Methylated phenanthrenes are more potent than phenanthrene in a bioassay of human aryl hydrocarbon receptor (AhR) signaling

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 hy...

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Bibliographic Details
Published in:Environmental toxicology and chemistry 2014-10, Vol.33 (10), p.2363-2367
Main Authors: Sun, Yue, Miller III, Charles A., Wiese, Thomas E., Blake, Diane A.
Format: Article
Language:English
Subjects:
Activation
Alkylated polycyclic aromatic hydrocarbons
Aromatic compounds
Aryl hydrocarbon receptor
Basic Helix-Loop-Helix Transcription Factors
Basic Helix-Loop-Helix Transcription Factors - genetics
Basic Helix-Loop-Helix Transcription Factors - metabolism
Bioassay
Bioassays
Biological Assay
chemistry
Crude oil
drug effects
Environmental Pollutants
Environmental Pollutants - chemistry
Environmental Pollutants - toxicity
Environmental Toxicology
Genetic Engineering
genetics
Human
Humans
Hydrocarbons
metabolism
Methylation
Methylphenanthrene
Petrogenic polycyclic aromatic hydrocarbons
petroleum
Petroleum hydrocarbons
Phenanthrene
phenanthrenes
Phenanthrenes - chemistry
Phenanthrenes - toxicity
Polycyclic aromatic hydrocarbons
Receptors
Receptors, Aryl Hydrocarbon
Receptors, Aryl Hydrocarbon - genetics
Receptors, Aryl Hydrocarbon - metabolism
Saccharomyces cerevisiae
Saccharomyces cerevisiae - drug effects
Saccharomyces cerevisiae - genetics
Saccharomyces cerevisiae - metabolism
Signal Transduction
Signal Transduction - drug effects
surveys
toxicity
Toxicity Tests
Toxicology
Yeast
Yeasts
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Summary: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. Environ Toxicol Chem 2014;33:2363–2367. © 2014 The Authors. Environmental Toxicology and Chemistry published by Wiley Periodicals, Inc. on behalf of SETAC.
ISSN:0730-7268
1552-8618
DOI:10.1002/etc.2687