Urinary Excretion of Thioethers Related to Styrene Exposure

Ginette TRUCHON; Denis BÉGIN; Jacques LESAGE; Diane TALBOT; Daniel DROLET; Michel GÉRIN; Mark GOLDBERG

doi:10.1539/joh.40.350

Ginette TRUCHON, Denis BÉGIN, Jacques LESAGE, Diane TALBOT, Daniel DROLET, Michel GÉRIN, Mark GOLDBERG

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Keywords: Styrene exposure, Global thioethers, Urinary specific mercapturic acids, Biological monitoring

JOURNAL FREE ACCESS

1998 Volume 40 Issue 4 Pages 350-355

DOI https://doi.org/10.1539/joh.40.350

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Published: 1998 Received: March 16, 1998 Available on J-STAGE: April 07, 2006 Accepted: September 14, 1998 Advance online publication: - Revised: -
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Date of correction: April 07, 2006 Reason for correction: - Correction: ABSTRACT Details: Wrong : Urinary Excretion of Thioethers Related to Styrene Exposure: Ginette TRUCHON et al. Institut de recherche en santé et en sécurité du travail, Montréal, Québeo, Canada-The objective of this study was to test the suitability of styrene-specific mercapturic acids as urinary bioindicators of occupational styrene exposure. The excretion of mandelic acid (MA), global thioethers and styrene-specific mercapturic acids was measured in urine samples from 64 workers employed in three companies fabricating glass fiber-reinforced polyester products. Global thioethers were measured by a spectrophotometric method while MA and specific mercapturic acids, N-acetyl-S-(1-phenyl-2-hydroxyethyl)-L-cysteine (M1) and N-acetyl-S-(2-phenyl-2-hydroxyethyl)-L-cysteine (M2), were measured by high pressure liquid chromatography with UV detection. Excretion of M1 and M2 was qualitatively verified by gas chromatography-mass spectrometry. The environmental measurements were carried out with passive dosimeters. Workers had 8-h TWA exposure levels ranging from O to 667 mg/m³. End-of-shift MA excretion ranged from O to 2.08 mmol/mmol creatinine and was well correlated with environmental styrene exposure (r=0.91, p<0.001). M1 and M2 were detected (i.e. above ca. I μmol/mmol creatinine) in urine samples of only three workers who were exposed to various concentrations of styrene. End-of-shift excretion of global thioethers was found to be significantly correlated to cigarette consumption as well as to styrene exposure, as measured by end-of-shift MA excretion. In opposition to data from rats, our results indicate that humans exposed to styrene excrete little styrene-specific thioethers. The apparent inter-individual variability in excretion of M1 and M2 suggests that they may not constitute suitable indicators of occupational styrene exposure.
Right : Urinary Excretion of Thioethers Related to Styrene Exposure: Ginette TRUCHON et al. Institut de recherche en santé et en sécurité du travail, Montréal, Québeo, Canada-The objective of this study was to test the suitability of styrene-specific mercapturic acids as urinary bioindicators of occupational styrene exposure. The excretion of mandelic acid (MA), global thioethers and styrene-specific mercapturic acids was measured in urine samples from 64 workers employed in three companies fabricating glass fiber-reinforced polyester products. Global thioethers were measured by a spectrophotometric method while MA and specific mercapturic acids, N-acetyl-S-(1-phenyl-2-hydroxyethyl)-L-cysteine (M1) and N-acetyl-S-(2-phenyl-2-hydroxyethyl)-L-cysteine (M2), were measured by high pressure liquid chromatography with UV detection. Excretion of M1 and M2 was qualitatively verified by gas chromatography-mass spectrometry. The environmental measurements were carried out with passive dosimeters. Workers had 8-h TWA exposure levels ranging from O to 667 mg/m³. End-of-shift MA excretion ranged from O to 2.08 mmol/mmol creatinine and was well correlated with environmental styrene exposure (r=0.91, p<0.001). M1 and M2 were detected (i.e. above ca. I μmol/mmol creatinine) in urine samples of only three workers who were exposed to various concentrations of styrene. End-of-shift excretion of global thioethers was found to be significantly correlated to cigarette consumption as well as to styrene exposure, as measured by end-of-shift MA excretion. In opposition to data from rats, our results indicate that humans exposed to styrene excrete little styrene-specific thioethers. The apparent inter-individual variability in excretion of M1 and M2 suggests that they may not constitute suitable indicators of occupational styrene exposure.

