Mercapturic acids: recent advances in their determination by liquid chromatography/mass spectrometry and their use in toxicant metabolism studies and in occupational and environmental exposure studies

References

• Ackermann BL, Berna MJ, Murphy AT. (2002). Recent advances in use of LC/MS/MS for quantitative high-throughput bioanalytical support of drug discovery. Curr Top Med Chem 2:21–34
   Google Scholar
• Albertini RJ, Sram RJ, Vacek PM, et al. (2003). Biomarkers in Czech workers exposed to 1,3-butadiene: a transitional epidemologic study. Res Rep Health Effects Institute 116:1–162
   PubMedGoogle Scholar
• Albertini RJ, Sram RJ, Vacek PM, et al. (2001). Biomarkers for assessing occupational exposures to 1,3-butadiene. Chem–Biol Interact 135–136:429–53
   PubMed Web of Science ®Google Scholar
• Alwis KU, Blount BC, Britt AS, et al. (2012). Simultaneous analysis of 28 urinary VOC metabolites using ultra high performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry (UPLC-ESI/MSMS). Anal Chim Acta 750:152–60
   PubMed Web of Science ®Google Scholar
• American Conference of Governmental Industrial Hygienists. (2014). TLVs and BEIs: threshold limit values for chemical substances and physical agents & biological expsoure indicies. Cincinnati (OH): ACGIH
   Google Scholar
• Ammenheuser MM, Bechtold WE, Abdel-Rahman SZ, et al. (2001). Assessment of 1,3-butadiene exposure in polymer production workers using HPRT mutations in lymphocytes as a biomarker. Environ Health Perspect 109:1249–55
   PubMed Web of Science ®Google Scholar
• Angerer J, Schildbach M, Kramer A. (1998). S-p-toluylmercapturic acid in the urine of workers exposed to toluene: a new biomarker for toluene exposure. Arch Toxicol 72:119–23
   PubMed Web of Science ®Google Scholar
• Arnold SM, Angerer J, Boogaard PJ, et al. (2013). The use of biomonitoring data in exposure and human health risk assessment: benzene case study. Crit Rev Toxicol 43:119–53
   PubMed Web of Science ®Google Scholar
• B'Hymer C, Cheever KL. (2004). Development of a gas chromatographic test for the quantification of the biomarker 3-bromopropionic acid in human urine. J Chromatogr B 802:361–6
   PubMed Web of Science ®Google Scholar
• B'Hymer C, Cheever KL. (2010). Biomarkers and metabolites: HPLC/MS analysis. In: Cazes J ed. Encyclopedia of chromatography. Baton Rouge (LA): Taylor and Francis, 238–46
   Google Scholar
• B'Hymer C, Cheever KL. (2007). Evaluation of extracton conditions and use of HPLC–MS for the simultaneous determination of acrylamide and its primary metabolite, N-acetyl-S-(2-carbamoylethyl).cysteine, in human urine. J Liq Chromatogr Relat Technol 30:1303–16
   Web of Science ®Google Scholar
• Baines PJ, Bray HG, James SP. (1977). Mercapturic acid formation in the developing rat. Xenobiotica 7:653–63
   PubMed Web of Science ®Google Scholar
• Barbieri A, Sabatini L, Accorsi A, et al. (2004). Simultaneous determination of t, t-muconic, S-phenylmercapturic and S-benzylmercapturic acids in urine by a rapid and sensitive liquid chromatography/electrospray tandem mass spectrometry method. Rapid Commun Mass Spectrom 18:1983–8
   PubMed Web of Science ®Google Scholar
• Barnsley EA, Grenby TH, Young L. (1966). Biochemical studies of toxic agents. The metabolism of 1- and 2-bromopropane in rats. Biochem J 100:282–8
   PubMed Web of Science ®Google Scholar
• Carrieri M, Bartolucci GB, Livieri M, et al. (2009). Quantitative determination of the 1,3-butadiene urinary metabolite 1,2-dihydroxybutyl mercapturic acid by high-performance liquid chromatography/tandem mass spectrometry using polynomial calibration curves. J Chromatogr B 887:1388–93
   Web of Science ®Google Scholar
• Carlson GP. (2002). Effect of the inhibition of the metabolism of 4-vinylphenol on its hepatotoxicity and pneumotoxicity in rats and mice. Toxicology 179:129–36
   PubMed Web of Science ®Google Scholar
• Carlson GP. (2004). Influence of selected inhibitors on the metabolism of the styrene metabolite 4-vinylphenol in wild-type and CYP2E1 knockout mice. J Toxicol Environ Hlth 67:905–9
   PubMed Web of Science ®Google Scholar
• Carlson GP. (2011). Hepatotoxicity and pneumotoxicity of styrene and its metabolites in glutathione S transferase-deficient mice. Drug Chem Toxicol 34:440–4
