Current experimental evidence suggests that oxidative stress, the overproduction of reactive oxygen species (ROS), plays a role in the development of numerous inflammatory diseases such as asthma, diabetic retinopathy, and atherosclerosis. The enzyme nicotinamide adenine disphosphonucleotide (NADPH) oxidase has been confirmed as the predominant source of ROS within endothelial cells, as well as in other cell types that are affected by inflammatory processes. Previous studies have confirmed that apocynin is an excellent inhibitors of NADPH oxidase. We have demonstrated that apocynin is a prodrug that is converted to the active metabolite, diapocynin, in the presence of hydrogen peroxide and myleoperoxidase. Various analogs of the diapocynin have been synthesized from the following monomers: 4-fluoro-2-methoxyphenol, 4-chloro-2-methoxyphenol, 4-bromo-2-methoxyphenol, and 4-hydroxy-3-methoxybenzonitrile. These dimers have been characterized by nuclear magnetic resonance spectroscopy (NMR) and their NADPH oxidase inhibitor activity is being explored.

Dimerization of apocynin and its derivatives

251st National Meeting (2016)

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