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Human carcinogen 1,3-butadiene (BD) undergoes metabolic activation to 3,4-epoxy-1-butene (EB), hydroxymethylvinyl ketone (HMVK), 3,4-epoxy-1,2-butanediol (EBD) and 1,2,3,4-diepoxybutane (DEB). Among these, DEB is by far the most genotoxic metabolite and is considered the ultimate carcinogenic species of BD. We have shown previously that BD-exposed laboratory mice form 8- to 10-fold more DEB–DNA adducts than rats exposed at the same conditions, which may be responsible for the enhanced sensitivity of mice to BD-mediated cancer. In the present study, we have identified 1,4- bis -( N -acetyl- l -cystein- S -yl)butane-2,3-diol ( bis -BDMA) as a novel DEB-specific urinary biomarker. Isotope dilution high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry was employed to quantify  bis -BDMA and three other BD-mercapturic acids, 2-( N -acetyl- l -cystein- S -yl)-1-hydroxybut-3-ene/1-( N -acetyl- l -cystein- S -yl)-2-hydroxy-but-3-ene (MHBMA, from EB), 4-( N -acetyl- l -cystein- S -yl)-1,2-dihydroxybutane (DHBMA, from HMVK) and 4-( N -acetyl- l -cystein- S -yl)-1,2,3-trihydroxybutane (THBMA, from EBD), in urine of confirmed smokers, occupationally exposed workers and BD-exposed laboratory rats.  Bis -BDMA was formed in a dose-dependent manner in urine of rats exposed to 0–200 p.p.m. BD by inhalation, although it was a minor metabolite (1%) as compared with DHBMA (47%) and THBMA (37%). In humans, DHBMA was the most abundant BD-mercapturic acid excreted (93%), followed by THBMA (5%) and MHBMA (2%), whereas no  bis -BDMA was detected. These results reveal significant differences in metabolism of BD between rats and humans.

Bis -butanediol-mercapturic acid ( bis -BDMA) as a urinary biomarker of metabolic activation of butadiene to its ultimate carcinogenic species