   PubMed Web of Science ®Google Scholar
• Carmella SG, Chen ML, Zhang Y, et al. (2007). Quantitation of acrolein-derived (3-hydroxypropyl) mercapturic acid in human urine by liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry: effects of cigarette smoking. Chem Res Toxicol 20:986–90
   PubMed Web of Science ®Google Scholar
• Cheever KL, Marlow KL, B'hymer C, et al. (2009). Development of an HPLC–MS procedure for the quantification of N-acetyl-S-(n-propyl)-L-cysteine, the major urinary metabolite of 1-bromopropane in human urine. J Chromatogr B Analyt Technol Biomed Life Sci 877:827–32
   PubMed Web of Science ®Google Scholar
• Chiang WC, Chen CY, Lee TC, et al. (2015). Fast and simple screening for the simultaneous analysis of seven metabolites derived from five volatile organic compounds in human urine using on-line solid-phase extraction coupled with liquid chromatography–tandem mass spectrometry. Talanta 132:469–78
   PubMed Web of Science ®Google Scholar
• Cosnier F, Brochard C, Burgart M, et al. (2012). Mercapturic acids derived from toluene in rat urine samples: identification and measurement by gas chromatography-tandem mass spectrometry. Anal Bioanal Chem 404:1907–17
   PubMed Web of Science ®Google Scholar
• Cosnier F, Cossec B, Burgart M, et al. (2013). Biomarkers of toluene exposure in rats: mercapturic acids versus traditional indicators (urinary hippuric acid and o-cresol and blood toluene). Xenobiotica 43:651–60
   PubMed Web of Science ®Google Scholar
• Cossec B, Cosnier F, Burgart M, et al. (2013). Glutathione pathway in ethylbenzene metabolism: novel biomarkers of exposure in the rat. Chemosphere 81:1334–41
   Web of Science ®Google Scholar
• De Palma G, Manini P, Mozzoni P, et al. (2001). Polymorphism of xenobiotic-metabolizing enzymes and excretion of styrene-specific mercapturic acids. Chem Res Toxicol 14:1393–400
   PubMed Web of Science ®Google Scholar
• De Rooij BM, Commandeur JNM, Vermeulen NPE. (1998). Mercapturic acids as biomarkers of exposure to electrophilic chemicals: applications to environmental and industrial chemicals. Biomarkers 3:239–303
   PubMed Web of Science ®Google Scholar
• Ding YS, Blount BC, Valentin-Blasini L, et al. (2009). Simultaneous determination of six mercapturic acid metabolites of volatile organic compounds in human urine. Chem Res Toxicol 22:1018–25
   PubMed Web of Science ®Google Scholar
• Eckert E, Drexler H, Goen T. (2010). Determination of six hydroxyalkyl mercapturic acids in human urine using hydrophilic interaction liquid chromatography with tandem mass spectrometry (HILIC-ESI-MS/MS). J Chromatogr B 878:2506–14
   PubMed Web of Science ®Google Scholar
• Eckert E, Goen T. (2014). Rapid determination of four short-chain alkyl mercapturic acids in human urine by column-switching liquid chromatography–tandem mass spectrometry. J Chromatog B 965:54–60
   PubMed Web of Science ®Google Scholar
• Friedman M. (2003). Chemistry, biochemistry, and safety of acrylamide. A review. J Agric Food Chem 51:4504–26
   PubMed Web of Science ®Google Scholar
• Frost-Pineda K, Zedler BK, Oliveri D, et al. (2008). Short-term clinical exposure evaluation of a third generation electrically heated cigarette smoking system (EHCSS) in adult smokers. Regul Toxicol Pharmacol 52:104–10
   PubMed Web of Science ®Google Scholar
• Fustinoni S, Campo L, Manini P, et al. (2008). An integrated approach to biomonitoring exposure to styrene and styrene-(7,8)-oxide using a repeated measurements sampling design. Biomarkers 13:560–78
   PubMed Web of Science ®Google Scholar
• Fustinoni S, Perbellini L, Soleo L, et al. (2004). Biological monitoring in occupational exposure to low levels of 1,3-butadiene. Toxicol Lett 149:353–60
   PubMed Web of Science ®Google Scholar
• Fustinoni S, Soleo L, Warholm M, et al. (2002). Influence of metabolic genotypes on biomarkers of exposure to 1,3-butadiene in humans. Cancer Epidemiol Biomarkers Prev 11:1082–90
   PubMed Web of Science ®Google Scholar
• Gonzalez-Reche LM, Schettgen T, Angerer J. (2003). New approaches to the metabolism of xylenes: verification of the formation of phenylmercapturic acid metabolites of xylenes. Arch Toxicol 77:80–5
