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Molecularly Imprinted Solidphase Extraction Combined With Research Article Received: 6 December 2010 Revised: 4 March 2011 Accepted: 5 April 2011 Published online in Wiley Online Library: 14 June 2011 (wileyonlinelibrary.com) DOI 10.1002/jsfa.4471 Molecularly imprinted solid-phase extraction combined with high-performance liquid chromatography for analysis of trace olaquindox residues in chick feeds Jiaming Song,a,b Xuguang Qiao,a Haihua Chen,b Dongyan Zhao,a Yue Zhang,a and Zhixiang Xua∗ Abstract BACKGROUND: Olaquindox, one of the antimicrobial growth accelerants, is usually used as a feed additive in livestock production to improve feed efficiency. Due to health concerns over possible carcinogenic, mutagenic and photoallergenic effects of olaquindox on animals, the development of a simple, rapid and sensitive analytical method for determination of olaquindox is crucial and necessary. RESULTS: In this paper, a novel and hydrophilic functionalised material of olaquindox-imprinted polymer was synthesised in aqueous solution by a surface molecular imprinting in combination with a sol–gel process. This imprinted material was characterised by Fourier transform infrared, scanning electron microscopy, and static and kinetic adsorption experiments, and results showed that it had good recognition and selective ability, and fast adsorption-desorption dynamics for olaquindox. Applying the prepared material as sorbent, a method of molecularly imprinted solid-phase extraction (MISPE) for separation and analysis of olaquindox residues in feeds coupled with HPLC was presented. Under the selected MISPE condition, the detection limit (S/N = 3) for olaquindox was 68.0 ng L−1, the RSD for five replicate extractions of 50 µgL−1 olaquindox was 9.8%. The blank chick feed samples spiked with olaquindox at 0.0025 and 0.010 mg g−1 levels were extracted and determined by the developed method, with recoveries ranging from 90% to 96%. CONCLUSION: This method was applied for enrichment and analysis of olaquindox in animal feed samples with good accuracy and repeatability. This study will provide a sensitive and fast method for the monitoring of olaquindox residues in foods. c 2011 Society of Chemical Industry Keywords: molecular imprinting; olaquindox; molecularly imprinted solid-phase extraction; high performance liquid chromatography INTRODUCTION animal feeds and foods are required for the assurance of consumer Olaquindox (2-(N-2-hydroxyethylcarbamonyl)-3-methyl-quino- health. xaline-N1,N4-dioxide), as one of the most known members of Much effort has been devoted to the development of analytical quinoxaline-1,4-dioxides (Fig. 1) and the antimicrobial growth ac- methods for assessing the presence of this compound residues celerants, is usually used as feed additives in livestock production based on high-performance liquid chromatography (HPLC) with ultra-violet (UV) detection.1,6,7 This method can be reliable, to improve feed efficiency, control swine dysentery and bacte- while it has several potential drawbacks, including tedious rial enteritis in young swine to prevent diseases in animals and procedure, time consumption, and insufficient sensitivity. Gas increase the rate of weight gain.1 However, with the incorrect chromatography–mass spectrometry (GC-MS) and LC coupled to use of olaquindox, several problems have been exposed. Previ- MS/MS (LC-MS/MS) for the detection of the olaquindox in feeds ous study indicated that the excessive use of olaquindox in fish have been reported;8,9 they would be more sensitive but require farm may have adverse effects on the environment.2 Other study showed that olaquindox could destroy antioxidant defence sys- 3 tem of animals. Furthermore, olaquindox can accumulate in rats ∗ 4 Correspondence to: Zhixiang Xu, College of Food Science and Engineering, and mice and induce strong toxic reactions, such as mortality. In Shandong Agricultural University, Taian, China. E-mail: [email protected] the European Union, due to health concerns over possible carcino- genic, mutagenic and photoallergenic effects of the olaquindox a College of Food Science and Engineering, Shandong Agricultural University, on animals, its use was prohibited in animal feeds as a feed antibi- Taian, China 2378 5 otic from the beginning of 1998. For these reasons, accurate and b College of Food Science and Engineering, Qingdao Agricultural University, reliable analytical methods for the determination of olaquindox in Qingdao, China J Sci Food Agric 2011; 91: 2378–2385 www.soci.org c 2011 Society of Chemical Industry Determination of olaquindox in chick feeds www.soci.org O O O N CH3 N CH3 N N O O O Mequindox Quinocetone O N CONHCH2CH2OH N CH3 O Olaquindox Figure 1. Chemical structures of olaquindox, quinocetone and mequindox. relatively expensive instruments,10 and cannot be widely used for EXPERIMENTAL routine analytical purposes. Furthermore, the low concentration Chemicals of olaquindox combined with the complexity of the matrix in Olaquindox, mequindox and quinocetone were obtained from implicated samples make its detection difficult, even with the