Chiral multisubstrate inhibitors of dopamine β-monooxygenase: Evidence for dual modes of interaction

Biochemistry

Volumn 36, Issue 23, 1997, Pages 7144-7153

  Wimalasena, Kandatege ^a   Wimalasena, D Shyamali ^a   Dharmasena, Silpadipathiyalage ^a   Haines, Donovan C ^a   Alliston, Kevin R ^a  

^a WICHITA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 PHENYL 1,5 BISTHIOGLUTARIMIDE; 5 PHENYL 2 THIOOXAZOLIDONE; COPPER; DOPAMINE BETA MONOOXYGENASE; ENZYME INHIBITOR; OXYGEN; TYRAMINE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ADRENERGIC ACTIVITY; ANIMAL CELL; ARTICLE; CHIRALITY; CONTROLLED STUDY; ENANTIOMER; ENZYME ACTIVE SITE; ENZYME INHIBITOR INTERACTION; ENZYME SPECIFICITY; INHIBITION KINETICS; METHYLATION; NONHUMAN; PRIORITY JOURNAL; STEREOSPECIFICITY; SYNTHESIS;

ANIMALS; BINDING SITES; CATTLE; DOPAMINE BETA-HYDROXYLASE; KINETICS; MODELS, CHEMICAL; MODELS, MOLECULAR; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

ANIMALIA; LYCAENINAE;

EID: 0030985907     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi963048r     Document Type: Article

References (63)

