Advertisement

Analytical and Bioanalytical Chemistry

, Volume 407, Issue 20, pp 6137–6148 | Cite as

A novel two-dimensional liquid-chromatography method for online prediction of the toxicity of transformation products of benzophenones after water chlorination

  • Jian Li
  • Li-yun Ma
  • Li Xu
  • Zhi-guo ShiEmail author
Research Paper

Abstract

Benzophenone-type UV filters (BPs) are ubiquitous in the environment. Transformation products (TPs) of BPs with suspected toxicity are likely to be produced during disinfection of water by chlorination. To quickly predict the toxicity of TPs, in this study, a novel two-dimensional liquid-chromatography (2D-LC) method was established in which the objective of the first dimension was to separate the multiple components of the BPs sample after chlorination, using a reversed-phase liquid-chromatography mode. A biochromatographic system, i.e. bio-partitioning micellar chromatography with the polyoxyethylene (23) lauryl ether aqueous solution as the mobile phase, served as the second dimension to predict the toxicity of the fraction from the first dimension on the basis of the quantitative retention–activity relationships (QRARs) model. Six BPs, namely 2,4-dihydroxybenzophenone, oxybenzone, 4-hydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone and 2,2'-dihydroxy-4-methoxybenzophenone, were the target analytes subjected to chlorination. The products of these BPs after chlorination were directly injected to the 2D-LC system for analysis. The results indicated that most TPs may be less toxic than their parent chemicals, but some may be more toxic, and that intestinal toxicity of TPs may be more obvious than blood toxicity. The proposed method is time-saving, high-throughput, and reliable, and has great potential for predicting toxicity or bioactivity of unknown and/or known components in a complex sample.

Graphical Abstract

The scheme for the 2D-LC online prediction of toxicity of the transformation products of benzophenone-type UV filters after chlorination

Keywords

Benzophenones Chlorination Two-dimensional liquid chromatography Toxicity simulation Biochromatography 

Notes

Acknowledgements

The authors gratefully acknowledge the financial support of this research by the Program for New Century Excellent Talents in University (No. NCET-12-0213), Ministry of Education of China and the Fundamental Research Funds for the Central Universities (No. 2015TS135).

