Artificial Systems for Molecular Recognition of Mycotoxins

Nowadays, public awareness about synthetic chemicals in food is high, and consumers continue to express concern about the health risks linked to the deliberate addition of chemicals to food. On the contrary, the perception of the health risks posed by food contamination due to mycotoxins is less marked. However, although effects are often difficult to link with a particular food, it is now largely accepted in academic circles and public health bodies that food and feed contamination from mycotoxins is a severe public health problem that can deeply affect health not only after a single massive exposure but, more often, after continuous exposure to low doses, and that such exposure can be related to several chronic diseases, including some types of cancer and serious hormonal dysfunctions (Lewis and Fenwick 1991; De Vries et al. 2002). Thus, good analytical protocols based on efficient analytical processes - sensitive, selective, fast, inexpensive and suitable for sample mass screenings - are required by legislation, health authorities and companies operating in the food market. At present, commercially available rapid assays based on the use of immunoanalytical techniques are widely diffused, as these analytical techniques assure the feasibility of fast sample mass screenings in a more affordable fashion compared to the older thin layer chromatographic methods (van Egmond 2004). However, a sample which is positive to toxicant contamination should be validated by using more sophisticated analytical methods. These methods are usually based on instrumental separative techniques coupled with mass spectrometry detectors of varying complexity. They have the sensitivity required for contamination detection and quantification, but direct application of these techniques on food and feed samples can be rarely performed. In fact, contaminants are usually present in food at low concentration (ng–μg/kg) levels, dispersed in highly complex (thousand of different components) and morphologically structured matrices, with an elevated degree of point-to-point and sample-to-sample variability. Thus, such a type of matrix introduces severe disturbances in the analytical separation step. Moreover, very “dirty” samples show the noxious property to influence strongly the background ion current in a mass spectrometry detector, reducing its sensitivity (Hajslova and Zrostlikova 2003; Niessen 2003). In consequence, quantitative analysis can be performed only after extensive clean-up and preconcentration steps (Buldini et al. 2002; Careri et al. 2002; Pichon et al. 2002; Hennion and Pichon 2003). Thus, economical, rapid and selective clean-up methods based on “intelligent” materials are needed.

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

[2]  M. Hennion,et al.  Chapter 33 Immunosorbents in sample preparation , 2002 .

[3]  Loretta Ricci,et al.  Recent applications of sample preparation techniques in food analysis. , 2002, Journal of chromatography. A.

[4]  E. Lai,et al.  Determination of ochratoxin A in red wines by multiple pulsed elutions from molecularly imprinted polypyrrole , 2007 .

[5]  J. Simon,et al.  Interaction of Ochratoxin A with Human Serum Albumin. Preferential Binding of the Dianion and pH Effects , 2002 .

[6]  E. Lai,et al.  N-phenylacrylamide functional polymer with high affinity for ochratoxin A , 2004 .

[7]  E. Turiel,et al.  Molecular recognition in a propazine-imprinted polymer and its application to the determination of triazines in environmental samples. , 2001, Analytical chemistry.

[8]  F. Navarro-Villoslada,et al.  Zearalenone sensing with molecularly imprinted polymers and tailored fluorescent probes , 2007 .

[9]  Olof Ramström,et al.  Molecularly Imprinted Materials : Science and Technology , 2004 .

[10]  L. Anfossi,et al.  Affinity chromatography techniques based on the immobilisation of peptides exhibiting specific binding activity. , 2003, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[11]  Jitka Zrostlíková,et al.  Matrix effects in (ultra)trace analysis of pesticide residues in food and biotic matrices. , 2003, Journal of chromatography. A.

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

[13]  I. Wilson,et al.  Methodology for assessing the properties of molecular imprinted polymers for solid phase extraction , 1999 .

[14]  T. Sano,et al.  Polymer-based adsorption medium prepared using a fragment imprinting technique for homologues of chlorinated bisphenol A produced in the environment. , 2004, Journal of chromatography. A.

[15]  Laura Anfossi,et al.  A combinatorial approach to obtain affinity media with binding properties towards the aflatoxins , 2003, Analytical and bioanalytical chemistry.

[16]  J. Stewart Solid Phase Peptide Synthesis , 1984 .

[17]  J. Haginaka Selectivity of affinity media in solid-phase extraction of analytes , 2005 .

[18]  R. B. Merrifield Solid phase peptide synthesis. I. the synthesis of a tetrapeptide , 1963 .

[19]  Sergey A. Piletsky,et al.  Molecular Imprinting of Polymers , 2006 .

[20]  B. Sellergren,et al.  Analysis of nicotine and its oxidation products in nicotine chewing gum by a molecularly imprinted solid-phase extraction. , 1998, Analytical chemistry.

