Molecularly-Imprinted Materials for Potentiometric Transduction: Application to the Antibiotic Enrofloxacin

REFERENCES

• Amemiya , S. 2007 . Potentiometric ion-selective electrodes . In Handbook of Electochemistry , ed. C. G. Zoski . Amsterdam : Elsevier , chap. 7.
   Google Scholar
• Andersson , L. I. 2000 . Molecular imprinting for drug bioanalysis – A review on the application of imprinted polymers to solid-phase extraction and binding assay . J. Chromatogr. B 739 : 163 – 173 .
   PubMed Web of Science ®Google Scholar
• Ariffin , M. M. , E. I. Miller , P. A. G. Cormack , and R. A. Anderson . 2007 . Molecularly imprinted solid-phase extraction of diazepam and its metabolites from hair samples . Anal. Chem. 79 : 256 – 262 .
   PubMed Web of Science ®Google Scholar
• Bakker , E. , E. Malinowaska , R. D. Schiller , and M. E. Meyerhoff . 1994 . Anion-selective membrane electrodes based on metalloporphyrins – the influence of lipophilic anionic and cationic sites on potentiometric selectivity . Talanta 41 : 881 – 890 .
   PubMed Web of Science ®Google Scholar
• Bossi , A. , F. Bonini , A. P. F. Turner , and S. A. Piletsky . 2007 . Molecularly imprinted polymers for the recognition of proteins: The state of the art . Biosens. Bioelectron. 22 : 1131 – 1137 .
   PubMed Web of Science ®Google Scholar
• Buck , R. P. , and E. Lindner . 1994 . Recommendations for nomenclature of ion-selective electrodes . Pure Appl. Chem. 66 : 2527 – 2536 .
   Web of Science ®Google Scholar
• Bucknall , S. , J. Silverlight , N. Coldham , L. Thorne , and R. Jackman . 2003 . Antibodies to the quinolones and fluoroquinolones for the development of generic and specific immunoassays for detection of these residues in animal products . Food Addit. Contam. 20 : 221 – 228 .
   PubMed Web of Science ®Google Scholar
• Busi , E. , R. Basosi , F. Ponticelli , and M. Olivucci . 2004 . An innovative approach to the design of plastic antibodies: Molecular imprinting via a non-polar transition state analogue . J. Mol. Catal. A 217 : 31 – 36 .
   Web of Science ®Google Scholar
• Cabello , F. C. 2004 . Antibiotics and aquaculture in Chile: Implications for human and animal health . Rev. Med. Chil. 132 : 1001 – 1006 .
   PubMed Web of Science ®Google Scholar
• Cabello , F. C. 2006 . Heavy use of prophylactic antibiotics in aquaculture: A growing problem for human and animal health and for the environment . Environment. Microb. 8 : 1137 – 1144 .
   PubMed Web of Science ®Google Scholar
• Cosofret , V. V. , and R. P. Buck . 1993 . Recent advances in pharmaceutical analysis with potentiometric membrane sensors . Crit. Rev. Anal. Chem. 24 : 1 – 58 .
   Web of Science ®Google Scholar
• Crumplin , G. C. 1986. The mechanism of action of quinolones, in quinolones – their future in clinical practice. Int. Congr. Symp. Ser. R. Soc. Med. 104: 1–15.
   Google Scholar
• Dickert , F. L. , and O. Hayden . 1999 . Molecular imprinting in chemical sensing . Trends Anal. Chem. 18 : 192 – 199 .
   Web of Science ®Google Scholar
• Duan , J. , and Z. H. Yuan . 2001 . Development of an indirect competitive ELISA for ciprofloxacin residues in food animal edible tissues . J. Agric. Food Chem. 49 : 1087 – 1089 .
   PubMed Web of Science ®Google Scholar
• Dufresne , G. , A. Fouquet , D. Forsyth , and S. A. Tittlemier . 2007 . Multiresidue determination of quinolone and fluoroquinolone antibiotics in fish and shrimp by liquid chromatography/tandem mass spectrometry . J. AOAC Int. 90 : 604 – 312 .
