The establishment of a practical method for the determination of piperazine residues using accelerated solvent extraction and UHPLC-FLD
Main Article Content
Keywords
piperazine, ASE, derivatisation, UHPLC-FLD
Abstract
This article describes a reliable method for estimating piperazine residues in chicken tissues (muscle, kidney and liver) and pork via ultra-high-performance liquid chromatography (UHPLC) coupled with a fluorescence detector (FLD) using dansyl chloride (DNS-Cl) as the derivatisation reagent. After extraction by accelerated solvent extraction (ASE), the analyte was purified on a strong cation-exchange solid-phase extraction (SPE) column. Separation was achieved using an Acquity UPLC HSS T3 (2.1 mm × 100 mm, 1.8 μm) column with ultrapure water–acetonitrile (15:85, V/V) as the mobile phase. The results showed that when the concentration of piperazine was between the limit of quantitation (LOQ) and 200.0 μg/kg, the peak area of the derivative had a good linear relationship with the piperazine concentration, and the coefficients of determination (R2) were greater than or equal to 0.9991. When the spiked concentration of piperazine was equal to the LOQ, maximum residue limit (MRL) of 0.5, 1.0 and 2.0, the recoveries ranged from 79.64 to 99.77% and the relative standard deviations (RSDs) were 1.14–5.63%. The limits of detection (LODs) and LOQs were 0.50–1.20 and 1.80–3.50 μg/kg, respectively. The method was applied to the quantification of piperazine residues in commercial chicken tissues and pork from local supermarkets.
References
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Llasera, M.P. and García-Cicourel, A.R., 2017. On-line SPE chromatography with spectrophotometric diode array detection as a simple and advantageous choice for the selective trace analysis of benzo(a)anthracene degradation products from microalgae. Talanta 165: 584–592. https://doi.org/10.1016/j.talanta.2017.01.011
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Matuszewski, B.K. and Chavezeng, C.M., 2003. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Analytical Chemistry 75(13): 3019–3030. https://doi.org/10.1021/ac020361s
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Peek, H.W. and Landman, W.J.M., 2011. Coccidiosis in poultry: anticoccidial products, vaccines and other prevention strategies. Veterinary Quarterly 31(3): 143–161. https://doi.org/10.1080/01652176.2011.605247
Richter, B.E., Jones, B.A., Ezzell, J.L., Porter, N.L., Avdalovic, N. and Pohl, C.,1996. Accelerated solvent extraction: a technique for sample preparation. Analytical Chemistry 68(6): 1033–1039. https://doi.org/10.1021/ac9508199
Sakaguchi, Y., Kinumi, T. and Takatsu, A., 2016. Quantification of peptides using N-terminal isotope coding and C-terminal derivatization for sensitive analysis by micro liquid chromatography-tandem mass spectrometry. Journal of Mass Spectrometry 51: 1111–1119. https://doi.org/10.1002/jms.3845
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Standardization Administration of the People’s Republic of China, 2008. Water for analytical laboratory use-specification and test methods, Standards Press of China, Beijing. Available at: https://www.sac.gov.cn.
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U.S. Food and Drug Administration, 2001. Guidance for industry: bioanalytical method validation, Government Printing Office, Washington, DC. Available at: https://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/UCM070107.pdf.
U.S. Food and Drug Administration, 2014. CFR-Code of federal regulations title 21 part 556 tolerances for residue of new animal drugs in food, Government Printing Office, Rockville, MD. Available at: https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?CFRPart287=556&showFR=1.
