Sensors based on cytochrome P450 and CYP mimicking systems

Electrochimica Acta

Volumn 110, Issue , 2013, Pages 63-72

  Yarman, Aysu ^a,b   Wollenberger, Ulla ^b   Scheller, Frieder W ^a,b  

^a FRAUNHOFER INSTITUTE FOR BIOMEDICAL ENGINEERING   (Germany)

^b UNIVERSITY OF POTSDAM   (Germany)

Author keywords

Biosensors; Catalytically active molecularly imprinted polymers; Cytochrome P450; Microperoxidases; Personalised medicine

Indexed keywords

CYTOCHROME P450; CYTOCHROME P450 ENZYMES; DIRECT ELECTRON TRANSFER; MICROPEROXIDASES; MOLECULARLY IMPRINTED POLYMER; PERSONALISED MEDICINES; PROTEIN ELECTROCHEMISTRY; SUBSTRATE CONVERSION;

BIOSENSORS; ELECTROCHEMISTRY; ELECTRODES; ELECTRON TRANSITIONS; ENZYME ELECTRODES; GLUCOSE OXIDASE; GLUCOSE SENSORS; OXYGEN SUPPLY; POLYMERS; PORPHYRINS; SENSORS;

SUBSTRATES;

EID: 84888287441     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2013.03.154     Document Type: Article

References (96)

