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

Author

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  • Kentaro Misaki

    (Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan
    School of Nursing, University of Shizuoka, Yada 52-1, Suruga-ku, Shizuoka 422-8526, Japan)

  • Nguyen Minh Tue

    (Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan
    Key Laboratory of Analytical Technology for Environmental Quality and Food Safety Control (KLATEFOS), VNU University of Science, Vietnam National University, 334 Nguyen Trai, Hanoi 11400, Vietnam)

  • 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
    Key Laboratory of Analytical Technology for Environmental Quality and Food Safety Control (KLATEFOS), VNU University of Science, Vietnam National University, 334 Nguyen Trai, Hanoi 11400, Vietnam)

  • Shin Takahashi

    (Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan
    Center of Advanced Technology for the Environment, Agricultural Faculty, Ehime University, Tarumi 3-5-7, Matsuyama 790-8566, Japan)

  • Shinsuke Tanabe

    (Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan)

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.

Suggested Citation

  • Kentaro Misaki & Nguyen Minh Tue & Takeji Takamura-Enya & Hidetaka Takigami & Go Suzuki & Le Huu Tuyen & Shin Takahashi & Shinsuke Tanabe, 2022. "Antiandrogenic and Estrogenic Activity Evaluation of Oxygenated and Nitrated Polycyclic Aromatic Hydrocarbons Using Chemically Activated Luciferase Expression Assays," IJERPH, MDPI, vol. 20(1), pages 1-17, December.
    • Handle: RePEc:gam:jijerp:v:20:y:2022:i:1:p:80-:d:1010417
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    1. Maryam Ghotbaddini & Joann B. Powell, 2015. "The AhR Ligand, TCDD, Regulates Androgen Receptor Activity Differently in Androgen-Sensitive versus Castration-Resistant Human Prostate Cancer Cells," IJERPH, MDPI, vol. 12(7), pages 1-13, July.
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