References

  1. 1.
    Ternes TA, Joss A, Siegrist H (2004) Scrutinizing pharmaceuticals and personal care products in wastewater treatment. Environ Sci Technol 38:392A–399ACrossRefGoogle Scholar
  2. 2.
    Kupper T, Plagellat C, Brandli RC, de Alencastro LF, Grandjean D, Tarradellas J (2006) Fate and removal of polycyclic musks, UV filters and biocides during wastewater treatment. Water Res 40:2603–2612CrossRefGoogle Scholar
  3. 3.
    Poiger T, Buser HR, Balmer ME, Bergqvist PA, Muller MD (2004) Occurrence of UV filter compounds from sunscreens in surface waters: regional mass balance in two Swiss lakes. Chemosphere 55:951–963CrossRefGoogle Scholar
  4. 4.
    Balmer ME, Buser HR, Muller MD, Poiger T (2005) Occurrence of some organic UV filters in wastewater, in surface waters, and in fish from Swiss. Lakes Environ Sci Technol 39:953–962CrossRefGoogle Scholar
  5. 5.
    Negreira N, Canosa P, Rodriguez I, Ramil M, Rubi E, Cela R (2008) Study of some UV filters stability in chlorinated water and identification of halogenated by-products by gas chromatography-mass spectrometry. J Chromatogr A 1178:206–214CrossRefGoogle Scholar
  6. 6.
    Deborde M, von Gunten U (2008) Reactions of chlorine with inorganic and organic compounds during water treatment-Kinetics and mechanisms: a critical review. Water Res 42:13–51CrossRefGoogle Scholar
  7. 7.
    DellaGreca M, Iesce MR, Pistillo P, Previtera L, Temussi F (2009) Unusual products of the aqueous chlorination of atenolol. Chemosphere 74:730–734CrossRefGoogle Scholar
  8. 8.
    Yang X, Shang C (2004) Chlorination byproduct formation in the presence of humic acid, model nitrogenous organic compounds, ammonia, and bromide. Environ Sci Technol 38:4995–5001CrossRefGoogle Scholar
  9. 9.
    Buth JM, Arnold WA, McNeill K (2007) Unexpected products and reaction mechanisms of the aqueous chlorination of cimetidine. Environ Sci Technol 41:6228–6233CrossRefGoogle Scholar
  10. 10.
    Liu Q, Chen Z, Wei D, Du Y (2014) Acute toxicity formation potential of benzophenone-type UV filters in chlorination disinfection process. J Environ Sci 26:440–447CrossRefGoogle Scholar
  11. 11.
    Xiao M, Wei D, Yin J, Wei G, Du Y (2013) Transformation mechanism of benzophenone-4 in free chlorine promoted chlorination disinfection. Water Res 47:6223–6233CrossRefGoogle Scholar
  12. 12.
    Suzuki T, Kitamura S, Khota R, Sugihara K, Fujimoto N, Ohta S (2005) Estrogenic and antiandrogenic activities of 17 benzophenone derivatives used as UV stabilizers and sunscreens. Toxicol Appl Pharmacol 203:9–17CrossRefGoogle Scholar
  13. 13.
    Zeiger E, Anderson B, Haworth S, Lawlor T, Mortelmans K, Speck W (1987) Salmonella mutagenicity tests: III Results from the testing of 255 chemicals. Environ Mutagen 9(Suppl 9):1–109CrossRefGoogle Scholar
  14. 14.
    French JE (1992) NTP technical report on the toxicity studies of 2-Hydroxy-4-methoxybenzophenone (CAS No 131-57-7) Administered Topically and in Dosed Feed to F344/N Rats and B6C3F1 Mice. Toxic Rep Ser 21:1–14Google Scholar
  15. 15.
    Maijo I, Fontanals N, Borrull F, Neususs C, Calull M, Aguilar C (2013) Determination of UV filters in river water samples by in-line SPE-CE-MS. Electrophoresis 34:374–382CrossRefGoogle Scholar
  16. 16.
    Siroka Z, Svobodova Z (2013) The toxicity and adverse effects of selected drugs in animals—overview. Pol J Vet Sci 16:181–191Google Scholar
  17. 17.
    Tiwari AK, Pragya P, Ravi RK, Chowdhuri DK (2011) Environmental chemical mediated male reproductive toxicity: Drosophila melanogaster as an alternate animal model. Theriogenology 76:197–216CrossRefGoogle Scholar
  18. 18.
    Scott CW, Peters MF, Dragan YP (2013) Human induced pluripotent stem cells and their use in drug discovery for toxicity testing. Toxicol Lett 219:49–58CrossRefGoogle Scholar
  19. 19.
    Greenhough S, Medine CN, Hay DC (2010) Pluripotent stem cell derived hepatocyte like cells and their potential in toxicity screening. Toxicology 278:250–255CrossRefGoogle Scholar
  20. 20.
    Escuder-Gilabert L, Martinez-Pla JJ, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ (2003) Biopartitioning micellar separation methods: modelling drug absorption. J Chromatogr B Analyt Technol Biomed Life Sci 797:21–35CrossRefGoogle Scholar
  21. 21.
