Effect of the orthoquinone moiety in 9,10-phenanthrenequinone on its ability to induce apoptosis in HCT-116 and HL-60 cells |
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Authors: | Noriyuki Hatae Jun Nakamura Tetsuo Okujima Minoru Ishikura Takumi Abe Satoshi Hibino Tominari Choshi Chiaki Okada Hiroko Yamada Hidemitsu Uno Eiko Toyota |
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Affiliation: | 1. School of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan;2. Department of Chemistry and Biology, Graduate School of Science and Engineering, Ehime University, Matsuyama, Ehime 790-8577, Japan;3. Graduate School of Pharmacy & Pharmaceutical Sciences, and Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan;4. Graduate School of Material Science, Nara Institute of Science and Technology, Takayama-cho, Ikoma, Nara 630-0192, Japan |
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Abstract: | 9,10-Phenanthrenequinone (9,10-PQ) is one of the most abundant quinones among diesel exhaust particulates. Recent data have suggested that quinones induce apoptosis in immune, epithelial and tumor cells, leading to respirator illness; however, the mechanisms by which quinones induce apoptosis and the structure required for this remain unknown. We studied the antitumor activity of 9,10-PQ analogs against two human tumor cell lines, HCT-116 colon tumor cells and HL-60 promyelocytic leukemia cells. The loss of the cis-orthoquinone unit in 9,10-PQ abrogated its ability to induce apoptosis in the two tumor cell lines, and the LC50 values of these analogs were indicated over 10 μM. An analog of 9,10-PQ in which the biaryl unit had been deleted displayed a reduced ability to induce tumor cell apoptosis, while the analogs 1,10-phenanthroline-5,6-dione (9) and pyrene-4,5-dione (10), which also had modified biaryl units, exhibited increased tumor cell apoptotic activity. The cis-orthoquinone unit in 9,10-PQ was identified as essential for its ability to induce apoptosis in tumor cells, and its biaryl unit is also considered to influence orthoquinone-mediated apoptotic activity. |
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Keywords: | 9,10-Phenanthrenequinone Orthoquinone Diesel exhaust particulates Antitumor activity Apoptosis |
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