Phenolic Biosensors

Bioelectrochemistry: Fundamentals, Experimental Techniques and Applications

Volumn , Issue , 2008, Pages 219-248

  Wollenberger, Ulla ^a   Lisdat, Fred ^b   Rose, Andreas ^a   Streffer, Katrin ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

^b TECHNICAL UNIVERSITY OF APPLIED SCIENCES WILDAU   (Germany)

Author keywords

Decomposition and polymerization; Enzyme based bioelectrochemical measurement; Folin Ciocalteau classical method; Phenol biosensor design; Phenol biosensor enzyme; Phenolic biosensors; QH GDH and CDH based biosensors and phenol index; QH GDH based sensors

Indexed keywords

EID: 81555204009     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470753842.ch6     Document Type: Chapter

References (192)

1. R. Koch and B. Wagner, Umweltchemikalien, VCH, Weinheim, 1989.
2. Z. Rappoport (ed.), The Chemistry of Phenols, John Wiley & Sons Ltd, Chichester, 2003.
3. M. Stob, Handbook of Natural Food Toxicants, CRC Press, London, 1983.
4. M. Castillo and D. Barceló, Analysis of industrial effluents to determine endocrine-disrupting chemicals, Trends Anal. Chem., 16, 574-583 (1997).
5. A. M. Soto, H. Justicia, J. W. Wray and C. Sonnenschein, p-Nonyl-phenol: an estrogenic xenobiotic released from 'modified' polystyrene, Environ Health Perspect, 92, 167-173 (1991).
6. T. Colborn, F. S. von Saal and A. M. Soto, Developmental effects of endrocrine-disruptin chemicals in wildlife and humans, Environ. Health Perspect., 101, 378-384 (1993).
7. K. Robards, P. D. Prenzler, G. Tucker, P. Swatsitang and W. Glover, Phenolic compounds and their role in oxidative processes in fruits, Food Chemistry, 66, 401-436 (1999).
8. J. E. O'Connel and P. F. Fox, Significance and applications of phenolic compounds in the production and quality of milk and dairy products: a review, Internat. Diary Journal, 11 (3) 103-120 (2001).
9. K. L. Tuck and P. J. Hayball, Major phenolic compounds in olive oil: metabolism and health effects, J. Nutritional Biochemistry, 13, 636-644 (2002).
10. P. Götz and H. G. Boman, Insect immunity, in Comprehensive Insect Physiology, G. A. Kerkut and L. I. Gilbert (eds.), Biochemistry and Pharmacology, Vol. 3, Pergamon Press, Oxford, pp. 453-485, 1985.
11. G. Prota, Melanins and Melanogenesis, Academic Press, London, 1992.
12. M. G. Peter, Die molekulare Architektur des Exoskeletts von Insekten, Chem. uns. Zeit, 27, 189-197 (1993).
13. D. Richardson, Water Analysis. Anal. Chem., 73, 2719-2734 (2001).
14. R. J. Robbins, Phenolic acids in foods: an overview of analytical methodology, J. Agric. Food Chem., 51, 2866-2887 (2003).
15. US EPA Methods for the Determination of Organic and Inorganic Compounds in Drinking Water, EPA-815-R-00-014 Vol. I., Office of Ground Water and Drinking Water, Technical Support Center, and the National Exposure Research Laboratory, Office of Research and Development, US EPA, Cincinnati, OH 45268, (2000).
16. F. Scheller and F. Schubert, Biosensors, Elsevier, Amsterdam, 1992.
17. M. Peter and U. Wollenberger, Phenol-oxidizing enzymes:mechanisms and applications in biosensors, in Frontiers in Biosensorics II, F.W. Scheller, F. Schubert and J. Fedrowitz (eds.), Birkhäuser Verlag, Basel, 1997.
18. K. Riedel, J. Hensel, S. Rothe, B. Neumann and F. Scheller, Microbial sensors for determination of aromatics and their chloro derivatives, Appl. Microbiol. Biotechnol., 502-506 (1993).
19. P. Skladal, Mushroom tyrosinase-modified carbon paste electrode as an amperometric biosensor for phenols, Coll. Czech. Chem. Comm., 56, 1427-1433 (1991).
20. J. Wang, N. Naser, H. S. Kwon and M. Y. Cho, Tissue bioelectrode for organic-phase enzymatic assays, Anal. Chim. Acta, 264, 7-12 (1992).
21. J. Wang and M. S. Lin, Mixed plant tissue-carbon paste bioelectrode, Anal. Chem., 60, 1545-1548 (1988).
22. Y. Chen and T. C. Tan, Selectivity enhancement of an immobilised apple powder enzymatic sensor for dopamine, Biosens. Bioelectr, 9, 401-410 (1994).
23. A. Navaratne, M. S. Lin and G. A. Rechnitz, Eggplantbased bioamperometric sensor for the detection of catechol, Anal. Chim. Acta, 237, 107 (1990).
24. F. Schubert, U. Wollenberger and F. Scheller, Plant tissuebased amperometric tyrosine electrode, Biotech. Lett., 5, 239-242 (1983).
25. S. Uchiyama, M. Tamata, Y. Tofuku and S. Suzuki, A catechol electrode based on spinach leaves, Anal. Chim. Acta, 208, 287-290 (1988).
26. S. Y. Seo, V. K. Sharma and N. Sharma, Myshroom tyrosinase: recent prospects, J. Agr. Food Chem., 51, 2837-2853 (2003).