the Institute for the Control of Agrochemicals of Ministry of Agri- most sophisticated instrumentation. In order to control the use culture (Beijing, China). Silica gel (80–100 mesh, Qingdao Ocean of olaquindox, developing a simple and effective method for Chemical Co., Qingdao, China) was used as the support mate- the extraction and analysis of olaquindox residues in animals of rial. Tetraethoxysilicane (TEOS) and γ -aminopropyltriethoxysilane (APTES) were purchased from WD Silicone Co., Ltd (Wuhan, China). food origin is of particular significance and necessity. To achieve The HPLC grade methanol and acetonitrile were purchased from the necessary levels of sensitivity, an extraction and separation Tianjin yongda Chemical Co. (Tianjin, China). All the other reagents step is needed. Solid-phase extraction (SPE) is a well established were analytical grade. Doubly deionised water (DDW) was used technique and has been used to substitute for liquid–liquid throughout the study. extraction (LLE) in biological samples prior to analysis.11 However, most of the commercial solid phase sorbent is C bonded silica. 18 Apparatus and HPLC analysis It can also concentrate other compounds present in the matrix, For determination of the adsorption capacity of the new imprinted which may interfere with the analysis. The preparation of selective and non-imprinted polymer, a Cary 50-Bio UV spectrometer sorbent for SPE is crucial. (Mulgrave, Victoria, Australia) was used. A 20.0 kV on a SS-35 Among the approaches applied one of the most interesting scanning electron microscope (Shimadzu, Kytoto, Japan) and a and promising method is using molecular imprinting technology. US-501 horizontal shaker (Jintian, Beijing, China) were used in this The resulting molecularly imprinted polymers (MIPs), not only study. The Strata Scx C18 SPE column (200 mg/3 mL) was obtained possess high selectivity and specificity for template molecules, but from Phenomenex (Torrance, California, USA). also exhibit far greater physiochemical stability and applicability The HPLC system consisted of two LC-10ATVP pumps and a Shi- in harsh chemical media.12 The applications of MIPs have madzu SPD-10AVP ultraviolet detector (Shimadzu). All separations been reported in many fields, such as affinity separation,13 wereachievedonananalyticalreversed-phaseThermoC18 column × immunoassays, microreactors, and antibody binding mimics,14 (4.6 mm 250 mm, Agela Technology, Newark, Delaware, USA) at a mobile phase flow rate of 0.8 mL min−1. Class-vp software was catalysis,15 enzymes mimics,16,17 biomimetic sensors.18 Their use used to acquire and process spectral and chromatographic data. as sorbent material for SPE is the most interesting and important The mobile phase was methanol/water (85 : 15, v/v). The sample applications of MIPs.19–25 volume injected was 15 µL and detection was at 372 nm. The aim of this study was to synthesize a highly selective olaquindox molecularly imprinted material by surface molecular Preparation of molecularly imprinted polymers imprinting in combination with a sol–gel process technique, The method to activate the silica gel followed that of Han which can be used as SPE sorbent. A convenient and effective et al.25 The imprinted polymer was prepared as follows: 1.5 g analytical technique for monitoring olaquindox in chick feeds by of olaquindox was dissolved in 30 mL of DDW, and mixed with molecularly imprinted solid-phase extraction (MISPE) technique 6 mL of APTES stirring for 20 min, then 0.5 g activated silica gel in combination with HPLC system was established. The factors and 10 mL of TEOS were added. After stirring for 10 min, the affecting preconcentration and separation of the analytes were mixture was mixed with 4 mL of acetic acid (0.1 mol L−1)and ◦ discussed in detail, and the applicability of this method was then was incubated for 10 h at 50 C. After polymerisation was 2379 evaluated. complete, the product was filtered, washed with methanol and J Sci Food Agric 2011; 91: 2378–2385 c 2011 Society of Chemical Industry wileyonlinelibrary.com/jsfa www.soci.org Zhixiang Xu et al. O H OCH2CH3 N CONHCH CH OH 2 2 + N CHC2HCH2 Si OCH2CH3 H OCH2CH3 N CH3 + - BMIM PF6 O H2O O H OCH2CH3 + N CONHCH2CH2O- H N CH2CH2CH2 Si OCH2CH3 H OCH2CH3 N CH3 TEOS O HAC Extraction Imprinted cavity Figure 2. Preparation process of the molecularly imprinted sol–gel polymer of olaquindox. DDW sequentially to remove the unreacted reagents and template for 4 h at room temperature with a horizontal shaker and then sep- ◦ molecules (Fig. 2), and dried in a vacuum oven at 100 Cfor8h. arated centrifugally at 4320 × g for 20 min. The supernatants were The polymer was extracted with 50 mL of ethanol and 15 mL measured for the unextracted olaquindox by UV spectrometry at of 1.0 mol L−1 HCl under magnetic stirring for 4 h to remove 372 nm and the adsorption capacity (Q) was calculated. Uptake olaquindox. The product was isolated by filtration, washed with kinetics of the imprinted polymer for 100 mg L−1 olaquindox was ethanol, and then neutralised with 0.1 mol L−1 NaOH and washed evaluated.
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