Wada, M., Yamahara, K., Ikeda, R., Kikura-Hanajiri, R., Kuroda, N. and Nakashima, K., 2015. Simultaneous determination of N-benzylpiperazine and 1-(3-trifluoromethylphenyl) piperazine in rat plasma by HPLC-fluorescence detection and its application to monitoring of these drugs. biomedical chromatography 26: 21–25. https://doi.org/10.1002/bmc.1619
Wang, B., Pang, M., Xie, X., Xie, K., Zhang, Y., Cui, L., Zhao, X., Wang, Y., Shi, H., Guo, Y., Wang, R., Zhang, G., Dai, G. and Wang, J., 2017. Quantification of piperazine in chicken and pig tissues by gas chromatography-electron ionization tandem mass spectrometry employing pre-column derivatization with acetic anhydride. Journal of Chromatography A 1519: 9–18. https://doi.org/10.1016/j.chroma.2017.08.079
Wang, N., Su, M., Liang, S. and Sun, H., 2016. Investigation of six bioactive anthraquinones in slimming tea by accelerated solvent extraction and high performance capillary electrophoresis with diode-array detection. Food Chemistry 199: 1–7. https://doi.org/10.1016/j.foodchem.2015.11.083
Xie, K., Liu, Y., Sun, L., Pang, M., Xie, X., Gao, Q., Wang, B., Zhang, Y., Wang, R., Zhang, G., Dai, G. and Wang, J., 2016. Quantification of piperazine in chicken muscle by ultra-Performance liquid chromatography-electrospray ionization tandem mass spectrometry. Food Analytical Methods 1–9. https://doi.org/10.1007/s12161-016-0717-x
Anna, P.G.N., Tiwari, S., Tube, J., Vyas, V. and Qureshi, G., 2017. Ultrasound assisted-synthesis and biological evaluation of piperazinylprop-1-en-2-yloxy-2H-chromen-2-ones as cytotoxic agents. Drug Design and Discovery 14: 1195–1205. https://doi.org/10.2174/1570180814666170322154750
Brachet, A., Rudaz, S., Mateus, L., Christen, P. and Veuthsy, J.L., 2015. Optimisation of accelerated solvent extraction of cocaine and benzoylecgonine from coca leaves. Journal of Separation Science 24(10/11): 865–873. https://doi.org/10.1002/1615-9314(20011101)24:10/11
Brennan, K.A., Lake, B., Hely, L.S., Jones, K., Gittings, D., Colussi-mass, J., Fitzmaurice, P.S., Lea, R.A. and Schenk, S., 2007. N-benzylpiperazine has characteristics of a drug of abuse. Behavioural Pharmacology 18(8): 785–790. https://doi.org/10.1097/fbp.0b013e3282f18d8f
Ciaccio, L.L., Missan, S.R., Mcmullen, W.H. and Grenfell, T.C., 1957. Nonaqueous titration of 1,4-Disubstituted piperazines. Analytical Chemistry 29(11): 1670–1673. https://doi.org/10.1021/ac60131a032
Demirci, S., Hayal, T.B., kiratli, B., Sisli, H.B., Demirci, S., Sahin F. and Dogan, A., 2019. Design and synthesis of phenylpiperazine derivatives as potent anticancer agents for prostate cancer. Chemical Biology & Drug Design 94: 1–12. https://doi.org/10.1111/cbdd.13575
Dong, S., Yan, Z. and Yang, H. …, 2016. A sensitive precolumn derivatization method for determination of piperazine in vortioxetine hydrobromide using a C8 column and high-performance liquid chromatography-mass spectrometry. Analytical Sciences 32(12): 1333–1338. https://doi.org/10.2116/analsci.32.1333
European Union, 2002. Commission decision of 2002/657/EC implementing council directive 96/23/EC concerning the performance of analytical methods and the interpretation of results, Official Journal of the European Union, London. Available at: https://ec.europa.eu/health/files/eudralex/vol-5/reg_2010_37/reg_2010_37_en.pdf.
