Structure-activity relationships of some complex I inhibitors

Biochimica et Biophysica Acta - Bioenergetics

Volumn 1364, Issue 2, 1998, Pages 236-244

  Miyoshi, Hideto ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Complex I; Mitochondrion; Respiratory inhibitor; Structure activity relationship

Indexed keywords

AGRICULTURAL CHEMICAL; CAPSAICIN; ENZYME INHIBITOR; PIERICIDIN A; PYRIDINIUM DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); ROTENONE; UBIQUINONE; UNCLASSIFIED DRUG;

BINDING SITE; ENZYME INHIBITION; ENZYME SUBSTRATE COMPLEX; NONHUMAN; PRIORITY JOURNAL; RESPIRATORY CHAIN; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0032490106     PISSN: 00052728     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0005-2728(98)00030-9     Document Type: Article

References (51)

1. [1] T. Friedrich, P. Van Heck, H. Leif, T. Ohnishi, E. Forche, B. Kunze, R. Jansen, W. Trowitzsch-Kienat, G. Höfle, H. Reichenbach, H. Weiss, Eur. J. Biochem. 219 (1993) 691-698.
2. [2] M. Degli Esposti, Biochim. Biophys. Acta, 1998, this special issue.
3. [3] T.R. Perrior, Chem. Ind., London, 1993, pp. 883-887.
4. [4] G. Büchi, L. Crombie, P.J. Godin, J.S. Kaltenbronn, K. Siddalingaiah, D.A. Whiting, J. Chem. Soc., 1961, pp. 2843-2860.
5. [5] T. Unai, I. Yamamoto, Agric. Biol. Chem. 37 (1973) 897-901.
6. [6] M.J. Begley, L. Crombie, A.H.A. Hadi, J.L. Josephs, J. Chem. Soc. Perkin Trans. I, 1989, pp. 204-205.
7. [7] S.K. Arora, R.B. Bates, R.A. Grady, N.E. Delfel, J. Am. Chem. Soc. 97 (1975) 5752-5755.
8. [8] J. Burgos, E.R. Redfearn, Biochim. Biophys. Acta 110 (1965) 475-483.
9. [9] H. Ueno, H. Miyoshi, K. Ebisui, H. Iwamura, Eur. J. Biochem. 225 (1994) 411-417.
10. [10] H. Ueno, H. Miyoshi, M. Inoue, Y. Niidome, H. Iwamura, Biochim. Biophys. Acta 1276 (1996) 195-202.
11. [11] P.C. Levett, D.A. Whiting, J. Cayley, G.S. Cockerill, J.B. Weston, Bioorg. Med. Chem. Lett. 4 (1994) 505-508.
12. [12] I.M. Møller, W. Lin, Annu. Rev. Plant Physiol. 37 (1986) 309-334.
13. [13] K. Matsushita, T. Ohnishi, H.R. Kaback, Biochemistry 26 (1987) 7732-7737.
14. [14] T. Yagi, Biochemistry 26 (1987) 2822-2828.
15. [15] T. Yagi, Y. Hatefi, J. Biol. Chem. 263 (1988) 16150-16155.
16. [16] G. Hofhaus, H. Weiss, K. Leonard, J. Mol. Biol., 1991, 1027-1043.
17. [17] N. Takahashi, A. Suzuki, S. Tamura, J. Am. Chem. Soc. 87 (1965) 2066-2074.
18. [18] S. Yoshida, S. Shiraishi, N. Takahashi, Agric. Biol. Chem. 41 (1977) 587-591.
19. [19] S. Yoshida, K. Yoneyama, S. Shiraishi, A. Watanabe, N. Takahashi, Agric. Biol. Chem. 41 (1977) 855-862.
20. [20] S. Yoshida, Y. Nagao, N. Takahashi, Agric. Biol. Chem. 44 (1980) 2913-2920.
21. [21] S. Yoshida, Y. Nagao, A. Watanabe, N. Takahashi, Agric. Biol. Chem. 44 (1980) 2921-2924.
22. [22] M. Gutman, S. Kliatchko, FEBS Lett. 67 (1976) 348-353.
23. [23] K.H. Chung, K.Y. Cho, Y. Asami, N. Takahashi, S. Yoshida, Z. Naturforsch. 44C (1989) 609-616.
