Design of acetylcholinesterases for biosensor applications

Biosensors and Bioelectronics

Volumn 18, Issue 2-3, 2002, Pages 201-209

  Schulze, Holger ^a   Vorlová, Sandra ^a   Villatte, Francois ^a   Bachmann, Till T ^a   Schmid, Rolf D ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Biosensor; Carbamates; Expression systems; Genetically engineered acetylcholinesterase; Organophosphates; Sensitivity

Indexed keywords

BIOASSAY; CATALYSIS; ENZYMES; INSECTICIDES; MUTAGENESIS; PHOSPHATES;

ORGANOPHOSPHATES;

BIOSENSORS;

ACETYLCHOLINESTERASE; CARBAMATE INSECTICIDE; ELEMENT; ENZYME VARIANT; INSECTICIDE; ORGANOPHOSPHATE INSECTICIDE; RECOMBINANT ENZYME;

AFFINITY CHROMATOGRAPHY; AMPEROMETRIC BIOSENSOR; ARTICLE; BIOSENSOR; BIOTECHNOLOGICAL PROCEDURES; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME PURIFICATION; ENZYME STRUCTURE; FLOW INJECTION ANALYSIS; GENE EXPRESSION SYSTEM; HUMAN; ION EXCHANGE CHROMATOGRAPHY; NONHUMAN; PIEZOELECTRICITY; POTENTIOMETRY; PROTEIN ENGINEERING; SITE DIRECTED MUTAGENESIS; X RAY ANALYSIS;

ACETYLCHOLINESTERASE; BIOSENSING TECHNIQUES; CHOLINESTERASE INHIBITORS; ENZYMES, IMMOBILIZED; EQUIPMENT DESIGN; GENE EXPRESSION REGULATION; INSECTICIDES; ORGANOPHOSPHORUS COMPOUNDS; PROTEIN ENGINEERING; RECOMBINANT PROTEINS;

EID: 0036523574     PISSN: 09565663     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0956-5663(02)00184-7     Document Type: Article

References (82)

