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The mutagenicities and endocrine-disrupting activities of two isomers of mononitrated 1-hydroxypyrene [1-hydroxy-x-nitropyrenes (1-OH-x-NPs); x = 2 and 5], which are not only photoreaction products of 1-nitropyrene (1-NP) but also constituent of ambient airborne particles, were evaluated for the first time using the Ames plate incorporation assay and the yeast two-hybrid assay, respectively. The mutagenicity of 1-OH-5-NP was weakly positive in the absence of rat liver S9, but was enhanced up to 3-fold with the metabolic activation by S9. On the contrary, 1-OH-2-NPdid not exhibit significant mutagenicity in the presence or absence of S9. 1-OH-5-NP showed weak estrogenic activity, but 1-OH-2-NP did not show any estrogenic activity. The concentration of 1-OH-5-NP that gave 10% of activity of 1.0 × 10-6M 17ß- estradiol (E2) was 5.4 × 10-7M. 1-OH-5-NP exhibited stronger antiestrogenic and antiandrogenic activities than 1-OH-2-NP. 1-OH-5-NP at a concentration of 1.0 × 10-6M inhibited 71 and 90%of ß-galactosidase activity induced by 1.0 × 10-9Mof E2 and 1.0 × 10-8M of 5a-dihydrotestosterone (DHT), respectively. On the other hand, 1.0 × 10-6M of 1-OH-2-NP inhibited 16 and 43% of ß-galactosidase activity induced by 1.0 × 10-9M of E2 and 1.0 × 10-8M of DHT, respectively. These findings point out the need for determining the environmental sources and distribution of 1-OH-2-NP and 1-OH-5-NP as well as the other hydroxynitropyrene isomers. © 2011 The Pharmaceutical Society of Japan

Mutagenicities and Endocrine-disrupting Activities of 1-Hydroxy-2-nitropyrene and 1-Hydroxy-5-nitropyrene