24. [24] T. Mitsui, T. Sagama, J. Fukami, K. Fukunaga, N. Takahashi, S. Tamura, Botyu-Kagaku 34 (1969) 135-142, (in Japanese).
25. [25] D.J. Horgan, H. Ohno, T.P. Singer, J.E. Casida, J. Biol. Chem. 243 (1968) 5967-5976.
26. [26] Y. Shimomura, T. Kawada, M. Suzuki, Arch. Biochem. Biophys. 270 (1989) 573-577.
27. [27] T. Yagi, Arch. Biochem. Biophys. 281 (1990) 305-311.
28. [28] J.M. Janusz, B.L. Buckwalter, P.A. Young, T.R. LaHann, R.W. Farmer, G.B. Kasting, M.E. Loomans, G.A. Kerckaert, C.S. Maddin, E.F. Berman, R.L. Bohne, T.L. Cupps, J.R. Milstein, J. Med. Chem. 36 (1993) 2595-2604.
29. [29] C.S.J. Walpole, S. Bevan, G. Bovermann, J.J. Boelsterli, R. Breckenridge, J.W. Davies, G.A. Hughes, I. James, L. Oberer, J. Winter, R. Wrigglesworth, J. Med. Chem. 37 (1994) 1942-1954.
30. [30] P. Chudapongse, W. Janthasoot, Biochem. Pharmacol. 30 (1981) 735-740.
31. [31] T. Satoh, H. Miyoshi, K. Sakamoto, H. Iwamura, Biochim. Biophys. Acta 1273 (1996) 21-30.
32. [32] I.J. Kopin, S.P. Markey, Annu. Rev. Neurosci. 11 (1988) 81-96.
33. [33] M.R. Gluck, M.J. Krueger, R.R. Ramsay, S.O. Sablin, T.P. Singer, W.J. Nicklas, J. Biol. Chem. 269 (1994) 3167-3174.
34. [34] M.P. Murphy, M.J. Krueger, S.O. Sablin, R.R. Ramsay, T.P. Singer, Biochem. J. 306 (1995) 359-365.
35. [35] D.J. Horgan, T.P. Singer, J.E. Casida, J. Biol. Chem. 243 (1968) 834-843.
36. [36] M. Gutman, T.P. Singer, J.E. Casida, J. Biol. Chem. 245 (1970) 1992-1997.
37. [37] D.S. Higgins, J.T. Greenamyre, J. Neurosci. 16 (1996) 3807-3816.
38. [38] R.R. Ramsay, M.J. Krueger, S.K. Youngster, T.P. Singer, Biochem. J. 273 (1991) 481-484.
39. [39] C.L. Koppel, D. Greenblatt, H.C. Kwok, P.K. Arora, M.P. Singh, L.M. Sayre, Biochem. Biophys. Res. Commun. 148 (1987) 684-693.
40. [40] L.M. Sayre, M.P. Singh, P.K. Arora, F. Wang, R.J. McPeak, C.L. Koppel, Arch. Biochem. Biophys. 280 (1990) 274-283.
41. [41] H. Miyoshi, M. Inoue, S. Okamoto, M. Ohshima, K. Sakamoto, H. Iwamura, J. Biol. Chem. 272 (1997) 16176-16183.
42. [42] J.R. Corbett, K. Wright, A.C. Baillie, The Biochemical Mode of Action of Pesticides, Academic Press, London, 1984, pp. 1-49.
43. [43] R.M. Hollingworth, K.I. Ahammadsahib, Rev. Pestic. Toxicol. 3 (1995) 277-302.
44. [44] P. Leroux, Pestic. Sci. 47 (1996) 191-197.
45. [45] K. Motoba, T. Suzuki, M. Uchida, Pestic. Biochem. Physiol. 43 (1992) 37-44.
46. [46] E. Wood, B. Latli, J.E. Casida, Pestic. Biochem. Physiol. 54 (1996) 135-145.
47. [47] R.M. Hollingworth, K.I. Ahammadsahib, G. Gadelhak, J.L. McLaughlin, Biochem. Soc. Trans. 22 (1994) 230-233.
48. [48] K. Motoba, H. Nishizawa, T. Suzuki, H. Hamaguchi, M. Uchida, Biosci. Biotechnol. Biochem. 56 (1992) 366-372.
49. [49] K. Motoba, T. Suzuki, M. Uchida, Pestic. Biochem. Physiol. 43 (1992) 37-44.
50. [50] T. Akagi, Y. Takahashi, S. Sasaki, Quant. Struct.-Act. Relatsh. 15 (1996) 290-295.
51. [51] U. Brandt, Biochim. Biophys. Acta 1318 (1997) 79-91.