27. A. Sánchez-Ferrer, J. N. Rodriguez-López, F. Garcia-Cánvas and F. Garcia-Carmona, Tyrosinase: a comprehensive review of its mechanism, Biochim. Biophys. Acta, 1247, 1-11 (1995).
28. V. Bernan, D. Filpula,W. Herber, M. Bibb and E. Katz, The nucleotide sequence of the tyrosinase gene from streptomyces antibioticus and characterisation of the gene product, Gene, 37, 101-110 (1985).
29. R. Z. Kazandijan and A. M. Klibanov, Regioselective oxidation of phenols catalysed by polyphenol oxidase in chlorophorm, J. Amer. Chem. Soc., 107, 5448-5450 (1985).
30. D. E. Wilcox, A. G. Porras, Y. T. Hwang et al., Substrate analogue binding to the coupled binuclear copper active site in tyrosinase, J. Amer. Chem. Soc., 107, 4015-4027 (1985).
31. J. N. Rodriguez-Lopez, J. Tudela, R. Varn, F. Garcia-Carmona and F. Garcia-Canvas, Analysis of a kinetic model for melanin biosynthesis pathway, J. Biol. Chem., 267, 3801-3810 (1992).
32. C. Gerdemann, C. Eicken and B. Krebs, The crystal structure of catechol oxidase: New insight into the function of type-3 copper protein, Acc. Chem. Res., 35, 183-191 (2002).
33. A. M. Mayer, Polyphenoloxidases in plants - recent progress, Phytochemistry, 26, 11-20 (1987).
34. A. M. Mayer and E. Harel, Polyphenoloxidases in plants, Phytochemistry, 18, 193-215 (1979).
35. F. Pelaez, M. J. Martinez and A. T. Martinez, Screening of 68 species of basidiomycetes for enzymes involved in lignin degradation, Mycol. Res., 99, 37-42 (1995).
36. S. O. Andersen, Sclerotization and tanning of the cuticle, in Comparative Insect Physiology, G. P. Kerkut and L. I. Gilbert (eds.), Biochem. and Pharmacol., Vol. 3, Pergamon Press, New York, pp. 59-74, 1985.
37. V. Ducros, A. M. Brzozowski, K. S. Wilson et al., Crystal structure of the type-2 Cu depleted laccase from Coprinus cinereus at 2.2 angstrom resolution, Nat. Struct. Biol., 5, 310-316 (1998).
38. E. I. Solomon, P. Chen, M. Metz, S. Lee and A. E. Palmer, Oxygen binding, activation and reduction to water by copper proteins, Ang. Chem. Int. Ed., 40, 4570-4590 (2001).
39. A. Messerschmidt and L. Huber, The blue oxidases, ascorbate oxidase, laccase and ceruloplasmin, Modelling and structural relationship, Eur. J. Biochem, 187, 341-352 (1990).
40. E. I. Solomon, M. J. Baldwin and M. D. Lowery, Electronic structures of active sites in copper proteins, Chem. Rev., 92, 521-542 (1992).
41. C. F. Thurston, The structure and function of fungal laccases, Microbiology, 140, 19-26 (1994).
42. A. I. Yaropolov, O. V. Skorobogatko, S. S. Vartanov and S. D. Varfolomeyev, Laccase-properties, catalytic mechanism and applicability, Appl. Biochem. Biotechnol., 49, 257-280 (1994).
43. A. Christensson, N. Dimcheva, E. E. Ferapontova et al., Direct electron transfer between ligninolytic redox enzymes and electrodes, Electroanal., 16, 1074-1092 (2004).
44. K. Piontek, M. Antorini and T. Choinowski, Crystal structure of a laccase from the fungus Trametes versicolor at 1.90-Angstrom resolution containing a full complement of coppers, J. Biol. Chem., 277, 37663-37669 (2002).
45. M. Antorini, I. Herpoel-Gimbert, T. Choinowski et al., Purification crystallisation and X-ray diffraction study of fully functional laccases from two ligninolytic fungi, Biochim. Biophys. Acta, 1594, 109-114 (2002).
46. L. E. Andreasson and B. Reinhammar, The mechanism of electron transfer in laccase catalyzed reactions, Biochim. Biophys. Acta, 558, 145-156 (1979).
47. N. K. Cenas and J. J. Kulys, Fermentativnuyi perenos electrona (russ.: Enzymatic electron transfer), Mokslas, Vilnius, 1988.
48. D. S. Yaver, F. Xu, E. J. Golightly et al., Purification, characterization, molecular cloning, and expression of two laccase genes from the white rot basidiomycete Trametes villosa, Appl. Environ. Microbiol., 62, 834-841 (1996).
49. J. Kulys, K. Kristopaites and A. Ziemys, Kinetics and thermodynamics of peroxidase and laccase-catalyzed oxidation of N-substituted phenoothiazines and phenoxazines, J. Biol. Inorg. Chem., 5, 333-340 (2000).
50. H. B. Dunford, Heme peroxidases, Wiley-VCH, New York, 1999.
51. H. Anni and T. Yonetani, Mechanism of action of peroxidases, in Metal Ions in Biological Systems, H. Siegel and A. Siegel (eds.), Marcel Dekker, New York, pp. 219-241, 1992.