    Yin CR, Ma LY, Huang JG, Xu L, Shi ZG (2013) Fast profiling ecotoxicity and skin permeability of benzophenone ultraviolet filters using biopartitioning micellar chromatography based on penetrable silica spheres. Anal Chim Acta 804:321–327CrossRefGoogle Scholar
  22. 22.
    Martinez-Pla JJ, Martin-Biosca Y, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ (2004) Evaluation of the pH effect of formulations on the skin permeability of drugs by biopartitioning micellar chromatography. J Chromatogr A 1047:255–262CrossRefGoogle Scholar
  23. 23.
    Molero-Monfort M, Escuder-Gilabert L, Villanueva-Camanas RM, Sagrado S, Medina-Hernandez MJ (2001) Biopartitioning micellar chromatography: an in vitro technique for predicting human drug absorption. J Chromatogr B Biomed Sci Appl 753:225–236CrossRefGoogle Scholar
  24. 24.
    Hu Z, Zhang W, He H, Feng Y, Da S (2009) Profiling of permeable compounds in Ligusticum chuanxiong by biopartitioning micellar chromatography. Chromatographia 69:637–644CrossRefGoogle Scholar
  25. 25.
    Quinones-Torrelo C, Sagrado-Vives S, Villanueva-Camanas RM, Medina-Hernandez MJ (2001) An LD50 model for predicting psychotropic drug toxicity using biopartitioning micellar chromatography. Biomed Chromatogr 15:31–40CrossRefGoogle Scholar
  26. 26.
    Bermudez-Saldana JM, Escuder-Gilabert L, Medina-Hernandez MJ, Villanueva-Camanas RM, Sagrado S (2005) Modelling bioconcentration of pesticides in fish using biopartitioning micellar chromatography. J Chromatogr A 1063:153–160CrossRefGoogle Scholar
  27. 27.
    Zhang C, Li J, Xu L, Shi ZG (2012) Fast immobilized liposome chromatography based on penetrable silica microspheres for screening and analysis of permeable compounds. J Chromatogr A 1233:78–84CrossRefGoogle Scholar
  28. 28.
    Hansch C, Leo A, Mekapati SB, Kurup A (2004) QSAR and ADME. Bioorg Med Chem 12:3391–3400CrossRefGoogle Scholar
  29. 29.
    Stoll DR, Li X, Wang X, Carr PW, Porter SE, Rutan SC (2007) Fast, comprehensive two-dimensional liquid chromatography. J Chromatogr A 1168:3–43CrossRefGoogle Scholar
  30. 30.
    Dugo P, Cacciola F, Kumm T, Dugo G, Mondello L (2008) Comprehensive multidimensional liquid chromatography: theory and applications. J Chromatogr A 1184:353–368CrossRefGoogle Scholar
  31. 31.
    Alexander AJ, Ma L (2009) Comprehensive two-dimensional liquid chromatography separations of pharmaceutical samples using dual Fused-Core columns in the 2nd dimension. J Chromatogr A 1216:1338–1345CrossRefGoogle Scholar
  32. 32.
    Zhu T, Row KH (2012) Monolithic materials and their applications in HPLC for purification and analysis of bioactive compounds from natural plants: a review. Instrum Sci Technol 40:78–89CrossRefGoogle Scholar
  33. 33.
    Shi Z, Feng Y (2008) Synthesis and characterization of hierarchically porous silica microspheres with penetrable macropores and tunable mesopores. Micropor Mesopor Mat 116:701–704CrossRefGoogle Scholar
  34. 34.
    Wei J, Shi Z, Chen F, Feng Y, Guo Q (2009) Synthesis of penetrable macroporous silica spheres for high-performance liquid chromatography. J Chromatogr A 1216:7388–7393CrossRefGoogle Scholar
  35. 35.
    Negreira N, Rodriguez I, Rodil R, Cela R (2012) Assessment of benzophenone-4 reactivity with free chlorine by liquid chromatography quadrupole time-of-flight mass spectrometry. Anal Chim Acta 743:101–110CrossRefGoogle Scholar
  36. 36.
    Zhang N, Li Z, Che W, Xu S, Wang S (2009) Biopartitioning micellar chromatography to predict dihydropyridine selective calcium channel antagonist toxicity. Chromatographia 70:685–690CrossRefGoogle Scholar
  37. 37.
    Wang SR, Chen C, Xiong MJ, Wu LP, Ye LM (2010) Quantitative retention-activity relationship models of angiotensin converting enzyme inhibitors using biopartitioning micellar chromatography. J Chromatogr Sci 48:134–139CrossRefGoogle Scholar
  38. 38.
    Molero-Monfort M, Martin-Biosca Y, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ (2000) Micellar liquid chromatography for prediction of drug transport. J Chromatogr A 870:1–11CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2015

Authors and Affiliations

  1. 1.Tongji School of PharmacyHuazhong University of Science and TechnologyWuhanChina
  2. 2.Department of ChemistryWuhan UniversityWuhanChina

Personalised recommendations