   PubMed Web of Science ®Google Scholar
• El-Maali , N. A. 2004 . Voltammetric analysis of drugs . Bioelectrochemistry 64 : 99 – 107 .
   PubMed Web of Science ®Google Scholar
• European Economic Community (EEC). Council Regulation 2377/90 of 26 June 1990. Consolidated with previous amendments and published by 19 November 2005 .
   Google Scholar
• Faridbod , F. , M. R. Ganjali , R. Dinarvand , and P. Norouzi . 2008 . Developments in the field of conducting and non-conducting polymer based potentiometric membrane sensors for ions over the past decade . Sensors 8 : 2331 – 2412 .
   PubMed Web of Science ®Google Scholar
• Gräslund , S. , and B. E. Bengtsson . 2001 . Chemicals and biological products used in south-east Asian shrimp farming, and their potential impact on the environment – a review . The Sc. Tot. Environ. 93 – 131 .
   PubMed Web of Science ®Google Scholar
• Guan , G. , B. Liu , Z. Wang , and Z. Zhang . 2008 . Imprinting of molecular recognition sites on nanostructures and its applications in chemosensors . Sensors 8 : 8291 – 8320 .
   PubMed Web of Science ®Google Scholar
• Hatano , K. 2004 . Simultaneous determination of quinolones in foods by LC/MS/MS . J. Food Hyg. Soc. Jap. 45 : 239 – 244 .
   PubMed Web of Science ®Google Scholar
• Hernandez-Arteseros , J. A. , I. Boronat , R. Compano , and M. D. Prat . 2000 . Liquid chromatographic separation of fluoroquinolone antibacterials used as veterinary drugs . Chromatographia 52 : 295 – 300 .
   Web of Science ®Google Scholar
• Hernando , M. D. , M. Mezcua , J. M. Suarez-Barcena , and A. R. Fernandez-Alba . 2006 . Liquid chromatography with time-of-flight mass spectrometry for simultaneous determination of chemotherapeutant residues in salmon . Anal. Chim. Acta. 562 : 176 – 184 .
   Web of Science ®Google Scholar
• Hirayama , K. , Y. Sakai , K. Kameoka , K. Noda , and R. Naganawa . 2002 . Preparation of a sensor device with specific recognition sites for acetaldehyde by molecular imprinting technique . Sens. Actuators. B 86 : 20 – 25 .
   Web of Science ®Google Scholar
• Holtzapple , K. , A. Buckley , and H. Stanker . 1997 . Production and characterization of monoclonal antibodies against sarafloxacin and cross-reactivity studies of related fluoroquinolones . J Agric. Food. Chem. 45 : 1984 – 1990 .
   Web of Science ®Google Scholar
• Horie , M. , K. Saito , N. Nose , and H. Nakazawa . 1994 . Simultaneous determination of benofloxacin, danofloxacin, enrofloxacin and ofloxacin in chicken tissues by high-performance liquid-chromatography . J. Chromatogr. B 653 : 69 – 76 .
   PubMed Web of Science ®Google Scholar
• Horie , M. , K. Saito , N. Nose , and H. Nakazawa . 1995 . Simultaneous determination of 8 quinolone antibacterials in meat and fish by high-performance liquid-chromatography . J. Food Hyg. Soc. Jap. 36 : 62 – 67 .
   Google Scholar
• Hormazabal , V. , A. Rogstad , I. Steffenak , and M. Yndestad . 1991 . Rapid assay for monitoring residues of enrofloxacin and sarafloxacin in fish-tissues by high-performance liquid-chromatography . J. Liq. Chromatogr. 14 : 1605 – 1614 .
   Web of Science ®Google Scholar
• Hosoya , K. , Y. Shirasu , K. Kimata , and N. Tanaka . 1998 . Molecularly imprinted chiral stationary phase prepared with racemic template . Anal. Chem. 70 : 943 – 945 .