52. J. Everse, K. E. Everse and M. B. Grisham (eds.), Peroxidases in Chemistry and Biology, Vol. 1 and 2, CRC Press, Boca Raton, 1991.
53. T. L. Poulos, Peroxidases, Current Opinion Biotech., 4, 484-489 (1993).
54. O. Ryan, M. R. Smyth and C. O'Fagain, Horseradish peroxidase: the analyst's friend, Essays in Biochem., 28, 129-146 (1994).
55. M. A. Ator and P. R. Ortiz de Montellano, Protein control of prosthetic heme reactivity. Reaction of substrates with the heme edge of horseradish peroxidase, J. Biol. Chem., 262, 1542-1551 (1987).
56. T. E. Barman (ed.), Enzyme Handbook, Vol. 1, Springer Verlag, Berlin, pp. 234-235, 1992.
57. P. Bielli and L. Calabrese, Structure to function relationships in ceruloplasmin: a 'moonlighting' protein, Cell Mol. Life Sci., 59, 1413-1427 (2002).
58. U. Wollenberger and B. Neumann, Quinoprotein glucose dehydrogenase modified carbon paste electrode for the detection of phenolic compounds, Electroanal., 9, 366-371 (1997).
59. A. F. Eremenko, A. Makower, W. Jin, P. Rüger and F. W. Scheller, Biosensor based on an enzyme modified electrode for highly-sensitive measurement of polyphenols, Biosens. Bioelectron., 10, 717-722 (1995).
60. A. Rose, D. Pfeiffer, F. W. Scheller and U. Wollenberger, Quinoprotein glucose dehydrogenase modified thick-film electrodes for the amperometric detection of phenolic compounds in flow injection analysis, Fres. J. Anal. Chem., 369, 145-152 (2001).
61. A. Lindgren, L. Stoica, T. Ruzgas, A. Ciucu and L. Gorton, Development of a cellobiose dehydrogenase modified electrode for amperometric detection of diphenols, Analyst, 124, 527-532 (1999).
62. C. Nistor, A. Rose, M. Farré et al., In-field monotoring of cleaning efficiency in wastewater treatment plants using two phenol-sensitive biosensors, Anal. Chim. Acta, 456, 3-17 (2002).
63. A. Oubrie, H. J. Rozeboom, K. H. Kalk et al., Structure and mechanism of soluble quinoprotein glucose dehydrogenase, EMBO J., 18, 5187-5194 (1999).
64. P. Dokter, J. Frank, J. A. Duine, Purification and characterisation of quinoprotein glucose dehydrogenase from Acinetobacter calcoaceticus l.m.d. 79.41., Biochem. J., 239, 163-167 (1986).
65. A. J. J. Olsthoorn and J. A. Duine, On the mechanism and specificity of soluble, quinoprotein glucose dehydrogenase in the oxidation of aldose sugars, Biochem., 37 (39), 13854-13861 (1998).
66. P. Dokter, J. T. Pronk, B. J. van Schie, J. P. van Dijken and J. A. Duine, The in vivo and in vitro substrate specificity of quinoprotein glucose dehydrogenase from Acinetobacter calcoaceticus l.m.d. 79.41, FEMS Microbiol. Lett., 43 (2), 195-200 (1987).
67. K. Matsushita, E. Shinagawa, O. Adachi and M. Ameyama, Quinoprotein D-glucose dehydrogenase in Actinobacter calcoaceticus LMD 79.41: purification and characterisation of the membrane-bound enzyme distinct from the soluble enzyme, Dordrecht, The Netherlands, in PQQ and Quinoproteins, Kluwer Academic Publishers, p. 122 1989.
68. J. A. Duine, J. J. Frank and J. K. van Zeeland, Glucose dehydrogenase from Acinetobacter calcoaceticus, FEBS Letters, 108 (2), 443-446 (1979).
69. A. V. Eremenko, A. Makower and F. W. Scheller, Measurement of nanomolar diphenols by substrate recycling coupled to a pH-sensitive electrode, Fres. J. Anal. Chem., 351, 729-731 (1995).
70. C. Anthony, The role of quinoproteins, in Bacterial Energy Transduction, Marcel Dekkerp, New York, p. 223, 1993.
71. D. Lehner, P. Zipper, G. Henriksson and G. Petterson, Small-angle X-ray scattering studies on cellobiose dehydrogenase from Phanerochaete chrysosporium, Biochim. Biophys. Acta, 1293 (1), 161-169 (1996).
72. B. M. Hallberg, T. Bergfors, K. Backbro, G. Pettersson, G. Henriksson and C. Divne, A new scaffold for binding haem in the cytochrome domain of the extracellular flavocytochrome cellobiose dehydrogenase, Structure, 8 (1), 79-88 (2000).
73. G. Henriksson, G. Johansson and G. J. Pettersson, A critical review of cellobiose dehydrogenases, J. Biotechnol., 78, 93-113 (2000).
74. M. Ameyama, E. Shinagawa, K. Matsushita and O. Adachi, D-Fructose dehydrogenase of Gluconobacter industrius:purification, characterization, and application to enzymatic microdetermination of D-fructose, J. Bacteriol., 145, 814-823 (1981).
75. C. G. Mowat, I. Beaudoin, R. C. E. Durley et al., Kinetic and crystallographic studies on the active site Arg289Lys mutant of flavocytochrome b2 (yeast L-lactate dehydrogenase), Biochem., 39, 3266-3275 (2000).