1. 2-dependent reactions of cytochrome P-450LM compared with peroxidase catalysis FEBS Letters 96 1978 349
2. N. Bistolas, U. Wollenberger, C. Jung, and F.W. Scheller Cytochrome P450 biosensors - a review Biosensors and Bioelectronics 20 2005 2408
3. S.J. Sadeghi, A. Fantuzzi, and G. Gilardi Breakthrough in P450 bioelectrochemistry and future perspectives Biochimica et Biophysica Acta 1884 2011 237
4. V.V. Shumyantseva, T.V. Bulko, E.V. Suprun, Y.M. Chalenko, M.Y. Vagin, Y.O. Rudakov, M.A. Shatskaya, and A.I. Archakov Electrochemical investigations of cytochrome P450 Biochimica et Biophysica Acta 1814 2011 94
5. K.S. Rabe, V.J. Gandubert, M. Spengler, M. Erkelenz, and C.M. Niemeyer Engineering and assaying of cytochrome P450 biocatalysts Analytical and Bioanalytical Chemistry 392 2008 1059
6. E. Schneider, and D.S. Clark Cytochrome P450 (CYP) enzymes and the development of CYP biosensors Biosensors and Bioelectronics 39 2013 1
7. A. Yarman, A. Badalyan, N. Gajovic-Eichelmann, U. Wollenberger, and F.W. Scheller Enzyme electrode for aromatic compounds exploiting the catalytic activities of microperoxidase-11 Biosensors and Bioelectronics 30 2011 320
8. A. Yarman, B. Neumann, N. Gajovic-Eichelmann, U. Wollenberger, and F.W. Scheller Intelligent biosensors unifying bioelectrocatalysis by minizymes with MIP-based selectivity Biosensors 2012 World Congress Cancun, Mexico, 15-18 May 2012
9. A. Yarman, F.W. Scheller, Unpublished results.
10. D.F.V. Lewis Guide to Cytochromes P450: Structure and Function 2001 Taylor and Francis New York
11. P.R. Ortiz de Montellano Cytochrome P450: Structure, Mechanism, and Biochemistry 3rd ed. 2004 Springer New York
12. I.G. Denisov, T.M. Makris, S.G. Sligar, and I. Schlichting Structure and chemistry of cytochrome P450 Chemical Reviews 105 2005 2253
13. F. Scheller, R. Renneberg, G. Strnad, K. Pommerening, and P. Mohr Electrochemical aspects of cytochrome P-450 system from liver microsomes Bioelectrochemistry and Bioenergetics 4 1977 500
14. G.E. Tsotsou, A.E.G. Cass, and G. Gilardi High throughput assay for cytochrome P450 BM3 for screening libraries of substrates and combinatorial mutants Biosensors and Bioelectronics 17 2002 119
15. H.M. Eggers, H.B. Halsall, and W.R. Heineman Enzyme immunoassay with flow-amperometric detection of NADH Clinical Chemistry 28 1982 1848
16. P.J. Elving, W. Bresnahan, J. Moiroux, and Z. Samec NAD/NADH as a model redox system: mechanism, mediation, modification by the environment Bioelectrochemistry and Bioenergetics 2 1982 365
17. M. Wodnicka, R.D. Guarino, J.J. Hemperly, M.R. Timmins, D. Stitt, and J.B. Pitner Novel fluorescent technology platform for high throughput cytotoxicity and proliferation assays Journal of Biomolecular Screening 5 2000 141
18. D. Yu, B. Blankert, E. Bodoki, J.-C. Viré, R. Sandulescu, A. Nomura, and J.-M. Kauffmann Amperometric biosensors based on horseradish peroxidase-immobilised magnetic microparticles Sensors and Actuators B-Chemical 113 2006 149
19. D. Yu, B. Blankert, and J.-M. Kauffmann Development of amperometric horseradish peroxidase based biosensors for clozapine and for the screening for thiol compounds Biosensors and Bioelectronics 22 2007 2707
20. D. Yu, O.D. Renedo, B. Blankert, E. Bodoki, V. Sima, R. Sandulescu, J. Arcos, and J.-M. Kauffmann A peroxidase-based biosensor supported by nanoporous silica microparticles for acetaminophen biotransformation and inhibition studies Electroanalysis 18 2006 1637
21. W. Scheller, W. Jin, E. Ehrentreich-Förster, B. Ge, F. Lisdat, R. Büttemeier, U. Wollenberger, and F.W. Scheller Cytochrome C based superoxide sensor for in vivo application Electroanalysis 11 1999 703
22. R.W. Estabrook, K.M. Faulkner, M.J. Shet, and C.W. Fisher Application of electrochemistry for P450-catalyzed reactions E.F. Johnson, M.R. Waterman, Methods in Enzymology vol. 272 1996 Academic Press U.S.A 44