Date of correction: April 07, 2006 Reason for correction: - Correction: AFFILIATION Details: Wrong :
1) Institut de recherche en santé et en sécurité du travail, Montréal, Quebec, Canada
2) Département de médecine du travail et d''hygiène du milieu, Université de Montréal, Montr6al, Québec, Canada
3) Unltéd''épidémiologie et de biostatistique, Institut Armand-Frappier, Laval, Québec, Canada

Right :
1) Institut de recherche en santé et en sécurité du travail, Montréal, Quebec, Canada
2) Département de médecine du travail et d'hygiène du milieu, Université de Montréal, Montr6al, Québec, Canada
3) Unltéd'épidémiologie et de biostatistique, Institut Armand-Frappier, Laval, Québec, Canada

Date of correction: April 07, 2006 Reason for correction: - Correction: CITATION Details: Wrong : 1) Bartolucci GB, Chiesura Corona P, DeRosa E, Brugnone F, Perbellini L. Environmental and Biological Monitoring of Workers Exposed to Styrene. In: Ho MH, Dillon HK. eds. Biological Monitoring of Exposure to Chemicals. Organic Compounds. New York: John Wiley & Sons, 1987: 155-168.
2) Engstrom K. Styrene. In: Aitio A, Riihimaki V, Vainio H, eds., Biological Monitoring and Surveillance of Workers Exposed to Chemicals. Washington: Hemisphere Publishing Corporation, 1984: 99-110.
3) Ryan AJ, James MD, Ben-Zvi Z, Law FCP, Bend JR. Hepatic and Extrahepatic Metabolism of ¹⁴C-Styrene Oxide. Environ Health Perspect 1976; 17: 135-144.
4) Malonova H, Bardodej Z. Urinary Excretion of Mercapturates as a Biological Indicator of Exposure to Electrophilic Agents. J Hyg Epidemiol Microbiol Immunol 1983; 27: 319-328.
5) Truchon G, Gérin M, Brodeur J. Urinary Excretion of Mandelic, Phenylglyoxylic, and Specific Mercapturic Acids in Rats Exposed Repeatedly by Inhalation to Various Concentrations of Styrene Vapors. Can J Physiol Pharmacol 1990; 68: 556-561.
6) Sorsa M, Hemminki K, Vainio H. Biological Monitoring of Exposure to Chemical Mutagens in the Occupational Environment. Teratog Carcinog Mutag 1982; 2: 137-150.
7) Berlin A, Draper M, Hemminki D, Vainio H. International Seminar on Methods of Monitoring Human Exposure to Carcinogenic and Mutagenic Agents. Int Arch Occup Environ Health 1 984; 54: 369-375.
8) Chasseaud LF. Determination of Thioethers as Biochemical Markers for Monitoring Exposure to Potential Toxicants. In: Sies H, Kefferer B, eds. Glutathione Conjugation. Mechanisms and Biological Significance. New York: Academic Press Limited, 1988: 391-413.
9) Triebig G, Schaller H-K, Wagner M, Weltle D, Moser W, Valentin H. A Pilot Study of the Diagnostic Validity of Urinary Thioether Excretion in Occupational Medecine. Sci Total Environ 1 988; 71: 231-234.
10) IRSST—Institut de recherche en santé et en sécurité du travail du Quebec. Air Styrene Analysis (in French). Analytical method 31-1, IRSST, Montréal, 1990.
ll) Truchon G, Brodeur J, Gérin M. Simultaneous Determination of Urinary Mandelic, Phenylglyoxylic, and Mercapturic Acids of Styrene by High-Performance Liquid Chromatography. J Anal Toxicol 1990; 14: 227-230.
12) Van Doorn R, Borm PJA, Leijdekkers Ch-M, Henderson PTh, Reuvers J, Van Bergen TJ. Detection and Identification of S-Methylcysteine in Urine of Workers Exposed to Methyl Chloride. Int Arch Occup Environ Health 1980; 46: 99-l09.