   PubMed Web of Science ®Google Scholar
• Huet , A. C. , C. Charlier , S. A. Tittlemier , G. Singh , S. Benrejeb , and P. Delahaut . 2006 . Simultaneous determination of (Fluoro)quinolone antibiotics in kidney, marine products, eggs, and muscle by enzyme-linked immunosorbent assay (ELISA) . J. Agric. Food Chem. 54 : 2822 – 2827 .
   PubMed Web of Science ®Google Scholar
• Hutchins , R. S. , and L. G. Bachas . 1995 . Nitrate-selective electrode developed by electrochemically mediated imprinting doping of polypyrrole . Anal. Chem. 67 : 1654 – 1660 .
   Web of Science ®Google Scholar
• Johnston , L. , L. Mackay , and M. Croft . 2002. Determination of quinolones and fluoroquinolones in fish tissue and seafood by high-performance liquid chromatography with electrospray ionisation tandem mass spectrometric detection. J. Chromatogr. A 982: 97–109.
   PubMed Web of Science ®Google Scholar
• Juan-Garcia , A. , G. Font , and Y. Pico . 2007 . Simultaneous determination of different classes of antibiotics in fish and livestock by CE-MS . Electrophoresis 28 : 4180 – 4191 .
   PubMed Web of Science ®Google Scholar
• Lima , J. L. , M. C. Montenegro , and M. G. Sales . 1996 . Construction and evaluation of PVC conventional and tubular tripelennamine-selective electrodes: Their application in pharmaceutical preparations . J. Pharm. Biomed. Anal. 14 : 931 – 938 .
   PubMed Web of Science ®Google Scholar
• Kamel , A. H. , S. A. A. Almeida , M. G. F. Sales , and F. T. C. Moreira . 2009 . Sulfadiazine-potentiometric sensors for flow and batch determinations of sulfadiazine in drugs and biological fluids . Anal. Sci. 25 : 365 – 371 .
   PubMed Web of Science ®Google Scholar
• Kamel , A. H. , F. T. C. Moreira , S. A. A. Almeida , and M. G. F. Sales . 2008 . Novel potentiometric sensors of molecular imprinted polymers for specific binding of chlormequat . Electroanalysis 20 : 194 – 202 .
   Web of Science ®Google Scholar
• Kato , M. , Y. Ihara , E. Nakata , M. Miyazawa , M. Sasaki , T. Kodaira , and H. Nakazawa . 2007 . Development of enrofloxacin ELISA using a monoclonal antibody tolerating an organic solvent with broad cross-reactivity to other new quinolones . Food Agric. Immunol. 18 : 179 – 187 .
   Web of Science ®Google Scholar
• Katz , A. , and M. E. Davis . 2000 . Molecular imprinting of bulk, microporous silica . Nature 403 : 286 – 289 .
   PubMed Web of Science ®Google Scholar
• Kisiel , A. , A. Michalska , and K. Maksymiuk . 2007 . Plastic reference electrodes and plastic potentiometric cells with dispersion cast poly(3,4-ethylenedioxythiophene) and poly(vinyl chloride) based membranes . Bioelectrochemistry 71 : 75 – 80 .
   PubMed Web of Science ®Google Scholar
• Kriz , O. , O. Ramstrom , and K. Mosbach . 1997 . Molecular imprinting – New possibilities for sensor technology . Anal. Chem. 69 : 345A – 349A .
   Web of Science ®Google Scholar
• Lanza , F. , and B. Sellergren . 2001 . The application of molecular imprinting technology to solid phase extraction . Chromatographia 53 : 599 – 611 .
   Web of Science ®Google Scholar
• Lavignac , N. , C. J. Allender , and K. R. Brain . 2004 . Current status of molecularly imprinted polymers as alternatives to antibodies in sorbent assays . Anal. Chim. Acta. 510 : 139 – 145 .