[21]  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.

[22]  Laura Anfossi,et al.  Chromatographic characterisation of an estrogen-binding affinity column containing tetrapeptides selected by a combinatorial-binding approach. , 2002, Journal of chromatography. A.

[23]  Kit S Lam,et al.  From combinatorial chemistry to cancer-targeting peptides. , 2007, Molecular pharmaceutics.

[24]  E. Lai,et al.  Molecularly imprinted polypyrrole modified carbon nanotubes on stainless steel frit for selective micro solid phase pre-concentration of ochratoxin A , 2006 .

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

[26]  M. Careri,et al.  Recent advances in the application of mass spectrometry in food-related analysis. , 2002, Journal of chromatography. A.

[27]  G. Theodoridis,et al.  Preparation of a molecularly imprinted polymer for the solid-phase extraction of scopolamine with hyoscyamine as a dummy template molecule. , 2003, Journal of chromatography. A.

[28]  Yun Shi,et al.  Selective solid-phase extraction of bisphenol A using molecularly imprinted polymers and its application to biological and environmental samples , 2006, Analytical and bioanalytical chemistry.

[29]  N. Chandra,et al.  Interaction of coumarin derivatives with human serum albumin: investigation by fluorescence spectroscopic technique and modeling studies. , 2001, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[30]  R. Beier,et al.  Natural Toxicants in Foods , 1992 .

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

[32]  A. Cepeda,et al.  Liquid chromatographic study of the interaction between aflatoxins and β-cyclodextrin , 1992 .

[33]  C. Baggiani,et al.  Solid phase extraction of food contaminants using molecular imprinted polymers. , 2007, Analytica chimica acta.

[34]  A. Rachkov,et al.  Towards molecularly imprinted polymers selective to peptides and proteins. The epitope approach. , 2001, Biochimica et biophysica acta.

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

[36]  C Cámara,et al.  Synthesis of a pH dependent covalent imprinted polymer able to recognize organotin species. , 2006, The Analyst.

[37]  Tingyu Li Peptide and peptidomimetic chiral selectors in liquid chromatography. , 2005, Journal of separation science.

[38]  B. Sellergren,et al.  Extraction of clenbuterol from calf urine using a molecularly imprinted polymer followed by quantitation by high-performance liquid chromatography with UV detection. , 2002, Journal of chromatography. A.

[39]  Hans P. van Egmond,et al.  Natural toxins: risks, regulations and the analytical situation in Europe , 2004 .

[40]  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.

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

[42]  C. Maragos,et al.  Synthesis and evaluation of molecularly imprinted polymers as sorbents of moniliformin , 2007, Food additives and contaminants.

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

[44]  E Anklam,et al.  Validation of analytical methods for determining mycotoxins in foodstuffs , 2002 .

[45]  Jeak Ling Ding,et al.  Antimicrobial peptides: Resistant‐proof antibiotics of the new millennium , 2004 .

[46]  E. Turiel,et al.  Clean-up of triazines in vegetable extracts by molecularly-imprinted solid-phase extraction using a propazine-imprinted polymer , 2003, Analytical and bioanalytical chemistry.

[47]  C. Creaser,et al.  Food contaminants: sources and surveillance. , 1991 .

[48]  D. Sherrington,et al.  Evaluation of methods aimed at complete removal of template from molecularly imprinted polymers. , 2001, The Analyst.

[49]  M. Moreno-Bondi,et al.  Molecularly imprinted polymers applied to the clean-up of zearalenone and α-zearalenol from cereal and swine feed sample extracts , 2006, Analytical and bioanalytical chemistry.

[50]  G. Bailey,et al.  Mechanisms of chlorophyllin anticarcinogenesis against aflatoxin B1: complex formation with the carcinogen. , 1995, Chemical research in toxicology.

[51]  C. Baggiani,et al.  Solid-phase extraction of ochratoxin A from wine based on a binding hexapeptide prepared by combinatorial synthesis. , 2007, Journal of chromatography. A.

[52]  Valérie Pichon,et al.  Immuno-based sample preparation for trace analysis. , 2003, Journal of chromatography. A.

[53]  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.

[54]  Jonathan W. DeVries,et al.  Mycotoxins and Food Safety , 2002, Advances in Experimental Medicine and Biology.

[55]  W. Niessen,et al.  Progress in liquid chromatography-mass spectrometry instrumentation and its impact on high-throughput screening. , 2003, Journal of chromatography. A.

[56]  M. Quaglia,et al.  Polymeric receptors for the recognition of folic acid and related compounds via substructure imprinting. , 2006, Analytical chemistry.