Abstract
Molecularly imprinted polymers (MIPs) were prepared by the bulk polymerization using crystal violet as the template molecule, and the methacrylic acid and ethylene glycol dimetheacrylate as functional monomer and cross-linker, respectively. Systematic investigations of synthetic conditions were conducted. The surface morphology and recognition mechanism of the obtained polymers were studied using scanning electron microscope and spectrophotometric analysis. MIPs showed high affinity to template molecule and were successfully applied as special solid-phase extraction sorbent for selective extraction of crystal violet from natural seawater. An off-line molecularly imprinted solid-phase extraction (MISPE) method followed by high-performance liquid chromatography with diodearray detection for the analysis of crystal violet was also established. MISPE columns have good recoveries for crystal violet standard solutions and good linearity was obtained over the concentration range of 0–200 μg L−1 (R 2 > 0.99). Finally, two natural seawater samples were investigated. The recoveries of spiked seawater on the MISPE columns were from 44.47% to 62.34%, the relative standard deviation (n=3) being in the range of 2.89%–5.96%.
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Attardi, M. E., Porcu, G., and Taddei, M., 2000. Malachite green, a valuable reagent to monitor the presence of free COOH on the solid-phase. Tetrahedron Letter, 41: 7391–7394, PII: S0040-4039(00)01257-0.
Baggiani, C., Anfossi, L., Giovannoli, C., and Tozzi, C., 2004. Binding properties of 2, 4, 5-trichlorophenoxyacetic acid-imprinted polymers prepared with different molar ratios between template and functional monomer. Talanta, 62: 1029–1034, DOI: 10.1016/ j.talanta.2003.10.027.
Culp, S. J., and Beland, F. A., 1996. Malachite green: A toxicological review. Journal of the American College of Toxicology, 15: 219–238, DOI: 10.3109/10915819609008715.
Dowling, G., Mulder, P. P. J., Regan, C. D. L., and Smyth, M. R., 2007. Confirmatory analysis of malachite green, leucomalachite green, crystal violet and leucocrystal violet in salmon by liquid chromatography-tandem mass spectrometry. Analytica Chimica Acta, 586: 411–419, DOI: 10.1016/j.aca.2006.08.045.
European Commission, 2004. Report for 2004 on the Results of Residue Monitoring in Food of Animal Origin in the Member States. SANCO/3400/2005.
Guo, Z. Y., Gai, P. P., Hao, T. T., Duan, J., and Wang, S., 2011. Determination of malachite green residues in fish using a highly sensitive electrochemiluminescence method combined with molecularly imprinted solid phase extraction. Journal of Agricultural and Food Chemistry, 59: 5257–5262, DOI: 10.1021/jf2008502.
Lin, C. I., Joseph, A. K., Chang, C. K., Wang, Y. C., and Lee, Y. D., 2003. Synthesis of molecular imprinted organic-inorganic hybrid polymer binding caffeine. Analytica Chimica Acta, 481: 175–180, DOI: 10.1016/S0003-2670(03)00095-3.
Mei, S. R., Wu, D., Jiang, M., Lu, B., Lim, J. M., Zhou, Y. K., and Lee, Y. I., 2011. Determination of trace bisphenol A in complex samples using selective molecularly imprinted solid-phase extraction coupled with capillary electrophoresis. Microchemical Journal, 98: 150–155, DOI: 10.1016/j.microc.2011.01.003.
Michailof, C., Manesiotis, P., and Panayiotou, C., 2008. Synthesis of caffeic acid and phydroxybenzoic acid molecularly imprinted polymers and their application for the selective extraction of polyphenols from olive mill waste waters. Journal of Chromatography A, 1182: 25–33, DOI: 10.1016/j.chroma.2008.01.001.
Oplatowska, M., Connolly, L., Stevenson, P., Stead, S., and Elliott, C. T., 2011. Development and validation of a fast monoclonal based disequilibrium enzyme-linked immunosorbent assay for the detection of triphenylmethane dyes and their metabolites in fish. Analytica Chimica Acta, 698: 51–60, DOI: 10.1016/j.aca. 2011.04.047.
Puoci, F., Curcio, M., Cirillo, G., Iemma, F., Spizzirri, U. G., and Picci, N., 2008. Molecularly imprinted solid-phase extraction for cholesterol determination in cheese products. Food Chemistry, 106: 836–842, DOI: 10.1016/j.foodchem.2007.06.043.
Rushing, L. G., and Bowman, M. C., 1980. Determination of gentian violet in animal feed, human urine, and wastewater by high pressure liquid chromatography. Journal of Chromatographic Science, 18: 224–232, DOI: 10.1093/chromsci/18.9.24A.