1. Abad J.M., Pariente F., Hernandez L., Abruna H.D., Lorenzo E. Determination of organophosphorus and carbamate pesticides using piezoelectric biosensors. Analytical Chemistry. 70:1998;2848-2855.
2. Aldridge W.N. Some properties of specific acetylcholinesterase with particular reference to the mechanism of inhibition by diethyl p-nitrophenyl thiophosphate (E605) and analogues. Biochemical Journal. 46:1950;451-456.
3. Andreescu S., Magearu V., Lougarre A., Fournier D., Marty J.-L. Immobilization of enzymes on screen-printed sensors via an histidine tail. Application to the detection of pesticides using modified cholinesterase. Analytical Letters. 34:2001;529-540.
4. Ashani Y., Radic Z., Tsigelny I., Vellom D.C., Pickering N.A., Quinn D.M., Doctor B.P., Taylor P. Amino acid residues controlling reactivation of organophosphonyl conjugates of acetylcholinesterase by mono- and bisquaternary oximes. The Journal of Biological Chemistry. 270:1995;6370-6380.
5. Bachmann T.T., Leca B., Villatte F., Marty J.-L., Fournier D., Schmid R.D. Improved multianalyte detection of organophosphates and carbamates with disposable multiresidue biosensors using recombinant mutants of Drosophila acetylcholinesterase and artificial neural networks. Biosensors and Bioelectronics. 15:2000;193-201.
6. Bachmann T.T., Schmid R.D. A disposable, multielectrode biosensor for rapid simultaneous detection of the insecticides paraoxon and carbofuran at high resolution. Analytica Chimica Acta. 401:1999;95-103.
7. Bazelyansky M., Robey E., Kirsch J.F. Fractional diffusion-limited component of reactions catalyzed by acetylcholinesterase. Biochemistry. 25:1986;125-130.
8. Boublik Y., Saint-Aguet P., Lougarre A., Arnaud M., Villatte F., Estrada-Mondaca S., Fournier D. Acetylcholinesterase engineering for detection of insecticide residues. Protein Engineering. 15:2002;43-50.
9. Cagnini A., Palchetti I., Lionti I., Mascini M., Turner A.P.F. Disposable ruthenized screen-printed biosensors for pesticide monitoring. Sensors and Actuators B. 24-25:1995;85-89.
10. Chaabihi H., Fournier D., Fedon Y., Bossy J.P., Ravallec M., Devauchelle G., Cerutti M. Biochemical characterization of Drosophila melanogaster acetylcholinesterase expressed by recombinant baculoviruses. Biochemical and Biophysical Research Communications. 203:1994;734-742.
11. Cousin X., Bon S., Duval N., Massoulie J., Bon C. Cloning and expression of acetylcholinesterase from Bungarus fasciatus venom. A new type of cooh-terminal domain; involvement of a positively charged residue in the peripheral site. The Journal of Biological Chemistry. 271:1996;15099-15108.
12. Cousin X., Hotelier T., Lievin P., Toutant J.P., Chatonnet A. A cholinesterase genes server (ESTHER): a database of cholinesterase-related sequences for multiple alignments, phylogenetic relationships, mutations and structural data retrieval. Nucleic Acid Research. 24:1996;132-136.
13. Coussen F., Bonnerot C., Massoulie J. Stable expression of acetylcholinesterase and associated collagenic subunits in transfected RBL cell lines: production of GPI-anchored dimers and collagen-tailed forms. European Journal of Cell Biology. 67:1995;254-260.
14. Duval N., Bon S., Silman I., Sussman J.L., Massoulie J. Site-directed mutagenesis of active-site-related residues in Torpedo acetylcholinesterase. Presence of a glutamic acid in the catalytic triad. FEBS Letters. 309:1992;421-423.
15. Duval N., Massoulie J., Bon S. H and T subunits of acetylcholinesterase from Torpedo, expressed in COS cells, generate all types of globular forms. The Journal of Cell Biology. 118:1992;641-653.
16. Estrada-Mondaca S., Fournier D. Stabilisation of recombinant Drosophila acetylcholinesterase. Protein Expression and Purification. 12:1998;166.
17. Estrada-Mondaca S., Lougarre A., Fournier D. Drosophila acetylcholinesterase: effect of post-translational modifications on the production in the baculovirus system and substrate metabolization. Archives of Insect Biochemistry and Physiology. 38:1998;84-90.
18. Evtugyn G.A., Ivanov A.N., Gogol E.V., Marty J.-L., Budnikov H.C. Amperometric flow-injection biosensor for the determination of cholinesterase inhibitors. Analytica Chimica Acta. 385:1999;13-21.
19. Faerman C., Ripoll D., Bon S., Le Feuvre Y., Morel N., Massoulie J., Sussman J.L., Silman I. Site-directed mutants designed to test back-door hypotheses of acetylcholinesterase function. FEBS Letters. 386:1996;65-71.
