Abstract
Chiral effects for the inhibition of acetylcholinesterase by organophosphorus pesticides were investigated for insecticide malathion and malaoxon, which is a metabolic product of malathion in living organisms. Studies were carried out using a bienzymatic biosensor with immobilized acetylcholinesterase, choline oxidase, and with Prussian Blue used as a mediator. In both cases the R enantiomers accelerate acetylocholinesterase inhibition. The chiral effect in inhibition was much more pronounced in fast flow measurements than in batch measurements.
[1] A. Amine, H. Mohammadi, I. Bourais, G. Palleschi, Biosensors Bioelectron. 21, 1405 (2006) http://dx.doi.org/10.1016/j.bios.2005.07.01210.1016/j.bios.2005.07.012Search in Google Scholar PubMed
[2] S. Andresscu, J.-L. Marty, Biomol. Eng. 23, 1 (2006) http://dx.doi.org/10.1016/j.bioeng.2006.01.00110.1016/j.bioeng.2006.01.001Search in Google Scholar PubMed
[3] Y. Boublik, P. Saint-Aguet, A. Loguarre, M. Arnaud, F. Villatte, S. Estrada-Mondaca, D. Fournier, Protein. Eng. 15, 43 (2002) http://dx.doi.org/10.1093/protein/15.1.4310.1093/protein/15.1.43Search in Google Scholar PubMed
[4] H. Schulze, S.B. Muench, F. Villatte, R.D. Schmid, T.T. Bachmann, Anal. Chem. 77, 5823 (2005) http://dx.doi.org/10.1021/ac050383p10.1021/ac050383pSearch in Google Scholar PubMed
[5] A. GaŁęzowska, T. Sikora, G. Istamboulie, M. Trojanowicz, I. PoŁeć, G.S. Nunes, T. Noguer, J.-L. Marty, Sens. Mater. 20, 299 (2008) Search in Google Scholar
[6] G. Valdes-Ramirez, M. Cortina, M.T. Ramirez-Silva, J.-L. Marty, Anal. Bioanal. Chem. 392, 699 (2008) http://dx.doi.org/10.1007/s00216-008-2290-710.1007/s00216-008-2290-7Search in Google Scholar PubMed
[7] G. Jeanty, A. Wojciechowska, J.-L. Marty, M. Trojanowicz, Anal. Bioanal. Chem. 373, 691 (2002) http://dx.doi.org/10.1007/s00216-002-1336-510.1007/s00216-002-1336-5Search in Google Scholar PubMed
[8] D. Du, J. Wang, J.N. Smith, C. Timchalk, Y. Lin, Anal. Chem. 81, 9314 (2009) http://dx.doi.org/10.1021/ac901673a10.1021/ac901673aSearch in Google Scholar PubMed PubMed Central
[9] A.G. Hadd, S.C. Jacobson, J.M. Ramsey, Anal. Chem. 71, 5206 (1999) http://dx.doi.org/10.1021/ac990591f10.1021/ac990591fSearch in Google Scholar
[10] X. Shen, F. Liang, G. Zhang, D. Zhang, Analyst 137, 2119 (2012) http://dx.doi.org/10.1039/c2an35154d10.1039/c2an35154dSearch in Google Scholar PubMed
[11] S. Viswanathan, H. Radecka, J. Radecki, Biosensors Bioelectron. 24, 2772 (2009) http://dx.doi.org/10.1016/j.bios.2009.01.04410.1016/j.bios.2009.01.044Search in Google Scholar PubMed
[12] I. Ion, A.C. Ion, Mater. Sci. Eng. C, 32, 1001 (2012) http://dx.doi.org/10.1016/j.msec.2012.01.00910.1016/j.msec.2012.01.009Search in Google Scholar
[13] K. Wang, H.-N. Li, J. Wu, C. Ju, J.-J. Yan, Q. Liu, B. Qiu, Analyst 136, 3349 (2011) http://dx.doi.org/10.1039/c1an15227k10.1039/c1an15227kSearch in Google Scholar PubMed
[14] Z. Zheng, Y. Zhou, X. Li, S. Liu, Z. Tang, Biosensors Bioelectron. 26, 3081 (2011) http://dx.doi.org/10.1016/j.bios.2010.12.02110.1016/j.bios.2010.12.021Search in Google Scholar PubMed
