Antiandrogenic and Estrogenic Activity Evaluation of Oxygenated and Nitrated Polycyclic Aromatic Hydrocarbons Using Chemically Activated Luciferase Expression Assays

Kentaro Misaki (), Nguyen Minh Tue, Takeji Takamura-Enya, Hidetaka Takigami, Go Suzuki, Le Huu Tuyen, Shin Takahashi and Shinsuke Tanabe
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Kentaro Misaki: Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan
Nguyen Minh Tue: Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan
Takeji Takamura-Enya: Department of Applied Chemistry, Kanagawa Institute of Technology, 1030 Shimo-Ogino, Atsugi 243-0292, Japan
Hidetaka Takigami: Center for Material Cycles and Waste Management Research, National Institute for Environmental Studies (NIES), Onogawa 16-2, Tsukuba 305-8506, Japan
Go Suzuki: Center for Material Cycles and Waste Management Research, National Institute for Environmental Studies (NIES), Onogawa 16-2, Tsukuba 305-8506, Japan
Le Huu Tuyen: Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan
Shin Takahashi: Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan
Shinsuke Tanabe: Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan

IJERPH, 2022, vol. 20, issue 1, 1-17

Abstract: To establish the risk of the endocrine disrupting activity of polycyclic aromatic compounds, especially oxygenated and nitrated polycyclic aromatic hydrocarbons (oxy-PAHs and nitro-PAHs, respectively), antiandrogenic and estrogenic activities were determined using chemically activated luciferase expression (CALUX) assays with human osteoblast sarcoma cells. A total of 27 compounds including 9 oxy-PAHs (polycyclic aromatic ketones and quinones) and 8 nitro-PAHs was studied. The oxy-PAHs of 7 H -benz[ de ]anthracen-7-one (BAO), 11 H -benzo[ a ]fluoren-11-one (B[ a ]FO), 11 H -benzo[ b ]fluoren-11-one (B[ b ]FO), and phenanthrenequinone (PhQ) exhibited significantly the potent inhibition of AR activation. All nitro-PAHs exhibited high antiandrogenic activities (especially high for 3-nitrofluoranthene (3-NFA) and 3-nitro-7 H -benz[ de ]anthracen-7-one (3-NBAO)), and the AR inhibition was confirmed as noncompetitive for 3-NFA, 3-NBAO, and 1,3-dinitropyrene (1,3-DNPy). Antiandrogenic activity of 3-NFA demonstrated characteristically a U-shaped dose–response curve; however, the absence of fluorescence effect on the activity was confirmed. The prominent estrogenic activity dependent on dose–response curve was confirmed for 2 oxy-PAHs (i.e., B[ a ]FO and B[ b ]FO). Elucidating the role of AR and ER on the effects of polycyclic aromatic compounds (e.g., oxy- and nitro-PAHs) to endocrine dysfunctions in mammals and aquatic organisms remains a challenge.

Keywords: polycyclic aromatic ketone; polycyclic aromatic quinone; nitrated polycyclic aromatic hydrocarbon; antiandrogenic activity; estrogenic activity; chemically activated luciferase expression assay (search for similar items in EconPapers)
JEL-codes: I I1 I3 Q Q5 (search for similar items in EconPapers)
Date: 2022
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