20. Fischer M., Ittah A., Liefer I., Gorecki M. Expression and reconstitution of biologically active human acetylcholinesterase from Escherichia coli. Cellular and Molecular Neurobiology. 13:1993;25-38.
21. Gäberlein S., Knoll M., Spener F., Zaborosch C. Disposable potentiometric enzyme sensor for direct determination of organophosphorus insecticides. Analyst. 125:2000;2274-2279.
22. Ghindilis A.L., Morzunova H.C., Barmin A.V., Kurochkin I.N. Potentiometric biosensors for cholinesterase inhibitor analysis based on mediatorless bioelctrocatalysis. Biosensors and Bioelectronics. 11:1996;837-880.
23. Gibson K., Guilbault G.G. A potentiometric assay of cholinesterase. Analytica Chimica Acta. 76:1975;245-251.
24. Guilbault G.G., Das J. Immobilization of cholinesterase and urease. Analytical Biochemistry. 33:1970;341-355.
25. Guilbault G.G., Iwase A. Assay of cholinesterase in an electrode system with an immobilized substrate. Analytica Chimica Acta. 85:1976;295-300.
26. Guilbault G.G., Kramer D.N. Fluorometric system employing immobilized cholinesterase for assaying anticholinesterase compounds. Analytical Chemistry. 37:1965;1675-1680.
27. Guilbault G.G., Kuan S.S., Tully J., Hackney D. New procedure for rapid and sensitive detection of cholinesterase separated by polyacrylamide gel electrophoresis. Analytical Biochemistry. 36:1970;72-77.
28. Guilbault G.G., Sadar M.H., Kuan S.S., Casey D. Effect of pesticides on liver cholinesterases from rabbit, pigeon, chicken, sheep and pig. Analytica Chimica Acta. 51:1970;83-93.
29. Guilbault G.G., Sadar M.H., Kuan S.S., Casey D. Enzymatic methods of analysis. Trace analysis of various pesticides with insect cholinesterase. Analytica Chimica Acta. 52:1970;75-82.
30. Guilbault, G.G., Schmid, R.D., 1991. In: Turner, A.P.F., Yevdokimov, Y.M. (Eds.) Advances in Biosensors 1. Electrochemical, Piezoelectric and Fibre-Optic Biosensors, pp. 257-289.
31. Günther A., Bilitewski U. Characterisation of inhibitors of acetylcholinesterase by an automated amperometric flow-injection system. Analytica Chimica Acta. 300:1995;117-125.
32. Harel M., Kryger G., Rosenberry T.L., Mallender T.L., Fletcher R.J., Guss J.M., Silman I., Sussman J.L. Three-dimensional structure of Drosophila melanogaster acetylcholinesterase and of its complexes with two potent inhibitors. Protein Science. 9:2000;1063-1072.
33. Hart A.L., Collier W.A., Janssen D. The response of screen-printed enzyme electrodes containing cholinesterases to organophosphates in solution and from commercial formulations. Biosensors and Bioelectronics. 12:1997;645-654.
34. Heim J., Schmidt-Dannert C., Atomi H., Schmid R.D. Functional expression of a mammalian acetylcholinesterase in Pichia pastoris: comparison to acetylcholinesterase, expressed and reconstituted from Escherichia coli. Biochimica Biophysica Acta. 1396:1998;306-319.
35. Herzsprung P., Weil L., Quentin K. Bestimmung von phosphorpestiziden und insektiziden carbamaten mittels cholinesterasehemmung; mitt. 1: hemmwirkung von phosphorpestiziden und insektiziden carbamaten auf immobilisierte cholinesterase. Zeitschrift Wasser-Abwasser-Forschung. 22:1989;67-72.
36. Huang Z., Villarta-Snow R., Lubrano G.J., Guilbault G.G. Development of choline and acetylcholine pt microelectrodes. Analytical Biochemistry. 215:1993;31-37.
37. Hussein A.S., Chacon M.R., Smith A.M., Tosado-Acevedo R., Selkirk M.E. Cloning, expression, and properties of a nonneuronal secreted acetylcholinesterase from the parasitic nematode Nippostrongylus brasiliensis. The Journal of Biological Chemistry. 274:1999;9312-9319.
38. Hussein A.S., Smith A.M., Chacon M.R., Selkirk M.E. Determinants of substrate specificity of a second non-neuronal secreted acetylcholinesterase from the parasitic nematode Nippostrongylus brasiliensis. European Journal of Biochemistry. 267:2000;2276-2282.
39. Jeanty G., Marty J.-L. Detection of paraoxon by continuous flow system based enzyme sensor. Biosensors and Bioelectronics. 13:1997;213-218.
40. Kaplan D., Ordentlich A., Barak D., Ariel N., Kronman C., Velan B., Shafferman A. Does 'butyrylization' of acetylcholinesterase through substitution of the six divergent aromatic amino acids in the active center gorge generate an enzyme mimic of butyrylcholinesterase? Biochemistry. 40:2001;7433-7445.
41. Kindervater R., Künnecke W., Schmid R.D. Exchangeable immobilized enzyme reactor for enzyme inhibition tests in flow-injection analysis using a magnetic device. Determination of pesticides in drinking water. Analytica Chimica Acta. 234:1990;113-117.
