Determination of Chlorpyrifos using enzymatic biosensors: A review
Keywords:
Cholinesterase, biosensor, pesticides, substrateAbstract
The need for monitoring organophosphate pesticides in food in a short time has led to research on the development of analytical tools capable of quantifying them simply, in situ, and at low cost. In this way, food with pesticide residues to concentration levels not allowed by normativity would be quickly discarded. In the food industry and especially in the production of milk for its mass consumption and constant turnover, it is required that the quality decision of the raw material is taken as soon as possible. The enzymatic biosensors based in cholinesterase have been developed for the analysis of organophosphorus pesticides in water, and there are reports that indicate their use in other arrays. To improve the sensitivity for quantification of pesticides using biosensors, enzyme immobilization techniques, materials and types of working electrodes have been studied.
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Schreinemachers, P., Tipraqsa, P. Agricultural pesticides and land use intensification in high, middle and low income countries. Food Policy, 37(6), 616–626. 2012.
Ferri, D., Gaviña, P., Costero, A. M., Parra, M., Vivancos, J.-L., Martínez-Máñez, R. Detection and discrimination of organophosphorus pesticides in water by using a colorimetric probe array. Sensors and Actuators B: Chemical, 202(2014), 727–731. 2014.
Wang, Y., Kruzik, P., Helsberg, A.,Helsberg, I., Rausch, W.-D. Pesticide poisoning in domestic animals and livestock in Austria: a 6 year’s retrospective study. Forensic Sci. Int. 169, 157–160. 2007.
Morales, C., Rodríguez, N., Restrepo, L. F., López, C. Relación entre residuos de clorpirifos en leche y sangre de vacas Holstein y niveles séricos de estradiol y tiroxina. Revista electrónica de Veterinaria, 11(1). 2010.
Loaiza, A., Jaramillo, J. A., León, F. Incidencia de factores sociales, económicos, culturales y técnicos en el uso de agroquímicos por pequeños productores del departamento de Antioquia (p. 174). 2000.
Rekha, K., Gouda, Thakur, Karanth, N.G. Ascorbate oxidase based amperometric biosensor for organophosphorous pesticide monitoring. Biosensors & Bioelectronics, 15(9-10), 499–502. 2000.
Vallecilla, C., Rodríguez, N., Restrepo, L. F., López, C. Relación entre residuos de clorpirifos en leche y sangre de vacas Holstein y niveles séricos de estradiol y tiroxina - Chlorpyrifos residues in milk and blood in Holstein cows and their relation to estradiol and thyroxin serum levels. Revista Electrónica de Veterinaria. REDVET, 11(1), 1–22. 2010.
Jiménez, C., León, D. Biosensores: Aplicaciones y perspectivas en el control y calidad de procesos y productos alimenticios. Revista de la facultad de química farmaceútica., 16(1), 144-154. 2009.
Rodríguez, D.C., Carvajal, S., Peñuela, G. Effect of chlorpyrifos on the inhibition of the enzyme acetylcholinesterase by cross-linking in watersupply samples and milk from dairy cattle. Talanta, 111, 1-7. 2013.
Borgmann, S., Schulte, A., Neugebauer, S., & Schuhmann, W. Amperometric Biosensors. En Advances in Electrochemical Science and Engineering. (págs. 1-84). Weinheim: WILEY-VCH Verlag GmbH & Co. KGaA, 2011.
Environmental Protection Agency. Human health risk an assessment. Chlorpyrifos. Obtenido de Environmental Protection Agency, Office of pesticide programs: http://www.epa.gov/scipoly/sap/meetings/2008/september/hed_ra.pdf [Consultado el 04 de noviembre de 2014].
Domínguez, J., Gossas, T., Villaverde, C., Danielson, H., & Sussman, F.. Experimental and ‘in silico’ analysis of the effect of pH on HIV-1 protease inhibitor affinity: Implications for the charge state of the protein ionogenic groups. Bioorganic & Medicinal Chemistry, 20, 4838–4847. 2012.
Arroyo, M. Inmovilización de enzimas. Fundamentos, métodos y aplicaciones Inmobilized. Ars Pharmaceutica, 39(2), 23–39. 1998.
Norouzi, P., Pirali-Hamedani, M., Ganjali, M.R., Faridbod, F.A. A novel acetyl cholinesterase biosensor based on chitosan–gold nanoparticles film for determination of monocrotophos using FFT continuous cyclic voltammetry, Int. J. Electrochem. Sci. 5, 1434–1446. 2010.
Di Tuoro, D., Portaccio, M., Lepore, M., Arduini, F., Moscone, D., Bencivenga, U., Mita, D. G. An acetylcholinesterase biosensor for determination of low concentrations of Paraoxon and Dichlorvos. New Biotechnology, 29(1), 132–8. 2011.
