Mechanism of Inhibition of Advanced Glycosylation by Aminoguanidine in Vitro

Abstract

A triazine and a bishydrazone were isolated from a solution of aminoguanidine incubated with an Amadori product (1-deoxy-1-propylamino-D-fructose) under physiological conditions. The new products were characterized by NMR and mass spectrometric analysis. The mechanism of the inhibition was proposed to involve the reactive intermediate 1, 4-dideoxy-1-(propylamino)-D-glycero-2, 3-hexodiulose (i.e., 1-propylamino-1, 4-dideoxyosone). The existence of this intermediate was supported by acetylation and characterization of the product. Formation of a proposed triazine and bis(amidinohydrazone) after the incubation of 1-propylamino-1, 4-dideoxyosone with aminoguanidine also supported the proposed mechanism.