Abstract

A series of mono, bis and mixed Schiff bases (1-7) were synthesised and evaluated for potential anti-glycation and anti-oxidant activities using the bovine serum albumin - glucose assay and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical assay respectively. All compounds showed significant (p < 0.05) antiglycating activities with IC50 values (4.02 x10-24 ± 0.1 – 2.88 x 10-1 ± 1.35 mM) which were lower than the standard positive control aminoguanidine (IC50 : 1.51 x 10-3 ± 2.11 mM). Moreover, compounds 1-7 were found to possess significant (p < 0.05) DPPH radical scavenging properties with SC50 values (1.31 x 10-19 ± 0.05 to 2.25 x 10-1 ± 1.24 mM) lower than the standard ascorbic acid (SC50 : 5.50 x 10-3 ± 2.11 mM). Compound 6 was found to be the most potent anti-glycating molecule (IC50 value: 4.02 x10-24 ± 0.1 mM) while compound 5 was the most potent anti-oxidant molecule (SC50: 1.31 x 10-19 ± 0.05 mM); both being significantly lower (p < 0.05) than the respective positive controls used. The present data showed that the number of phenolic OH together with structural changes influence both the anti-glycation and anti-oxidant observed herein. This study provides for the first time a series of potential template molecules for possible pharmaceutical applications that warrant further investigation as potential anti-glycation and anti-oxidant agents which could be of importance in metabolic diseases including diabetes mellitus.

Keywords: 2, 3-Diaminopyridine, Schiff bases, Anti-glycation, Anti-oxidant, Hydroxyl analogues, Diabetes mellitus, scavenging, bovine serum albumin