A novel and selective monoamine oxidase B substrate

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 20, 2005, Pages 5808-5813

  Rimoldi, John M ^a   Puppali, Satish G ^a   Isin, Emre ^b   Bissel, Philippe ^b   Khalil, Ashraf ^b   Castagnoli Jr , Neal ^b  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

Cyclic iminium metabolite; Cyclopropyltetrahydropyridine; Monoamine oxidase B selective substrate; Regioselectivity

Indexed keywords

1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; CARBON; CYCLOPROPANE DERIVATIVE; FLAVOPROTEIN; HEPTANE DERIVATIVE;

ARTICLE; CATALYSIS; CONJUGATION; ELECTRON; ENZYME SUBSTRATE; MOLECULAR STABILITY; OXIDATION;

ANIMALS; CATALYSIS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MONOAMINE OXIDASE; PAPIO; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SUBSTRATE SPECIFICITY;

EID: 24344455130     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.05.059     Document Type: Article

References (40)

1. N.S. Scrutton Nat. Prod. Rep. 21 2004 722
2. A.S. Kalgutkar, D.K. Dalvie, N. Castagnoli Jr., and T.J. Taylor Chem. Res. Toxicol. 14 2001 1139
3. M. Strolin-Benedetti, and K.F. Tipton J. Neural. Transm. Suppl. 52 1998 149
4. B. Rochat, M. Kosel, G. Boss, B. Testa, M. Gillet, and P. Baumann Biochem. Pharmacol. 56 1998 15
5. C.M. Dixon, G.R. Park, and M.H. Tarbit Biochem. Pharmacol. 47 1994 1253
6. A possible exception to this generalization will be found in a report [Hemrick-Leucke, S. K.; Robertson, D. W.; Krushinski, J. H.; Fuller, R. W. Life Sci. 1992, 50, 573] describing the substrate properties of racemic 3-hydroxy-1-methyl-4-phenylpiperidine. However, the experimental details did not rule out the not unreasonable possibility that the actual substrate was the corresponding dehydration product, MPTP.
7. A.S. Kalgutkar, D.K. Dalvie, N. Castagnoli Jr., and T.J. Taylor Chem. Res. Toxicol. 14 2001 1139
8. T.P. Singer F. Müller Chemistry and Biochemistry of Flavoenzymes (II) 1991 CRC Press London 437 470
9. J. Weisman, A. Trevor, K. Chiba, L. Peterson, and N. Castagnoli Jr. J. Med. Chem. 28 1985 997
10. N.A. Naiman, H. Rollema, A. Johnson, and N. Castagnoli Jr. Chem. Res. Toxicol. 3 1990 133
11. S. Kuttab, A. Kalgutkar, and N. Castagnoli Jr. Chem. Res. Toxicol. 7 1994 740
12. J. Rimoldi, Y.-X. Wang, S. Nimkar, S. Kuttab, A. Anderson, H. Burch, and N. Castagnoli Jr. Chem. Res. Toxicol. 8 1995 703
13. R.B. Silverman The Organic Chemistry of Enzyme-Catalyzed Reactions 2000 Academic Press San Diego pp. 132-141
14. R.G. Silverman Acc. Chem. Res. 28 1995 335
15. L.A. Peterson, P.S. Caldera, A. Trevor, K. Chiba, and N. Castagnoli Jr. J. Med. Chem. 28 1985 1432
16. A.G. Ishkiv, N.V. Ermaov, S.V. Mikerov, Y. Klyatskii, and E.F. Miroshnichenko Voprosy Meditsinskoi Khimii 38 1992 25
17. R.E. Heikkila, A. Hess, and R.C. Duvoisin Life Sci. 36 1985 231
18. J.W. Langston, I. Irwin, E.B. Langston, and L.S. Forno Neurosci. Lett. 50 1984 289 We have confirmed the lack of substrate properties of 6 with a sensitive GC-EI/MS assay.
19. Y. Lee, K.-Q. Ling, X. Lu, R.G. Silverman, E.M. Shepard, D.M. Dooley, and L.M. Sayre J. Am. Chem. Soc. 124 2002 12135
20. Y.-X. Wang, S. Mabic, and N. Castagnoli Jr. Bioorg. Med. Chem. 6 1998 143
21. T.T. Tidwell The Chemistry of the Cyclopropyl Group 1987 John Wiley & Sons Ltd pp. 565-622.
22. M.A. Battiste, M.W. Couch, and R. Rehberg J. Phys. Chem. 81 1977 64
23. K.B. Wiberg, and K.E. Laidign J. Org. Chem. 57 1992 5092
24. S. Kimura, S. Ito, M. Yoshifuji, and T. Veszprémi J. Org. Chem. 68 2003 6820
25. Handbook of Chemistry and Physics, 73rd ed.; 1992-1993; pp. 9-2.
26. X. Lu, S. Yang, and R.B. Silverman J. Org. Chem. 61 1996 8961
27. V.K. Aggarwal, G.Y. Fang, and G. Meek Org. Lett. 5 2003 4417
28. Y. Kita, J. Futamura, Y. Ohba, Y. Sawama, J.K. Ganesh, and H. Fujioka J. Org. Chem. 68 2003 5917
29. H. Inoue, K. Castagnoli, S. Mabic, K. Igarashi, and N. Castagnoli Jr. J. Pharmacol. Exp. Ther. 291 1999 856
30. J.I. Salach, T.P. Singer, N. Castagnoli Jr., and A. Trevor Biochem. Biophys. Res. Commun. 125 1984 831
31. K. Magyar, and B. Szende Neurotoxicology 25 2004 233
32. J. Knoll, and K. Magyar Adv. Biochem. Psychopharmacol. 5 1972 393
33. R.E. Heikkila, L. Manzino, S.C. Felicitas, and C.R. Duvoisin Nature 311 1984 467
34. K. Auclair, H. Zhengbo, D.M. Little, P.R. Ortiz de Montellano, and J.T. Groves J. Am. Chem. Soc. 124 2002 6020
35. S.-Y. Choi, P.H. Toy, and M. Newcomb J. Org. Chem. 63 1998 8609
36. M. Newcomb, C.C. Johnson, M.B. Manek, and T.R. Varick J. Am. Chem. Soc. 114 1992 10915
37. L.A. Paquette J. Am Chem. Soc. 86 1964 4092
38. K. Chiba, A.J. Trevor, and N. Castagnoli Jr. Biochem. Biophys. Res. Commun. 120 1984 574
39. S.M. Pitts, S.P. Markey, D.L. Murphy, and A. Weiss S.P. Markey N. Castagnoli Jr. A.J. Trevor I.J. Kopin Recommended Practices for the Safe Handling of MPTP 1995 Academic Press New York 703
40. J.I. Salach, and W. Weyler S. Kaufman Methods in Enzymology Vol. 142 1987 Academic Press London 627