76. J. P. Roth and J. P. Klinman, Catalysis of electron transfer during activation of O2 by the flavoprotein glucose oxidase, PNAS, 100 (1), 62-67 (2003).
77. K. R. Frederick, J. Tung, R. S. Emerick et al., Glucose oxidase from Aspergillus niger. Cloning, gene sequence, secretion from Saccharomyces cerevisiae and kinetic analysis of a yeast-derived enzyme, J. Biol. Chem., 265, 3793-3802 (1990).
78. L. Macholan and L. Schanel, Enzyme electrode with immobilized polyphenol oxidase for determination of phenolic substrates, Coll. Czech. Chem. Commun., 42, 3667-3675 (1977).
79. D. Pfeiffer, U. Wollenberger, A. Makower, F. Scheller, L. Risinger and G. Johansson, Amperometric amino acid electrodes, Electroanal., 2, 517-523 (1990).
80. L. Campanella, T. Beone, M. P. Sammartino and M. Tomassetti, Determination of phenol in wastes and water using an enzyme sensor, Analyst, 118, 979-986 (1993).
81. J. Metzger, M. Reiss and W. Hartmeier, Amperometric phenol biosensor based on a thermostable phenol hydroxylase, Biosens. Bioelectr., 13, 1077-1082 (1998).
82. L. Macholan, Phenol-sensitive enzyme electrode with substrate cycling for quantification of certain inhibitory aromatic acids and thio compounds, Coll. Czech. Chem. Commun., 55, 2152 (1990).
83. F. Lisdat, U. Wollenberger, A. Makower, H. Hörtnagel, D. Pfeiffer and F. W. Scheller, Catecholamine detection using enzymatic amplification, Biosens. Bioelectr, 12, 1199-1211 (1997).
84. L. Campanella, G. Favero, M. Pastorino and M. Tomassetti, Monitoring the rancidification process in olive oils using biosensor operating in organic solvents, Biosens. Bioelectr, 14, 179-186 (1999).
85. L. Campanella, G. Favero, M. P. Sammartino and M. Tomassetti, Further development of catalase, tyrosinase and glucose oxidase based organic phase enzyme electrode response as a function of organic solvent properties, Talanta, 46 (4), 595-606 (1998).
86. Y. Hasebe, K. Yokobori, K. Fukasawa, T. Kogure and S. Uchiyama, Highly sensitive electrochemical determination of Escherichia coli density using tyrosinase-based chemically amplified biosensor, Anal. Chim. Acta, 357 (1-2), 51-54 (1997).
87. K. Streffer, E. Vijgenboom, A. W. J. W. Tepper et al., Determination of phenolic compounds using recombinant tyrosinase from streptomyces antibioticus, Anal. Chim. Acta, 427, 201 (2001).
88. A. Makower, A. V. Eremenko, K. Streffer, U. Wollenberger and F. W. Scheller, Tyrosinase-glucose dehydrogenase substrate-recycling biosensor: highly-sensitive measurement of phenolic compounds, J. Chem. Tech. Biotech., 65, 39-44 (1996).
89. Y. Hasebe, T. Hirano and S. Uchiyama, Determination of catecholamines and uric acid in biological fluids without pretreatment, using chemically amplified biosensors, Sensors and Actuators, B 24-25, 94-97 (1995).
90. A. L. Ghindilis, A. Makower, C. G. Bauer, F. F. Bier and F. Scheller, Picomolar determination of p-aminophenol and catecholamines based on recycling enzyme amplification, Anal. Chim. Acta, 304, 25-31 (1995).
91. J. Szeponik, B. Moller, D. Pfeiffer et al., Ultrasensitive bienzyme sensor for adrenaline, Biosens. Bioel., 12, 947-952 (1997).
92. U. Wollenberger, F. Schubert, D. Pfeiffer and F. Scheller, Enhancing biosensor performance using multienzyme systems, Trends Biotechnology., 11, 255-262 (1993).
93. F. F. Bier, E. Ehrentreich-Förster, F. W. Scheller et al., Ultrasensitive biosensors, Sens. Actuators, 33 (1-3), 5-12 (1996).
94. F. F. Bier, E. Ehrentreich-Förster, A. Makower and F. W. Scheller, An enzymatic amplification cycle for high sensitive immunoassays, Anal. Chim. Acta, 328, 27 (1996).
95. F. Scheller, U.Wollenberger, F. Schubert, D. Pfeiffer and V. A. Bogdanovskaya, Amplification and switching by enzymes in biosensors, GBF Monographs, 10, 39-49 (1987).
96. P. D. Hansen, J. Köhler and D. Nowak (eds.), Two European Technical Meetings, Biosensors for environmental monitoring, Report, European Commission, (1998).
97. C. G. Bauer, A. V. Eremenko, E. Ehrentreich-Förster et al., Zeptomole-detecting biosensor for alkaline phosphatase in an electrochemical immunoassay for 2,4-dichlorophenoxy acetic acid, Anal. Chem., 68 (15), 2453-2458 (1996).
98. A. L. Ghindilis, N. Michael and A. Makower, A new sensitive and simple method for detection of catecholamines from adrenal chromaffin cells, Pharmazie, 50, 599-600 (1995).
99. P. Skladal, Mushroom tyrosinase-modified carbon paste electrode as an amperometric biosensor for phenols, Coll. Czech. Chem. Commun., 56, 1427-1433 (1991).