   PubMed Web of Science ®Google Scholar
• Garner CE, Sumner SCJ, Davis JG, et al. (2006). Metabolism and disposition of 1-bromopropane in rats and mice following inhalation or intravenous administration. Toxicol Appl Pharmacol 215:23–36
   PubMed Web of Science ®Google Scholar
• Goddlett DR, Gale DC, Guiles S, et al. (2001). Mass spectrometry in pharmeceutical analysis. In: Meyers RA, ed. Encyclopedia of analytical chemistry: applications, theory and instrumentation. New York (NY): John Wiley & Sons, 7209–78
   Google Scholar
• Hallberg LM, Bechtold WE, Grady J, et al. (1997). Abnormal DNA repair activities in lymphocytes of workers exposed to 1,3-butadiene. Mutat Res 383:213–21
   PubMed Web of Science ®Google Scholar
• Haufroid V, Jakubowski M, Janasik B, et al. (2002). Interest of genotyping and phenotyping of drug-metabolizing enzymes for the interpretation of biological monitoring of exposure to styrene. Pharmacogen 12:691–702
   PubMedGoogle Scholar
• Hayes RB, Zhang L, Yin S, et al. (2000). Genotoxic markers among butadiene polymer workers in China. Carcinogenesis 21:55–62
   PubMed Web of Science ®Google Scholar
• Hecht SS, Berg JZ, Hochalter JB. (2009). Preferential glutathione conjugation of a reverse diol epoxide compared to a bay region diol epoxide of phenanthrene in human hepatocytes: relevance to molecular epidemiology studies of glutathione-S-transferase polymorphisms and cancer. Chem Res Toxicol 22:426–32
   PubMed Web of Science ®Google Scholar
• Hecht SS, Villalta PW, Hochalter JB. (2008). Analysis of phenanthrene diol epoxide mercapturic acid detoxification products in human urine: relevance to molecular epidemiology studies of glutathione S-transferase polymorphisms. Carcinogenesis 29:937–43
   PubMed Web of Science ®Google Scholar
• Hemstrom P, Irgum K. (2006). Hydrophilic interaction chromatography. J Sep Sci 29:1784–821
   PubMed Web of Science ®Google Scholar
• Holland JF, Enke CG, Allison J, et al. (1983). Mass-spectrometry on the chromatographic time scale – realistic expectations. Anal Chem 55:997A–1012A
   Web of Science ®Google Scholar
• Horowitz BZ. (1997). Bromism from excessive cola consumption. J Toxicol Clin Toxicol 35:315–20
   PubMed Web of Science ®Google Scholar
• Hou HW, Xiong W, Gao N, et al. (2012). A column-switching liquid chromatography–tandem mass spectrometry method for quantitation of 2-cyanoethylmercapturic acid and 2-hydroxyethylmercapturic acid in Chinese smokers. Anal Biochem 430:75–82
   PubMed Web of Science ®Google Scholar
• International Agency for Research on Cancer. (1982). IARC monographs on the evaluation of carcinogenic risks to humans: benzene. Lyon: World Health Organization, IARC Publications
   Google Scholar
• International Agency for Research on Cancer. (1989). IARC monographs on the evaluation of carcinogenic risks to humans: some organic solvents, resinsmonomers and related compounds, pigments and occupational exposures in paint manufacture and painting. IARC monographs on the evaluation of carcinogenic risks to humans: benzene. Lyon: World Health Organization, IARC Publications
   Google Scholar
• International Agency for Research on Cancer. (1994). IARC monographs on the evaluation of carcinogenic risks to humans: some industrial chemicals. Lyon: World Health Organization, IARC Publications
   Google Scholar
• International Agency for Research on Cancer. (1999). IARC monographs on the evaluation of carcinogenic risks to humans: re-evaluation of some organic chemicals, hydrazine and hydrogen peroxide. Lyon: World Health Organization, IARC Publications
   Google Scholar
• International Agency for Research on Cancer. (2008). IARC monographs on the evaluation of carcinogenic risks in humans: 1,3-butadiene, ethylene bromide and vinyl halide. Lyon: World Health Organization, IARC Publications
   Google Scholar
• Ichihara G. (2005). Neuro-reproductive toxicities of 1-bromopropane and 2-bromopropane. Int Arch Occup Environ Health 78:79–96
   PubMed Web of Science ®Google Scholar
• Ichihara G, Amarnath K, Amarnath V, et al. (2001). Detection of N-acetyl-S-propylcysteine in the urine of workers exposed to 1-bromopropane. Toxicologist 60:82
   Google Scholar
