title: Methylated phenanthrenes are more potent than phenanthrene in a bioassay of human aryl hydrocarbon receptor (AhR) signaling.
abstract: Alkylated polycyclic aromatic hydrocarbons (APAHs) are abundant in petroleum, but data regarding their toxicological properties are limited. A survey of all monomethylated phenanthrene structures revealed that they were 2 times to 5 times more potent than phenanthrene for activation of human aryl hydrocarbon receptor in a yeast bioassay. Phenanthrenes with equatorial methyl groups had the greatest potency. The greater potency of the methylated phenanthrenes highlights the need for more toxicological data on APAHs.
authors.affiliation: Department of Biochemistry and Molecular Biology, Tulane University School of Medicine, New Orleans, Louisiana, USA.
authors.forename: Yue
authors.initials: Y
authors.lastname: Sun
authors.forename: Charles A
authors.initials: CA
authors.lastname: Miller
authors.forename: Thomas E
authors.initials: TE
authors.lastname: Wiese
authors.forename: Diane A
authors.initials: DA
authors.lastname: Blake
mesh_terms: D051792:Basic Helix-Loop-Helix Proteins / Q000235:genetics / Q000378:metabolism*; D001681:Biological Assay; D004785:Environmental Pollutants / Q000737:chemistry* / Q000633:toxicity*; D005818:Genetic Engineering; D006801:Humans; D008745:Methylation; D010616:Phenanthrenes / Q000737:chemistry* / Q000633:toxicity*; D018336:Receptors, Aryl Hydrocarbon / Q000235:genetics / Q000378:metabolism*; D012441:Saccharomyces cerevisiae / Q000187:drug effects / Q000235:genetics / Q000378:metabolism; D015398:Signal Transduction / Q000187:drug effects; D018675:Toxicity Tests
chemical_list: D051792:Basic Helix-Loop-Helix Proteins; D004785:Environmental Pollutants; D010616:Phenanthrenes; D018336:Receptors, Aryl Hydrocarbon; C111235:AHR protein, human; C031181:phenanthrene
keywords: Alkylated polycyclic aromatic hydrocarbons; Aryl hydrocarbon receptor; Methylphenanthrene; Petrogenic polycyclic aromatic hydrocarbons; Phenanthrene