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Synthesis of Hapten for Indirect Competitive Immunoassay for Measuring 3,5,6-trichloro-2-pyridinol

  • Kim, Areumnuri (Chemical Safety Division, National Institute of Agricultural Sciences) ;
  • Kim, Joong-Young (BIONAST Co., Ltd.) ;
  • Jeong, Sang-Hee (Department of Applied Biotoxicology, Hoseo University) ;
  • Cho, Myung-Haing (College of Veterinary Medicine, Seoul National University) ;
  • Park, Kyung-Hun (Chemical Safety Division, National Institute of Agricultural Sciences) ;
  • Cho, Namjun (Chemical Safety Division, National Institute of Agricultural Sciences) ;
  • Paik, Min Kyoung (Chemical Safety Division, National Institute of Agricultural Sciences)
  • Received : 2015.09.10
  • Accepted : 2015.10.24
  • Published : 2015.12.31

Abstract

BACKGROUND: In this study, we have attempted to identify a urinary biomarker to assess chlorpyrifos exposure in farmers. The major metabolite and the excretion pathway of chlorpyrifos is 3,5,6-trichloro-2-pyridinol (TCP) in urine. Herein, we describe an adequate synthetic method for TCP hapten for measuring urinary TCP of farmers. METHODS AND RESULTS: First, TCP was prepared by spacer attachment through hydrolysis of thiophosphate ester from chlorpyrifos. After reaction with benzyl bromide, the TCP was transformed into 2,3,5-trichloro-6-benzyloxypyridine. Next, the chlorine in the 2 nd position of the pyridyl ring was substituted into 3-mercaptopropanoic acid spacer arm. Finally, the phenyl group attached to the 6 th position in pyridyl ring was removed for producing the targeted product, 3-(3,5-Dichloro-6-hydroxy-2-pyridyl) thiopropanoic acid. CONCLUSION: Henceforth, this TCP hapten would be used in developing immunoassay studies for the detection and quantitation of urinary TCP of farmers.

Keywords

References

  1. Chuang, J. C., Van Emon, J. M., Reed, A. W., & Junod, N. (2004). Comparison of immunoassay and gas chromatography/mass spectrometry methods for measuring 3, 5, 6-trichloro-2-pyridinol in multiple sample media. Analytica Chimica Acta, 517(1), 177-185. https://doi.org/10.1016/j.aca.2004.04.034
  2. Gorton, L. (Ed.). (2005). Biosensors and modern biospecific analytical techniques (p. 331), Elsevier B. V., The Netherlands.
  3. Kim, Y. A., Lee, E. H., Kim, K. O., Lee, Y. T., Hammock, B. D., & Lee, H. S. (2011). Competitive immunochromatographic assay for the detection of the organophosphorus pesticide chlorpyrifos. Analytica Chimica Acta, 693(1), 106-113. https://doi.org/10.1016/j.aca.2011.03.011
  4. Manclús, J. J. & Montoya, A. (1995). Development of immunoassays for the analysis of chlorpyrifos and its metabolite 3,5,7-trichloro-2-pyridinol in the aquatic environment. Analytica Chimica Acta, 311, 341-348. https://doi.org/10.1016/0003-2670(95)00044-Z
  5. Manclús, J. J., Primo, J., & Montoya, A. (1994). Development of a chlorpyrifos immunoassay using antibodies obtained from a simple hapten design. Journal of Agricultural and Food Chemistry, 42(6), 1257-1260. https://doi.org/10.1021/jf00042a001
  6. Mauriz, E., Calle, A., Manclus, J. J., Montoya, A., & Lechuga, L. M. (2007). On-line determination of 3, 5, 6-trichloro-2-pyridinol in human urine samples by surface plasmon resonance immunosensing. Analytical and Bioanalytical Chemistry, 387(8), 2757-2765. https://doi.org/10.1007/s00216-007-1175-5
  7. Zhang, W., Tang, Y., Du, D., Smith, J., Timchalk, C., Liu, D., & Lin, Y. (2013). Direct analysis of trichloropyridinol in human saliva using an Au nanoparticles-based immunochromatographic test strip for biomonitoring of exposure to chlorpyrifos. Talanta, 114, 261-267. https://doi.org/10.1016/j.talanta.2013.06.012