• Jian W, Edom RW, Xu Y, et al. (2010). Recent advances in application of hydrophilic interaction chromatography for quantitative bioanalysis. J Sep Sci 33:681–97
   PubMed Web of Science ®Google Scholar
• Jones AR, Walsh DR. (1979). The oxidative metabolism of 1-bromopropane in the rat. Xenobiotica 9:763–72
   PubMed Web of Science ®Google Scholar
• Kawai T, Takeuchi A, Miyama Y, et al. (2001). Biological monitoring of occupational exposure to 1-bromopropane by means of urinalysis for 1-bromopropane and bromide ion. Biomarkers 6:303–12
   PubMed Web of Science ®Google Scholar
• Kawai T, Zhang ZW, Moon CS, et al. (2002). Comparison of urinary bromide levels among people in East Asia, and the effects of dietary intakes of cereals and marine products. Toxicol Lett 134:285–93
   PubMed Web of Science ®Google Scholar
• Kebarle P, Tang L. (1993). From ions in solution to ions in the gas-phase – the mechanism of electrospray mass-spectrometry. Anal Chem 65:A972–86
   Web of Science ®Google Scholar
• King R, Bonfiglio R, Fernandez-Metzler C, et al. (2000). Mechanistic investigation of ionization suppression in electrospray ionization. J Am Soc Mass Spectrom 11:942–50
   PubMed Web of Science ®Google Scholar
• Kellert M, Scholz K, Wagner S, et al. (2006). Quantitation of mercapturic acids from acrylamide and glycidamide in human urine using a column switching tool with two trap columns and electrospray tandem mass spectrometry. J Chromatogr A 1131:58–66
   PubMed Web of Science ®Google Scholar
• Kelsey KT, Wiencke JK, Ward J, et al. (1995). Sister-chromatid exchanges, glutatione-S-transferase theta-deletion and cytogenic sensitivity to diepoxybutane in lymphocytes from butadiene monomer production workers. Mutat Res 35:267–73
   Web of Science ®Google Scholar
• Kirman CR, Albertini RA, Gargas ML. (2010a). 1,3-Butadiene: III. Assessing carcinogenic modes of action. Crit Rev Toxicol 40:74–92
   PubMed Web of Science ®Google Scholar
• Kirman CR, Albertini RJ, Sweeney LM, et al. (2010b). 1,3-Butadiene: I. Review of metabolism and the implications to human health risk assessment. Crit Rev Toxicol 40:1–11
   PubMed Web of Science ®Google Scholar
• Kopp EK, Sieber M, Kellert M, et al. (2008). Rapid and sensitive HILIC-ESI-MS/MS quantitation of polar metabolites of acrylamide in human urine using column switching with an online trap column. J Agric Food Chem 56:9828–34
   PubMed Web of Science ®Google Scholar
• Korfmacher WA. (2005). Principles and applications of LC–MS in new drug discovery. Drug Discovery Today 10:1357–67
   PubMed Web of Science ®Google Scholar
• Kotapati S, Matter BA, Grant AL, et al. (2011). Quantitative analysis of trihydroxybutyl mercapturic acid, a urinary metabolite of 1,3-butadiene, in humans. Chem Res Toxicol 24:1516–26
   PubMed Web of Science ®Google Scholar
• Kotapati S, Sangaraju D, Esades A, et al. (2014). Bis-butanediol-mercapturic acid (bis-BDMA). as a urinary biomarker of metabolic activation of butadiene to its ultimate carcinogenic species. Carcinogenesis 35:1371–8
   PubMed Web of Science ®Google Scholar
• Kuklenyik Z, Calafat AM, Barr JR, et al. (2011). Design of online solid phase extraction-liquid chromatography-tandem mass spectrometry (SPE-LC–MS/MS). hyphenated systems for quantitative analysis of small organic compounds in biological matrices. J Sep Sci 34:3606–18
   PubMed Web of Science ®Google Scholar
• Kuklenyik Z, Panuwet P, Jayatilaka NK, et al. (2012). Two-dimensional high performance liquid chromatography separation and tandem mass spectrometry detection of atrazine and its metabolic and hydrolysis products in urine. J Chromatogr B Analyt Technol Biomed Life Sci 901:1–8
   PubMed Web of Science ®Google Scholar
• Li W, Chen J, Jiang D, et al. (2015a). Sensitive determination of two major mercapturic acid metabolites of 1,3-butadiene in human urine based on the isotopic dilution ultrahigh performance liquid chromatography–tandem mass spectrometry. Anal Methods 7:4691–8
   Web of Science ®Google Scholar
• Li CM, Hu CW, Wu KY. (2005). Quantification of urinary N-acetyl-S-(propionamide) cysteine using an on-line clean-up system coupled with liquid chromatography/tandem mass spectrometry. J Mass Spectrom 40:511–15