100. F. Ortega, E. Dominguez, E. Burestedt et al., Phenol oxidase- based biosensors as selective detection units in chromatography for the determination of phenolic compounds, J. Chromatogr. A, 675, 65 (1994).
101. P. Önnerfjord, J. Emneus, G. Marko-Varga and L. Gorton, Tyrosinase graphite epoxy based composite electrodes for detection of phenols, Biosens. Bioelectr., 10, 607-619 (1995).
102. J. Wang, L. Fang and D. Lopez, Amperometric biosensor for phenols based on a tyrosinase-graphite-epoxy biocomposite, Analyst, 119, 455-458 (1994).
103. T.Wasa, K. Akimoto, T. Yao and S. Murao, Development of laccase membrane electrode by using carbon electrode impregnated with epoxy resin and ist response characteristics, Nippon Kagaku Koishi, 9, 1398-1403 (1984).
104. T. Ruzgas, J. Emneus, L. Gorton and G. Marko-Varga, The development of a peroxidase biosensor for monitoring phenol and related aromatic compounds, Anal. Chim. Acta, 311, 245-253 (1995).
105. J. Kulys and R. Schmid, A sensitive enzyme electrode for phenol monitoring, Anal. Lett., 23, 589-597 (1990).
106. A. Lindgren, J. Emneus, T. Ruzgas, L. Gorton and G. Marko-Varga, Amperometric detection of phenols using peroxidase-modified graphite electrodes, Anal. Chim. Acta, 347, 51-62 (1997).
107. F.-D. Munteanu, A. Ciucu, A. Lindgren et al., Bioelectrochemical Monitoring of Phenol and aromatic amines in flow injection using novel plant peroxidases, Anal. Chem., 70, 2596-2600 (1998).
108. C. Nistor, J. Emneus, L. Gorton and A. Ciucu, Improved stability and altered selectivity of tyrosinase based graphite electrodes for detection of phenolic compounds, Anal. Chim. Acta, 387 (3), 309-326 (1999).
109. R. S. Freire, N. Duran and L. T. Kubota, Development of a laccase based flow-injection electrochemical biosensor for determination of phenolic compounds and its application for monitoring remediation of Kraft E1 paper mill effluent, Anal. Chim. Acta, 463, 229-238 (2002).
110. A. Jarosz-Wilkolazka, T. Ruzgas and L. Gorton, Use of laccase-modified electrode for amperometric detection of plant flavonoids, Enzyme Microbial Technol., 35, 238-241 (2004).
111. F. Ortega, E. Dominguez, G. Jönsson-Pettersson and L. Gorton, Amperometric biosensor for the determination of phenolic compounds using a tyrosinase graphite electrode in a flow injection system, J. Biotech., 31, 289-300 (1993).
112. M. Lutz, E. Burestedt, J. Emneus, H. Linden, S. Gobhadi, L. Gorton and G. Marko-Varga, Effect of different additives on a tyrosinase based carbon paste electrode, Anal. Chim. Acta, 305, 8-17 (1995).
113. F. Lisdat, W. O. Ho, U. Wollenberger et al., Recycling systems based on screen-printed electrodes, Electroanal., 10, 803-807 (1998).
114. A. I. Yaropolov, A. N. Kharybin, J. Emneus, G. Marko-Varga and L. Gorton, Flow-injection analysis of phenols at a graphite electrode modified with co-immobilized laccase and tyrosinase, Anal. Chim. Acta, 308, 137-144 (1995).
115. L. Coche-Guerente, S. Cosnier and C. Innocent, Poly (amphiphilic pyrrole)-PPO electrodes for organic-phase enzymatic assay, Anal. Lett., 28, 1005-1016 (1995).
116. O. Adeyoju, E. I. Iwuoha, M. R. Smyth and D. Leech, Highperformance liquid chromatographic determination of phenols using a tyrosinase-based amperometric biosensor detection system, The Analyst, 121, (12), 1885-1889 (1996).
117. M. Hedenmo, A. Narvaez, E. Dominguez and I. Katakis, Improved mediated tyrosinase amperometric enzyme electrodes, J. of Electroanal. Chem., 425 (1-2), 1-11 (1997).
118. F. Daigle and D. Leech, Reagentless tyrosinase enzyme electrodes: effects of enzyme loading, electrolyte pH, ionic strength and temperature, Anal. Chem., 69, 4108-4112 (1997).
119. H. Kotte, B. Grundig, K. D. Vorlop, B. Strehlitz and U. Stottmeister, Methylphenazonium-modified enzyme sensor-based on polymer thick-film for subnanomolar detection of phenols, Anal. Chem., 67, 65-70 (1995).
120. M. Bonakdar, J. L. Vilechez and H. A. Mottola, Bioamperometric sensor for phenol based on carbon paste electrodes, J. Electroanal. Chem., 266, 47-55 (1989).
121. J. Parellada, A. Narvaez, M. A. Lopez et al., Amperometric immunosensors and enzyme electrodes for environmental applications, Anal. Chim. Acta, 362, 47-57 (1998).
122. J. Wang, Y. Lin, A. V. Eremenko, A. L. Ghindilis and I. N. Kurochkin, A laccase electrode for organic-phase enzymatic assays, Anal. Lett., 26, 197-207 (1993).
123. J. Wang, Y. Lin and Q. Chen, Organic-phase biosensors based on entrapment of enzymes within poly(ester-sulfonic acid) coatings, Electroanal., 5, 23-28 (1993).