   Web of Science ®Google Scholar
• Lizondo , M. , M. Pons , M. Gallardo , and J. Estelrich . 1997 . Physicochemical properties of enrofloxacin . J. Pharm. Biomed. Anal. 15 : 1845 – 1849 .
   PubMed Web of Science ®Google Scholar
• Lucchetti , D. , L. Fabrizi , E. Guandalini , E. Podesta , L. Marvasi , A. Zaghini , and E. Coni . 2004 . Long depletion time of enrofloxacin in rainbow trout (Oncorhynchus mykiss) . Antimicrob. Agents Chemother. 48 : 3912 – 3917 .
   PubMed Web of Science ®Google Scholar
• Maki , T. , I. Hirono , H. Kondo , and T. Aoki . 2008 . Drug resistance mechanism of the fish-pathogenic bacterium Lactococcus garvieae . J. Fish Diseases 31 : 461 – 468 .
   PubMed Web of Science ®Google Scholar
• Manesiotis , P. , A. J. Hall , J. Courtois , K. Irgum , and B. Sellergren . 2005 . An artificial riboflavin receptor prepared by a template analogue imprinting strategy . Angew. Chem. 114 : 3970 – 3974 .
   Google Scholar
• Marx , S. , A. Zaltsman , A. I. Turyan , and D. Mandler . 2004 . Parathion sensor based on molecularly imprinted sol-gel films . Anal. Chem. 76 : 120 – 126 .
   Web of Science ®Google Scholar
• Mayes , A. G. , and M. Whitcombe . 2005 . Synthetic strategies for the generation of molecularly imprinted organic polymers . Adv. Drug Delivery Rev. 57 : 1742 – 1778 .
   PubMed Web of Science ®Google Scholar
• McCourt , J. , G. Bordin , and A. R. Rodriguez . 2003 . Development of a capillary zone electrophoresis-electrospray ionisation tandem mass spectrometry method for the analysis of fluoroquinolone antibiotics . J. Chromatogr. A 990 : 259 – 269 .
   PubMed Web of Science ®Google Scholar
• Nilsson , K. , J. Lindell , O. Norrlow , and B. Sellergren . 1994 . Imprinted polymers as antibody mimetics and new affinity gels for selective separations in capillary electrophoresis . J. Chromatogr. A 680 : 57 – 61 .
   Web of Science ®Google Scholar
• Park , S. K. , M. Kim , Y. S. Sho , S. Y. Chung , S. Hu , J. O. Lee , M. K. Hong , M. C. Kim , J. S. Kang , and O. H. Jhee . 2007. Microbiological and chemical detection of antibiotic residues in livestock and seafood products in the Korean market. Food Sci. Biotechn. 16: 868–872.
   Web of Science ®Google Scholar
• Pearson , M. , and V. Inglis . 1993 . A sensitive microbioassay for the detection of antibacterial agents in the aquatic environment . J. Fish Dis. 16 : 255 – 260 .
   Web of Science ®Google Scholar
• Peter , S. , L. Schweitz , and S. Nilsson . 2003 . Molecularly imprinted polymers in capillary electrochromatography: Recent developments and future trends . Electrophoresis 24 : 3892 – 3899 .
   PubMed Web of Science ®Google Scholar
• Qiao , F. X. , H. W. Sun , H. Y. Yan , and K. H. Row . 2006 . Molecularly imprinted polymers for solid phase extraction . Chromatographia 64 : 625 – 634 .
   Web of Science ®Google Scholar
• Ramos , M. , A. Aranda , E. Garcia , T. Reuvers , and H. Hooghuis . 2003 . Simple and sensitive determination of five quinolones in food by liquid chromatography with fluorescence detection . J. Chromatogr. B 789 : 373 – 381 .
   PubMed Web of Science ®Google Scholar
• Rimmer , S. 1998 . Synthesis of molecular imprinted polymer networks . Chromatographia 47 : 470 – 474 .