   PubMed Web of Science ®Google Scholar
• Li WH, Shibata E, Zhou ZJ, et al. (2010). Dose-dependent neurologic abnormalities in workers exposed to 1-bromopropane. J Occup Environ Med 52:769–77
   PubMed Web of Science ®Google Scholar
• Li G, Wang L, Fei T, et al. (2015b). Ionic liquid-based ultrasonic-assisted extraction combined with HPLC–MS/MS for the determination of seven mercapturic acids in human urine. Chromatographa 78:641–8
   Web of Science ®Google Scholar
• Linhart I, Mráz J, Dabrowská L, et al. (2012). Vinylphenylmercapturic acids in human urine as biomarkers of styrene ring oxidation. Toxicol Lett 213:260–5
   PubMed Web of Science ®Google Scholar
• Linhart I, Mráz J, Scharff J, et al. (2010). New urinary metabolites formed from ring-oxidized metabolic intermediates of styrene. Chem Res Toxicol 23:251–7
   PubMed Web of Science ®Google Scholar
• Linhart I, Smejkal J, Mladkova I. (1998). Stereochemical aspects of styrene biotransformation. Toxicol Lett 94:127–35
   PubMed Web of Science ®Google Scholar
• Lovreglio P, Barbieri A, Carrieri M, et al. (2010). Validity of new biomarkers of internal dose for use in the biological monitoring of occupational and environmental exposure to low concentrations of benzene and toluene. Int Arch Occupat Environ Hlth 83:341–56
   PubMed Web of Science ®Google Scholar
• Maestri L, Negri S, Ferrari M, et al. (2005). Determination of urinary S-phenylmercapturic acid, a specific metabolite of benzene, by liquid chromatography/single quadrupole mass spectrometry. Rapid Commun Mass Spectrom 19:1139–44
   PubMed Web of Science ®Google Scholar
• Majersik JJ, Caravati EM, Steffens JD. (2007). Severe neurotoxicity associated with exposure to the solvent 1-bromopropane (n-propyl bromide). Clin Toxicol 45:270–6
   PubMed Web of Science ®Google Scholar
• Mallet CR, Lu ZL, Fisk R, et al. (2003). Performance of an ultra-low elution-volume 96-well plate: drug discovery and development applications. Rapid Commun Mass Spectrom 17:163–70
   PubMed Web of Science ®Google Scholar
• Manini P, Andreoli R, Bergamaschi E, et al. (2000). A new method for the analysis of styrene mercapturic acids by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom 14:2055–60
   PubMed Web of Science ®Google Scholar
• Manini P, Andreoli R, Poli D, et al. (2002). Liquid chromatography/electrospray tandem mass spectrometry characterization of styrene metabolism in man and in rat. Rapid Commun Mass Spectrom 16:2239–48
   PubMed Web of Science ®Google Scholar
• Manini P, Buzio L, Andreoli R, et al. (2003). Assessment of biotransformation of the arene moiety of styrene in volunteers and occupationally exposed workers. Toxicol Appl Pharmacol 189:160–9
   PubMed Web of Science ®Google Scholar
• Mascher DG, Mascher HJ, Scherer G, et al. (2001). High-performance liquid chromatographic–tandem mass spectrometric determination of 3-hydroxypropylmercapturic acid in human urine. J Chromatogr B 750:163–9
   PubMed Web of Science ®Google Scholar
• Mathias PI, Cheever KL, Hanley KW, et al. (2012). Comparison and evaluation of urinary biomarkers for occupational exposure to spray adhesives containing 1-bromopropane. Toxicol Mech Methods 22:526–32
   PubMed Web of Science ®Google Scholar
• Matuszewski BK, Constanzer ML, Chavez-Eng CM. (1998). Matrix effect in quantitative LC/MS/MS analyses of biological fluids: a method for determination of finasteride in human plasma at picogram per milliliter concentrations. Anal Chem 70:882–9
   PubMed Web of Science ®Google Scholar
• Matuszewski BK, Constanzer ML, Chavez-Eng CM. (2003). Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC–MS/MS. Anal Chem 75:3019–30
   PubMed Web of Science ®Google Scholar
• Melikian AA, O'connor R, Prahalad AK, et al. (1999). Determination of the urinary benzene metabolites S-phenylmercapturic acid and trans,trans-muconic acid by liquid chromatography–tandem mass spectrometry. Carcinogenesis 20:719–26
   PubMed Web of Science ®Google Scholar
• Miller RR, Newhook R, Poole A. (1994). Styrene production, use, and human exposure. Crit Rev Toxicol 24:S1–10
   Google Scholar
• Morbidity Mortality Weekly Report. (2008). Neurologic illness associated with occupational exposure to the solvent 1-bromopropane – New Jersey and Pennsylvania (2007–2008). Atlanta (GA): Centers for Disease Control and Prevention