124. J. Wang, N. Naser and U. Wollenberger, Use of tyrosinase for enzymatic elimination of acetaminophen interference in amperometric sensing, Anal. Chim. Acta, 285, 19-24 (1993).
125. Q. Deng and S. Dong, Construction of a tyrosinase-based biosensor in pure organic phase, Anal. Chem., 67, 1357-1360 (1995).
126. Q. Deng and S. Dong, The effect of substrate and solvent properties on the response of an organic phase tyrosinase electrode, J. of Electroanal. Chem., 435, 11-15 (1997).
127. J. Kulys and R. Vidziunaite, Amperometric biosensors based on recombinant laccases for phenol determination, Biosens. Bioelectr., 18, 319-325 (2003).
128. S. C. Chang, K. Rawson and C. J. McNeil, Disposable tyrosinase-peroxidase bi-enzyme sensor for amperometric detection of phenols, Biosens. Bioelectr., 17, 1015-1023 (2002).
129. K. Streffer, Highly sensitv measurements of substrates and inhibitors on the basis of tyrosinase sensors and recycling systems, Thesis, University of Potsdam, 2002.
130. G. F. Hall, D. A. Best and A. P. F. Turner, Amperometric enzyme electrode for the determination of phenols in chloroform, Enzyme Microb. Technol., 10, 543-546 (1988).
131. J. Yu and H. Ju, Pure organic phase phenol biosensor based on tyrosinase entrapped in a vapor deposited titania sol-gel membrane, Electroanal., 16 (16), 1305-1310 (2004).
132. M. J. Dennison, J. M. Hall and A. P. F. Turner, Gas-phase microbiosensor for monitoring phenol vapor at ppb levels, Anal. Chem., 67, 3922-3927 (1995).
133. A. Kaisheva, I. Iliev, R. Kazareva, S. Christov, J. Petkova, U. Wollenberger and F. Scheller, Enzyme/gas diffusion electrodes for determination of phenol, Sensors and Actuators, B33, 39-43 (1996).
134. P. Pantano and W. G. Kuhr, Enzyme-modified microelectrodes for in vivo neurochemical measurements, Electroanal., 7, 405-416 (1995).
135. S. Cosnier, J. J. Fombon, P. Labbe and D. Limosin, Development of a PPO-poly(amphiphilic pyrrole) electrode for on site monitoring of phenol in aqueous effluents, Sensors and Actuators B, 59, 134-139 (1999).
136. W. Jin, F. F. Bier, U. Wollenberger and F. Scheller, Construction and characterization of a multi-layer enzyme electrode: covalent binding of quinoprotein glucose dehydrogenase onto gold electrodes, Biosens Bioelectr., 10, 823-829 (1995).
137. L. Stoica, A. Lindgren-Sjölander, T. Ruzgas and L. Gorton, Biosensor based on cellobiose dehydrogenase for detection of catecholamines, Anal. Chem., 76, 4690-4696 (2004).
138. D. Barcelo, J. Dachs and S. Alcock (eds.), BIOSET: Final Report, Biosensors for evaluation of the performance of waste water treatment works, European Commission, Environment and Climate programme, Barcelona, 2000.
139. A. Rose, C. Nistor, J. Emnéus, D. Pfeiffer and U. Wollenberger, GDH biosensor based off-line capillary immunoassay for alkylphenols and their ethoxylates, Biosens. Bioelectr, 17, 1033-1043 (2002).
140. C. Nistor, A. Osvik, R. Davidsson et al., Detection of Escherichia coli in water by culture-based amperometric and luminometric methods, Water Sci. Technol., 45, 191-199 (2002).
141. E. Dock, J. Christensen, M. Olsson et al., Multivariate data analysis of dynamic amperometric biosensor responses from binary analyte mixtures - application of sensitivity correction algorithms, Talanta, 65, 298-305 (2005).
142. R. Solna, S. Sapelnikowa, P. Skladal et al., Multienzyme electrochemical array sensor for determination of phenols and pesticides, Talanta, 65, 349-357 (2005).
143. I. Czolkos, J. Selbig, A. Scholz, J. Szeponik and U. Wollenberger, Multienzyme array-measurement and data evaluation, in preparation.
144. U. Wollenberger, K. Streffer and F. Scheller, in Two European Technical Meetings: Biosensors for Environmental Monitoring, P. D. Hansen, J. Köhler and D. Nowak (eds.), Report, European Commission, 1998.
145. E. Dominguez and A. Narvaez, in Two European Technical Meetings: Biosensors for Environmental Monitoring, P. D. Hansen, J. Köhler and D. Nowak (eds.), Report, European Commission, 1998.
146. B. Strelitz, in Two European Technical Meetings: Biosensors for Environmental Monitoring, P. D. Hansen, J. Köhler and D. Nowak (eds.), Report, European Commission, 1998.
147. A. Narvaez, J. Parellada and E. Dominguez, Tyrosinase screen-printed electrodes for the analysis of phenolic compounds in environmental samples using an automatic flow injection system, in D. Barcelo, J. Dachs and S. Alcock (eds.), BIOSET: Final Report, Biosensors for Evaluation of the Performance of Waste Water Treatment Works. European Commission, Environment and Climate programme, Barcelona, pp. 37-41, 2000.