Andreescu, S., Marty, J.-L. Twenty years research in cholinesterase biosensors: from basic research to practical applications. Biomolecular Engineering, 23(1), 1–15. 2006.
Purves, D., Augustine, G.J., Fitzpatrick, D., Hall, W.C., LaMantia, A.S., McNamara, J.O., White, L.E. Neuroscience, fourth ed., Sinauer Associates, Sunderland, MA. 2008.
Krasinski, A., Radic, Z., Manetsch, R., Raushel, J., Taylor, P., Sharpless, K.B., Kolb, H.C. In situ selection of lead compounds by click chemistry: target-guided optimization of acetylcholinesterase inhibitors, J. Am. Chem. Soc. 127, 6686–6692. 2005.
Manetsch, R., Krasinski, A., Radic, Z., Raushel, J., Taylor, P., Sharpless, K.B., Kolb H.C. In situ click chemistry: enzyme inhibitors made to their own specifications, J. Am. Chem. Soc. 126, 12809–12818. 2004.
Lin, G., Lee, Y.R., Liu, Y.C., Wu, Y.G. Ortho effect for inhibition mechanisms of butyrylcholinesterase by o-substitute phenyl L-butyl carbamates and comparison with acetylcholinesterase, cholesterol esterase, and phenol, Chem. Res. Toxicol. 18, 1124–1131. 2005.
Hosea, N.A., Berman, H.A., Taylor, P. Specificity and orientation of trigonal carboxi esters and tetrahedral alkilphosphonyl esters in cholinesterases. Biochemistry 34, 11528–11536. 1995.
Pohanka, M. Musilek, K. Kuca, K. Progress of biosensors based on cholinesterase inhibition, Curr. Med. Chem. 16, 1790–1798. 2009.
Lin, Y.H., Lu, F., Wang, J., Disposable carbon nanotube modified screen- printed biosensor for amperometric detection of organophosphorus pesticides and nerve agents. Electroanalysis 16, 145– 149. 2004.
Cremisini, C., Di Sario, S., Mela, J., Pilloton, R., Palleschi, G., Evaluation of the use of free and immobilised acetylcholinesterase for paraoxon detection with an amperometric choline oxidase based biosensor. Anal. Chim. Acta 311, 273–280. 1995.
Marty, J.-L., Sode, K., Karube, I. Biosensor for detection of organophosphate and carbamate insecticides. Electroanalysis 4, 249–252. 1992.
Rouillon, R., Mionetto, N., Marty, J.-L., Acetylcholine biosensor invol- ving entrapment of two enzymes. Optimization of operational and storage conditions. Anal. Chim. Acta 268, 347–350. 1992.
Bernabei, M., Cremisini, C., Mascini, M., Palleschi, G. Determination of organophosphorus and carbamic pesticides with a choline and acetylcholine electrochemical biosensor. Anal. Lett. 24, 1317–1331. 1991.
Palleschi, G., Bernabei, M., Cremisini, C., Mascini, M. Determination of organophosphorus insecticides with a choline electrochemical biosensor. Sens. Actuators B 7, 513–517. 1992.
Kumaran, S., Morita, M., Application of a cholinesterase biosensor to screen for organophosphorus pesticides extracted from soil. Talanta 4, 649– 655. 1995.
Ghindilis, A.L., Morzunova, T.G., Barmin, A.V., Kurochin, I.N., Potentiometric biosensors for cholinesterase inhibitor analysis based on mediatorless bioelectrocatalysis. Biosens. Bioelectron. 11, 873–880. 1996.
Imato, T., Ishibashi, N., Potentiometric butyrylcholine sensor for organophosphate pesticides. Biosens. Bioelectron. 10, 435–441. 1995.
Fernando, J.F., Rogers, K.R., Anis, N.A., Valdes, J.J., Thompson, R.G., Eldefrawi, A.T., Eldefrawi, M.E., Rapid detection of anticholinesterase insecticides by a reusable light addressable potentiometric biosensor. J. Agric. Food Chem. 41, 511–516. 1993.
Nunes, G.S., Barcelo, D., Grabaric, B.S., Diaz-Cruz, J.M., Ribeiro, M.L., Evaluation of highly sensitive amperometric biosensor with low cholinesterase charge immobilized on a chemically modified carbon paste electrode for trace determination of carbamates in fruit, vegetable and water samples. Anal. Chim. Acta 399, 37–49.1999.
Hart, A.L., Collier, W.A., Janssen, D. The response of screen-printed electrodes containing cholinesterases to organo-phosphate in solution and from commercial formulation. Biosens. Bioelectron. 12, 645–654. 1997.
Scouten, W. H., Luong, J. H. T., Brown, R. S. Enzyme or protein immobilization techniques for applications in biosensor design. TIBTECH, 13, 178–185. 1995.
La Rosa, C., Pariente, F., Hernandez, L., Lorenzo, E. Determination of organophosphorus and carbamic pesticides with an acetylcholinesterase amperometric biosensor using 4-aminophenyl acetate as substrate. Anal. Chim. Acta 295, 237–282. 1994.