   Google Scholar
• Nguyen HP, Schug KA. (2008). The advantages of ESI-MS detection in conjunction with HILIC mode separations: fundamentals and applications. J Sep Sci 31:1465–80
   PubMed Web of Science ®Google Scholar
• National Institute for Occupational Safety and Health. (2013). OSHA/NIOSH hazard alert: 1-bromopropane. Cincinnati (OH): NIOSH Publication. No. 2013-150
   Google Scholar
• Norrgran J, Bravo R, Bishop AM, et al. (2006). Quantification of six herbicide metabolites in human urine. J Chromatogr B Analyt Technol Biomed Life Sci 830:185–95
   PubMed Web of Science ®Google Scholar
• Paci E, Pigini A, Cialdella AM. (2007). Determination of free and total S-phenylmercapturic acid by HPLC/MS/MS in the biological monitoring of benzene exposure. Biomarkers 12:111–23
   PubMed Web of Science ®Google Scholar
• Panuwet P, Nguyen JV, Kuklenyik P, et al. (2008). Quantification of atrazine and its metabolites in urine by on-line solid-phase extraction-high-performance liquid chromatography–tandem mass spectrometry. Anal Bioanal Chem 391:1931–9
   PubMed Web of Science ®Google Scholar
• Perbellini L, Veronese N, Princivalle A. (2002). Mercapturic acids in the biological monitoring of occupational exposure to chemicals. J Chromatogr B Analyt Technol Biomed Life Sci 781:269–90
   PubMed Web of Science ®Google Scholar
• Perico A, Baglioni S, Bavazzano P. (2004). Determination of N-acetyl-S-(N-methylcarbamoyl)cysteine (AMCC) in urine by high-performance liquid chromatography combined with mass spectrometry. Rapid Commun Mass Spectrom 18:1865–8
   PubMed Web of Science ®Google Scholar
• Perez HL, Lahdetie J, Landin HH, et al. (1997). Haemoglobin adducts of epoxybutanediol from exposure to 1,3-butadiene or butadiene epoxides. Chem Biol Interact 105:181–98
   PubMed Web of Science ®Google Scholar
• Pfaffli P, Hesso A, Vainio H, et al. (1981). 4-Vinylphenol excretion suggestive of arene oxide formation in workers occupationally exposed to styrene. Toxicol Appl Pharmacol 60:85–90
   PubMed Web of Science ®Google Scholar
• Pluym N, Gilch G, Scherer G, et al. (2015). Analysis of 18 urinary mercapturic acids by two high-throughput multiplex-LC–MS/MS methods. Anal Bioanal Chem 407:5463–76
   PubMed Web of Science ®Google Scholar
• Pombrio JM, Giangreco A, Li LQ, et al. (2001). Mercapturic acids (N-acetylcysteine S-conjugates) as endogenous substrates for the renal organic anion transporter-1. Mol Pharmacol 60:1091–9
   PubMed Web of Science ®Google Scholar
• Princivalle A, Pasini F, Pervellini L. (2010). S-(acetamidomethyl)mercapturic acid (AMMA): a new biomarker for occupational exposure to N, N-dimethylacetamide. J Chromotog B 878:2515–19
   PubMed Web of Science ®Google Scholar
• Raymond LW, Ford MD. (2007). Severe illness in furniture makers using a new glue: 1-bromopropane toxicity confounded by arsenic. J Occup Environ Med 49:1009–19
   PubMed Web of Science ®Google Scholar
• Reska M, Ochsmann E, Kraus T, et al. (2010). Accurate quantification of mercapturic acids of styrene (PHEMAs) in human urine with direct sample injection using automated column-switching high-performance liquid chromatography coupled with tandem mass spectrometry. Anal Bioanal Chem 397:3563–74
   PubMed Web of Science ®Google Scholar
• Richardson KA, Peters M, Wong BA, et al. (1999). Quantitative and qualitative differences in the metabolism of 14C-1,3-butadiene in rats and mice: relevance to cancer susceptibility. Toxicol Sci 49:186–201
   PubMed Web of Science ®Google Scholar
• Sabatini L, Barbieri A, Indiveri P, et al. (2008). Validation of an HPLC–MS/MS method for the simultaneous determination of phenylmercapturic acid, benzylmercapturic acid and o-methylbenzyl mercapturic acid in urine as biomarkers of exposure to benzene, toluene and xylenes. J Chromatogr B Analyt Technol Biomed Life Sci 863:115–22
   PubMed Web of Science ®Google Scholar
• Sapkota A, Halden RU, Dominici F, et al. (2006). Urinary biomarkers of 1,3-butadiene in environmental settings using liquid chromatography isotope dilution tandem mass spectrometry. Chem Biol Interact 160:70–9
   PubMed Web of Science ®Google Scholar
