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An approach based on liquid chromatography/electrospray ionization-mass spectrometry to detect diol metabolites as biomarkers of exposure to styrene and 1,3-butadiene.

Analytical biochemistry (2008-12-30)
Shuijie Shen, Fan Zhang, Su Zeng, Jiang Zheng
ABSTRACT

Styrene and 1,3-butadiene are important intermediates used extensively in the plastics industry. They are metabolized mainly through cytochrome P450-mediated oxidation to the corresponding epoxides, which are subsequently converted to diols by epoxide hydrolase or through spontaneous hydration. The resulting styrene glycol and 3-butene-1,2-diol have been suggested as biomarkers of exposure to styrene and 1,3-butadiene, respectively. Unfortunately, poor ionization of the diols within electrospray mass spectrometers becomes an obstacle to the detection of the two diols by liquid chromatography/electrospray ionization-mass spectrometry (LC/ESI-MS). We developed an LC/ESI-MS approach to analyze styrene glycol and 3-butene-1,2-diol by means of derivatization with 2-bromopyridine-5-boronic acid (BPBA), which not only dramatically increases the sensitivity of diol detection but also facilitates the identification of the diols. The analytical approach developed was simple, quick, and convincing without the need for complicated chemical derivatization. To evaluate the feasibility of BPBA as a derivatizing reagent of diols, we investigated the impact of diol configuration on the affinity of a selection of diols to BPBA using the established LC/ESI-MS approach. We found that both cis and trans diols can be derivatized by BPBA. In conclusion, BPBA may be used as a general derivatizing reagent for the detection of vicinal diols by LC/MS.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
3,4-Dihydroxy-1-butene, ≥99%
Sigma-Aldrich
(S)-(+)-1-Phenyl-1,2-ethanediol, 99%
Sigma-Aldrich
1-Phenyl-1,2-ethanediol, 97%
Sigma-Aldrich
(R)-(−)-1-Phenyl-1,2-ethanediol, 99%