1. Ahn, N., & Klinman, J. P. (1983) Biochemistry 22, 3096-3106.
2. Ash, D. E., Papadopoulos, N. J., Colombo, G., & Villafranca, J. J. (1984) J. Biol. Chem. 259, 3395-3398
3. Berg, U., & Sandstrom, J. (1966) Acta Chem. Scand. 20, 689-697.
4. Blackburn, N. J., Collison, D., Sutton, J., & Mabbs, F. E. (1984) Biochem. J. 220, 447-454.
5. Blackburn, N. J., Pettingill, T. M., Seagraves, K. S., & Shigeta, R. T. (1990) J. Biol. Chem. 265, 15383-15386.
6. Blumberg, W. E., Desai, P. R., Powers, L., Freedman, J. H., & Villafranca, J. J. (1989) J. Biol. Chem. 264, 6029-6032.
7. Bossard, M. J., & Klinman, J. P. (1986) J. Biol. Chem. 261, 16421-16427.
8. Byers, L. D. (1978) J. Theor. Biol. 74, 501-512.
9. Cava, M. P., & Levinson, M. L. (1985) Tetrahedron 41, 5061-5087.
10. Cleland, W. W. (1979) Methods Enzymol. 63, 103-108.
11. Creveling, C. R., Daly, J. W., Witkop, B., & Udenfriend, S. (1962) Biochim. Biophys. Acta 64, 125-134.
12. Diliberto, E. J., Jr., & Allen, P. L. (1981) J. Biol. Chem. 256, 3385-3393.
13. Ettlinger, M. G. (1950) J. Am. Chem. Soc. 72, 4792-4796.
14. Fitzpatrick, P. F., & Villafranca, J. J. (1987) Arch. Biochem. Biophys. 257, 231-250.
15. Goldstein, M., Lauber, E., & McKereghan, M. R. (1965) J. Biol. Chem. 240, 2066-2072.
16. Hasnain, S. S., Diakum, G. P., Knowles, P. F., Binsted, N., Garner, C. D., & Blackburn, N. J. (1984) Biochem. J. 221, 545-548.
17. Herman, H. H., Husain, P. A., Colbert, J. E., Schweri, M. M., Pollock, S. H., Fowler, L. C., & May, S. W. (1991) J. Med. Chem. 34, 1082-1085.
18. Kaufman, S., & Friedman, S. (1965) Pharmacol. Rev. 17, 71-100.
19. Kaufman, S., Bridges, W. F., Eisenberg, F., & Friedman, S. (1962) Biochem. Biophys. Res. Commun. 9, 497-502.
20. Kirshner, N. (1962) J. Biol. Chem. 237, 2311-2317.
21. Kjaer, A., & Gmelin, R. (1958) Acta Chem. Scand. 12, 1693-1694.
22. Klinman, J. P., Humphries, H., & Voet, J. D. (1980) J. Biol. Chem. 255, 11648-11651.
23. Klinman, J. P., & Krueger, M. (1982) Biochemistry 21, 67-75.
24. Klinman, J. P., Krueger, M., Brenner, M., & Edmondson, D. E. (1984) J. Biol. Chem. 259, 3399-3402.
25. Kruse, L. I., De Wolf, W. E., Chambers, P. A., & Goodhard, P. J. (1986) Biochemistry 25, 7271-7278.
26. Ljones, T., & Skotland, T. (1986) in Copper Proteins and Copper Enzymes (Lontie, R., Ed.) Vol. 2, pp 131-157, CRC Press, Boca Raton, FL.
27. Ljones, T., Skotland, T., & Flatmark, T. (1976) Eur. J. Biochem. 6, 525-533.
28. Mangold, J. B., & Klinman, J. P. (1984) J. Biol. Chem. 259, 7772-7779.
29. May, S. W., & Phillips, R. S. (1980) J. Am. Chem. Soc. 102, 5981-5983.
30. May, S. W., Phillips, R. S., Mueller, P. W., & Herman, H. H. (1981) J. Biol. Chem. 256, 2258-2261.
31. May, S. W., Phillips, R. S., Herman, H. H., & Mueller, P. W. (1982) Biochem. Biophys. Res. Commun. 104, 38-44.
32. May, S. W., Mueller, P. W., Padgette, S. R., Herman, H. H., & Phillips, R. S. (1983) Biochem. Biophys. Res. Commun. 110, 161-168.
33. May, S. W., Herman, H. H., Roberts, S. F., & Cicarello, M. C. (1987) Biochemistry 26, 8470-8475.
34. Miller, S. M., & Klinman, J. P. (1983) Biochemistry 22, 3096-3106.
35. Miller, S. M., & Klinman, J. P. (1985) Biochemistry 24, 2114-2127.
36. Munakata, M., Kitagawa, S. (1982) in copper coordination chemistry (Karlin, K. D., & Zubieta, J., Eds) pp 473-495, Adenine Press, Guilderland, NY.
37. Nagao, Y., Kumagai, T., Yamada, S., & Fugita, E. (1985) J. Chem. Soc., Perkin Trans. 1 2361-2367.
38. Njus, D., & Radda, G. K. (1979) Biochem J. 180, 579-585.
39. Padgette, S. R., Wimalasena, K., Herman, H. H., Sirimanne, S. R., & May, S. W. (1985) Biochemistry 24, 5826-5839.
40. Pettingill, T. M., Strange, R. W., & Blackburn, N. J. (1991) J. Biol. Chem. 266, 16996-17003.
41. Preaux, T., & Gielens, C. (1984) in Copper Proteins and Copper Enzymes (Lontie, R., Ed.) Vol. 2, pp 159-205, CRC, Boca Raton, FL.
42. Reedy, B. J., & Blackburn, N. J. (1994) J. Am. Chem. Soc. 116, 1924-1931.
43. Reedy, B. J., Murthy, N. N., Karlin, K. D., & Blackburn, N. J. (1995) J. Am. Chem. Soc. 117, 9826-9831.
44. Rorabacher, D. B., Martin, M. J., Koenigbauer, M. J., Malik, M., Schroeder, R. R., Endicott, J. F., & Ochrymowycz, L. A. (1983) in Copper Coordination Chemistry: Biochemical and Inorganic Perspectives (Karlin, K. D., & Zubieta, J., Eds.) pp 167-202, Adenine Press, Guilderland, NY.
45. Rosenberg, R. C., & Lovenberg, W. (1980) in Essays in Neurochemistry and Neuropharmacology (Youdim, M. B. H., Lovenberg, W., Sharman, D. F., & Lagnado, J. R., Eds.) Vol. 4, pp 163-209.
46. Scott, R. A., Sullivan, R. J., De Wolf, W. E., Dolle, R. E., & Kruse, L. I. (1988) Biochemistry 27, 5411-5417.
47. Sirimanne, S. R., & May, S. W. (1988) J. Am. Chem. Soc. 110, 7560-7561.
48. Skotland, T., & Ljones, T. (1980) Biochim. Biophys. Acta 630, 30-35.
49. Skotland, T., Peterssen, L., Backstrom, D., Ljones, T., Flatmark, T., & Ehrenberg, A. (1980) Eur. J. Biochem. 105, 5-11.
50. Solomon, E. I. (1981) in Copper Proteins (Spiro, T. G., Ed.) pp 41-108, Wiley, New York.
51. Stewart, L. C., & Klinman, J. P. (1987) Biochemistry 26, 5302-5309.
52. Stewart, L. C., & Klinman, J. P. (1988) Annu. Rev. Biochem. 57, 551-592.
53. Taylor, K. B. (1974) J. Biol. Chem. 249, 454-458.
54. Testa, V. E., Fontanella, L., Cristiani, G. F., & Fava, F. (1958) Liebigs Ann. Chem. 614, 167-170.
55. Testa, V. E., Fontanella, L., Cristiani, G. F., & Mariani, L. (1961) Liebigs Ann. Chem. 639, 166-180.
56. Weinhard, K., Wallach, M. B., & Marx, M. (1985) J. Med. Chem. 28, 694-698.
57. Wimalasena, K., & May, S. W. (1987) J. Am. Chem. Soc. 109, 4036-4046.
58. Wimalasena, K., & May, S. W. (1989) J. Am. Chem. Soc. 111, 2729-2731.
59. Wimalasena, K., & Wimalasena, D. S. (1991a) Biochem. Biophys. Res. Commun. 175, 920-927.
60. Wimalasena, K., & Wimalasena, D. S. (1991b) Anal. Biochem. 197, 353-361.
61. Wimalasena, K., Dharmasena, S., & Wimalasena, D. S. (1994) Biochem. Biophys. Res. Commun. 200, 113-119.
62. Wimalasena K., Dharmasena, S., Wimalasena, D. S., & Hughbanks-Wheaton, D. K. (1996) J. Biol. Chem. 271, 26032-26043.
63. Zenker, N., Hubbard, L. S., & Wright, J. (1988) J. Nat. Prod. 51, 862-865.