An innovative in vitro assay to study the effects of aromatic pollutants on porphyrin systems

Abstract

Interactions between aromatic pollutants (APs) and porphyrin nucleus as physiological receptors have a significant effect on biological functions of porphyrin-based systems in organism. However, the details on the interaction at molecule level are still elusive. Herein, interaction mechanisms between two typical APs (methylene blue, MB and benzo[a]pyrene, B[a]P) and meso-tetra (4-carboxyphenyl) porphine (TCPP) as physiological receptors were systematically investigated. Adsorption behaviors of TCPP to B[a]P was dominated by pi-pi interaction, while interaction between TCPP and MB coupled with a multi-force field including hydrophobic, pi-pi, electrostatic, and H-bonding interactions. The relative contributions of these four forces obeyed an order: H-bonding > pi-pi > electrostatic > hydrophobic, regardless of the pH value and the initial concentration of MB. H-bonding assisted by hydrogen/hydroxide ion was the most influential force. According to the effect of pH and temperature, organisms exposed to cellular environment with high alkalinity and high temperature might uptake more APs molecules with chemical properties similar to MB and suffered greater health risks. In detail, APs might replace amino acid molecules surrounding porphyrin and change the distortion type of porphyrin molecule, and then affect biological functions of porphyrin and related proteins. This study facilitates a better understanding of potential toxicity of organisms in contaminated environment.