Title page for ETD etd-05222007-091412

Type of Document Dissertation
Author Kalgutkar, Amit S.
URN etd-05222007-091412
Title Synthesis and biological evaluation of novel MPTP analogs as potential monoamine oxidase B inhibitors
Degree PhD
Department Chemistry
Advisory Committee
Advisor Name Title
Castagnoli, Neal Jr. Committee Chair
Gibson, Harry W. Committee Member
Kingston, David G. I. Committee Member
Merola, Joseph S. Committee Member
Tanko, James M. Committee Member
  • Cyclic teriary amines
Date of Defense 1993-09-01
Availability restricted
The Parkinsonian-inducing neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and close structural analogs are the only known cyclic tertiary amines with good monoamine oxidase substrate properties. In addition to its substrate properties, MPTP is a weak mechanism-based inactivator of monoamine oxidase-B (MAC)-B). In an attempt to exploit the special interactions between this cyclic tertiary allylamine and MAO-B, studies were initiated to develop novel mechanism-based inactivators of this flavoenzyme. Analogs of MPTP bearing a variety of functional groups at either N or the C(4) position have been synthesized and their interactions with purified MAO-l3 have been characterized. The substituents selected included functionalities which were considered potential sources of enzyme generated electrophilic or radical intermediates that might alkylate and inactivate the enzyme. None of the C(4)-substituted compounds displayed significant enzyme inhibitor properties while the 4-phenyl-I-propargyl analog was a good mechanism-based inactivator of MAO-B but not MAO-A.

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