The toxicity of methylenecyclopropylglycine: Studies of the inhibitory effects of (methylenecyclopropyl)formyl-CoA on enzymes involved in fatty acid metabolism and the molecular basis of its inactivation of enoyl-CoA hydratases

Journal of the American Chemical Society

Volumn 121, Issue 39, 1999, Pages 9034-9042

  Li, Ding ^a,b   Agnihotri, Gautam ^a   Dakoji, Srikanth ^a,c   Oh, Eugene ^a,d   Lantz, Marily ^e   Liu, Hung Wen ^a  

^a University of Minnesota   (United States)

^b CASE WESTERN RESERVE UNIVERSITY   (United States)

^c TEXAS A AND M UNIVERSITY   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e Samsung Advanced Institute of Technology (SAIT)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

(METHYLENECYCLOPROPYL)FORMYL COENZYME A; CYCLOPROPANE DERIVATIVE; ENOYL COENZYME A HYDRATASE; FATTY ACID; GLYCINE DERIVATIVE; METHYLENECYCLOPROPYLGLYCINE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATTLE; ENZYME INACTIVATION; ENZYME INHIBITION; ENZYME PURIFICATION; FATTY ACID METABOLISM; HYPOGLYCEMIA; KIDNEY; LIVER; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; SWINE;

EID: 0032833997     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991908w     Document Type: Article

References (53)

