Oxidative stress is caused by free radicals in the human body and may lead to pathogenesis of many diseases. Antioxidants are well known for their ability to protect cells against oxidative stress by scavenging free radicals. However, many antioxidants in the presence of transition metal ions such as Cu2+ and Fe3+ cause oxidative damage to biomolecules like DNA, protein, and fatty acid through pro-oxidant activities.  This study focused on synthesizing antioxidant that can separate the antioxidant activity from pro-oxidant activity by joining multiple hindered phenolic groups together in dendritic structure to produce high antioxidant activity and by incorporating internal cavities consisting of poly ethylene glycolic moieties to chelate metal ions and thus prevent pro-oxidant effect.  The synthesized dendrimer is generation 2(G2) and consists of a total of 36 phenolic units, 24 units on the surface and 12 units inside. It was built on a D-mannitol-based core onto which bis-(4-hydroxybenzyl)propargylamine was attached to form G1 dendrimer via microwave assisted-copper metal-catalyzed 1,3-dipolar cycloaddition, so called click chemistry. The reaction was highly efficient, yielding 89.3% of product. The G1 dendrimer was further reacted with branching unit to form G1.5 (yield=46%), which was in turn reacted with bis-(syringyl)propargylamine to form the G2 target dendrimer (yield=15%).

Organic synthesis of a D-mannitol core-based generation 2 antioxidant dendrimer

248th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.