42. Kronman C., Velan B., Gozes Y., Leitner M., Flashner Y., Lazar A., Marcus D., Sery T., Papier Y., Grosfeld H., et al. Production and secretion of high levels of recombinant human acetylcholinesterase in cultured cell lines: microheterogeneity of the catalytic subunit. Gene. 121:1992;295-304.
43. Kumaran S., Tran-Minh C. Determination of organophosphorous and carbamate insecticides by flow injection analysis. Analytical Biochemistry. 200:1992;187-194.
44. Legay C., Bon S., Massoulie J. Expression of a cDNA encoding the glycolipid-anchored form of rat acetylcholinesterase. FEBS Letters. 315:1993;163-166.
45. Martinez C.R., Gonzales R.E., Moran A.M.J., Mendez H.J. Sensitive method for the determination of organophosphorus pesticides in fruits and surface waters by high-performance liquid chromatography with ultraviolet detection. Journal of Chromatography. 607:1992;37-45.
46. Massoulie J., Bon S. Affinity chromatography of acetylcholinesterase. The importance of hydrophobic interactions. European Journal of Biochemistry. 68:1976;531-539.
47. Millard C.B., Broomfield C.A. Anticholinesterases: medical applications of neurochemical principles. Journal of Neurochemistry. 64:1995;1909-1918.
48. Mionetto N., Morel N., Massoulie J., Schmid R.D. Biochemical determination of insecticides via cholinesterases. 1. Acetylcholinesterase from rat brain: functional expression using a baculovirus system, and biochemical characterization. Biotechnology Techniques. 11:1997;805-812.
49. Montesinos T., Perez-Munguia S., Marty J.-L., Mitsubayashi K. Screen-printed electrodes, with genetically modified cholinesterase, for detection of pesticides in water-miscible organic solvent. Journal of Advanced Science. 12:2000;217-222.
50. Mor T.S., Sternfeld M., Soreq H., Arntzen C.J., Mason H.S. Expression of recombinant human acetylcholinesterase in transgenic tomato plants. Biotechnology and Bioengineering. 75:2001;259-266.
51. Morel N., Massoulie J. Expression and processing of vertebrate acetylcholinesterase in the yeast Pichia pastoris. Biochemical Journal. 328:1997;121-129.
52. Morel N., Massoulie J. Comparative expression of homologous proteins. A novel mode of transcriptional regulation by the coding sequence folding compatibility of chimeras. The Journal of Biological Chemistry. 275:2000;7304-73012.
53. Mulchandani A., Mulchandani P., Chen W. Amperometric thick-film strip electrodes for monitoring organophosphate nerve agents based on immobilized organophosphorus hydrolase. Analytical Chemistry. 71:1999;2246-2249.
54. Mulchandani P., Chen W., Mulchandani A. Flow injection amperometric enzyme biosensor for direct determination of organophosphate nerve agents. Environmental Science and Technology. 35:2001;2562-2565.
55. Mulchandani P., Mulchandani A., Kaneva I., Chen W. Biosensor for direct determination of organophosphate nerve agents. 1. Potentiometric enzyme electrode. Biosensors and Bioelectronics. 14:1999;77-85.
56. Ordentlich A., Barak D., Kronman C., Ariel N., Segall Y., Velan B., Shafferman A. The architecture of human acetylcholinesterase active center probed by interactions with selected organophosphate inhibitors. The Journal of Biological Chemistry. 271:1996;11953-11962.
57. Ordentlich A., Barak D., Kronman C., Ariel N., Segall Y., Velan B., Shafferman A. Functional characteristics of the oxyanion hole in human acetylcholinesterase. The Journal of Biological Chemistry. 273:1998;19509-19517.
58. Ordentlich A., Barak D., Kronman C., Flashner Y., Leitner M., Segall Y., Ariel N., Cohen S., Velan B., Shafferman A. Dissection of the human acetylcholinesterase active center determinants of substrate specificity. Identification of residues constituting the anionic site, the hydrophobic site, and the acyl pocket. The Journal of Biological Chemistry. 268:1993;17083-17095.
59. Palchetti I., Cagnini A., Carlo M.D., Coppi C., Mascini M., Turner A.P.F. Determination of pesticides in real samples using a disposable biosensor. Analytica Chimica Acta. 337:1997;315-321.
60. Pleiss J., Mionetto N., Schmid R.D. Protein engineering of rat brain acetylcholinesterase: a point mutation enhances sensitivity to pesticides. Protein Engineering. 10:(Suppl):1997;66.
61. Pleiss J., Mionetto N., Schmid R.D. Probing the acyl binding site of acetylcholinesterase by protein engineering. Journal of Molecular Catalyis B: Enzymatic. 6:1999;287-296.
