{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T07:15:02Z","timestamp":1790838902515,"version":"4.1.0"},"reference-count":83,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2022,12,21]],"date-time":"2022-12-21T00:00:00Z","timestamp":1671580800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Grant-in-Aid for Scientific Research (S)","award":["20221003"],"award-info":[{"award-number":["20221003"]}]},{"name":"Grant-in-Aid for Scientific Research (S)","award":["20H00646"],"award-info":[{"award-number":["20H00646"]}]},{"name":"the Japan Society for the Promotion of Science (JSPS)","award":["20221003"],"award-info":[{"award-number":["20221003"]}]},{"name":"the Japan Society for the Promotion of Science (JSPS)","award":["20H00646"],"award-info":[{"award-number":["20H00646"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJERPH"],"abstract":"<jats:p>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 7H-benz[de]anthracen-7-one (BAO), 11H-benzo[a]fluoren-11-one (B[a]FO), 11H-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-7H-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\u2013response curve; however, the absence of fluorescence effect on the activity was confirmed. The prominent estrogenic activity dependent on dose\u2013response 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.<\/jats:p>","DOI":"10.3390\/ijerph20010080","type":"journal-article","created":{"date-parts":[[2022,12,22]],"date-time":"2022-12-22T02:59:06Z","timestamp":1671677946000},"page":"80","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Antiandrogenic and Estrogenic Activity Evaluation of Oxygenated and Nitrated Polycyclic Aromatic Hydrocarbons Using Chemically Activated Luciferase Expression Assays"],"prefix":"10.3390","volume":"20","author":[{"given":"Kentaro","family":"Misaki","sequence":"first","affiliation":[{"name":"Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan"},{"name":"School of Nursing, University of Shizuoka, Yada 52-1, Suruga-ku, Shizuoka 422-8526, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nguyen Minh","family":"Tue","sequence":"additional","affiliation":[{"name":"Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan"},{"name":"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"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Takeji","family":"Takamura-Enya","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry, Kanagawa Institute of Technology, 1030 Shimo-Ogino, Atsugi 243-0292, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hidetaka","family":"Takigami","sequence":"additional","affiliation":[{"name":"Center for Material Cycles and Waste Management Research, National Institute for Environmental Studies (NIES), Onogawa 16-2, Tsukuba 305-8506, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Go","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Center for Material Cycles and Waste Management Research, National Institute for Environmental Studies (NIES), Onogawa 16-2, Tsukuba 305-8506, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Le Huu","family":"Tuyen","sequence":"additional","affiliation":[{"name":"Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan"},{"name":"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"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shin","family":"Takahashi","sequence":"additional","affiliation":[{"name":"Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan"},{"name":"Center of Advanced Technology for the Environment, Agricultural Faculty, Ehime University, Tarumi 3-5-7, Matsuyama 790-8566, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shinsuke","family":"Tanabe","sequence":"additional","affiliation":[{"name":"Center for Marine Environmental Studies (CMES), Ehime University, Bunkyo-cho 2-5, Matsuyama 790-8577, Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,12,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1080\/10408440091159176","article-title":"Health effects of endocrine-disrupting chemicals on wildlife, with special reference to the European situation","volume":"30","author":"Vos","year":"2000","journal-title":"Crit. 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