23. V.V. Shumyantseva, T.V. Bulko, T.T. Bachmann, U. Bilitewski, R.D. Schmid, and A.I. Archakov Electrochemical reduction of flavocytochromes 2B4 and 1A2 and their catalytic activity Archives of Biochemistry and Biophysics 377 2000 43
24. V. Reipa, M.P. Mayhew, M.J. Holden, and V.L. Vilker Redox control of the CYP101 catalytic cycle: effects of Y96F active site mutations and binding of a non-natural substrate Chemical Communications 21 2002 318
25. E.I. Iwuoha, S. Joseph, Z. Zhang, M.R. Smyth, U. Fuhr, and P.R. Ortiz de Montellano Drug metabolism biosensors: electrochemical reactivities of cytochrome CYP101 immobilised in synthetic vesicular systems Journal of Pharmaceutical and Biomedical Analysis 17 1998 1101
26. V.V. Shumyantseva, T.V. Bulko, S.A. Usanov, R.D. Schmid, C. Nicolini, and A.I. Archakov Construction and characterization of bioelectrocatalytic sensors based on cytochromes P450 Journal of Inorganic Biochemistry 87 2001 185
27. J. Nazor, S. Dannenmann, R.O. Adjei, Y.B. Fordjour, I.T. Ghampson, M. Blanusa, D. Roccatano, and U. Schwaneberg Laboratory evolution of P450BM3 for mediated electron transfer yielding an activity-improved and reductase independent variant Protein Engineering Design and Selection 21 2008 29
28. S. Krishnan, D. Wasalathanthri, L.L. Zhao, J.B. Schenkman, and J.F. Rusling Efficient bioelectronic actuation of the natural catalytic pathway of human metabolic cytochrome P450s Journal of the American Chemical Society 133 2011 1459
29. G. Gilardi, A. Fantuzzi, and S.J. Sadeghi Engineering and design in the bioelectrochemistry of metalloproteins Current Opinion in Structural Biology 11 2001 491
30. A. Sideri, A. Goyal, G. Di Nardo, G.E. Tsotsou, and G. Gilardi Hydroxylation of non-substituted polycyclic aromatic hydrocarbons by cytochrome P450 BM3 engineered by directed evolution Journal of Inorganic Biochemistry 120 2013 1
31. T.S. Wong, and U. Schwaneberg Protein engineering in bioelectrocatalysis Current Opinion in Biotechnology 14 2003 590
32. V. Reipa, M.P. Mayhew, and V.L. Vilker A direct electrode-driven CYP cycle for biocatalysis Proceedings of the National Academy of Science of the United Stares of America 94 1997 13554
33. M.P. Mayhew, V. Reipa, M.J. Holden, and V.L. Vilker Improving the cytochrome CYP enzyme for electrode-driven biocatalysis of styrene epoxidation Biotechnology Progress 16 2000 610
34. G. Gilardi, Y.T. Meharenna, G.E. Tsotsou, S.J. Sadeghi, M. Fairhead, and S. Giannini Molecular Lego: design of molecular assemblies of P450 enzymes for nanobiotechnology Biosensors and Bioelectronics 17 2002 133
35. V.R. Dodhia, C. Sassone, A. Fantuzzi, G. Di Nardo, S.J. Sadeghi, and G. Gilardi Modulating the coupling efficiency of human cytochrome P450 CYP3A4 at electrode surfaces through protein engineering Electrochemistry Communications 10 2008 1744
36. P. Panicco, V.R. Dodhia, A. Fantuzzi, and G. Gilardi Enzyme-based amperometric platform to determine the polymorphic response in drug metabolism by cytochromes P450 Analytical Chemistry 83 2011 2179
37. J. Kazlauskaite, A.C.G. Westlake, L.-L. Wong, and H.A.O. Hill Direct electrochemistry of cytochrome P450cam 1996 2189 2190
38. S. Carrara, A. Cavallini, V. Erokhin, and G. De Micheli Multi-panel drugs detection in human serum for personalized therapy Biosensors and Bioelectronics 26 2011 3914
39. Z. Zhang, A.-E.F. Nassar, Z. Lu, J.B. Schenkman, and J.F. Rusling Direct electron injection from electrodes to cytochrome P450cam in biomembrane-like films Journal of the Chemical Society, Faraday Transactions 93 1997 1769
40. A. Fantuzzi, M. Fairhead, and G. Gilardi Direct electrochemistry of immobilized human cytochrome P450 2E1 Journal of the American Chemical Society 126 2004 5040
41. Y. Wu, X. Liu, L. Zhang, and C. Wang An amperometric biosensor based on rat cytochrome p450 1A1 for benzo[a]pyrene determination Biosensors and Bioelectronics 26 2011 2177