148. U. Wollenberger, A. Rose and D. Pfeiffer, Portable prototype device with integrated biosensor using PQQ-dependent glucose dehydrogenase modified thick-film electrodes for the determination of phenolic compounds in aqueous solution, in D. Barcelo, J. Dachs and S. Alcock (eds.), BIOSET: Final Report, Biosensors for Evaluation of the Performance of Waste Water Treatment Works. European Commission, Environment and Climate programme, Barcelona, pp. 31-35, 2000.
149. J. Emneus, C. Nistor, A. Lindgren, T. Ruzgas and L. Gorton, A cellobiose dehydrogenase biosensor in a flow injection system for measurement of diphenols and aminophenols, in D. Barcelo, J. Dachs and S. Alcock (eds.), BIOSET: Final Report, Biosensors for Evaluation of the Performance of Waste Water Treatment Works. European Commission, Environment and Climate programme, Barcelona, pp. 25-30, 2000.
150. C. Nistor and J. Emnéus, An enzyme flow immunoassay using alkaline phosphatase as the label and a tyrosinase biosensor as the label detector, Anal. Commun., 35, 417-419 (1998).
151. S. Yamaguchi, S. Ozawa, T. Ikeda and M. Senda, Sensitive amperometry of 4-aminophenol based on catalytic current involving enzymatic recycling with diaphorase and its application to alkaline phosphatase assay, Anal. Sci., 8, 87-88 (1992).
152. F. W. Scheller, A. Makower, A. Ghindilis et al., Enzyme sensors for subnanomolar concentrations, in Biosensor and Chemical Sensor Technology, ACS Symposium Series 613, K. R. Rogers, A. Mulchandani and W. Zhou (eds.), American Chemical Society, Washington, DC, Chapter 7, pp. 71-81, 1995.
153. D. Ratge, G. Baumgardt, E. Knoll and H. Wisser, Plasma free and conjugated catecholamines in diagnosis and localization of pheochromocytoma, Clin. Chim. Acta, 132, 229-243 (1983).
154. D. S. Goldstein, Plasma-catecholamines in clinical-studies of cardiovascular-diseases, Acta Physiologica Scandinavica, 527, 39-41 (1984).
155. S. D. Anker, Catecholamine levels and treatment in chronic heart failure, Europ. Heart J., 19, F56-F61 (1998).
156. J.W. M. Lenders, K. Pacak and G. Eisenhofer, New advances in the biochemical diagnosis of pheochromocytoma -Moving beyond catecholamines, Endocrine Hypertension Ann. New York Acad. Sci., 970, 29-40 (2002).
157. B. Bruguerolle and N. Simon, Biologic rhythms and Parkinson's disease: a chronopharmacologic approach to considering fluctuations in function, Clin. Neuropharm., 25, 194-201 (2002).
158. P. Hjemdahl, P. T. Larsson, T. Bradley et al., Catecholamine measurements in urine by high-performance liquid chromatography with amperometric detection-comparison with an autoanalyser flourescence method, J. Chrom., 494, 53-66 (1989).
159. A. H. Liu and E. K. Wang, Amperometric detection of catecholamines with liquid-chromatography at a polypyrrole- phosphomolybdic anion-modified electrode, Anal. Chim. Acta, 296, 171-180 (1994).
160. Y. Ferry and D. Leech, Amperometric detection of catecholamine neurotransmitters using electrocatalytic substrate recycling at a laccase electrode, Electroanal., 17, 113-119 (2005).
161. K. T. Kawagoe, J. A. Jankowski and R. M. Wightman, Etched carbon-fiber electrodes as amperometric detectors of Catecholamine secretion from isolated biological cells, Anal. Chem., 63, 1589-1594 (1991).
162. T. K. Chen, G. O. Luo and A. G. Ewing, Amperometric monitoring of stimulated catecholamine release from rat pheochromocytoma (PC12) cells at the zeptomole level, Anal. Chem., 66, 3031-3035 (1994).
163. R. D. O'Neill, Microvoltammetric techniques and for monitoring neurochemical dynamics, Analyst, 119, 767-779 (1994).
164. F. Lisdat, U. Wollenberger, M. Paeschke, and, F. W. Scheller, Sensitive catecholamine measurement using a monoenzymatic recycling system, Anal. Chim. Acta, 368, 233-241 (1998).
165. A. L. Ghindilis, A. Makower and F. Scheller, A laccaseglucose dehydrogenase recycling-enzyme electrode based on potentiometric mediatorless electrocatalytic detection, Anal. Meth. Instr., 2, 129-132 (1995).
166. U. Wollenberger and F. Lisdat, F. Scheller, Enzymatic substrate recycling electrodes, in Frontiers in Biosensorics, F. W. Scheller, F. Schubert and J. Fedrowitz (eds.), Birkhäuser Verlag, Basel, pp. 45-69, 1997.
167. F. Lisdat and U. Wollenberger, Trienzymatic amplification system for the detection of catechol and catecholamines using internal co-substrate regeneration, Anal. Lett., 31, 1275-1285 (1998).
168. B. Haghighi, L. Gorton, T. Ruzgas and L. J. Jönsson, Characterization of graphite electrodes modified with laccase from Trametes versicolor and their use for bioelectrochemical monitoring of phenolic compounds in flow injection analysis, Anal. Chim. Acta, 487, 3-14 (2003).
