Skip to main content

Advertisement

Log in

Quantification of urinary conjugates of bisphenol A, 2,5-dichlorophenol, and 2-hydroxy-4-methoxybenzophenone in humans by online solid phase extraction–high performance liquid chromatography–tandem mass spectrometry

  • Original Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

Urinary concentrations of phenols or their metabolites have been used as biomarkers to assess the prevalence of exposure to these compounds in the general population. Total urinary concentrations, which include both free and conjugated (glucuronide and sulfated) forms of the compounds, are usually reported. From a toxicologic standpoint, the relative concentrations of the free species compared with their conjugated analogs can be important because conjugation may reduce the potential biologic activity of the phenols. In this study, we determined the percentage of glucuronide and sulfate conjugates of three phenolic compounds, bisphenol A (BPA), 2,5-dichlorophenol (2,5-DCP), and 2-hydroxy-4-methoxybenzophenone (benzophenone-3, BP-3) in 30 urine samples collected between 2000 and 2004 from a demographically diverse group of anonymous adult volunteers. We used a sensitive on-line solid phase extraction–isotope dilution–high performance liquid chromatography–tandem mass spectrometry method. These three phenols were detected frequently in the urine samples tested. Only small percentages of the compounds (9.5% for BPA, and 3% for 2,5-DCP and BP-3) were excreted in their free form. The percentage of the sulfate conjugate was about twice that of the free compound. The glucuronide conjugate was the major metabolite, representing 69.5% (BPA), 89% (2,5-DCP), and 84.6% (BP-3) of the total amount excreted in urine. These results are in agreement with those reported before which suggested that BPA-glucuronide was an important BPA urinary metabolite in humans. To our knowledge, this is the first study describing the distribution of urinary conjugates of BP-3 and 2,5-DCP in humans.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3a–c

Similar content being viewed by others

References

  1. Sajiki J, Yonekubo J (2003) Chemosphere 51:55–62

    Article  PubMed  CAS  Google Scholar 

  2. Howe SR, Borodinsky L, Lyon RS (1998) J Coat Technol 70:69–74

    Article  CAS  Google Scholar 

  3. Arenholt-Bindslev D, Breinholt V, Preiss A, Schmalz G (1999) Clin Oral Investig 3:120–125

    Article  PubMed  CAS  Google Scholar 

  4. Safe SH, Pallaroni L, Yoon K, Gaido K, Ross S, McDonnell D (2002) Environ Health Perspect 110:925–929

    CAS  Google Scholar 

  5. Safe SH, Pallaroni L, Yoon K, Gaido K, Ross S, Saville B, McDonnell D (2001) Reprod Fertil Dev 13:307–315

    Article  PubMed  CAS  Google Scholar 

  6. Kuiper GGJM, Lemmen JG, Carlsson B, Corton JC, Safe SH, van der Saag PT, van der Burg P, Gustafsson JA (1998) Endocrinology 139:4252–4263

    Article  PubMed  CAS  Google Scholar 

  7. Andersen HR, Andersson AM, Arnold SF, Autrup H, Barfoed M, Beresford NA, Bjerregaard P, Christiansen LB, Gissel B, Hummel R, Jorgensen EB, Korsgaard B, Le Guevel R, Leffers H, McLachlan J, Moller A, Nielsen JB, Olea N, Oles-Karasko A, Pakdel F, Pedersen KL, Perez P, Skakkeboek NE, Sonnenschein C, Soto AM, Sumpter JP, Thorpe SM, Grandjean P (1999) Environ Health Perspect 107:89–108

    Article  CAS  Google Scholar 

  8. Elsby R, Maggs JL, Ashby J, Park BK (2001) J Pharmacol Exp Ther 297:103–113

    PubMed  CAS  Google Scholar 

  9. Snyder RW, Maness SC, Gaido KW, Welsch F, Sumner SCJ, Fennell TR (2000) Toxicol Appl Pharmacol 168:225–234

    Article  PubMed  CAS  Google Scholar 

  10. Volkel W, Colnot T, Csanady GA, Filser JG, Dekant W (2002) Chem Res Toxicol 15:1281–1287

    Article  PubMed  CAS  Google Scholar 

  11. Calafat AM, Kuklenyik Z, Reidy JA, Caudill SP, Ekong J, Needham LL (2005) Environ Health Perspect 113:391–395

    Article  CAS  Google Scholar 

  12. ATSDR (2004) Toxicological profile for dichlorobenzenes. Draft for Public Comment, Agency for Toxic Substances and Disease Registry, Atlanta, GA

