochemistry 1984, 23, 5398.
42. Townsley, J. D.; Possanza, G.J.; Brodie, H. J. Fed. Proc., Fed. Am. Soc. Exp. Biol. 1966, 25, 282 (Abstract 520).
43. Caspi, E.; Dharmaratne, H. R. W.; Shackleton, C. J. Chem. Soc., Chem. Commun. 1989, 1699.
44. Stevenson, D. E.; Wright, J. N.; Akhtar, M. J. Chem. Soc., Chem. Commun. 1985, 1078.
45. Stevenson, D. E.; Wright, J. N.; Akhtar, M. J. Chem. Soc., Perkin Trans. 1 1988, 2043.
46. Cole, P. A.; Robinson, C. H. J. Chem. Soc., Chem. Commun. 1986, 1651.
47. Cole, P. A.; Robinson, C. H. J. Chem. Soc., Perkin Trans. 1 1990, 2119.
48. Cole, P. A.; Robinson, C. H. J. Am. Chem. Soc. 1988, 110, 1284.
49. Cole, P. A.; Bean, J. M.; Robinson, C. H. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 2999.
50. Akhtar, M.; Alexander, K.; Boar, R. B.; McGhie, J. F.; Barton, D. H. R. Biochem. J. 1978, 169, 449.
51. Kominami, S.; Shinzawa, K.; Takemori, S. Biochem. Biophys. Res. Commun. 1982, 109, 916.
52. Shimizu, K. Biochim. Biophys. Acta 1979, 575, 37.
53. Schwarzel, W. C.; Krugel, W. G.; Brodie, H. J. Endocrinology 1973, 92, 866.
54. Furth, P. S., Rosenberger, J. G., Marcotte, P. A.; Robinson, C. H. J. Enzyme Inhib. 1990, in press.
55. Brueggemeier, R. W.; Li, P.K.; Snider, C. E.; Darby, M. V.; Katlic, N. E. Steroids 1987, 50, 163.
56. Miyairi, S.; Fishman, J. J. Biol. Chem. 1986, 261, 6772.
57. Marcotte, P. A.; Robinson, C. H. Steroids 1982, 39, 325.
58. Naruta, Y.; Maruyama, K. Tetrahedron Lett. 1987, 28, 4553.
59. Kellis, J. T., Jr.; Vickery, L. E. J. Biol. Chem. 1987, 262, 4413.
60. Numazawa, M.; Mutsumi, A.; Hoshi, K.; Koike, R. Biochem. Biophys. Res. Commun. 1989, 160, 1009.
61. Santen, R. J.; Worgul, W. J.; Samojlik, E.; Interrante, A.; Boucher, A. E.; Lipton, A.; Harvey, H. A.; White, D. S.; Smart, E.; Cox, C.; Wells, S. New Engl. J. Med. 1981, 305, 545.
62. Shaw, M. A.; Nicholls, P. J.; Smith, H. J. J. Steroid Biochem. 1988, 31, 137.
63. Foster, A. B.; Jarman, M.; Leung, C. S.; Rowlands, M. G.; Taylor, G. N.; Plevey, R. G.; Sampson, P. J. Med. Chem. 1985, 28, 200.
64. Hartmann, R. W.; Batzl, C. J. Med. Chem. 1986, 29, 1362.
65. Graves, P. E.; Salhanick, H. A. Endocrinology 1979, 105, 52.
66. Mason, J. I.; Carr, B. R.; Murry, B. A. Steroids 1987, 50, 179.
67. Steele, R. E.; Mellor, L. B.; Sawyer, W. K.; Wasvary, J. M.; Browne, L. J. Steroids 1987, 50, 147.
68. Hirsch, K. S.; Jones, C. D.; Lindstrom, T. D.; Stamm, N.B.; Sutton, G. P.; Taylor, H. M.; Weaver, D. E. Steroids 1987, 50, 201.