42. E.I. Iwuoha, A. Wilson, M. Howel, N.G.R. Mathebe, K. Montane-Jaime, D. Narinesingh, A. Gueseppi-Elie, and P-4502D6 Cytochrome (CYP2D6) bioelectrode for fluoxetine Analytical Letters 37 2004 929
43. L. Asturias-Arribas, M.A. Alonso-Lomillo, O. Domiguez-Renedo, and M.J. Arcos-Martinez CYP450 biosensors based on screen-printed carbon electrodes for the determination of cocaine Analytica Chimica Acta 685 2011 15
44. H. Colas, K.M. Ewen, F. Hannemann, N. Bistolas, U. Wollenberger, R. Bernhardt, and P. de Oliveira Direct and mediated electrochemical response of the cytochrome P450 106A2 from Bacillus megaterium ATCC 13368 Bioelectrochemistry 87 2012 71
45. P. Vatsyayan, M. Chakraborty, S. Bordoloi, and P. Goswami Electrochemical investigations of fungal cytochrome P450 Journal of Electroanalytical Chemistry 662 2011 312
46. V.V. Shumyantseva, T.V. Bulko, G.P. Kumetsova, A.V. Lisitsa, E.A. Ponomarenko, I.I. Karuzina, and A.I. Archakov Electrochemical reduction of Sterol-14 alpha-demethylase from Mycobacterium tuberculosis (CYP51b1) Biochemistry-Moscow 72 2007 658
47. S.Q. Liu, L. Peng, X.D. Yang, Y.F. Wu, and L. He Electrochemistry of cytochrome P450 enzyme on nanoparticle-containing membrane-coated electrode and its applications for drug sensing Analytical Biochemistry 375 2008 209
48. L. Peng, X. Yang, Q. Zhang, and S. Liu Electrochemistry of cytochrome P450 2B6 on electrodes modified with zirconium dioxide nanoparticles and platin components Electroanalysis 20 2008 803
49. M.L. Yang, J.L. Kabulski, L. Wollenberg, X.Q. Chen, M. Subramanian, T.S. Tracy, D. Lederman, P.M. Gannett, and N. Wu Electrocatalytic drug metabolism by CYP2C9 bonded to a self-assembled monolayer-modified electrode Drug Metabolism and Disposition 37 2009 892
50. S.Y. Rhieu, D.R. Ludwig, V.S. Siu, and G.T.R. Palmore Direct electrochemistry of cytochrome P450 27B1 in surfactant films Electrochemistry Communications 11 2009 1857
51. Y. Mie, M. Ikegami, and Y. Komatsu Gold sputtered electrode surfaces enhance direct electron transfer reactions of human cytochrome P450s Electrochemistry Communications 12 2010 680
52. L.H. Mak, S.J. Sadeghi, A. Fantuzzi, and G. Gilardi Control of human cytochrome P450 2E1 electrocatalytic response as a result of unique orientation on gold electrodes Analytical Chemistry 82 2010 5357
53. A. Fantuzzi, E. Capria, L.H. Mak, V.R. Dodhia, S.J. Sadeghi, S. Collins, G. Somers, E. Hug, and G. Gilardi An electrochemical microfluidic platform for human P450 drug metabolism profiling Analytical Chemistry 82 2010 10222
54. Y. Wu Direct electrochemistry of cytochrome P450 6A1 in mimic bio-membrane and its application for pesticides sensing Sensors and Actuators B-Chemical 156 2011 773
55. E.V. Suprun, F. Arduini, D. Moscone, G. Palleschi, V.V. Shumyantseva, and A.I. Archakov Direct electrochemistry of heme proteins on electrodes modified with didodecyldimethyl ammonium bromide and carbon black Electroanalysis 24 2012 1923
56. B. Munge, C. Estavillo, J.B. Schenkman, and J.F. Rusling Optimization of electrochemical and peroxide-driven oxidation of styrene with ultrathin polyion films containing cytochrome CYP101 and myoglobin ChemBioChem 4 2003 82
57. C. Baj-Rossi, C. De Micheli, and S. Carrara Electrochemical detection of anti-breast-cancer agents in human serum by cytochrome P450-coated carbon nanotubes Sensors 12 2012 6520
58. X. Zu, Z. Lu, Z. Zhang, J.B. Schenkman, and J.F. Rusling Electroenzyme-catalyzed oxidation of styrene and cis-β-methylstyrene using thin films of cytochrome CYP101 and myoglobin Langmuir 15 1999 7372
59. V.V. Shumyantseva, Y.D. Ivanov, N. Bistolas, F.W. Scheller, A.I. Archakov, and U. Wollenberger Direct electron transfer of cytochrome P450 2B4 at electrodes modified with non-ionic detergent and colloidal clay nanoparticles Analytical Chemistry 76 2004 6046
60. S. Joseph, J.F. Rusling, Y.M. Lvov, T. Fredberg, and U. Fuhr An amperometric biosensor with human CYP3A4 as a novel drug screening tool Biochemical Pharmacology 65 2003 1817