1. Gray, D. O.; Fowden, L. Biochem. J. 1962, 82, 385-389.
2. Melde, K.; Buettner, H.; Boschert, W.; Wolf, H. P. O.; Ghisla, S. Biochem. J. 1989, 259, 921-924.
3. Melde, K.; Jackson, S.; Bartlett, K.; Sherratt, H. S. A.; Ghisla, S. Biochem. J. 1991, 274, 395-400.
4. Tanaka, K. In Handbook of Clinical Neurology; Vinken, P. J., Bruyn, G. W., Eds.; Elsevier-North-Holland: Amsterdam, The Netherlands, 1979; Vol. 37, Chapter 17, pp 511-539.
5. Sherratt, H. S. A. Trends Pharmacol. Sci. 1986, 7, 186-191.
6. Tanaka, K.; Ikeda, Y. In Fatty Acid Oxidation; Clinical, Biochemical, and Molecular Aspects; Tanaka, K., Coates, P. M., Eds.; Alan R. Liss, Inc.: New York, 1990; pp 167-172.
7. Tanaka, K.; Isselbacher, K. J.; Shih, V. Science 1972, 175, 69-71.
8. Ghisla, S.; Wenz, A.; Thorpe, C. In Enzyme Inhibitors; Brodbeck, U., Ed.; Verlag Chim: Weinheim, Germany, 1980; pp 43-60.
9. Wenz, A.; Thorpe, C.; Ghisla, S. J. Biol. Chem. 1981, 256, 9809-9812.
10. Ghisla, S.; Melde, K.; Zeller, H. D.; Boschert, W. In Fatty Acid Oxidation; Clinical, Biochemical, and Molecular Aspects; Tanaka, K., Coates, P. M., Eds.; Alan R. Liss, Inc.: New York, 1990; pp 185-192.
11. Li, D.; Guo, Z.; Liu, H.-w. J. Am. Chem. Soc. 1996, 118, 275-276.
12. Bradford, M. M. Anal. Biochem. 1976, 72, 248-254.
13. Laemmli, U. K. Nature 1970, 227, 680-685.
14. Wu, W. J.; Anderson, V. E.; Raleigh, D. P.; Tonge, P. J. Biochemistry 1997, 36, 2211-2220.
15. Becker, D. F.; Fuchs, J. A.; Banfield, D. K.; Walter, F. D.; MacGillivray, R. T. A.; Stankovich, M. T. Biochemistry 1993, 32, 10736-10742.
16. Thorpe, C. Methods Enzymol. 1981, 71, 366-374.
17. Schulz, H.; Staack, H. Methods Enzymol. 1981, 71, 398-403.
18. Middleton, B. Methods Enzymol. 1975, 35, 128-136.
19. Staack, H.; Binstock, J. F.; Schulz, H. J. Biol. Chem. 1978, 253, 1827-1831.
20. Miyazawa, S.; Furuta, S.; Osumi, T.; Hashimoto, T.; Ui, N. J. Biochem. 1981, 90, 511-519.
21. Steinman, H. M.; Hill, R. L. Methods Enzymol. 1975, 35, 136-151.
22. Engel, P. C. Methods Enzymol. 1981, 71, 359-366.
23. Bieber, L. L.; Fiol, C. Methods Enzymol. 1986, 123, 276-284.
24. Bradshaw, R. A.; Noyes, B. E. Methods Enzymol. 1975, 35, 122-128.
25. Belcher, M. Methods Enzymol 1981, 72, 404-408.
26. Lai, M.-t.; Li, D.; Oh, E.; Liu, H.-w. J. Am. Chem. Soc. 1993, 115 1619-1628.
27. Buettner, H. Ph.D. Thesis, University of Konstanz, 1988.
28. Lai, M.-t.; Liu, L.-d.; Liu, H.-w. J. Am. Chem. Soc. 1991, 113, 7388-7397.
29. Baldwin, J. E.; Parker, D. W. J. Org. Chem. 1987, 52, 1475-1477.
30. Miyazawa, S.; Ozasa, H.; Osumi, T.; Hashimato, T. J. Biochem. 1983, 94, 529-542.
31. McGarry, J. D.; Woeltje, K. F.; Schroeder, J. G.; Cox, W. F.; Foster, D. W. In Fatty Acid Oxidation; Clinical, Biochemical, and Molecular Aspects; Tanaka, K., Coates, P. M., Eds.; Alan R. Liss, Inc.: New York, 1990; pp 193-208.
32. Schulz, H. In Fatty Acid Oxidation: Clinical, Biochemical, and Molecular Aspects; Tanaka, K., Coates, P. M., Eds.; Alan R. Liss: New York, 1990; pp 23-36.
33. Engel, P. C. In Chemistry and Biochemistry of Flavoenzymes; Müller, F., Ed.; CRC Press: New York, 1992; Vol. III, pp 597-655.
34. Izai, K.; Uchida, Y.; Orii, T.; Yamamoto, S.; Hashimoto, T. J. Biol. Chem. 1992, 267, 1027-1033.
35. Waterson, R. M.; Hill, R. L. J. Biol. Chem. 1972, 247, 5258-5265.
36. Riddles, P. W.; Blakeley, R. L.; Zerner, B. Methods Enzymol. 1983, 91, 49-60.
37. The stoichiometry of the bound CoA cannot be precisely determined due to the differences in the predicted molar absorptivity values of the possible enzyme-inhibitor adducts shown in Scheme 3.
38. Schulz, H. Biochim. Biophys. Acta 1991, 1081, 109-120.
39. Kunau, W. H.; Dommes, V.; Schulz, H. Prog. Lipid Res. 1995, 34, 267-342.
40. Bieber, L. L. Annu. Rev. Biochem. 1988, 57, 261-283.
41. Minami-Ishii, N.; Taketani, S.; Osumi, T.; Hashimoto, T. Eur. J. Biochem. 1989, 185, 73-78.
42. Engel, C. K.; Mathieu, M.; Zeelen, J. P.; Hiltunen, J. K.; Wierenga, R. K. EMBO J. 1996, 15, 5135-5145.
43. Engel, C. K.; Kiema, TR. R.; Hiltunen, J. K.; Wierenga, R. K. J. Mol. Biol. 1998, 275, 847-859.
44. Suckling, C. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 537-552.
45. Liu, H.-w.; Walsh, C. T. In The Chemistry of the Cydopropyl Group; Pappoport, Z., Ed.; Wiley-Interscience: New York, 1987; part 2, pp 969-1025.
46. Haddow, J.; Suckling, C. J.; Wood, H. C. S. J. Chem. Soc., Perkin Trans. 1 1989, 1297-1304.
47. Silverman, R. B.; Ding, C. Z.; Borrillo, L.; Chang, J. T. J. Am. Chem. Soc. 1993, 115, 2982-2983.
48. MacInnes, I.; Nonhebel, D. C.; Orszulik, S. T.; Suckling, C. J.; Wrigglesworth, R. J. Chem. Soc. Perkin Trans, 1 1983, 2771-2776.
49. Croteau, R.; Alonso, W. R.; Koepp, A. E.; Shim, J. H.; Cane, D. E. Arch. Biochem. Biophys. 1993, 307, 397-404.
50. Li, K.; Du, W.; Que, N. L. S.; Liu, H.-w. J. Am. Chem. Soc. 1996, 118, 8763-8764.
51. D'Ordine, R. L.; Tonge, P. J.; Carey, P. R.; Anderson, V. E. Biochemistry 1994, 33, 12635-12693.
52. D'Ordine, R. L.; Bahnson, B. J.; Tonge, P. J.; Anderson, V. E. Biochemistry 1994, 33, 14733-14742.
53. Austin, J. C.; Kuliopoulos, A.; Mildvan, A. S.; Spiro, T. G. Protein Sci. 1992, 1, 259-270.