Title page for ETD etd-08252008-162914

Type of Document Master's Thesis
Author Harris, Dana N.
URN etd-08252008-162914
Title Quantitative structure activity relationships of monamine oxidase catalyzed oxidation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine analogs
Degree Master of Science
Department Chemistry
Advisory Committee
Advisor Name Title
Castagnoli, Neal Jr. Committee Chair
Bell, Harold M. Committee Member
Bevan, David R. Committee Member
Tanko, James M. Committee Member
  • Parkinson's disease
  • QSAR
  • MAO
  • MPTP
Date of Defense 1996-05-15
Availability restricted

Studies into the quantitative structure act! Vlty relationships of rate s of I-methyl-4-phenyl-l,2,3,6-tetrahydropyridine oxidation catalyzed by monoamine oxidases A and B were performed to elucidate active site substrate conformation and oxidation mechanisms. Plotting experimental kinetic activity against molecular properties obtained by experiment and by computational chemistry methods demonstrated correlations with lipophilic, steric, and electronic factors. Compounds studied were 4-aryloxy analogs, 4- aromatic heterocycle analogs, and 4-phenyl analogs. The conformer with phenyl ring to tetrahydropyridine dihedral angles similar to a low energy conformer of I-methyl-4-(2'-methyl-phenyl)-1,2,3,6- tetrahydropyridine is the most active conformer. Results indicate that rate limiting single electron transfer mechanisms are more viable than hydrogen atom abstraction mechanisms. Results indicate that binding or dissociation is the rate limiting step for aryloxy-analog oxidation catalyzed by monoamine oxidase B whereas the catalytic event itself is the rate limiting step for the other analogs. Several equations were developed to describe quantitative structure activity relationships of oxidation rates.

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