62. Pylypiw H.M. Rapid gas chromatographic method for the multiresidue screening of fruits and vegetables for organochlorine and organophosphate pesticides. Journal of AOAC International. 76:1993;1369-1373.
63. Radic Z., Gibney G., Kawamoto S., MacPhee-Quigley K., Bongiorno C., Taylor P. Expression of recombinant acetylcholinesterase in a baculovirus system: kinetic properties of glutamate 199 mutants. Biochemistry. 31:1992;9760-9767.
64. Radic Z., Pickering N.A., Vellom D.C., Camp S., Taylor P. Three distinct domains in the cholinesterase molecule confer selectivity for acetyl- and butyrylcholinesterase inhibitors. Biochemistry. 32:1993;12074-12084.
65. Ralston J.S., Main A.R., Kilpatrick B.F., Chasson A.L. Use of procainamide gels in the purification of human and horse serum cholinesterase. Biochemical Journal. 211:1983;243-250.
66. Rosenberry T.L. Acetylcholinesterase. Advances in Enzymology and Related Areas of Molecular Biology. 43:1975;103-218.
67. Rosenberry T.L., Scoggin D.M. Structure of human erythrocyte acetylcholinesterase. The Journal of Biological Chemistry. 259:1984;5643-5652.
68. Saxena A., Redman A.M., Jiang X., Lockridge O., Doctor B.P. Differences in active site gorge dimension of cholinesterase revealed by binding of inhibitors to human butyrylcholinesterase. Biochemistry. 36:1997;14642-14651.
69. Schulze, H., Scherbaum, E., Anastassiades, M., Vorlová, S., Schmid, R.D. and Bachmann, T.T., Development, validation, and application of an acetylcholinesterase-biosensor test for the direct detection of insecticide residues in infant food. Biosensors and Bioelectronics, in press.
70. Shafferman A., Kronman C., Flashner Y., Leitner M., Grosfeld H., Ordentlich A., Gozes Y., Cohen S., Ariel N., Barak D., Harel M., Silman I., Sussman J.L., Velan B. Mutagenesis of human acetylcholinesterase. The Journal of Biological Chemistry. 267:1992;17640-17648.
71. Shafferman A., Velan B., Ordentlich A., Kronman C., Grosfeld H., Leitner M., Flashner Y., Cohen S., Barak D., Ariel N. Substrate inhibition of acetylcholinesterase: residues affecting signal transduction from the surface to the catalytic center. EMBO Journal. 11:1992;3561-3568.
72. Simon S., Massoulie J. Cloning and expression of acetylcholinesterase from Electrophorus. Splicing pattern of the 3′ exons in vivo and in transfected mammalian cells. The Journal of Biological Chemistry. 272:1997;33045-33055.
73. Skladal P., Mascini P. Sensitive detection of pesticides using amperometric sensors based on cobalt phthalocyanine-modified composite electrodes and immobilized cholinesterases. Biosensors and Bioelectronics. 7:1992;335-343.
74. Sussman J.L., Harel M., Frolow F., Oeffner C., Goldman A., Toker L., Silman I. Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholinesterase-binding protein. Science. 253:1991;872-879.
75. Van Sant, M.J., 1986. Applications of the Piezoelectric Crystal Detector in Environmental Analysis. PhD Thesis, University of New Orleans.
76. Velan B., Grosfeld H., Kronman C., Leitner M., Gozes Y., Lazar A., Flashner Y., Markus D., Cohen S., Shafferman A. The effect of elimination of intersubunit disulfide bonds on the activity, assembly, and secretion of recombinant human acetylcholinesterase. The Journal of Biological Chemistry. 266:1991;23977-23984.
77. Velan B., Kronman C., Grosfeld H., Leitner M., Gozes Y., Flashner Y., Sery T., Cohen S., Ben-Aziz R., Seidman S., et al. Recombinant human acetylcholinesterase is secreted from transiently transfected 293 cells as a soluble globular enzyme. Cellular and Molecular Neurobiology. 11:1991;143-156.
78. Vellom D.C., Radic Z., Li Y., Pickering N.A., Camp S., Taylor P. Amino acid residues controlling acetylcholinesterase and butyrylcholinesterase specificity. Biochemistry. 32:1993;12-17.
79. Villatte F., Bachmann T.T., Hussein A.S., Schmid R.D. Acetylcholinesterase assay for rapid expression screening in liquid and solid media. Biotechniques. 30:(81-84):2001;86.
80. Villatte F., Marcel V., Estrada-Mondaca S., Fournier D. Engineering sensitive acetylcholinesterase for detection of organophosphate and carbamate insecticides. Biosensors and Bioelectronics. 13:1998;157-164.
81. Villatte F., Ziliani P., Marcel V., Menozzi P., Fournier D. A high number of mutations in insect acetylcholinesterase may provide insecticide resistance. Pesticide Biochemistry and Physiology. 67:2000;95-102.
82. von Storp L.H., Guilbault G.G. A new assay for cholinesterase potentiometric determinations in flow streams. Analytica Chimica Acta. 62:1972;425-430.