Glamkowski, E.J., StrupczewskiJ., Wolf, E. and Woodward, D.L., 1974. Antihypertensive activity of 1-dimethylphosphinylmethyl-4-arylpiperazines. Journal of Medicinal Chemistry 17: 1008–1009. https://doi.org/10.1021/jm00255a021
Gomes, S.V.F., Portugal, L.A., Anjos, J.P., Jesus, O.N., Oliveira, E.J., David, J.P. and David, J.M., 2017. Accelerated solvent extraction of phenolic compounds exploiting a box-behnken design and quantification of five flavonoids by HPLC-DAD in passiflora species. Microchemical Journal 132: 28–35. https://doi.org/10.1016/j.microc.2016.12.021
Hayat, F., Zia-ur, R. and Muhammad Haleem, K., 2017. Two new heteroleptic ruthenium (II) dithiocarbamates: synthesis, characterization, DFT calculation and DNA binding. Journal of Coordination Chemistry 70(2): 279–295. https://doi.org/10.1080/00958972.2016.1255328
Lalka, D. and Bardos, T.J., 2010. Reactions of 2,2-dimethylaziridine-type alkylating agents in biological systems I: colorimetric estimation and stability in physiological media. Journal of Pharmaceutical Sciences 62(8): 1294–1298. https://doi.org/10.1002/jps.2600620813
Lee, S., Casteel, D.A. and Fleckenstein, L., 1997. Specific gas chromatographic analysis of diethylcarbamazine in human plasma using solid-phase extraction. Journal of Chromatography B 704(1–2): 181–185. https://doi.org/10.1016/s0378-4347(97)00424-6
Lin, H., Tian, Y., Zhang, Z., Wu, L. and Chen, Y., 2010. Quantification of piperazine phosphate in human plasma by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry employing precolumn derivatization with dansyl chloride. Analytica Chimica Acta 664(1): 40–48. https://doi.org/10.1016/j.aca.2010.02.003
Llasera, M.P. and García-Cicourel, A.R., 2017. On-line SPE chromatography with spectrophotometric diode array detection as a simple and advantageous choice for the selective trace analysis of benzo(a)anthracene degradation products from microalgae. Talanta 165: 584–592. https://doi.org/10.1016/j.talanta.2017.01.011
Marchetti, M.L., Errecalde, J. and Mestorino, N., 2012. Effect of 1-(1-naphthylmethyl)-piperazine on antimicrobial agent susceptibility in multidrug-resistant isogenic and veterinary Escherichia coli field strains. Journal of Medical Microbiology 61: 786–792. https://doi.org/10.1099/jmm.0.040204-0
Matuszewski, B.K. and Chavezeng, C.M., 2003. Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Analytical Chemistry 75(13): 3019–3030. https://doi.org/10.1021/ac020361s
McClintic, C., Remick, D.M., Perterson, J.A. and Risley, D.S., 2003. Novel method for the determination of piperazine in pharmaceutical drug substances using hydrophilic interaction chromatography and evaporative light scattering detection. Journal of Liquid Chromatography & Related Technologies 26(18): 3093–3104. https://doi.org/10.1081/JLC-120025426
Ministry of Agriculture of the People’s Republic of China. 2002. Maximum residue limit of veterinary drugs in animal food Bulletin No. 235 (Appendix 4), Beijing. Available at: https://www.moa.gov.cn/.
Moawed, E.A., Abulkibash, A.B. and El-shahat, M.F., 2015. Synthesis of tannic acid azo polyurethane sorbent and its application for extraction and determination of atrazine and prometryn pesticides in foods and water samples. Environmental Nanotechnology, Monitoring & Management 3: 61–66. https://doi.org/10.1016/j.enmm.2015.02.001
Navaneeswari, R. and Reddy, P.R., 2012. Analytical method for piperazine in an active pharmaceutical ingredient using chemical derivatization and HPLC-UV. Journal of Chemical and Pharmaceutical Research 4(6): 2854–2859. https://doi.org/10.1080/10826071003608959
Nnaji, N.J.N., Ujam, O.T., Ibisi, N.E., Ani, J.U., Onuegbu, T.O. and Olasunkanmi, L.O., 2017. Morpholine and piperazine based carboxamide derivatives as corrosion inhibitors of mild steel in HCl medium. Journal of Molecular Liquids 230: 652–661. https://doi.org/10.1016/j.molliq.2017.01.075
Park, J.A., Zhang, D., Kim, S., Cho, S., Jeong, D., Kim, J., Shim, J., Abd el-aty, A.M. and Shin, H., 2016. Development of a high-performance liquid chromatography with fluorescence detection method for quantification of piperazine in animal products by using precolumn derivatization. Food Chemistry 196: 1331–1337. https://doi.org/10.1016/j.foodchem.2015.10.081
