STUDIES ON THE OXIDATION OF 1,4-DISUBSTITUTED-1,2,3,6-TETRAHYDROPYRIDINES

REFERENCES

• Guengerich F.P. Common and Uncommon Cytochrome P450 Reactions Related to Metabolism and Chemical Toxicity. Chem. Res. Toxicol. 2001; 14: 612–860
   Google Scholar
• Testa B. Monooxygenase-Catalyzed N–C Cleavage. The Metabolism of Drugs and Other Xenobiotics. Biochemistry of Redox Reactions. Academic Press, New York 1995; 203–234
   Google Scholar
• Coutts R.T., Su P., Baker G.B. Involvement of CYP2D6, CYP3A4, and Other Cytochrome P-450 Isoenzymes in N-Dealkylation Reactions. J. Pharmacol. Toxicol. Methods 1994; 31: 177–186
   PubMed Web of Science ®Google Scholar
• Guengerich F.P. Sequential Electron Transfer and Base Catalysis in the N-Dealkylation of Amines by Cytochrome P450 Enzymes. Organic Reactivity: Physical and Biological Aspects. R. Soc. Chem. 1995; Vol. 148: 185–195
   Google Scholar
• Guengerich F.P., Yun C.-H., MacDonald T.L. Evidence for a 1-Electron Oxidation Mechanism in N-Dealkylation of N,N-Dialkylanilines by Cytochrome P450 2B1. Kinetic Hydrogen Isotope Effects, Linear Free Energy Relationships, Comparisons with Horseradish Peroxidase, and Studies with Oxygen Surrogates. J. Biol. Chem. 1996; 271: 27321–27329
   PubMed Web of Science ®Google Scholar
• Guengerich F.P., Okazaki O., Seto Y., MacDonald T.L. Radical Cation Intermediates in N-Dealkylation Reactions. Xenobiotica 1995; 25: 689–709
   PubMed Web of Science ®Google Scholar
• Manchester J.I., Dinnocenzo J.P., Higgins L., Jones J.P. A New Mechanistic Probe for Cytochrome P450: An Application of Isotope Effect Profiles. J. Am. Chem. Soc. 1997; 119: 5069–5070
   Web of Science ®Google Scholar
• Karki S.B., Dinnocenzo J.P. On The Mechanism of Amine Oxidations by P450. Xenobiotica 1995; 25: 711–724
   PubMed Web of Science ®Google Scholar
• Karki S.B., Dinnocenzo J.P., Jones J.P., Korzekwa K.R. Mechanism of Oxidative Amine Dealkylation of Substituted N,N-Dimethylanilines by Cytochrome P450: Application of Isotope Effect Profiles. J. Am. Chem. Soc. 1995; 117: 3657–3664
   Web of Science ®Google Scholar
• Wang Y.-X., Mabic S., Castagnoli N., Jr. 1-Methyl-3-pyrrolines and 2-Methylisoindolines: New Classes of Cyclic Tertiary Amine Monoamine Oxidase B Substrates. Bioorg. Med. Chem. 1998; 6: 143–149
   PubMed Web of Science ®Google Scholar
• Kalgutkar A.S., Dalvie D.K., Castagnoli N., Jr., Taylor T.J. Interactions of Nitrogen-Containing Xenobiotics with Monoamine Oxidase (MAO) Isozymes A and B: SAR Studies on MAO Substrates and Inhibitors. Chem. Res. Toxicol. 2001; 14: 1139–1164
   PubMed Web of Science ®Google Scholar
• Kuttab S., Kalgutkar A., Castagnoli N., Jr. Mechanistic Studies on the Monoamine Oxidase B Catalyzed Oxidation of 1,4-Disubstituted Tetrahydropyridines. Chem. Res. Toxicol. 1994; 7: 740–744
   PubMed Web of Science ®Google Scholar
• Rimoldi J.M., Wang Y.-X., Nimkar S.K., Kuttab S., Anderson A.H., Burch H., Castagnoli N., Jr. Probing the Mechanism of Bioactivation of MPTP Type Analogs by Monoamine Oxidase B: Structure Activity Studies on Substituted 4-Phenyl-, 4-Phenoxy- and 4-Thiophenoxy-1-Cyclopropyl-1,2,3,6-Tetrahydropyridines. Chem. Res. Toxicol. 1995; 8: 703–710
   PubMed Web of Science ®Google Scholar
• Silverman R.B. Radical Thoughts About the Life of MAO. Prog. Brain Res. 1995; 106: 23–31
   PubMed Web of Science ®Google Scholar
• Bondon A., Macdonald T.L., Harris T.M., Guengerich F.P. Oxidation of Cycloalkylamines by Cytochrome P-450. Mechanism-Based Inactivation, Adduct Formation, Ring Expansion, and Nitrone Formation. J. Biol. Chem. 1989; 264: 1988–1997
   PubMed Web of Science ®Google Scholar
• Macdonald T.L., Zirvi K., Burka L.T., Peyman P., Guengerich F.P. Mechanism of Cytochrome P-450 Inhibition by Cyclopropylamines. J. Am. Chem. Soc. 1982; 104: 2050–2052
   Web of Science ®Google Scholar
• Guengerich, F.P.; Willard, R.J.; Shea, J.P.; Richards, L.E.; Macdonald, T.L. Mechanism-Based Inactivation of Cytochrome P-450 by Heteroatom-Substituted Cyclopropanes and Formation of Ring-Opened Products. 1984, 106, 6446–6447.