l3) IRSST-Institut de recherche en santé et en sécurité du travail du Québec. Urinary Creatinine Determination (in French). Analytical method 163-1, IRSST, Montréal, 1990.
14) Aringer L, Lidums V. Influence of Diet and other Factors on Urinary Levels of Thioethers. Int Arch Occup Environ Health 1988; 61: 123-130.
15) ACGIH-American Conference of Governmental Industrial Hygienists. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices, ACGIH, Cincinnati, 1994.
16) Seutter-Berlage F, Delbressine LPC, Smeets FLM, Ketelaars HCJ. Identification of Three Sulphur-Containing Urinary Metabolites of Styrene in the Rat. Xenobiotica, 1978; 8: 413-418.
17) Delbressine LPC, van Bladeren PJ, Smeets FLM, Seutter-Berlage F. Stereoselective Oxidation of Styrene to Styrene Oxide in Rats as Measured by Mercapturic Acid Excretion. Xenobiotica 1981; 11: 589-594.
18) Aringer L, Löf A, Elinder C-G. The Applicability of the Measurement of Urinary Thioethers. A Study of Humans Exposed to Styrene During Diet Standardization. Int. Arch. Occup. Environ. Health, 1991; 63: 341-346.
19) Norström A, Löf A, Aringer L, Samuelsson R, Andersson B, Levin J-O, Näslund P. Determination of N-Acetyl-S-(2-phenyl-2-hydroxyethyl) cysteine in Human Urine After Experimental Exposure to Styrene. Chemosphere 1992; 24: 1553-1561.
20) Hallier E, Goergens HW, Karels H, Golka K.ANote on Individual Differences in the Urinary Excretion of Optical Enantiomers of Styrene Metabolites and of Styrene-derived Mercapturic Acids in Humans. Arch Toxicol 1995; 69: 300-305.
21) Ghittori S, Maestri L, Imbriani M, Capodaglio E, Cavalleri A. Urinary Excretion of Specific Mercapturic Acids in Workers Exposed to Styrene. Am J Ind Med 1997; 31: 636-644.
22) Van Doorn R, Bos RP, Leijdekkers ChM, Wagenaas-Zegers JLG, Henderson Pth. Thioether Concentration and Mutagenicity of Urine from Cigarette Smokers. Int Arch Occup Environ Health 1979; 43: 159-166.
23) Heinonen T, Kytöniemi V, Sorsa M, Vainio H. Urinary Excretion of Thioethers among Low-tar and Mediumtar Cigarette Smokers. Int Arch Occup Environ Health, 1983; 52: 11-16.
24) Vainio H, Salvolainen H, Kilpikari I. Urinary Thioether of Employees of a Chemical Plant. Brit J Ind Med 1978; 35: 232-234.
25) Jakubowski M, Linhart I, Pielas G, Kopecky J. 2-Cyanoethylmercapturic Acid (CEMA) in the Urine as a Possible Indicator of Exposure to Acrylonitrile. Br J Ind Med 1987; 44: 83l-840.
26) Stommel P, Mütler G, Stücker W, Verkoyen C, Schöbel S, Norpoth K. Determination of S-phenylmercapturic acid in the urine-an improvement in the biological monitoring of benzene exposure. Carcinogenesis 1989; 10: 279-282.
27) Warholm M, Guthenberg C, Mannervik B. Molecular and catalytic properties of glutathione-S-transferases from human liver: an enzyme efficiently conjugating epoxides. Biochem 1983; 22: 3610-3617.
28) Warholm M, Guthenberg C, Mannervik B, Von Bahr C. Purification of a new glutathione-S-transferase (transferase μ) from human liver having high activity with benzo(a)pyrene-4, 5-oxide. Biochem Biophys Res Commun 1981; 98: 512-5 19.
29) Pacifici GM, Warholm M, Guthenberg C, Mannervik B, Rane A. Detoxification of styrene oxide by human liver glutathione transferase. Human Toxicol 1987; 6: 483-489.