  13. Tegethoff K, Herbold BA, Bomhard EM (2000) Mutat Res Genet Toxicol Environ Mutagen 470:161–167

    Article  CAS  Google Scholar 

  14. Hissink AM, Dunnewijk R, VanOmmen B, VanBladeren PJ (1997) Chem-Biol Interact 103:17–33

    Article  CAS  Google Scholar 

  15. Nedelcheva V, Gut I, Soucek P, Frantik E (1998) Chem-Biol Interact 115:53–70

    Article  PubMed  CAS  Google Scholar 

  16. Hissink AM, Oudshoorn MJ, VanOmmen B, VanBladeren PJ (1997) Toxicol Appl Pharmacol 145:1–9

    Article  PubMed  CAS  Google Scholar 

  17. CDC (2003) Second National Report on human exposure to environmental chemicals. National Center for Environmental Health, Division of Laboratory Sciences, Centers for Disease Control and Prevention, Atlanta, GA

  18. Hill RH, Head SL, Baker S, Gregg M, Shealy DB, Bailey SL, Williams CC, Sampson EJ, Needham LL (1995) Environ Res 71:99–108

    Article  CAS  Google Scholar 

  19. Schlumpf M, Cotton B, Conscience M, Haller V, Steinmann B, Lichtensteiger W (2001) Environ Health Perspect 109:239–244

    Article  CAS  Google Scholar 

  20. Okereke CS, Kadry AM, Abdelrahman MS, Davis RA, Friedman MA (1993) Drug Metab Dispos 21:788–791

    PubMed  CAS  Google Scholar 

  21. Felix T, Hall BJ, Brodbelt JS (1998) Anal Chim Acta 371:195–203

    Article  CAS  Google Scholar 

  22. Okereke CS, Abdelrahman MS, Friedman MA (1994) Toxicol Lett 73:113–122

    Article  PubMed  CAS  Google Scholar 

  23. Kim YH, Kim CS, Park S, Han SY, Pyo MY, Yang MH (2003) Biochem Biophys Res Commun 312:441–448

    Article  PubMed  CAS  Google Scholar 

  24. Hill RH, Shealy DB, Head SL, Williams CC, Bailey SL, Gregg M, Baker SE, Needham LL (1995) J Anal Toxicol 19:323–329

    PubMed  CAS  Google Scholar 

  25. Kuklenyik Z, Ekong J, Cutchins CD, Needham LL, Calafat AM (2003) Anal Chem 75:6820–6825

    Article  PubMed  CAS  Google Scholar 

  26. Lerch O, Zinn P (2003) J Chromatogr A 991:77–97

    Article  PubMed  CAS  Google Scholar 

  27. Zafra A, del Olmo M, Pulgar R, Navalon A, Vilchez JL (2002) Chromatographia 56:213–218

    Article  CAS  Google Scholar 

  28. Rosenfeld JM, Moharir Y, Hill R (1991) Anal Chem 63:1536–1541

    Article  CAS  Google Scholar 

  29. Taylor JK (1987) Quality assurance of chemical measurements. Lewis, Chelsea, MI

  30. Albro PW, Hass JR, Peck CC, Odam DG, Corbett JT, Bailey FJ, Blatt HE, Barrett BB (1981) Drug Metabol Dispos 9:223–225

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Antonia M. Calafat.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ye, X., Kuklenyik, Z., Needham, L.L. et al. Quantification of urinary conjugates of bisphenol A, 2,5-dichlorophenol, and 2-hydroxy-4-methoxybenzophenone in humans by online solid phase extraction–high performance liquid chromatography–tandem mass spectrometry. Anal Bioanal Chem 383, 638–644 (2005). https://doi.org/10.1007/s00216-005-0019-4

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-005-0019-4

Keywords

Navigation