Synthesis and evaluation of molecularly imprinted polymers as sorbents of moniliformin

Moniliformin is a low molecular weight mycotoxin that has worldwide potential to contaminate cereal grains. Although several traditional methods have been developed to detect moniliformin, the lack of anti-moniliformin antibodies has created a need for materials that recognize moniliformin at the molecular level through a binding mechanism. To address this issue, the authors synthesized molecularly imprinted polymers that bind moniliformin. Imprinted and non-imprinted polymers were evaluated by equilibrium binding assays and moniliformin concentrations were measured by LC analysis using ultraviolet light detection. Successful polymers were imprinted with toxin analogues as the templates; non-imprinted polymers exhibited minimal binding in acetonitrile under the assay conditions. Selected imprinted polymers also bound moniliformin in ethanol, methanol and dimethyl formamide. Significant differences in moniliformin binding by the polymers were dependent on polymer composition, and these differences were highly dependent on the template used to imprint the polymer. Polymers were further evaluated as sorbents for molecularly imprinted solid-phase extraction (MISPE), and an imprinted polymer was used for preconcentration and clean-up of a moniliformin spiked corn extract.

[1]  R. Krska,et al.  Advances in the analysis of mycotoxins and its quality assurance , 2005, Food additives and contaminants.

[2]  P. Patel,et al.  Food analyses using molecularly imprinted polymers. , 2001, Journal of agricultural and food chemistry.

[3]  Zheng Liu,et al.  A computational and experimental investigation of the interaction between the template molecule and the functional monomer used in the molecularly imprinted polymer , 2005 .

[4]  R. Krska,et al.  Improving methods of analysis for mycotoxins: molecularly imprinted polymers for deoxynivalenol and zearalenone , 2003, Food additives and contaminants.

[5]  A. Visconti,et al.  Recent advances on the use of adsorbent materials for detoxification of Fusarium mycotoxins , 2005, Food additives and contaminants.

[6]  J. Miller,et al.  Analysis of wheat extracts for ochratoxin A by molecularly imprinted solid-phase extraction and pulsed elution , 2004, Analytical and bioanalytical chemistry.

[7]  Edward P. C. Lai,et al.  Interaction of ochratoxin A with molecularly imprinted polypyrrole film on surface plasmon resonance sensor , 2005 .

[8]  C. Baggiani,et al.  A molecular imprinted polymer with recognition properties towards the carcinogenic mycotoxin ochratoxin A , 2001, Bioseparation.

[9]  S. Chung,et al.  Enzyme-assisted extraction of moniliformin from extruded corn grits. , 2005, Journal of Agricultural and Food Chemistry.

[10]  Wolfgang Lindner,et al.  Towards ochratoxin A selective molecularly imprinted polymers for solid-phase extraction. , 2002, Journal of chromatography. A.

[11]  M. Sharman,et al.  A survey of the occurrence of the mycotoxin moniliformin in cereal samples from sources worldwide. , 1991, Food additives and contaminants.

[12]  J. Hofmeyr,et al.  Inhibition of pyruvate dehydrogenase complex by moniliformin. , 1986, The Biochemical journal.

[13]  Sarah C. Baxter,et al.  Application of the Freundlich adsorption isotherm in the characterization of molecularly imprinted polymers , 2001 .

[14]  Naisyin Wang,et al.  Development of a multi-tiered approach to the in vitro prescreening of clay-based enterosorbents , 2001 .

[15]  H. Seidel,et al.  Fusarial toxins and their role in animal diseases. , 2003, Veterinary journal.

[16]  Börje Sellergren,et al.  Molecularly imprinted polymers : man-made mimics of antibodies and their applications in analytical chemistry , 2001 .

[17]  M. Moreno-Bondi,et al.  Molecularly imprinted polymers with a streamlined mimic for zearalenone analysis. , 2006, Journal of chromatography. A.

[18]  C. Maragos Detection of moniliformin in maize using capillary zone electrophoresis. , 2004, Food additives and contaminants.

[19]  I. Nicholls,et al.  1H nuclear magnetic resonance study of the molecular imprinting of (-)-nicotine: template self-association, a molecular basis for cooperative ligand binding. , 2004, Journal of chromatography. A.

[20]  S. Bursian,et al.  Efficacy of a commercial mycotoxin binder in alleviating effects of ochratoxin A, fumonisin B1, moniliformin and zearalenone in adult mink. , 2004, Veterinary and human toxicology.

[21]  W. Marasas,et al.  Determination of the mycotoxin moniliformin in cultures of Fusarium subglutinans and in naturally contaminated maize by high-performance liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. , 1999, Journal of chromatography. A.

[22]  R. J. Cole,et al.  Structure and synthesis of moniliformin, a novel cyclobutane microbial toxin. , 1974, Journal of the American Chemical Society.

[23]  S. Baxter,et al.  Characterization of the heterogeneous binding site affinity distributions in molecularly imprinted polymers. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[24]  Sergey A. Piletsky,et al.  Recognition of ephedrine enantiomers by molecularly imprinted polymers designed using a computational approach , 2001 .

[25]  J. Startin,et al.  Derivatization of the Fusarium mycotoxin moniliformin for gas chromatography-mass spectrometry analysis , 1986 .

[26]  M. C. Blanco-López,et al.  Computational approach to the rational design of molecularly imprinted polymers for voltammetric sensing of homovanillic acid. , 2005, Analytical chemistry.

[27]  E. Da̧bek-Złotorzyńska,et al.  Molecularly-imprinted polypyrrole-modified stainless steel frits for selective solid phase preconcentration of ochratoxin A , 2005, Analytical and bioanalytical chemistry.

[28]  Naresh Magan,et al.  Effect of the solvent on recognition properties of molecularly imprinted polymer specific for ochratoxin A. , 2004, Biosensors & bioelectronics.

[29]  Wolfgang Lindner,et al.  Molecularly imprinted polymer-assisted sample clean-up of ochratoxin A from red wine: merits and limitations. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[30]  W. Lindner,et al.  Determination of the mycotoxin moniliformin in cereals by high-performance liquid chromatography and fluorescence detection , 1996 .

[31]  P. Cormack,et al.  Molecularly imprinted polymers: synthesis and characterisation. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[32]  K. Mosbach,et al.  Receptor binding mimetics: a novel molecularly imprinted polymer , 1995 .