• Sarkar M, Kapur S, Frost-Pineda K, et al. (2008). Evaluation of biomarkers of exposure to selected cigarette smoke constituents in adult smokers switched to carbon-filtered cigarettes in short-term and long-term clinical studies. Nicotine Tob Res 10:1761–72
   PubMed Web of Science ®Google Scholar
• Scherer G, Urban M, Hagedorn HW, et al. (2010). Determination of methyl-, 2-hydroxyethyl- and 2-cyanoethylmercapturic acids as biomarkers of exposure to alkylating agents in cigarette smoke. J Chromatogr B 878:2520–8
   PubMed Web of Science ®Google Scholar
• Schettgen T, Bertram J, Kraus T. (2012). Accurate quantification of the mercapturic acids of acrylonitrile and its genotoxic metabolite cyanoethylene-epoxide in human urine by isotope-dilution LC-ESI/MS/MS. Talanta 98:11–19
   Web of Science ®Google Scholar
• Schettgen T, Musiol A, Alt A, et al. (2008a). Fast determination of urinary S-phenylmercapturic acid (SPMA) and S-benzylmercapturic acid (S-BMA) by column-switching liquid chromatography–tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 863:283–92
   PubMed Web of Science ®Google Scholar
• Schettgen T, Musiol A, Alt A, et al. (2009). A method for the quantification of biomarkers of exposure to acrylonitrile and 1,3-butadiene in human urine by column-switching liquid chromatography–tandem mass spectrometry. Anal Bioanal Chem 393:969–81
   PubMed Web of Science ®Google Scholar
• Schettgen T, Musiol A, Kraus T. (2008b). Simultaneous determination of mercapturic acids derived from ethylene oxide (HEMA), propylene oxide (2-HPMA), acrolein (3-HPMA), acrylamide (AAMA) and N, N-dimethylformamide (AMCC) in human urine using liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom 22:2629–38
   PubMed Web of Science ®Google Scholar
• Sclar G. (1999). Encephalomyeloradiculoneuropathy following exposure to an industrial solvent. Clin Neurol Neurosurg 101:199–202
   PubMed Web of Science ®Google Scholar
• Sklan NM, Barnsley EA. (1968). The metabolism of S-methyl-L-cysteine. Biochem J 107:217–23
   PubMed Web of Science ®Google Scholar
• Snyder LR, Kirkland JJ, Dolan JW. (2010) Normal-phase chromatography. In: Introduction of modern liquid chromatography, 3rd ed. Hoboken (NJ): John Wiley & Sons Inc., 362–401
   Google Scholar
• Sohn JH, Han MJ, Lee MY, et al. (2005). Simultaneous determination of N-hydroxymethyl-N-methylformamide, N-methylformamide and N-acetyl-S-(N-methylcarbamoyl)cystein in urine samples from workers exposed to N, N-dimethylformamide by liquid chromatography–tandem mass spectrometry. J Pharmaceut Biomed Anal 37:165–70
   PubMed Web of Science ®Google Scholar
• Sterz K, Kohler D, Schettgen T, et al. (2010). Enrichment and properties of urinary pre-S-phenylmercapturic acid (pre-PMA). J Chromatogr B 878:2502–5
   PubMed Web of Science ®Google Scholar
• Sterz K, Scherer G, Krumsiek J, et al. (2012). Identification and quantification of 1-hydroxybutene-2-yl mercapturic acid in human urine by UPLC–HILIC-MS/MS a novel biomarker for 1,3-butadiene exposure. Chem Res Toxicol 25:1565–7
   PubMed Web of Science ®Google Scholar
• Swenberg JA, Boysen G, Georgieva N, et al. (2007). Future directions in butadiene risk assessment and the role of cross-species internal dosimetry. Chem Biol Interact 166:78–83
   PubMed Web of Science ®Google Scholar
• Tachizawa H, Macdonald TL, Neal RA. (1982). Rat liver microsomal metabolism of propyl halides. Mol Pharmacol 22:745–51
   PubMed Web of Science ®Google Scholar
• Tornqvist M. (2005). Acrylamide in food: the discovery and its implications. In: Friedman M, Mottram D, eds. New York (NY): Springer Science and Business Media, 1–19
   Google Scholar
• Upadhyaya P, Hochalter JB, Balbo S, et al. (2010). Preferential glutathione conjugation of a reverse diol epoxide compared with a bay region diol epoxide of benzo[a]pyrene in human hepatocytes. Drug Metab Dispos 38:1397–402
   PubMed Web of Science ®Google Scholar
• Upadhyaya P, Rao P, Hochalter JB, et al. (2006). Quantitation of N-acetyl-S-(9,10-dihydro-9-hydroxy-10-phenanthryl)-L-cysteine in human urine: comparison with glutathione-S-transferase genotypes in smokers. Chem Res Toxicol 19:1234–40
   PubMed Web of Science ®Google Scholar