69. Wouters, W.; De Coster, R.; Krekels, M.; van Dun, J.; Beerens, D.; Haelterman, C.; Raeymaekers, A.; Freyne, E.; Van Gelder, J.; Venet, M.; Janssen, P. A. J. J. Steroid Biochem. 1989, 32, 781.
70. Lipton, A.; Harvey, H. A.; Demers, L. M.; Hanagan, J.; Mulagha, M.; Sanders, S.; Fitzsimmons, S.; Santen, R. J. 13th Congress of the European Society for Medical Oncology, Lugano, Switzerland, October 30, 1988.
71. Lipton, A.; Harvey, H.A.; Demers, L. M.; Hanagan, J. R.; Mulagha, M. T.; Kochak, G. M.; Fitzsimmons, S.; Sanders, S. I.; Santen, R. J. Cancer 1990, 65, 1279.
72. Stein, R. C.; Dowsett, M.; Davenport, J.; Hedley, A.; Ford, H. T.; Gazet, J. C.; Coombes, R. C. Cancer Res. 1990, 50, 1381.
73. Abeles, R. H. Drug Dev. Res. 1987, 10, 221.
74. Sheets, J. J.; Vickery, L. E. Proc. Natl. Acad. Sci. U.S.A. 1982,79, 5773.
75. Sheets, J. J.; Vickery, L. E. J. Biol. Chem. 1983,258, 1720.
76. Sheets, J. J.; Vickery, L. E. J. Biol. Chem. 1983, 258, 11446.
77. Wright, J. N.; van Leersum, P. T.; Chamberlin, S. G.; Akhtar, M. J. Chem. Soc., Perkin Trans. 1 1989, 1647.
78. Wright, J. N.; Calder, M. R.; Akhtar, M. J. Chem. Soc., Chem. Commun. 1985, 1733.
79. Shih, M.-.J.; Carrell, M. H.; Carrell, H. L.; Wright, C. L.; Johnston, J. O.; Robinson, C. H. J. Chem. Soc., Chem. Commun. 1987, 213.
80. Childers, W. E.; Robinson, C. H. J. Chem. Soc., Chem. Commun. 1987, 320.
81. Kellis, J. T.; Childers, W.E.; Robinson, C. H.; Vickery, L. E. J. Biol. Chem. 1987, 262, 4421.
82. Childers, W. E.; Shih, M.-J.; Furth, P. S.; Robinson, C.H. Steroids 1987, 50, 121.
83. Bednarski, P. J.; Nelson, S. D. J. Med. Chem. 1989, 32, 203.
84. Personal communication from L. E. Vickery, University of California, Irvine.
85. Unpublished work in the laboratory of J. O. Johnston, Merrell Dow.
86. Njar, V.; Safi, E.; Robinson, C. H. Abstracts of Papers, 199th National Meeting of the American Chemical Society, Division of Organic Chemistry, Boston, MA, Spring 1990; American Chemical Society: Washington, DC, 1990; Abstract 44.
87. Organon company communication, March 1988.
88. Kellis, J. T., Jr.; Vickery, L. E. Science 1984,225,1032.
89. Kellis, J. T., Jr.; Vickery, L. E. Biochem. Pharmacol. 1986, 35, 2887.
90. Covey, D. F.; Hood, W. F.; Parikh, V. D. J. Biol. Chem. 1981, 256, 1076.
91. Metcalf, B. W.; Wright, C. L.; Burkhart, J. P.; Johnston, J. O. J. Am. Chem. Soc. 1981, 103, 3221.
92. Marcotte, P. A.; Robinson, C. H. Fed. Proc. 1981, 40, 1867.
93. Johnston, J. O. Steroids 1987, 50, 105.
94. Ortiz de Montellano, P. R.; Kunze, K. L.; Beilan, H. S.; Wheeler, C. Biochemistry 1982, 21, 1331.
95. Kunze, K. L.; Mangold, B. L. K.; Wheeler, C.; Beilan, H. S.; Ortiz de Montellano, P. R. J. Biol. Chem. 1983, 258, 4202.