Right : 1) Bartolucci GB, Chiesura Corona P, DeRosa E, Brugnone F, Perbellini L. Environmental and Biological Monitoring of Workers Exposed to Styrene. In: Ho MH, Dillon HK. eds. Biological Monitoring of Exposure to Chemicals. Organic Compounds. New York: John Wiley & Sons, 1987: 155-168.
2) Engstrom K. Styrene. In: Aitio A, Riihimaki V, Vainio H, eds., Biological Monitoring and Surveillance of Workers Exposed to Chemicals. Washington: Hemisphere Publishing Corporation, 1984: 99-110.
3) Ryan AJ, James MD, Ben-Zvi Z, Law FCP, Bend JR. Hepatic and Extrahepatic Metabolism of ¹⁴C-Styrene Oxide. Environ Health Perspect 1976; 17: 135-144.
4) Malonova H, Bardodej Z. Urinary Excretion of Mercapturates as a Biological Indicator of Exposure to Electrophilic Agents. J Hyg Epidemiol Microbiol Immunol 1983; 27: 319-328.
5) Truchon G, Gérin M, Brodeur J. Urinary Excretion of Mandelic, Phenylglyoxylic, and Specific Mercapturic Acids in Rats Exposed Repeatedly by Inhalation to Various Concentrations of Styrene Vapors. Can J Physiol Pharmacol 1990; 68: 556-561.
6) Sorsa M, Hemminki K, Vainio H. Biological Monitoring of Exposure to Chemical Mutagens in the Occupational Environment. Teratog Carcinog Mutag 1982; 2: 137-150.
7) Berlin A, Draper M, Hemminki D, Vainio H. International Seminar on Methods of Monitoring Human Exposure to Carcinogenic and Mutagenic Agents. Int Arch Occup Environ Health 1 984; 54: 369-375.
8) Chasseaud LF. Determination of Thioethers as Biochemical Markers for Monitoring Exposure to Potential Toxicants. In: Sies H, Kefferer B, eds. Glutathione Conjugation. Mechanisms and Biological Significance. New York: Academic Press Limited, 1988: 391-413.
9) Triebig G, Schaller H-K, Wagner M, Weltle D, Moser W, Valentin H. A Pilot Study of the Diagnostic Validity of Urinary Thioether Excretion in Occupational Medecine. Sci Total Environ 1 988; 71: 231-234.
10) IRSST—Institut de recherche en santé et en sécurité du travail du Quebec. Air Styrene Analysis (in French). Analytical method 31-1, IRSST, Montréal, 1990.
ll) Truchon G, Brodeur J, Gérin M. Simultaneous Determination of Urinary Mandelic, Phenylglyoxylic, and Mercapturic Acids of Styrene by High-Performance Liquid Chromatography. J Anal Toxicol 1990; 14: 227-230.
12) Van Doorn R, Borm PJA, Leijdekkers Ch-M, Henderson PTh, Reuvers J, Van Bergen TJ. Detection and Identification of S-Methylcysteine in Urine of Workers Exposed to Methyl Chloride. Int Arch Occup Environ Health 1980; 46: 99-l09.
l3) IRSST-Institut de recherche en santé et en sécurité du travail du Québec. Urinary Creatinine Determination (in French). Analytical method 163-1, IRSST, Montréal, 1990.
14) Aringer L, Lidums V. Influence of Diet and other Factors on Urinary Levels of Thioethers. Int Arch Occup Environ Health 1988; 61: 123-130.
15) ACGIH-American Conference of Governmental Industrial Hygienists. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices, ACGIH, Cincinnati, 1994.
16) Seutter-Berlage F, Delbressine LPC, Smeets FLM, Ketelaars HCJ. Identification of Three Sulphur-Containing Urinary Metabolites of Styrene in the Rat. Xenobiotica, 1978; 8: 413-418.
17) Delbressine LPC, van Bladeren PJ, Smeets FLM, Seutter-Berlage F. Stereoselective Oxidation of Styrene to Styrene Oxide in Rats as Measured by Mercapturic Acid Excretion. Xenobiotica 1981; 11: 589-594.
18) Aringer L, Löf A, Elinder C-G. The Applicability of the Measurement of Urinary Thioethers. A Study of Humans Exposed to Styrene During Diet Standardization. Int. Arch. Occup. Environ. Health, 1991; 63: 341-346.
19) Norström A, Löf A, Aringer L, Samuelsson R, Andersson B, Levin J-O, Näslund P. Determination of N-Acetyl-S-(2-phenyl-2-hydroxyethyl) cysteine in Human Urine After Experimental Exposure to Styrene. Chemosphere 1992; 24: 1553-1561.
20) Hallier E, Goergens HW, Karels H, Golka K.ANote on Individual Differences in the Urinary Excretion of Optical Enantiomers of Styrene Metabolites and of Styrene-derived Mercapturic Acids in Humans. Arch Toxicol 1995; 69: 300-305.
21) Ghittori S, Maestri L, Imbriani M, Capodaglio E, Cavalleri A. Urinary Excretion of Specific Mercapturic Acids in Workers Exposed to Styrene. Am J Ind Med 1997; 31: 636-644.
22) Van Doorn R, Bos RP, Leijdekkers ChM, Wagenaas-Zegers JLG, Henderson Pth. Thioether Concentration and Mutagenicity of Urine from Cigarette Smokers. Int Arch Occup Environ Health 1979; 43: 159-166.
23) Heinonen T, Kytöniemi V, Sorsa M, Vainio H. Urinary Excretion of Thioethers among Low-tar and Mediumtar Cigarette Smokers. Int Arch Occup Environ Health, 1983; 52: 11-16.
24) Vainio H, Salvolainen H, Kilpikari I. Urinary Thioether of Employees of a Chemical Plant. Brit J Ind Med 1978; 35: 232-234.
25) Jakubowski M, Linhart I, Pielas G, Kopecky J. 2-Cyanoethylmercapturic Acid (CEMA) in the Urine as a Possible Indicator of Exposure to Acrylonitrile. Br J Ind Med 1987; 44: 83l-840.
26) Stommel P, Mütler G, Stücker W, Verkoyen C, Schöbel S, Norpoth K. Determination of S-phenylmercapturic acid in the urine-an improvement in the biological monitoring of benzene exposure. Carcinogenesis 1989; 10: 279-282.
27) Warholm M, Guthenberg C, Mannervik B. Molecular and catalytic properties of glutathione-S-transferases from human liver: an enzyme efficiently conjugating epoxides. Biochem 1983; 22: 3610-3617.
28) Warholm M, Guthenberg C, Mannervik B, Von Bahr C. Purification of a new glutathione-S-transferase (transferase μ) from human liver having high activity with benzo(a)pyrene-4, 5-oxide. Biochem Biophys Res Commun 1981; 98: 512-5 19.
29) Pacifici GM, Warholm M, Guthenberg C, Mannervik B, Rane A. Detoxification of styrene oxide by human liver glutathione transferase. Human Toxicol 1987; 6: 483-489.

