title: Electrochemistry of the anticancer agents methotrexate and alpha-difluoromethylornithine in iminium form.
abstract: The electrochemical characteristics of the antitumor agents methotrexate and alpha-difluoromethylornithine were determined as their iminium derivatives. Iminium formation from methotrexate is accomplished in vivo via protonation by enzyme. The requisite imine precursor is generated from alpha-difluoromethylornithine by condensation with enzyme containing pyridoxal phosphate. Electroreduction occurs in the range of -0.2 to -0.6 V. The relationship of reduction to structure is discussed. A possible mode of anticancer action involving electron transfer is presented.
authors.affiliation: Department of Chemistry, University of Wisconsin-Milwaukee 53201.
authors.forename: P
authors.initials: P
authors.lastname: Kovacic
authors.forename: J R
authors.initials: JR
authors.lastname: Ames
authors.forename: E C
authors.initials: EC
authors.lastname: Taylor
authors.forename: M D
authors.initials: MD
authors.lastname: Ryan
mesh_terms: D055598:Chemical Phenomena; D002621:Chemistry; D000518:Eflornithine / Q000032:analysis*; D004563:Electrochemistry; D006863:Hydrogen-Ion Concentration; D008727:Methotrexate / Q000032:analysis*; D011732:Pyridoxal Phosphate / Q000032:analysis
chemical_list: D011732:Pyridoxal Phosphate; D008727:Methotrexate; D000518:Eflornithine