96. Ortiz de Montellano, P. R.; Komives, E. A. J. Biol. Chem. 1985, 260, 3330.
97. Marcotte, P. A.; Robinson, C. H. Biochemistry 1982, 21, 2773.
98. Furth, P. S.; Robinson, C. H. Biochemistry 1989, 28, 1254.
99. Mann, J.; Pietrzak, B. J. Chem. Sac., Perkin Trans. 1 1987, 385.
100. Bednarski, P. J.; Porubek, D. J.; Nelson, S. D. J. Med. Chem. 1985, 28, 775.
101. Brodie, A. M. H.; Schwarzel, W. C.; Shaikh, A. A.; Brodie, H. J. Endocrinology 1977, 100, 1684.
102. Brodie, A. M. H.; Garrett, W. M.; Hendrickson, J. R.; Tsai-Morris, C.; Marcotte, P. A.; Robinson, C. H. Steroids 1981,38, 693.
103. Covey, D. F.; Hood, W. F. Mol. Pharmacol. 1982, 21, 173.
104. Newitt, J. A.; Robinson, C. H. Fed. Proc. 1986, 45, 1885 (Abstract 2362).
105. Marsh, D. A.; Brodie, H. J.; Garrett, W.; Tsai-Morris, C.-H.; Brodie, A. M. H. J. Med. Chem. 1985, 28, 788.
106. Abul-Hajj, Y. J. J. Med. Chem. 1986, 29, 582.
107. Abul-Hajj, Y. J. Steroid Biochem. 1990, 35, 139.
108. di Salle, E.; Giudici, D.; Ornati, G.; Briatico, G.; Lombardi, P. Conference on Aromatase: Future Perspectives, Miami, FL, March 4, 1987 (Abstract 18).
109. Coombes, R. C.; Goss, P. E.; Dowsett, M.; Hutchinson, G.; Cunningham, D.; Jarman, M.; Brodie, A. M. H. Steroids 1987, 50, 245.
110. Reed, M. J.; Lai, L. C.; Owen, A. M.; Singh, A.; Coldham, N. G.; Purohit, A.; Ghilchik, M. W.; Shaikh, N. A.; James, V. H. T. Cancer Res. 1990, 50, 193.
111. Barone, R. M.; Shamonki, I. M.; Siiteri, P. K.; Judd, H. L. J. Clin. Endocrinol. Metab. 1979, 49, 672.
112. Covey, D. F.; Hood, W. F. Cancer Res. (Suppl.) 1982, 42, 3327.
113. Ryan, K. J. J. Biol. Chem. 1959, 221, 268.
114. Gual, C.; Morato, T.; Hyano, M.; Gut, M.; Dorfman, R. I. Endocrinology 1962, 71, 920.
115. Covey, D. F. In Sterol Biosynthesis Inhibitors: Pharmaceutical and Agrochemical Aspects; Berg, D., Plempel, M., Eds.; Ellis Horwood, Ltd.: Chichester, England, 1988; p 534.
116. Covey, D. F.; Hood, W. F. Endocrinology 1981, 108, 1597.
117. Snider, C. E.; Brueggemeier, R. W. J. Biol. Chem. 1987, 262, 8685
118. Henderson, D.; Norbisrath, G.; Kerb, U. J. Steroid Biochem. 1986, 24, 303.
119. Giudici, D.; Ornati, G.; Briatico, G.; Buzzetti, F.; Lombardi, P.; di Salle, E. 8th International Symposium of the Journal of Steroid Biochemistry, Paris, France, 1987 (Abstract 53P).
120. Sherwin, P. F.; McMullan, P. C.; Covey, D. F. J. Med. Chem. 1989, 32, 651.
121. Numazawa, M.; Tsuji, M.; Osawa, Y. Steroids 1986, 48, 347.
122. Snider, C. E.; Brueggemeier, R. W. J. Steroid Biochem. 1985, 22, 325.
123. Brueggemeier, R. W.; Snider, C. E.; Kimball, J. G. Steroids 1982, 40, 679.