61. M.J. Eddowes, and H.A.O. Hill Novel method for the investigation of the electrochemistry of metalloproteins: cytochrome c Journal of the Chemical Society, Chemical Communications 21 1977 771
62. P. Yeh, and T. Kuwana Reversible electron reaction of cytochrome c Chemistry Letters 10 1977 1145
63. J. Lazarou, B.H. Pomeranz, and P.N. Corey Incidence of adverse drug reactions in hospitalized patients: a meta-analysis of prospective studies Journal of the American Medical Associations 279 15 1998 1200
64. C. Baj-Rossi, G. De Micheli, and S. Carrara P450-based nano-bio-sensors for personalized medicine P.A. Serra, Biosensors-emerging Materials and Applications 2011 INTECH 10.5772/16328
65. J. Kirchheiner, and A. Seeringer Clinical implications of pharmacogenetics of cytochrome P450 drug metabolizing enzymes Biochimica et Biophysica Acta 1770 2007 489
66. P.A. Adams, D.A. Baldwin, and H.M. Marques The hemepeptides from cytochrome c: preparation, physical, and chemical properties and their use as model compounds for the hemoproteins R.A. Scott, A.G. Mauk, Cytochrome c: A Multidisciplinary Approach 1996 University Science Books Sausalito, California 635
67. J. Babul, E.B. Mccovan, and E. Stellwagen The structure of hemopeptide 1-65 from cytochrome c Archives of Biochemistry and Biophysics 148 1972 141
68. T.W. Ni, and F.A. Tezcan Structural characterization of a microperoxidase inside a metal-directed protein cage Angewandte Chemie. International Edition in English 49 2010 7014
69. W. Lohmann, and U. Karst Biomimetic modelling of oxidative drug metabolism: strategies, advantages and limitations Analytical and Bioanalytical Chemistry 391 2011 79
70. C. Veeger Does P450-type catalysis proceed through a peroxo-iron intermediate? A review of studies with microperoxidase Journal of Inorganic Biochemistry 91 2002 35
71. J.H. Spee, M.G. Boersma, C. Veeger, B. Samyn, J. Van Beeumen, G. Warmerdam, G.W. Canters, V.M. Van Dongen, and I.-M. Rietjens The influence of the peptide chain on the kinetics and stability of microperoxidases European Journal of Biochemistry 24 1996 215
72. 2-catalyzed aromatic hydroxylation proceeds by a cytochrome-P-450-type oxygen-transfer reaction mechanism European Journal of Biochemistry 240 1996 232
73. K.J. Reszka, M.L. McCormick, and B.E. Britigan Oxidation of anthracycline anticancer agents by the peroxidase mimic microperoxidase 11 and hydrogen peroxide Free Radical Biology and Medicine 35 2003 78
74. M. Rodriguez, C. Claparols, A. Robert, and B. Meunier Alkylation of microperoxidase-11 by the antimalarial drug artemisinin ChemBioChem 11 2002 1147
75. B. Mohajerani, M. Soleymani-Jamarani, K. Nazari K., A. Mahmoudib, and A.A. Moosavi-Movahedi Microperoxidase-11-NH2-FSM16 biocatalyst: a heterogeneous enzyme model for peroxidative reactions Journal of Molecular Catalysis A: Chemical 296 2008 28
76. W.Y. Jeng, Y.H. Tsai, and W.J. Chuang The catalase activity of N-acetyl-microperoxidase-8 Journal of Peptide Research 64 2004 104
77. J.S. Ranweiler, and G.S. Wilson Structural effects on cytochrome electron transfer: properties of HPI-65 from horse heart cytochrome C Bioelectrochemistry and Bioenergetics 3 1976 113
78. T. Lötzbeyer, W. Schuhmann, E. Katz, J. Falter, and H.-L. Schmidt Direct electron transfer between the covalently immobilised enzyme microperoxidase MP-11 and a cystamine-modified gold electrode Journal of Electroanalytical Chemistry 377 1994 291
79. E. Csöregi, G. Jönsson-Petterson, and L. Gorton Mediatorless electrocatalytic reduction of hydrogen peroxide at graphite electrodes chemically modified with peroxidases Journal of Biotechnology 30 1993 315
80. T. Lötzbeyer, W. Schuhmann, and H.-L. Schmidt Minienzymes: a review for the development of reagentless amperometric biosensors based on direct electron-transfer process Bioelectrochemistry and Bioenergetics 42 1997 1