[15] A.W. Garrison, Environ Sci Technol. 40, 16 (2006) http://dx.doi.org/10.1021/es063022f10.1021/es063022fSearch in Google Scholar PubMed
[16] I. J. Buerge, T. Poiger, M. D. Müller, H-R. Buser. Environ. Sci. Technol. 37, 2668 (2003) http://dx.doi.org/10.1021/es020241210.1021/es0202412Search in Google Scholar PubMed
[17] A. W. Garrison, P. Schmitt, D. Martens, A. Kettrup, Environ. Sci. Technol. 30, 2449 (1996) http://dx.doi.org/10.1021/es950552v10.1021/es950552vSearch in Google Scholar
[18] A. Miyazaki, T. Nakamura, M. Kawaradani, S. Marumo, J. Agric. Food. Chem. 36, 835 (1988) http://dx.doi.org/10.1021/jf00082a04210.1021/jf00082a042Search in Google Scholar
[19] Q. Zhou, C. Xu, Y. Zhang, W. Liu, J. Agric. Food Chem. 57, 1624 (2009) http://dx.doi.org/10.1021/jf803673e10.1021/jf803673eSearch in Google Scholar PubMed
[20] N. Kurihara, J. Miyamoto, G.D. Paulson, B. Zeeh, M.W. Skidmore, R.M. Hollingworth, H.A. Kuiper, Pure Appl Chem. 69, 2007 (1997) http://dx.doi.org/10.1351/pac19976909200710.1351/pac199769092007Search in Google Scholar
[21] J. Miyamoto, H. Kaneko, Y. Takamatsu, J. Biochem Toxicol. 1, 79 (1986) http://dx.doi.org/10.1002/jbt.257001020810.1002/jbt.2570010208Search in Google Scholar PubMed
[22] M.G. Nillos, G. Rodriguez-Fuentes, J. Gan, D. Schlenk, Environm. Toxicol. Chem. 26, 1949 (2007) http://dx.doi.org/10.1897/07-001R.110.1897/07-001R.1Search in Google Scholar
[23] K.D. Lin, F. Zang, S.S. Zhou, W. Lui, J. Gan, Z. Pan, Environm. Toxicol. Chem. 26, 2339 (2007) http://dx.doi.org/10.1897/07-255R.110.1897/07-255R.1Search in Google Scholar
[24] S. Zhou, K. Lin, H. Yang, L. Li, W. Liu, J. Li, Chem. Res. Toxicol. 20, 400 (2007) http://dx.doi.org/10.1021/tx600281n10.1021/tx600281nSearch in Google Scholar
[25] C.E. Berkman, D.A. Quinn, C.M. Thompson, Chem. Res. Toxicol. 6, 724 (1993) http://dx.doi.org/10.1021/tx00035a01910.1021/tx00035a019Search in Google Scholar
[26] O.P. Rodriguez, G.W. Muth, C.E. Berkman, K. Kim, C.M. Thompson, Bull. Environ. Contam. Toxicol. 58, 171 (1997) http://dx.doi.org/10.1007/s00128990031610.1007/s001289900316Search in Google Scholar
[27] F. Arduini, F. Ricci, C.S. Tuta, D. Moscone, A. Amine, G. Palleschi, Anal. Chim. Acta 580, 155 (2006) http://dx.doi.org/10.1016/j.aca.2006.07.05210.1016/j.aca.2006.07.052Search in Google Scholar
[28] A. Ivanov, G. Evtugyn, H. Budnikov, F. Ricci, D. Moscone, G. Palleschi, Anal. Bioanal. Chem. 377, 624 (2003) http://dx.doi.org/10.1007/s00216-003-2174-910.1007/s00216-003-2174-9Search in Google Scholar
[29] M. Wcislo, D. Compagnone, M. Trojanowicz, Bioelectrochemistry 71, 91 (2007) http://dx.doi.org/10.1016/j.bioelechem.2006.09.00110.1016/j.bioelechem.2006.09.001Search in Google Scholar
[30] I. PoŁeć, L. Cieślak, B. Śledziński, H. Ksycińska, Pestic. Sci. 53, 165 (1998) http://dx.doi.org/10.1002/(SICI)1096-9063(199806)53:2<165::AID-PS747>3.0.CO;2-010.1002/(SICI)1096-9063(199806)53:2<165::AID-PS747>3.0.CO;2-0Search in Google Scholar
[31] C.E. Berkman, C.M. Thompson, S.R. Perrin, Chem. Res. Toxicol. 6, 718 (1993 http://dx.doi.org/10.1021/tx00035a01810.1021/tx00035a018Search in Google Scholar
© 2012 Versita Warsaw
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.