Comparative Characteristics of Physical, Chemical, and Biochemical Methods for Determining Nitrofuran Metabolites in Food
Keywords:Nitrofurans, Sample preparation, Nitrofuran metabolites, Nitrofuran detection methods
Background. Nitrofurans belong to a class of synthetic antibiotics, which are widely used in various livestock sectors due to their high effectiveness in control over infectious diseases and as a growth activator. Nitrofurans are rapidly metabolized compounds, but the metabolites of these drugs are able to bind to protein structures and accumulate in the body of animals. Nitrofuran metabolites show carcinogenic properties, therefore it is necessary to control their content in food products of animal origin.
Objective. The aim of the paper is to summarise modern methods for nitrofurans analysis.
Methods. The modern methods of sample preparation of food products of animal origin for extracting nitrofuran metabolites and methods for detecting these analytes are systematized and analyzed.
Results. Modern analysis methods have a sufficient sensitivity level of nitrofurans determination in the form of final products – furaltadone and furazolidone metabolites. There are several methods of detection, among which are chromatographic methods and enzyme immunoassay.Conclusions. Analysis of the literature has shown that use of combined techniques combining selective removal of nitrofuran metabolites from the sample matrix and their quantification, allows screening and confirmatory test for the presence of nitrofurans in food and also allows detecting analytes at 1 mg/kg.
R. Draisci et al., “Determination of nitrofuran residues in avian eggs by liquid chromatography UV photodiode array detection and confirmation by liquid chromatography ionspray mass spectrometry”, J. Chromatogr. A, vol. 777, no. 1, pp. 201–211, 1997. doi: 10.1016/S0021-9673(97)00247-1
Commission Regulation (EC) No 1442/95 amending Annexes I, II, III and IV of Council Regulation (EEC) No 2377/90 laying down a Community procedure for the establishment of maximum residue limits of veterinary medicinal products in foodstuffs of animal origin, Official J. Europ. Commun., L143, pp. 26–30, Rep. (EC) No 1442/95, June 1995. Available: http://eulex.europa.eu/smartapi/cgi/sga_doc?smartapi!celexapi!prod!CELEXnumdoc&numdoc=31995R1442&model=guichett&lg=en
D.R. Mccalla, “Mutagenicity of nitrofuran derivatives: Review,” Environ. Molecular Mutagenesis, vol. 5, no. 5, pp. 745–765, 1983. doi: 10.1002/em.2860050512
L.H. Vroomen et al., “In vivo and in vitro metabolic studies of furazolidone: a risk evaluation”, Drug Met. Rev., vol. 22, no. 6-8, pp. 663–676, 1990. doi: 10.3109/03602539008991460
J.E.M. van Koten-Vermeulen, “Report of the 40th meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA)”, World Health Organisation, Geneva, 85, 1993.
J.F.M. Nouws and J. Laurensen, “Postmortal degradation of furazolidone and furaltadone in edible tissues of calves”, Vet. Quarterly, vol. 12, no. 1, pp. 56–59, 1990. doi: 10.1080/01652176.1990.9694243
R.J. McCracken et al., “Determination of furazolidone in porcine tissue using thermospray liquid chromatography-mass spectrometry and a study of the pharmacokinetics and stability of its residues”, Analyst, vol. 120, pp. 2347–2351, 1995.
