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J.Health Sci., 46(4), 299-303, 2000

Characterization of Hydroxy-biphenyl-O-sulfates in Urine and Urine Crystals Induced by Biphenyl and KHCO3 Administration in Rats

Makoto Ohnishi,*,a Hirofumi Yajima,b Tetsuo Takemura,c Seigo Yamamoto,a Taijiro Matsushima,a and Tadahiro Ishiib

aJapan Bioassay Research Center, Japan Industrial Safety and Health Association, Hadano-shi, Kanagawa 257-0015, Japan, bDepartment of Applied Chemistry, Faculty of Science, Science University of Tokyo, 1-3 Shinjuku-ku, Tokyo 162-8601, Japan, and cDepartment of Chemistry, Faculty of Science, Science University of Tokyo, 1-3 Shinjuku-ku, Tokyo 162-8601, Japan

In order to obtain information on the relationship between calculi and urine-crystal constituents, component analyses of the biphenyl sulfate conjugates in urine and urine crystals in rats fed a diet containing biphenyl and KHCO3 were performed by LC-MS/MS and FT-IR. LC-MS/MS analysis revealed the presence of biphenyl metabolites, i.e., three isomers of monohydroxy-biphenyl-O-sulfate (HBPOS) and five isomers of dihydroxy-biphenyl-O-sulfate (DHBPOS), in rat urine. The same results were obtained for the crystals in rat urine. These findings suggested that the metabolism of biphenyl resulting in the formation of sulfate conjugates follows the process: biphenyl -> mono- or dihydroxylation -> sulfate conjugation. FT-IR analysis of the urine crystals indicated that the major constituent was the potassium salt of 4-hydroxy-biphenyl-O-sulfate (4-HBPOS), which is known to be the main constituent of urinary bladder calculi. Consequently, in view of the similarity of the major constituent, the potassium salt of 4-HBPOS, in both the urine crystals and calculi, it is thought that the formation of the calculi can be attributed to the lower solubility of the potassium salt of 4-HBPOS, as compared to the other sulfate conjugates.