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Molecularly imprinted polymers (MIPs) for nitrofurantoin (NFT) recognition addressing in parallel of two complementary functional groups were created using a noncovalent imprinting approach. Specific tailor-made functional monomers were synthesized: a diaminopyridine derivative as the receptor for the imide residue and three (thio)urea derivatives for the interaction with the nitro group of NFT. A significantly improved binding of NFT to the new MIPs was revealed from the imprinting factor, efficiency of binding, affinity constants and maximum binding number as compared to previously reported MIPs, which addressed either the imide or the nitro residue. Substances possessing only one functionality (either the imide group or nitro group) showed significantly weaker binding to the new imprinted polymers than NFT. However, the compounds lacking both functionalities binds extremely weak to all imprinted polymers. The new imprinted polymers were applied in a flow-through thermistor in organic solvent for the first time. The MIP-thermistor allows the detection of NFT down to a concentration of 5 μM in acetonitrile + 0.2% dimethyl sulfoxide (DMSO). The imprinting factor of 3.91 at 0.1 mM of NFT as obtained by thermistor measurements is well comparable to the value obtained by batch binding experiments., (© 2011 American Chemical Society)

Nitrofurans are used widely to treat animal diseases and were identified as the major compounds in many worldwide drug residue violations. To develop a rapid and convenient detection method to measure the residue of nitrofurantoin, we designed an immunogen and prepared a polyclonal antibody to develop an immunoassay in this study. The antibodies obtained were characterized by an indirect cELISA method and showed excellent specificity and sensitivity with IC50 of 3.2 ppb and no cross-reaction with most related species and compounds. Considering that nitrofurans often are used illegally to feed animals through drinking water, we measured the residue of nitrofurantoin in water spiked by the drug. The recovery rates are in the ranges of 88-103% for interassay and 90-103% for intra-assay. The CVs are in the ranges of 3.1-11.4% for interassay and 2.7-6.2% for intra-assay. The detection limit was determined to be 0.2 ppb. The immunoassay developed in this study is suitable to be used as a screening method to detect residues of nitrofurantoin in drinking water for animals.