A. Leitner et al., “Determination of the metabolites of nitrofuran antibiotics in animal tissue by high-performance liquid chromatographytandem mass spectrometry”, J. Chromatogr. A, vol. 939, no. 1-2, pp. 49–58, 2001. doi: 10.1016/S0021-9673(01)01331-0
K.M. Cooper and D.G. Kennedy, “Stability studies of the metabolites of nitrofuran antibiotics during storage and cooking”, Food Addit. Contam., vol. 24, no. 9, pp. 935–942, 2007. doi: 10.1080/02652030701317301
R.J. McCracken and D.G. Kennedy, “Detection, accumulation and distribution of nitrofuran residues in egg yolk, albumen and shell”, Food Addit. Contam., vol. 24, no. 1, pp. 26–33, 2007. doi: 10.1080/02652030600967214
E. Verdon et al., “Multi-residue monitoring for the simultaneous determination of five nitrofurans (furazolidone, furaltadone, nitrofurazone, nitrofurantoine, nifursol) in poultry muscle tissue through the detection of their five major metabolites (AOZ, AMOZ, SEM, AHD, DNSAH) by liquid chromatography coupled to electrospray tandem mass spectrometry – In-house validation in line with Commission Decision 657/2002/EC”, Anal. Chim. Acta, vol. 586, no. 1-2, pp. 336–347, 2007. doi: 10.1016/j.aca.2007.01.024
L. Rodziewicz and I. Zawadzka, “Determination of nitrofuran metabolite residues in animal tissues by LC-MS/MS method”, Roczniki Panstwowego Zakladu Higieny, vol. 58, no. 4, pp. 625–632, 2007.
K.M. Cooper et al., “Enzyme immunoassay for semicarbazide – the nitrofuran metabolite and food contaminant”, Anal. Chim. Acta., vol. 592, no. 1, pp. 64–71, 2007. doi: 10.1016/j.aca.2007.04.013
S. Szilagyi and B. de la Calle, “Development and validation of an analytical method for the determination of semicarbazide in fresh egg and in egg powder based on the use of liquid chromatography tandem mass spectrometry”, Anal. Chim. Acta, vol. 572, no. 1, pp. 113–120, 2006. doi: 10.1016/j.aca.2006.05.012
M. Vass et al., “In-house validation of an ELISA method for screening of semicarbazide in eggs”, Food Addit. Contam. Part A Chem. Anal. Control. Expo Risk Assess, vol. 25, no. 8, pp. 930–936, 2008. doi: 10.1080/02652030701883203
P.S. Chu and M.I. Lopez, “Liquid chromatographytandem mass spectrometry for the determination of protein-bound residues in shrimp dosed with nitrofurans”, J. Agricult. Food Chem., vol. 53, no. 23, pp. 8934–8939, 2005. doi: 10.1021/jf051615o
K.M. Cooper et al., “Detection of 3-amino-2-oxazolidinone (AOZ), a tissuebound metabolite of the nitrofuran furazolido- ne, in prawn tissue by enzyme immunoassay”, Food. Addit. Contam., vol. 21, no. 9, pp. 841–848, 2004. doi: 10.1080/02652030412331272476
A. Roychowdhury et al., “Emergence of tetracyclineresistant Vibrio cholerae O1 serotype Inaba, in Kolkata, India”, Jpn J. Infec. Dis., vol. 61, no. 2, pp. 128–129, 2008.
A. Conneely et al., “Use of solid phase extraction for the isolation and clean-up of a derivatised furazolidone metabolite from animal tissues”, Analyst, vol. 127, no. 6, pp. 705–709, 2002.
R.J. McCracken et al., “Evaluation of the residues of furazolidone and its metabolite, 3-amino-2-oxazolidinone (AOZ) in eggs”, Food Addit. Contam., vol. 18, no. 11, pp. 954–959, 2001. doi: 10.1080/02652030110050375
R.J. McCracken and D.G. Kennedy, “Determination of the furazolidone metabolite, 3-amino-2-oxazolidinone, in porcine tissues using liquid chromatography thermospray mass spectrometry and the occurrence of residues in pigs produced in Northern Ireland”, J. Chromatogr. B: Biomed. Sci. Appl., vol. 691, no. 1, pp. 87–94, 1997.
R.J. McCracken and D.G. Kennedy, “The bioavailability of residues of the furazolidone metabolite 3-amino- 2-oxazolidinone in porcine tissues and the effect of cooking upon residue concentrations”, Food Addit. Contam., vol. 14, no. 5, pp. 507–513, 1997. doi: 10.1080/02652039709374558
E. Horne et al., “Analysis of protein-bound metabolites of furazolidone and furaltadone in pig liver by high-performance liquid chromatography and liquid chromatography mass spectrometry”, Analyst, vol. 121, no. 10, pp. 1463–1468, 1996.