Rushing, L. G., and Hansen, E. B., 1997. Confirmation of malachite green, gentian violet and their leuco analogs in catfish and trout tissue by high-performance liquid chromatography utilizing electrochemistry with ultraviolet-visible diode array detection and fluorescence detection. Journal of Chromatography B, 700: 223–231.
Safarik, I., and Safarikova, M., 2002. Detection of low concentrations of malachite green and crystal violet in water. Water Research, 36: 196–200, PII: S0043-1354(01) 00243-3.
Shen, Y. D., Deng, X. F., Xu, Z. L., Wang, Y, Lei, H. T., Wang, H., Yang, J. Y., Xiao, Z. L., and Sun, Y. M., 2011. Simultaneous determination of malachite green, brilliant green and crystal violet in grass carp tissues by a broad-specificity indirect competitive enzyme-linked immunosorbent assay. Analytica Chimica Acta, 707: 148–154, DOI: 10.1016/j.aca. 2011.09.006.
Shivaji, S., Ranjana, S., and Roy, D., 2004. Toxicological effects of malachite green. Journal of Aquatic Toxicology, 66: 319–329, DOI: 10.1016/j.aquatox.2003.09.008.
Singh, K. P., Gupta, S., Singh, A. K., and Sinha, S., 2011. Optimizing adsorption of crystal violet dye from water by magnetic nanocomposite using response surface modeling approach. Journal of Hazardous Materials, 186: 1462–1473, DOI: 10.1016/j.jhazmat.2010.12.032.
Song, X. L., Li, J. H., and Wang, J. T., 2009. Quercetin molecularly imprinted polymers: Preparation, recognition characteristics and properties as sorbent for solid-phase extraction. Talanta, 80: 694–702, DOI: 10.1016/j.talanta.2009.07.051.
Stubbings, G., Tarbin, J., Cooper, A., Sharman, M., Bigwood, T., and Robb, P., 2005. A multi-residue cation-exchange clean up procedure for basic drugs in produce of animal origin. Analytica Chimica Acta, 547: 262–268, DOI: 10.1016/j.aca.2005.05.001.
Stubbings, G., and Bigwood, T., 2009. The development and validation of a multiclass liquid chromatography tandem mass spectrometry (LC-MS/MS) procedure for the determination of veterinary drug residues in animal tissue using a QuEChERS (QUick, Easy, CHeap, Effective, Rugged and Safe) approach. Analytica Chimica Acta, 637: 68–78, DOI: 10.1016/j.aca. 2009.01.029.
U. S. Food Drug Administration, 2003. Guideline for industry: Mass spectrometry for confirmation of the identity of animal drug residues. Federal Register, 68: 25617–25618.
Villar-Pulido, M., Gilbert-López, B., García-Reyes, J. F., Martos, N. R., and Molina-Díaz, A., 2011. Multiclass detection and quantitation of antibiotics and veterinary drugs in shrimps by fast liquid chromatography time-of-flight mass spectrometry. Talanta, 85: 1419–1427, DOI: 10.1016/j.talanta.2011.06.036.
Wang, J. T., and Song, X. L., 2010. Synthesis, evaluation and adsorption behavior of naphthalene analog-imprinted polymer by immobilized template on modified silica gel in seawater. Chinese Journal of Analytical, 38: 1121–1126.
Wang, Y. X., Liu, Q. M., Rong, F., and Fu, D. G., 2012. Comparison of three cross-linking agents for imprinting diethylstilbestrol in solid-phase extraction. Polymers for Advanced Technologies, 23: 720–727, DOI: 10.1002/pat.1911.
Yan, S., Gao, Z., Fang, Y., Cheng, Y., Zhou, H., and Wang, H., 2007. Characterization and quality assessment of binding properties of malachite green molecularly imprinted polymers prepared by precipitation polymerization in acetonitrile. Dye sand Pigments, 74: 572–577, DOI: 10.1016/j.dyepig.2006.03.021
Zhou, J., and He, X. W., 1999. Study of the nature of recognition in molecularly imprinted polymer selective for 2-aminopyridine. Analytica Chimica Acta, 381: 85–91, PII: S0003-2670(98)00716-8.
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Lian, Z., Wang, J. Molecularly imprinted polymers for selective extraction of crystal violet from natural seawater coupled with high-performance liquid chromatographic determination. J. Ocean Univ. China 13, 236–242 (2014). https://doi.org/10.1007/s11802-014-2087-6
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DOI: https://doi.org/10.1007/s11802-014-2087-6