169. A. Lindgren, Electrochemistry of heme containing enzymes - fundamentals and applications, PhD-Thesis, Lund, 2000.
170. E. Burestedt, C. Nistor, U. Schlagerlöf and J. Emneus, An enzyme flow immunoassay that uses beta-galactosidase as the enzyme label and a cellobiose dehydrogenase biosensor as label detector, Anal. Chem., 72, 4171-4177 (2000).
171. A. Kaisheva, I. Iliev, S. Christov and R. Kazareva, Electrochemical gas biosensor for phenol, Sensors and Actuators B, 44, 571-577 (1997).
172. S. Ito, S. Yamazaki, K. Kano and T. Ikeda, Highly sensitive electrochemical detection of alkaline phosphatase, Anal. Chim. Acta, 424, 57-63 (2000).
173. F. Mizutani, S. Yabuki and M. Asai, Highly-sensitive measurement of hydroquinone with an enzyme electrode, Biosens. Bioelectr, 6, 305-310 (1991).
174. F. Vianello, A. Cambria, S. Ragusa, M. T. Cambria, L. Zennaro and A. Rigo, A high sensitivity amperometric biosensor using a monomolecular layer of laccase as biorecognition element, Biosens. Bioelectr., 20, 315-321 (2004).
175. C. Saby, K. B. Male and J. H. T. Luong, A combined chemical and electrochemical approach using bis(trifluoroacetoxy) iodobenzene and glucode oxidase for the detection of chlorinated phenols, Anal. Chem., 69, 4324-4330 (1997).
176. A. S. S. Gomes, J. M. F. Nogueira and M. J. F. Rebelo, An amperometric biosensor for polyphenolic compounds in red wine, Biosens,. Bioelectr., 20, 1211-1216 (2004).
177. T. Ikeda, I. Katasho, M. Kamei and M. Senda, Electrocatalysis with glucose oxidase immobilized graphite electrode, J. Electroanal. Chem., 48, 1969-1979 (1984).
178. M. D. Rubianes and G. A. Rivas, Amperometric biosensor for phenols and catechols based on iridium-polyphenol oxidase-modified carbon paste, Electroanal, 12, 1159-1162 (2000).
179. H. Notsu and T. Tatsuma, Simultaneous determination of phenolic compounds by using a dual enzyme electrodes system, J. Electroanal. Chem., 566, 379-384 (2004).
180. E. Dempsey, D. Diamond and A. Collier, Development of a biosensor for endocrine disrupting compounds based on tyrosinase entrapped within a poly(thionine) film, Biosens. Bioelectr., 20, 367-377 (2004).
181. S. S. Rosatto, P. T. Sotomayor, L. T. Kubota and Y. Gushikem, Si2/Nb2O5 sol-gel as a support for HRP immobilization in biosensor preperation for phenol detection, Electrochim. Acta, 47, 4451-4458 (2002).
182. P. Mailley, E. A. Cummings, S. Mailley et al., Amperometric detection of phenolic compounds by polypyrrole-based composite carbon paste electrodes, Bioelectrochemistry, 63, 291-296 (2004).
183. A. Romani, M. Minunni, N. Mulinacci, P. Pinelli and F. F. Vincieri, Comparison among differential pulse voltammetry, amperometric biosensor, and HPLC/DAD analysis for polyphenol determination, J. Agric. Food Chem., 48, 1197-1203 (2000).
184. N. Loew, F. W. Scheller, U. Wollenberger, Characterization of self-assembling of glucose dehydrogenase in mono- and multilayers on gold electrodes, Electroanal., 16, 1149-1154 (2004).
185. D. Shan, S. Cosnier and C. Mousty, Layered double hydoxides: an attractive material for electrochemical biosensor design, Anal. Chem., 75, 3872-3879 (2003).
186. D. Shan, C. Mousty, S. Cosnier and S. Mu, A composite poly azure B-clay-enzyme senor for the mediated electrochemical determination of phenols, J. Electroanal. Chem., 537, 103-109 (2002).
187. J. Norberg, J. Emneus, J. A. Jönsson, L. Mathiasson, E. Burestedt, M. Knutsson and G. Marko-Varga, On-line supported liquid membrane liquid chromatography with a phenol oxidase-based biosensor as a selective detection unit for the determination of phenols in blood plasma, J. Chromatogr. B, 701, 39-46 (1997).
188. J. Wang, F. Lu, S. A. Kane et al., Hydrocarbon pasting liquids for improved tyrosinase-based carbon-paste phenol biosensors, Electroanal., 9, 1102 (1997).
189. E. A. Cummings, S. Linquette-Mailley, P. Mailley, S. Cosnier and E. T. McAdams, A comparison of amperometric screen-printed carbon electrodes and their application to the analysis of phenolic compounds present in beers, Talanta, 55, 1015-1027 (2001).
190. D. Quan and W. Shin, Amperometric detection of catechol and catecholamines by immobilized laccase from DeniLite, Electroanal., 16 (19), 1576-1582 (2004).
191. J. J. Roy, T. E. Abraham, K. S. Abhijith, P. V. S. Kumar and M. S. Thakur, Biosensor for the determination of phenols based on crosslinked enzyme crystals of laccase, Biosens. Bioelectr., 21 206-211 (2005).
192. J. Li, L. S. Chia, N. K. Goh and S. N. Tan, Silica sol-gel immobilised amperometric biosensor for the determination of phenolic compounds, Anal. Chim. Acta, 362, 203-211 (1998).