   Google Scholar
• Guengerich F.P., Macdonald T.L. Sequential Electron-Transfer Reactions Catalyzed by Cytochrome P-450 Enzymes. Advances in Electron-Transfer Chemistry, P.S. Mariano. JAI Press, Greenwich, CT 1993; Vol. 3: 191–241
   Google Scholar
• Hanzlik R.P., Tullman R.H. Sucidal Inactivation of Cytochrome P-450 by Cyclopropylamines. Evidence for Cation-Radical Intermediates. J. Am. Chem. Soc. 1982; 104: 2048–2050
   Web of Science ®Google Scholar
• Vazquez M.L., Silverman R.B. Revised Mechanism for Inactivation of Mitochondrial Monoamine Oxidase by N-Cyclolpropylbenzylamine. Biochemistry 1985; 24: 6538–6543
   PubMed Web of Science ®Google Scholar
• Mitchell D.J., Nikolic D., Rivera E., Sablin S.O., Choi S., van Breemen R.B., Singer T.P., Silverman R.B. Spectrometric Evidence for the Flavin-1-Phenylcyclopropylamine Inactivator Adduct with Monoamine Oxidase. Biochemistry 2001; 40: 5447–5456
   PubMed Web of Science ®Google Scholar
• Silverman R.B. Effect of Alpha-Methylation on Inactivation of Monoamine Oxidase by N-Cyclopropylbenzylamine. Biochemistry 1984; 23: 5206–5213
   PubMed Web of Science ®Google Scholar
• Zhong B., Silverman R.B. Identification of the Active Site Cysteine in Bovine Liver Monoamine Oxidase B. J. Am. Chem. Soc. 1997; 119: 6690–6691
   Web of Science ®Google Scholar
• Hall, L.; Murray, S.; Castagnoli, K.; Castagnoli, N., Jr. Studies on 1,2,3,6-Tetrahydropyridine Derivatives as Potential Monoamine Oxidase Inactivators. 1992, 5, 625–623.
   Google Scholar
• Nimkar S.K., Anderson A.H., Rimoldi J.M., Stanton M., Castagnoli K.P., Mabic S., Wang Y.-X., Castagnoli N., Jr. Synthesis and Monoamine Oxidase B Catalyzed Oxidation of C-4 Heteroaromatic Substituted 1,2,3,6-Tetrahydropyridine Derivatives. Chem. Res. Toxicol. 1996; 9: 1013–1022
   PubMed Web of Science ®Google Scholar
• Anderson A.H., Kuttab S., Castagnoli N., Jr. Deuterium Isotope Effect Studies on the MAO-B Catalyzed Oxidation of 4-Benzyl-1-Cyclopropyl-1,2,3,6-Tetrahydropyridine. Biochemistry 1996; 35: 3335–3340
   PubMed Web of Science ®Google Scholar
• Nguyen M.T., Creve S., Ha T.-K. On the Formation of the CH2CH2CH= NH2+ Distonic Radical Cation upon Ionization of the Cyclopropylamine and Allylamine. Chem. Phys. Lett. 1998; 293: 90–96
   Web of Science ®Google Scholar
• Maeda Y., Ingold K.U. Kinetic Applications of Electron Paramagnetic Resonance Specroscopy. 35. The Search for a Dialkylaminyl Rearrangement Ring Opening of N-Cyclobutyl-N-n-propylaminyl. J. Am. Chem. Soc. 1980; 102: 328–331
   Web of Science ®Google Scholar
• Zhao Z., Mabic S., Kuttab S., Franot C., Castagnoli K., Castagnoli N., Jr. Rat Liver Microsomal Enzyme Catalyzed Oxidation of 1-Cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine. Bioorg. Med. Chem. 1998; 6: 2531–2539
   PubMed Web of Science ®Google Scholar
• Schlesener C.J., Amatore C., Kochi J.K. Rates and Mechanism of Proton Transfer from Transient Carbon Acids. The Acidity of Methylbenzene Cation Radicals. J. Am. Chem. Soc. 1984; 106: 7472–7482
   Web of Science ®Google Scholar
• Franot C., Mabic S., Castagnoli N., Jr. Chemical Model Studies on the Monoamine Oxidase-B Catalyzed Oxidation of 4-Substituted 1-Cyclopropyl-1,2,3,6-tetrahydopyridines. Bioorg. Med. Chem. 1998; 6: 283–291
   PubMed Web of Science ®Google Scholar
• Park K.K., Han D., Shin D. Reduction of N-Arylpyridinium Compounds by Sodium Borohydride and Dithionite: Regioselectivity and Isomerization of Reduction Products. Bull. Korean Chem. Soc. 1986; 7: 201–204
   Web of Science ®Google Scholar
• Kuttab S., Shang J., Castagnoli N., Jr. Rat Liver Microsomal Enzyme Catalyzed Oxidation of 4-Phenyl-trans-1-(2-phenylcyclopropyl)-1,2,3,6-tetrahydropyridine. Bioorg. Med. Chem. 2001; 9: 1685–1689
   PubMed Web of Science ®Google Scholar
• Weissman J., Trevor A., Chiba K., Peterson L.A., Caldera P., Castagnoli N., Jr. Metabolism of the Nigrostriatal Toxin 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine by Liver Homogenate Fractions. J. Med. Chem. 1985; 28: 997–1001
   PubMed Web of Science ®Google Scholar
• Chiba K., Kubota E., Miykawa E.T., Kato Y., Ishizaki T. Characterization of Hepatic Microsomal Metabolism as an In Vivo Detoxication Pathway of 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine in Mice. J. Pharmacol. Exp. Ther. 1988; 246: 1108–1115
   PubMed Web of Science ®Google Scholar
• Binda C., Newton-Vinson P., Hubalek F., Edmondson D., Mattevi A. Structure of Human Monoamine Oxidase B: A Drug Target for the Treatment of Neurological Disorders. Nat. Struct. Biol. 2002; 9: 22–26
   PubMedGoogle Scholar