• Urban M, Gilch G, Schepers G, et al. (2003). Determination of the major mercapturic acids of 1,3-butadiene in human and rat urine using liquid chromatography with tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 796:131–40
   PubMed Web of Science ®Google Scholar
• US Department of Health and Human Services, Food and Drug Administration. (May 2001). Guidance for industry: bioanalytical method validation. Maryland: Rockford
   Google Scholar
• US Department of Health and Human Services, Public Health Service. National Toxicology Program. (2014). In: Report on carcinogens. 13th ed. NC: Research Triangle Park
   Google Scholar
• Vacek PM, Albertini RJ, Sram RJ, et al. (2010). Hemoglobin adducts in 1,3-butadiene exposed Czech workers: female–male comparisons. Chem Biol Interact 188:668–76
   PubMed Web of Science ®Google Scholar
• Valentine H, Amarnath K, Amarnath V, et al. (2007). Globin S-propyl cysteine and urinary N-acetyl-S-propylcysteine as internal biomarkers of 1-bromopropane exposure. Toxicol Sci 98:427–35
   PubMed Web of Science ®Google Scholar
• Van Bladeren P, Buys W, Breimer DD, et al. (1980). The synthesis of mercapturic acids and their esters. Eur J Medicinal Chem 15:495–7
   Web of Science ®Google Scholar
• van Sittert NJ, Megens H, Watson WP, et al. (2000). Biomarkers of exposure to 1,3-butadiene as a basis for cancer risk assessment. Toxicol Sci 56:189–202
   PubMed Web of Science ®Google Scholar
• Vanwelie RTH, Vandijck R, Vermeulen NPE, et al. (1992). Mercapturic acids, protein adducts, and DNA adducts as biomarkers of electrophilic chemicals. Crit Rev Toxicol 22:271–306
   PubMed Web of Science ®Google Scholar
• Varma D, Jansen SA, Ganti S. (2010). Chromatography with higher pressure, smaller particles and higher temperature: a bioanalytical perspective. Bioanalysis 2:2019–34
   PubMed Web of Science ®Google Scholar
• Ward JB, Ammenheuser MM, Whorton EB, et al. (1996). Biological monitoring for mutagenic effects of occupational exposure to butadiene. Toxicology 113:84–90
   PubMed Web of Science ®Google Scholar
• Watabe T, Hiratsuka A, Aizawa T, et al. (1982). 1-Vinylbenzene 3,4-oxide, a potent mutagen formed as a possible intermediate in the metabolism of styrene. Mutat Res 93:45–55
   PubMed Web of Science ®Google Scholar
• Wu CF, Uang SN, Chiang SY, et al. (2012). Simultaneous quantitation of urinary cotinine and acrylonitrile-derived mercapturic acids with ultraperformance liquid chromatography–tandem mass spectrometry. Anal Bioanal Chem 402:2113–20
   PubMed Web of Science ®Google Scholar
• Wu NJ, Clausen AM. (2007). Fundamental and practical aspects of ultrahigh pressure liquid chromatography for fast separations. J Sep Sci 30:1167–82
   PubMed Web of Science ®Google Scholar
• Yan WY, Byrd GD, Brown BG, et al. (2010). Development and validation of a direct LC–MS–MS method to determine the acrolein metabolite 3-HPMA in urine. J Chromatogr Sci 48:194–9
   PubMed Web of Science ®Google Scholar
• Zhang ZW, Kawai T, Takeuchi A, et al. (2001). Urinary bromide levels probably dependent to intake of foods such as sea algae. Arch Environ Contam Toxicol 40:579–84
   PubMed Web of Science ®Google Scholar
• Zhang F, Lowe ER, Rick DL, et al. (2011). In vitro metabolism, glutathione conjugation, and CYP isoform specificity of epoxidation of 4-vinylphenol. Xenobiotica 41:6–23
   PubMed Web of Science ®Google Scholar
• Zhang Y, Wang Q, Cheng J, et al. (2015). Comprehensive profiling of mercapturic acid metabolites from dietary acrylamide as short-term exposure biomarkers for evaluation of toxicokinetics in rats and daily internal exposure in humans using isotopic dilution ultra-high performance liquid chromatography tandem mass spectrometry. Anal Chim Acta 894:54–64
   PubMed Web of Science ®Google Scholar
• Zhang X, Xiong W, Shi L, et al. (2014). Simultaneous determination of five mercapturic acids derived from volatile organic compounds in human urine by LC–MS/MS and its application to relationship study. J Chromatog B 967:102–9
   PubMed Web of Science ®Google Scholar
• Zimmer D. (2003). Introduction to quantitative liquid chromatography-tandem mass spectrometry (LC–MS–MS). Chromatographia 57:S325–32
   Web of Science ®Google Scholar