81. Y. Astuti, and E. Topoglidis Use of microperoxidase-11 to functionalize tin dioxide electrodes for the optical and electrochemical sensing of hydrogen peroxide Analytica Chimica Acta 686 2011 126
82. H. Korri-Youssoufi, N. Desbenoit, R. Ricoux, J.-P. Mahy, and S. Lecomte Elaboration of a new hydrogen peroxide biosensor using microperoxidase 8 (MP8) immobilised on a polypyrrole coated electrode Materials Science and Engineering C 28 2008 855
83. M. Wang, Y. Shen, Y. Liu, T. Wang, F. Zhao, F. Liu, and S. Dong Direct electrochemistry of microperoxidase 11 using carbon nanotube modified electrodes Journal of Electroanalytical Chemistry 578 2005 121
84. M. Jänchen, F. Scheller, H.-J. Prümke, and P. Mohr Polarographic studies on the peroxidase activity of liganded deuterohemin Acta Biologica et Medica Germanica 34 1975 319
85. A. Yarman, B. Neumann, M. Bosserdt, N. Gajovic-Eichelmann, and F.W. Scheller Peroxide-dependent analyte conversion by the heme prosthetic group, the heme peptide microperoxidase-11 and cytochrome c on chitosan capped gold nanoparticles Modified electrodes Biosensors 2 2012 189
86. G. Wulff Molekulares Prägen (imprinting) in vernetzten Materialen mit Hilfe von Matrizenmolekülen-auf dem Weg zu künstlichen Antikörpern Angewandte Chemie 107 1995 1958
87. K. Lettau, A. Warsinke, M. Katterle, B. Danielsson, and F.W. Scheller A bifunctional molecularly imprinted polymer (MIP): analysis of binding and catalysis by a thermistor Angewandte Chemie. International Edition in English 45 2006 6986
88. D. Lakshmi, A. Bossi, M.J. Whitcombe, I. Chianella, S.A. Fowler, S. Subrahmanyam, E.V. Piletska, and S.A. Piletsky Electrochemical sensor for catechol and dopamine based on catalytic molecularly imprinted polymer-conducting polymer hybrid recognition element Analytical Chemistry 81 2009 3576
89. Z. Cheng, L. Zhang, and Y. Li Synthesis of an enzyme-like imprinted polymer with the substrate as the template, and its catalytic properties under aqueous conditions Chemistry-A European Journal 10 2004 3555
90. G. Díaz-Díaz, Y. Diñeiro, M.I. Meńendez, M.C. Blanco-López, M.J. Lobo-Castañón, A.J. Miranda-Ordieres, and P. Tuñón-Blanco Molecularly imprinted catalytic polymers with biomimetic chloroperoxidase activity Polymer 52 2011 2468
91. W. de Jesus Rodrigues Santos, P.R. Lima, C.R. Tarley, and T.L. Kubota A catalytically active molecularly imprinted polymer that mimics peroxidase based on hemin: application to the determination of p-aminophenol Analytical and Bioanalytical Chemistry 389 2007 1919
92. W. de Jesus Rodrigues Santos, P.R. Lima, C.R. Tarley, N.F. Höerh, and L.T. Kubota L.T Synthesis and application of a peroxidase-like molecularly imprinted polymer based on hemin for selective determination of serotonin in blood serum Analytica Chimica Acta 31 2009 170
93. J. Wang, Z.Y. Chen, M.P. Zhao, and Y.Z. Li Catalytical oxidation of styrene by molecularly imprinted polymer with phenylacetic acid as template and hemin as co-monomer Chinese Chemical Letters 18 2007 981
94. F. Berti, T. Todros, D. Lakshmi, M.J. Whitcombe, I. Chianella, M. Ferroni, S.A. Piletsky, A.P.F. Turner, and G. Marrazza Quasi-monodimensional polyaniline nanostructures for enhanced molecularly imprinted polymer-based sensing Biosensors and Bioelectronics 26 2010 497
95. J.R.M. Neto, W. de Jesus Rodrigues Santos, P.R. Lima, S.M.C.N. Tanaka, A.A. Tanaka, and L.T. Kubota A hemin-based molecularly imprinted polymer (MIP) grafted onto a glassy carbon electrode as a selective sensor for 4-aminophenol amperometric Sensors and Actuators B-Chemical 152 2011 220
96. A. Yarman, B. Neumann, N. Gajovic-Eichelmann, and F.W. Scheller Peroxide-dependent analyte conversion by heme, microperoxidase-11 and cytochrome c - analytical applications and medical implications The 63rd Annual Meeting of the International Society of Electrochemistry Prague, Czech Republic, 19-24 August 2012