MECHANISM OF INHIBITION OF ADVANCED GLYCOSYLATION BY AMINOGUANIDINE IN-VITRO

A triazine and a bishydrazone were isolated from a solution of aminogu anidine incubated with an Amadori product (1-deoxy-1-propylamino-D-fru ctose) under physiological conditions. The new products were character ized by NMR and mass spectrometric analysis. The mechanism of the inhi bition was proposed to involve the reactive intermediate -dideoxy-1-(p ropylamino)-D-glycero-2,3-hexodiulose (i.e., 1-propylamino-1,4-deoxyos one). 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-di deoxyosone with aminoguanidine also supported the proposed mechanism.,