The tert-butoxyl radical mediated hydrogen atom transfer reactions of the Parkinsonian proneurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and selected tertiary amines

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 18, 2008, Pages 8557-8562

  Suleman, N Kamrudin ^a   Flores, Joey ^a   Tanko, James M ^b   Isin, Emre Mehmet ^b   Castagnoli Jr , Neal ^b,c  

^a UNIVERSITY OF GUAM   (Guam)

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

^c EDWARD VIA COLLEGE OF OSTEOPATHIC MEDICINE   (United States)

Author keywords

Hydrogen atom transfer reactions; MPTP; Regioselectivity; tert Butoxyl

Indexed keywords

1,2,3,6 TETRAHYDRO 1 METHYL 4 PHENYLPYRIDINE; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; DEUTERIUM; HYDROGEN; NEUROTOXIN; RADICAL;

ARTICLE; CATALYSIS; ENZYME ACTIVITY; HYDROGEN ATOM TRANSFER REACTION; HYDROGEN BOND; MOLECULAR INTERACTION; NEUROTOXICITY; PARKINSONISM; SPECTROPHOTOMETER;

1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE; AMINES; CARBON; CATALYSIS; DEUTERIUM; HUMANS; HYDROGEN; KINETICS; MONOAMINE OXIDASE; NEUROTOXINS; OXIDATION-REDUCTION; PARKINSONIAN DISORDERS; STRUCTURE-ACTIVITY RELATIONSHIP; TERT-BUTYLHYDROPEROXIDE;

PARKINSONIA;

EID: 51649087084     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.08.013     Document Type: Article

References (35)

1. Chung K.K.K., Dawson V.L., and Dawson T.M. J. Neurol. 250 Suppl. 3 (2003) III/15-III/24
2. Lozano A.M., Lang A.E., Hutchison W.D., and Dostrovski J.O. Curr. Opin. Neurobiol. 8 (1998) 783-790
3. Ahlskog J.E., Petersen R.C., Waring S.C., Esteban-Santillan C., Craig U.-K., Maraganore D.M., Lennon V.A., and Kurland L.T. Neurology 48 5 (1997) 1356-1362
4. Plato C.C., Galasko D., Garruto R.M., Plato M., Gamst A., Craig U.-K., Torres J.M., and Wiederholt W. Neurology 58 5 (2002) 765-773
5. Galasko D., Salmon D.P., Craig U.-K., Thal L.J., Schellenberg G., and Wiederholt W. Neurology 58 1 (2002) 90-97
6. Sebeo J., Hof P.R., and Perl D.P. Acta Neuropathol. 107 6 (2004) 497-503
7. Khabazian I., Bains J.S., Williams D.E., Cheung J., Wilson J.M.B., Pasqualotto B.A., Pelech S.L., Andersen R.J., Wang Y.-T., Liu L., Nagai A., Kim S.U., Craig U.-K., and Shaw C.A. J. Neurochem. 82 3 (2002) 516-528
8. Thiruchelvam M., Richfield Eric.K., Goodman B.M., Baggs R.B., and Cory-Slechta D.A. Neurotoxicology 23 (2002) 621-633
9. Silverman R.B. Acc. Chem. Res. 28 8 (1995) 335-342
10. Binda C., Newton-Vinson P., Hubalek F., Edmondson D.E., and Mattevi A. Nat. Struct. Biol. 9 1 (2002) 22-26
11. Rinne U.K. J. Neural. Transm. 25 Suppl. (1987) 149-155
12. Savitt J.M., Dawson V.L., and Dawson T.M. J. Clin. Invest. 116 (2006) 1744-1754
13. Chrisp P., Mammen G.L., and Sorkin E.M. Drugs Aging 1 (1991) 228-248
14. Mitchell D.J., Nikolic D., van Breeman R.B., and Silverman R.B. Bioorg. Med. Chem. Lett. 11 (2001) 1757-1760
15. Edmondson D.E. Xenobiotica 25 (1995) 735-753
16. Edmondson D.E., Mattevi A., Binda C., Li M., and Hubalek F. Curr. Med. Chem. 11 (2004) 1983-1993
17. Rigby S.E.J., Hynson R.M.G., Ramsay R.R., Munro A.W., and Scrutton N.S. J. Biol. Chem. 6 (2005) 4627-4631
18. Scrutton N.S. Nat. Prod. Rep. 21 (2004) 722-730
19. Langston J.W., Forno L.S., Tetrud J., Reeves A.G., Kaplan J.A., and Karluk D. Ann. Neurol. 46 4 (1999) 598-605
20. Chiba K., Trevor A.J., and Castagnoli Jr. N. Biochem. Biophys. Res. Commun. 120 (1984) 574-578
21. Lindsay Smith J.R., Nagatomi E., Stead A., Waddingtong D.J., and Beviere S.D. J. Chem. Soc. Perkin Trans. 2 (2000) 1193-1198
22. Adam W., Marquardt S., Kemmer D., Saha-Moeller C.R., and Schreier P. Org. Lett. 4 (2002) 225-228
23. Hudson A., Waterman D., and Alberti A. J. Chem. Soc. Perkin Trans. 2 (1995) 2091-2093
24. Karki S.B., Dinnocenzo J.P., Jones J.P., and Korzekwa K.R. J. Am. Chem. Soc. 117 13 (1995) 3657-3664
25. Choi S.-Y., Eaton P.E., Hollenberg P.F., Liu K.E., Lippard S.J., Newcomb M., Putt D.A., Upadhyaya S.P., and Xiong Y. J. Am. Chem. Soc. 118 (1996) 6547-6555
26. Franot C., Mabic S., and Castagnoli Jr. N. Bioorg. Med. Chem. 6 3 (1998) 283-291
27. Tanko J.M., Friedline R., Suleman N.K., and Castagnoli Jr. N. J. Am. Chem. Soc. 123 24 (2001) 5808-5809
28. Finn M., Friedline R., Suleman N.K., Wohl C.J., and Tanko J.M. J. Am. Chem. Soc. 126 24 (2004) 7578-7584
29. Paul H., Small Jr. R.D., and Scaiano J.C. J. Am. Chem. Soc. 100 14 (1978) 4520-4527
30. Griller D., Howard J.A., Marriott P.R., and Scaiano J.C. J. Am. Chem. Soc. 103 3 (1981) 619-623
31. Ottoboni S., Caldera P., Trevor A., and Castagnoli Jr. N. J. Biol. Chem. 264 23 (1989) 13684-13688
32. Dombrowski G.W., Dinnocenzo J.P., Farid S., Goodman J.L., and Gould I.R. J. Org. Chem. 64 2 (1999) 427-431
33. Lalevée J., Graff B., Allonas X., and Fouassier J.P.J. Phys. Chem. A 111 (2007) 6991-6998
34. Foti M., Ingold K.U., and Lusztyk J. J. Am. Chem. Soc. 116 (1994) 9440-9447
35. Pitts S.M., Markey S.P., Murphy D.L., Weisz A., and Lunn G. Recommended practices for the safe handling of MPTP. MPTP-A Neurotoxin Producing a Parkinsonian Syndrome (1986), Academic, New York 703-716