Andreescu, S. Barthelmebs, L. Barthelmebs, J.-L., Immobilisation of AChE on screen-printed electrodes: comparative study between three immobilization methods applications to the detection of organophosphorus insecticides, Anal. Chim. Acta 464, 171–180. 2002.
Bonnet, C., Andreescu, S., Marty, J.-L., Adsorption: an easy and efficient immobilisation of acetylcholinesterase on screen-printed electrodes. Anal. Chim. Acta 481, 209–211. 2003.
Andreescu, S., Noguer, T., Magearu, V., Marty, J.-L., Screen-printed electrode based on AChE for the detection of pesticides in presence of organic solvents. Talanta 57, 169–176. 2002.
Sotiropoulou, S. Chaniotakis, N.A. Tuning the sol–gel microenvironment for acetylcholinesterase encapsulation, Biomaterials. 26, 6771–6779. 2005.
Skladal, P. Biosensors based on cholinesterases for detection of pesti- cides. Food Technol. Biotechnol. 34, 43–49. 1996.
Skladal, P., Fiala, M., Krejci, J., Detection of pesticides in the environ- ment using biosensors based on cholinesterases. Intern. J. Environ. Anal. Chem. 65, 139–148. 1996.
Lee, H.S., Kim, Y.A., Chao, Y.A., Lee, Y.T., Oxidation of organopho- sphorus pesticides for the sensitive detection by a cholinesterase-based biosensor. Chemosphere 46, 571–576. 2002.
Li, Y.G., Zhou,Y.X., Feng, J.L., Jiang, Z.H., Ma, L.R., Immobilisation of enzyme on screen-printed electrode by exposure to glutaraldehyde vapour for the construction of amperometric acetylcholinesterase electrodes. Anal. Chim. Acta 382, 272–282, 1999.
Vakurov, A. Simpson, C.E. Daly, C.L. Gibson, T.D. Millner, P.A. Acetylcholinesterase based biosensor electrodes for organophosphate pesticide detection: I. Modification of carbon surface for immobilization of acetylcholinesterase, Biosens. Bioelectron. 20 1118–1125. 2004.
Upadhyay, S. Rao, G.R. Sharma, M.K. Bhattacharya, B.K . Rao, V.K. Vijayaraghavan, R. Immobilization of acetylcholinesterase–choline oxidase on a gold–platinum bimetallic nanoparticles modified glassy carbon electrode for the sensitive detection of organophosphate pesticides, carbamates, and nerve agents, Biosens. Bioelectron. 25 832–83. 2009.
Wink, T. Van Zuilen, S.J. Bult, A. Van Bennekom, W.P. Self-assembled monolayers for biosensors, Analyst 122 43R–50R. 1997.
Gooding, J.J. Hibbert, D.B. The application of alkanethiols self-assembled monolayers to enzyme electrodes, Trends Anal. Chem. 18, 525–532. 1999.
Andreescu, S., Fournier, D., Marty, J.-L., Development of highly sensitive sensor based on bio-engineered acetylcholinesterase immobilized by affinity method. Anal. Lett. 39, 1865–1885. 2003.
Martorell, D., Cespedes, F., Martinez-Fabregas, E., Alegret, S. Determination of organophosphorus and carbamate pesticides using a biosensor based on polyshable 7,7,8,8- tetracyanoquinodimethane-modified graphite-epoxy biocomposite. Anal. Chim. Acta 337, 305–313. 1997.
Skladal, P., Nunes, G.S., Yamanaka, H., Ribeiro, M.L. Detection of carbamate pesticides in vegetable samples using cholinesterase-based biosensors. Electroanalysis 9, 1083–1087. 1997.
Hartley, I.C., Hart, H.P., Amperometric measurement of organophosphate pesticides using a screen-printed disposable sensor and biosensor based on cobalt phtalocyanine. Analytical Proceedings Including Analytical Communications 31, 333–337. 1994.
Noguer,T., Leca, B., Jeanty, G., Marty, J.-L., Biosensors based on enzyme inhibition. Detection of organophosphorus and carbamate insecticides and dithiocarbamate fungicides. Field Anal. Chem. Technol. 3, 171–178. 1999.
Andreescu, D., Andreescu, S., Sadik, O.A., Newmaterials for biosensors, biochips and molecular bioelectronics. In: Gorton, L. (Ed.), Biosensors and Modern Biospecific Analytical Techniques. Elsevier, Amsterdam, pp. 285– 329. 2005.
Joshi, K.A., Tang, J., Haddon, R.,Wang, J., Chen,W.,Mulchaldani, A., A disposable biosensors for organophosphorus nerve agents based on carbon nanotubes modified thick film strip electrodes. Electroanalysis 17, 54–58. 2005.
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