Molecular dynamics of dibenz[a,h]anthracene and its metabolite interacting with lung surfactant phospholipid bilayers

Abstract

The interaction of dibenz[a,h]anthracene and its ultimate carcinogenic 3,4-diol-1,2-epoxide with lung surfactant phospholipid bilayers was successfully performed using molecular dynamics. The DPPC/DPPG/cholesterol bilayer (64 : 64 : 2) was used as the lung surfactant phospholipid bilayer model and compared with the DPPC bilayer as a reference. Dibenz[a,h]anthracene and its 3,4-diol-1,2-epoxide were inserted in water and lipid phases in order to investigate their interactions with the lung surfactant phospholipid bilayers. The radial distribution function between two P atoms in polar heads shows that the 3,4-diol-1,2-epoxide affects the order between the P atoms in the DPPC/DPPG/cholesterol model more than dibenz[a,h]anthracene, which is a consequence of its preference for the polar heads and dibenz[a,h]anthracene prefers to be located in the hydrocarbon chain of the phospholipid bilayers. Dibenz[a,h]anthracene and its 3,4-diol-1,2-epoxide may form aggregates in water and lipid phases, and in the water–lipid interface. The implications for the possible effect of dibenz[a,h]anthracene and its 3,4-diol-1,2-epoxide in the lung surfactant phospholipid bilayers are discussed.