Date of correction: April 07, 2006 Reason for correction: - Correction: PDF FILE Details: -

Abstract

Urinary Excretion of Thioethers Related to Styrene Exposure: Ginette TRUCHON et al. Institut de recherche en santé et en sécurité du travail, Montréal, Québeo, Canada-The objective of this study was to test the suitability of styrene-specific mercapturic acids as urinary bioindicators of occupational styrene exposure. The excretion of mandelic acid (MA), global thioethers and styrene-specific mercapturic acids was measured in urine samples from 64 workers employed in three companies fabricating glass fiber-reinforced polyester products. Global thioethers were measured by a spectrophotometric method while MA and specific mercapturic acids, N-acetyl-S-(1-phenyl-2-hydroxyethyl)-L-cysteine (M1) and N-acetyl-S-(2-phenyl-2-hydroxyethyl)-L-cysteine (M2), were measured by high pressure liquid chromatography with UV detection. Excretion of M1 and M2 was qualitatively verified by gas chromatography-mass spectrometry. The environmental measurements were carried out with passive dosimeters. Workers had 8-h TWA exposure levels ranging from O to 667 mg/m³. End-of-shift MA excretion ranged from O to 2.08 mmol/mmol creatinine and was well correlated with environmental styrene exposure (r=0.91, p<0.001). M1 and M2 were detected (i.e. above ca. I μmol/mmol creatinine) in urine samples of only three workers who were exposed to various concentrations of styrene. End-of-shift excretion of global thioethers was found to be significantly correlated to cigarette consumption as well as to styrene exposure, as measured by end-of-shift MA excretion. In opposition to data from rats, our results indicate that humans exposed to styrene excrete little styrene-specific thioethers. The apparent inter-individual variability in excretion of M1 and M2 suggests that they may not constitute suitable indicators of occupational styrene exposure.

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