Structure-Activity Relationships in the Oxidation of Benzylamine Analogues by Bovine Liver Mitochondrial Monoamine Oxidase B

Biochemistry

Volumn 33, Issue 23, 1994, Pages 7088-7098

  Walker, Mark C ^a   Edmondson, Dale E ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; LIVER ENZYME; MITOCHONDRIAL ENZYME;

ARTICLE; BINDING AFFINITY; CATTLE; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME BINDING; ENZYME KINETICS; ENZYME STRUCTURE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMAL; BENZYLAMINES; CATTLE; KINETICS; MITOCHONDRIA, LIVER; MONOAMINE OXIDASE; OXIDATION-REDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T; SUPPORT, U.S. GOV'T, P.H.S.;

BOS TAURUS; BOVINAE; FELIS CATUS; GYMNOMYZA SAMOENSIS;

EID: 0028278443     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi00189a011     Document Type: Article

References (59)

1. Ammundsen, L. H., & Nelson, L. S. (1951) J. Am. Chem. Soc. 73, 242–244.
2. Bach, A. W. J., Lan, N. C., Johnson, D. L., Abell, C. W., Bembenek, M. E., Kwan, S.W., Seeburg, P. H., & Shih, J. C. (1988) Proc. Natl. Acad. Sci. U.S.A. 85, 4934–4938.
3. Barber, J. M., Pollock, V., & Spence, J. T. (1988) Biochem. J. 256, 657–659.
4. Barnes, K. K., & Mann, C. K. (1967) J. Org. Chem. 32, 1474–1479.
5. Bondi, A. (1964) J. Phys. Chem. 68, 441–451.
6. Bright, H., & Porter, D. J. (1975) in The Enzymes (Boyer, P., Ed.) 3rd ed., Vol. 12, pp 421–505, Academic Press, New York.
7. Cottrell, T. L. (1958) The Strengths of Chemical Bonds, 2nd ed., Butterworth & Co., London.
8. Dinnocenzo, J. P., & Banach, T. E. (1989) J. Am. Chem. Soc. 111, 8646–8653.
9. Dinnocenzo, J. P., Karki, S. B., & Jones, J. P. (1993) J. Am. Chem. Soc. 115, 7111–7116.
10. Duggleby, R. G. (1981) Anal. Biochem. 110, 9–18.
11. Edmondson, D. E., Ackrell, B. A. C., & Kearney, E. B. (1981) Arch. Biochem. Biophys. 208, 69–74.
12. Edmondson, D. E., Bhattacharyya, A. K., & Walker, M. C. (1993) Biochemistry 32, 5196–5202.
13. Frost, A. A., & Pearson, R. G. (1961) Kinetics and Mechanism, 2nd ed., J. Wiley & Sons, New York.
14. Fuller, R. W., Marsh, M. M., & Mills, J. (1968) J. Med. Chem. 11, 397–398.
15. Fujita, T., Iwasa, J., & Hansch, C. (1964) J. Am. Chem. Soc. 86, 5176–5180.
16. Griller, D., Howard, J. A., Marriott, P. R., & Scaiano, J, C. (1981) J. Am. Chem. Soc. 103, 619–623.
17. Hansch, C., & Leo, A. (1979) Substituent Constants For Correlation Analysis in Chemistry and Biology, J. Wiley & Sons, New York.
18. Hartmann, C., & Klinman, J. P. (1991) Biochemistry 30, 4605–4611.
19. Hellerman, L., & Erwin, V. G. (1968) J. Biol. Chem. 243, 5234–5243.
20. Hellerman, L., Chuang, H. Y. K., & DeLuca, D. (1972) Adv. Biochem. Psychopharmacol. 5, 327–337.
21. Hull, L. A., Davis, G. T., Rosenblatt, D. H., Williams, H. K. R., & Weglein, R. C. (1967) J. Am. Chem. Soc. 89, 1163–1170.
22. Hull, L. A., Davis, G. T., Rosenblatt, D. H., & Mann, C. K. (1969) J. Phys. Chem. 73, 2142–2146.
23. Husain, M., Edmondson, D. E., & Singer, T. P. (1982) Biochemistry 21, 595–600.
24. Janes,S. M., Mu,D., Wemmer, D., Smith, A. J., Kaur, S., Maltby, D., Burlingame, A. L., & Klinman, J. P. (1990) Science 248, 981–987.
