Structure-activity relationship study on the bioreduction of azo dyes by Clostridium paraputrificum

Seven commercially available, structurally related azo dyes have been bioreduced by the anaerobic bacterium Clostridium paraputrificum. The rates of reduction of these dyes were found to vary between 24 and 74 nmoles reduced/mg protein/h. Acid red 1 and desmethyl acid red 106 were found to be the most readily reduced, while chromotrope 2R and cibacron brilliant red 3B-A were reduced at the slowest rates. The differences in reduction rates can be rationalized on the basis of structural differences and are consistent with the possible intermediacy of low molecular-weight electron carriers as the mediators of reduction. The incorporation of electron-withdrawing groups into the dyes, even if remotely placed, was found to increase the rate of reduction of dyes under controlled conditions, supporting the inversely proportional relationship between the electron density of the azo bond and the ease of bioreduction.