Enhanced anaerobic degradation of polymeric azo compounds by Escherichia coli in the presence of low-molecular-weight redox mediators.

Abstract

The effects of the redox mediator lawsone (2-hydroxy-1,4-naphthoquinone) on the ability of Escherichia coli to reduce anaerobically polymeric azo compounds were analysed. Two types of polymeric azo compounds were tested, that have been proposed as putative tools for the site-specific targeting of drugs to the colon. The first group of polymers consisted basically of linear chains of polymethacrylic acid or polymethylmethacrylate which were interrupted by subunits of 4,4'-bis(methacryloylamino)azobenzene. These polymers differed significantly in their hydrophilicity according to the relative proportion of polymethacrylic acid used for the polymerization procedure. The second group of polymers consisted of almost water-insoluble poly(ether-ester)azo polymers that were composed of 4-(6-hydroxyhexyl)oxy-phenylazobenzoate and 16-hydroxyhexadecanoate. The addition of lawsone to the anaerobically incubated cultures of E. coli resulted in a pronounced increase in the reduction rates of the water-soluble poly(methacrylate-co-4,4'-bis(methacryloylamino)azobenzene) and in a much smaller, but significant, increase in the reduction rates of the hydrophobic poly(ether-ester)azo polymers. An increase in the amount of azo groups resulted, for the hydrophobic poly(ether-ester)azo polymers, in an increased reduction rate in the presence of the redox mediator lawsone.