K.M. Cooper and D.G. Kennedy, “Nitrofuran antibiotic metabolites detected at parts per million concentrations in retina of pigs – a new matrix for enhanced monitoring of nitrofuran abuse”, Analyst, vol. 130, no. 4, pp. 466–468, 2005. doi: 10.1039/B418374F
C. Bock et al., “Matrix-comprehensive in-house validation and robustness check of a confirmatory method for the determination of four nitrofuran metabolites in poultry muscle and shrimp by LC-MS/MS”, J. Chromatogr. B, vol. 856, no. 1-2, pp. 178–189, 2007. doi: 10.1016/j.jchromb.2007.05.044
T.G. Diaz et al., “Determination of nitrofurantoin, furazolidone and furaltadone in milk by high-performance liquid chromatography with electrochemical detection”, J. Chromatogr. A, vol. 764, no. 2, pp. 243–248, 1997. doi: 10.1016/S0021-9673(96)00899-0
K.M. Cooper et al., “Production and characterisation of polyclonal antibodies to a derivative of 3-amino-2-oxazolidinone, a metabolite of the nitrofuran furazolidone”, Anal. Chim. Acta, vol. 520, no. 1-2, pp. 79–86, 2004. doi: 10.1016/j.aca.2004.05.074
I. Diblikova et al., “Monoclonal antibody-based ELISA for the quantification of nitrofuran metabolite 3-amino-2- oxazolidinone in tissues using a simplified sample preparation”, Anal. Chim. Acta, vol. 540, no. 2, pp. 285–292, 2005. doi: 10.1016/j.aca.2005.03.039
K.M. Cooper et al., “Residues of nitrofuran antibiotic parent compounds and metabolites in eyes of broiler chickens”, Food Addit. Contam. Part A: Chem. Anal. Control. Expo Risk Assess, vol. 25, no. 5, pp. 548–556, 2008. doi: 10.1080/02652030701586657
C. Bock et al., “Validation of a confirmatory method for the determination of residues of four nitrofurans in egg by liquid chromatography-tandem mass spectrometry with the software InterVal”, Anal. Chim. Acta, vol. 586, no. 1-2, pp. 348–358, 2007. doi: 10.1016/j.aca.2006.11.001
N.A. Botsoglou, “Determination of furazolidone in eggs by high-performance liquid-chromatography”, J. Agric. Food Chem., vol. 36, no. 6, pp. 1224–1227, 1988. doi: 10.1021/jf00084a024
J.K. Finzi et al., “Determination of nitrofuran metabolites in poultry muscle and eggs by liquid chromatography-tandem mass spectrometry”, J. Chromatogr B: Anal. Technol. Biomed. Life Sci., vol. 824, no. 1-2, pp. 30–35, 2005. doi: 10.1016/j.jchromb.2005.05.012
P. Mottier et al., “Quantitative determination of four nitrofuran metabolites in meat by isotope dilution liquid chromatography-electrospray ionisation-tandem mass spectrometry”, J. Chromatogr. A, vol. 1067, no. 1-2, pp. 85–91, 2005. doi: 10.1016/j.chroma.2004.08.160
A. Conneely et al., “Isolation of bound residues of nitrofuran drugs from tissue by solid-phase extraction with determination by liquid chromatography with UV and tandem mass spectrometric detection”, Anal. Chim. Acta, vol. 483, no. 1-2, pp. 91–98, 2003. doi: 10.1016/S0003-2670(02)01023-1
L. Rodziewicz, “Determination of nitrofuran metabolites in milk by liquid chromatography-electrospray ionisation tandem mass spectrometry”, J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., vol. 864, no. 1-2, pp. 156–160, 2008. doi: 10.1016/j.jchromb.2008.01.008
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