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

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Kim, Areumnuri;Kim, Joong-Young;Jeong, Sang-Hee;Cho, Myung-Haing;Park, Kyung-Hun;Cho, Namjun;Paik, Min Kyoung

  • 투고 : 2015.09.10
  • 심사 : 2015.10.24
  • 발행 : 2015.12.31

초록

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.

키워드

Chlorpyrifos;Hapten;TCP

참고문헌

  1. 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
  2. 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
  3. 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
  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. 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
  6. Gorton, L. (Ed.). (2005). Biosensors and modern biospecific analytical techniques (p. 331), Elsevier B. V., The Netherlands.
  7. 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

과제정보

연구 과제번호 : 급만성 농약노출 예측을 위한 생체 바이오마커 개발