25. Jonsson, T., Klinman, J. P., & Edmondson, D. E. (1994) Flavins and Flavoproteins (Yagi, K., & Shin, M., Eds.) W. de Gruyter, Inc., Hawthorne, NY (in press).
26. Klinman, J. P. (1976) Biochemistry 15, 2018–2026.
27. Klinman, J. P., & Matthews, R. G. (1985) J. Am. Chem. Soc. 107, 1058–1060.
28. Lewis, F. D. (1986) Acc. Chem. Res. 19, 401–405.
29. MacDonald, T. L., Gutheim, W. G., Martin, R. B., & Guengerich, F. P. (1989) Biochemistry 28, 2071–2077.
30. Miller, S. M., & Klinman, J. P. (1985) Biochemistry 24, 2114–2127.
31. Miwa, G. T., Walsh, J. S., Keddeirs, G. L., & Hollenberg, P. F. (1983) J. Biol. Chem. 258, 14445–14449.
32. Neuman, R., Hevey, R., & Abeles, R. H. (1975) J. Biol. Chem. 250, 6362–6367.
33. Northrop, D. B. (1981) Biochemistry 20, 4056–4061.
34. Ottoboni, S., Caldera, P., Trevor, A., & Castagnoli, N. (1989) J. Biol. Chem. 264, 13684–13688.
35. Palcic, M. M., & Klinman, J. P. (1983) Biochemistry 22, 5957–5966.
36. Pearce, L. B., & Roth, J. A. (1985) Biochemistry 24, 1821–1826.
37. Ramsay, R. R., Koerber, S. C., & Singer, T. P. (1987) Biochemistry 26, 3045–3050.
38. Ramsay, R. R., Sablin, S. O., & Singer, T. P. (1994) in Flavins and Flavoproteins (Yagi, K., & Shin, M., Eds.) W. de Gruyter, Inc., Hawthorne, NY (in press).
39. Robinson, J., & Cooper, J. M. (1970) Anal. Biochem. 33, 390–399.
40. Salach, J. I. (1979) Arch. Biochem. Biophys. 192, 128–137.
41. Silverman, R. B. (1991) Biochem. Soc. Trans. 19, 201–206.
42. Silverman, R. B., Hoffman, S. J., & Catus, W. B., III (1980) J. Am. Chem. Soc. 102, 7126–7128.
43. Simondsen, R. P., Weber, P. C., Salemme, F. R., & Tollin, G. (1982) Biochemistry 21, 6366–6375.
44. Simpson, J. T., Krantz, A., Lewis, F. D., & Kokel, B. (1982) J. Am. Chem. Soc. 104, 7155–7161.
45. Singer, T. P., & Ramsay, R. R. (1993) Monoamine oxidase, basic and clinical aspects (Yasubara, H., Parvez, S. H., Oguchi, K., Sandler, M., & Nagatsu, T., Eds.) pp 23–43, VSP, Utrecht.
46. Stankovich, M. T. (1991) in Chemistry and Biochemistry of Flavoenzymes (Müller, F., Ed.) pp 401–425, CRC Press Inc., Boca Raton, FL.
47. Strickland, S., Palmer, G., & Massey, V. (1975) J. Biol. Chem. 250, 4048–4052.
48. Stubbe, J. (1990) J. Biol. Chem. 265, 5329–5332.
49. Surdhar, P. S., & Armstrong, D. A. (1987) in Flavins and Flavoproteins (Edmondson, D. E., & McCormick, D. B., Eds.) pp 695–698, W. de Gruyter & Co., Berlin.
50. Tiller, G. E., Mueller, T. P., Dochtev, M. E., & Struve, W. G. (1984) Anal. Biochem. 141, 262–266.
51. Wakamatsu, T., Inaki, H., Ogawa, A., Watanabe, M., & Ban, Y. (1980) Heterocycles 14, 1437–1440.
52. Wei, M.-M., & Stewart, R. (1966) J. Am. Chem. Soc. 88, 1974–1979.
53. Weyler, W., & Salach, J. I. (1981) Arch. Biochem. Biophys. 212, 147–153.
54. Weyler, W., Hsu, Y., & Breakefield, X. O. (1990) Arch. Biochem. Biophys. 47, 391–417.
55. Xu, W., & Mariano, P. S. (1991) J. Am. Chem. Soc. 113,1431–1432.
56. Xu, W., Zhang, X.-M., & Mariano, P. S. (1991) J. Am. Chem. Soc. 113, 8863–8878.
57. Yu, P. H., Bailey, B. A., Durden, D. A., & Boulton, A. A. (1986) Biochem. Pharmacol. 35, 1027–1036.
58. Yue, K. T., Bhattacharyya, A. K., Zhelyaskov, V. R., & Edmondson, D. E. (1993) Arch. Biochem. Biophys. 300, 178–185.
59. Zeller, E. A., Hsu, M., Li, P. K., Ohlsson, J., & Subba Rao, R. (1971) Biochem. Pharmacol. 25, 403–405.