title: 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.
authors.affiliation: Departamento de Química, Pontifícia Universidade Católica do Rio de Janeiro, Rua Marques de São Vicente, 225, Gávea, CP 38097, 22451-900, Rio de Janeiro, RJ, Brazil. a_pimentel@puc-rio.br.
authors.forename: Helmut I
authors.initials: HI
authors.lastname: Padilla-Chavarría
authors.forename: Teobaldo R C
authors.initials: TR
authors.lastname: Guizado
authors.forename: Andre S
authors.initials: AS
authors.lastname: Pimentel
mesh_terms: D001551:Benz(a)Anthracenes / Q000737:chemistry* / Q000378:metabolism; D008051:Lipid Bilayers / Q000737:chemistry* / Q000378:metabolism; D056004:Molecular Dynamics Simulation; D015394:Molecular Structure; D010743:Phospholipids / Q000737:chemistry* / Q000378:metabolism; D011663:Pulmonary Surfactants / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001551:Benz(a)Anthracenes; D008051:Lipid Bilayers; D010743:Phospholipids; D011663:Pulmonary Surfactants; C026486:1,2,5,6-dibenzanthracene