Peek, H.W. and Landman, W.J.M., 2011. Coccidiosis in poultry: anticoccidial products, vaccines and other prevention strategies. Veterinary Quarterly 31(3): 143–161. https://doi.org/10.1080/01652176.2011.605247
Richter, B.E., Jones, B.A., Ezzell, J.L., Porter, N.L., Avdalovic, N. and Pohl, C.,1996. Accelerated solvent extraction: a technique for sample preparation. Analytical Chemistry 68(6): 1033–1039. https://doi.org/10.1021/ac9508199
Sakaguchi, Y., Kinumi, T. and Takatsu, A., 2016. Quantification of peptides using N-terminal isotope coding and C-terminal derivatization for sensitive analysis by micro liquid chromatography-tandem mass spectrometry. Journal of Mass Spectrometry 51: 1111–1119. https://doi.org/10.1002/jms.3845
Silva, D.P.B., Florentino, I.F., Oliveira, L.P., Lino, R.C., Galdino, P.M., Menegatti, R. and Costa, E.A., 2015. Anti-nociceptive and anti-inflammatory activities of 4-[(1-phenyl-1H-pyrazol-4-yl) methyl] 1-piperazine carboxylic acid ethyl ester: a new piperazine derivative. Pharmacology Biochemistry and Behavior 137: 86–92. https://doi.org/10.1016/j.pbb.2015.08.008
Staack, R.F. and Maurer, H.H., 2003. Toxicological detection of the new designer drug 1-(4-methoxyphenyl) piperazine and its metabolites in urine and differentiation from an intake of structurally related medicaments using gas chromatography-mass spectrometry. Journal of Chromatography B 798(2): 333–342. https://doi.org/10.1016/j.jchromb.2003.10.004
Standardization Administration of the People’s Republic of China, 2008. Water for analytical laboratory use-specification and test methods, Standards Press of China, Beijing. Available at: https://www.sac.gov.cn.
The European Medicines Agency, 2010. Commission regulation (EU) No. 37/2010 of 22 December 2009 on pharmacologically active substances and their classification regarding maximum residue limits in foodstuffs of animal origin, Official Journal of the European Union, London. Available at: https://ec.europa.eu/health/files/eudralex/vol-5/reg_2010_37/reg_2010_37_en.pdf.
The Japan Food Chemical Research Foundation, 2015. Maximum residue limits (MRLs) list of agricultural chemicals in foods, National Printing Bureau, Tokyo. Available at: https://www.m5.ws001.squarestart.ne.jp/foundation/agrdtl.php?a_inq=53500.
U.S. Food and Drug Administration, 2001. Guidance for industry: bioanalytical method validation, Government Printing Office, Washington, DC. Available at: https://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/UCM070107.pdf.
U.S. Food and Drug Administration, 2014. CFR-Code of federal regulations title 21 part 556 tolerances for residue of new animal drugs in food, Government Printing Office, Rockville, MD. Available at: https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfCFR/CFRSearch.cfm?CFRPart287=556&showFR=1.
Wada, M., Yamahara, K., Ikeda, R., Kikura-Hanajiri, R., Kuroda, N. and Nakashima, K., 2015. Simultaneous determination of N-benzylpiperazine and 1-(3-trifluoromethylphenyl) piperazine in rat plasma by HPLC-fluorescence detection and its application to monitoring of these drugs. biomedical chromatography 26: 21–25. https://doi.org/10.1002/bmc.1619
Wang, B., Pang, M., Xie, X., Xie, K., Zhang, Y., Cui, L., Zhao, X., Wang, Y., Shi, H., Guo, Y., Wang, R., Zhang, G., Dai, G. and Wang, J., 2017. Quantification of piperazine in chicken and pig tissues by gas chromatography-electron ionization tandem mass spectrometry employing pre-column derivatization with acetic anhydride. Journal of Chromatography A 1519: 9–18. https://doi.org/10.1016/j.chroma.2017.08.079
Wang, N., Su, M., Liang, S. and Sun, H., 2016. Investigation of six bioactive anthraquinones in slimming tea by accelerated solvent extraction and high performance capillary electrophoresis with diode-array detection. Food Chemistry 199: 1–7. https://doi.org/10.1016/j.foodchem.2015.11.083
Xie, K., Liu, Y., Sun, L., Pang, M., Xie, X., Gao, Q., Wang, B., Zhang, Y., Wang, R., Zhang, G., Dai, G. and Wang, J., 2016. Quantification of piperazine in chicken muscle by ultra-Performance liquid chromatography-electrospray ionization tandem mass spectrometry. Food Analytical Methods 1–9. https://doi.org/10.1007/s12161-016-0717-x
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