   Web of Science ®Google Scholar
• Roybal , J. E. , C. C. Walker , A. P. Pfenning , S. B. Turnipseed , J. M. Storey , S. A. Gonzales , and J. A. Hurlbut . 2002 . Concurrent determination of four fluoroquinolones in catfish, shrimp, and salmon by liquid chromatography with fluorescence detection . J. AOAC Int. 85 : 1293 – 1301 .
   PubMed Web of Science ®Google Scholar
• Scheer , M. 1987 . Studies of the antibacterial activity of Baytril . Vet. Med. Rev. 2 : 90 – 97 .
   Google Scholar
• Schneider , M. J. , A. M. Darwish , and D. W. Freeman . 2007 . Simultaneous multiresidue determination of tetracyclines and fluoroquinolones in catfish muscle using high performance liquid chromatography with fluorescence detection . Anal. Chim. Acta. 586 : 269 – 274 .
   PubMed Web of Science ®Google Scholar
• Schneider , M. J. , L. Vazquez-Moreno , M. D. Bermudez-Almada , R. B. Guardado , and M. Ortega-Nieblas . 2005 . Multiresidue determination of fluoroquinolones in shrimp by liquid chromatography-fluorescence-mass spectrometry . J. AOAC Int. 88 : 1160 – 1166 .
   PubMed Web of Science ®Google Scholar
• Sellergren , B. 1994 . Imprinted dispersion polymers – a new class of easily accessible affinity . J. Chromatogr. A 673 : 133 – 141 .
   Web of Science ®Google Scholar
• Telting-Diaz , M. , and E. Bakker . 2001 . Effect of lipophilic ion-exchanger leaching on the detection limit of carrier-based ion-selective electrodes . Anal. Chem. 73 : 5582 – 5589 .
   PubMed Web of Science ®Google Scholar
• Turnipseed , S. B. , J. E. Roybal , A. P. Fenning , and P. J. Kijak . 2003 . Use of ion-trap liquid chromatography-mass spectrometry to screen and confirm drug residues in aquacultured products . Anal. Chim. Acta 483 : 373 – 386 .
   Web of Science ®Google Scholar
• Turnipseed , S. B. , C. C. Walker , J. E. Roybal , A. P. Pfenning , and J. A. Hurlbut . 1998 . Confirmation of fluoroquinolones in catfish muscle by electrospray liquid chromatography mass spectrometry . J. AOAC Int. 81 : 554 – 562 .
   PubMed Web of Science ®Google Scholar
• Verdon , E. , P. Couedor , B. Roudaut , and P. Sanders . 2005 . Multiresidue method for simultaneous determination of ten quinolone antibacterial residues in multimatrix/multispecies animal tissues by liquid chromatography with fluorescence detection: Single laboratory validation study . J. AOAC Int. 88 : 179 – 1192 .
   Google Scholar
• Vlatakis , G. , L. I. Andersson , R. Miller , and K. Mosbach . 1993 . Drug assay using antibody mimics made by molecular imprinting . Nature 361 : 645 – 647 .
   PubMed Web of Science ®Google Scholar
• Wang , L. , X. P. Wu , and Z. H. Xie . 2005 . Determination of enrofloxacin and its metabolite ciprofloxacin by high performance capillary electrophoresis with end-column amperometric detection . J. Separation Sci. 28 : 1143 – 1148 .
   PubMed Web of Science ®Google Scholar
• Wulff , G. 2002 . Enzyme-like catalysis by molecularly imprinted polymers . Chem. Rev. 102 : 1 – 27 .
   PubMed Web of Science ®Google Scholar
• Xu , W. H. , X. B. Zhu , X. T. Wang , L. P. Deng , and G. Zhang . 2006 . Residues of enrofloxacin, furazolidone and their metabolites in Nile tilapia (Oreochromis niloticus) . Aquaculture 254 : 1 – 8 .
   Web of Science ®Google Scholar
• Ye , L. , and K. Mosbach . 2001 . Molecularly imprinted microspheres as antibody binding mimics . React. Funct. Polym. 48 : 149 – 157 .
   Web of Science ®Google Scholar