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J.Health Sci., 50(6), 625-633, 2004

Detection of Mutagenic 1-Chloro-3-, -6-, and -8-Nitropyrenes in Surface Soil Collected in Kyoto, Japan

Tsuyoshi Murahashi,a Mitokazu Kawabata,a Hidetoshi Sugiyama,b Tomohiro Hasei,a Tetsushi Watanabe,a and Teruhisa Hirayama*, a

aKyoto Pharmaceutical University, 5 Nakauchi-cho Misasagi Yamashina-ku, Kyoto 607-8414, Japan and bKanagawa Environmental Research Center, 842 Nakaharashimojuku, Hiratsuka 254-0072, Japan

Mutagenic 1-chloro-3-nitropyrene (1,3-CNP), 1,6-CNP and 1,8-CNP were detected in surface soil collected in Kyoto, Japan. First, 1,3-, 1,6- and 1,8-CNPs were synthesized by chlorination of 1-nitropyrene. Mutagenic activities obtained by Ames assay using Salmonella typhimurium strain TA98 under conditions without S9 mix were 1.22 revertants per nmol for 1,3-CNP, 1.14 for 1,6-CNP and 0.83 for 1,8-CNP. Miller's aryl hydrocarbon receptor (AhR) yeast reporter gene assay showed that the three CNPs had no AhR ligand activity. Surface soil was collected in Kyoto, Japan and analyzed for 1,3-, 1,6- and 1,8-CNPs by two-dimensional high-performance liquid chromatography with fluorescence detection and a zinc on-line catalytic column. 1,3-CNP, 1,6-CNP and 1,8-CNP were detected in the ranges 9.2-13.8, 3.4-4.6 and 4.3-5.0 pg per gram of soil (n = 2), respectively.