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

Volumn 2, Issue 2, 2012, Pages 189-204

  Yarman, Aysu ^a   Neumann, Bettina ^a   Bosserdt, Maria ^a   Gajovic Eichelmann, Nenad ^a   Scheller, Frieder W ^a  

^a FRAUNHOFER INSTITUTE FOR BIOMEDICAL ENGINEERING   (Germany)

Author keywords

Cytochrome c; Hemin; Microperoxidase 11; Peroxide dependent catalysis

Indexed keywords

BIOCOMPATIBILITY; CELL DEATH; CHITOSAN; DEGRADATION; ENZYMES; FIBER OPTIC SENSORS; GLASS MEMBRANE ELECTRODES; GOLD NANOPARTICLES; HYDROGEN PEROXIDE; METAL NANOPARTICLES; OXIDATION; PEPTIDES; PHENOLS; PORPHYRINS; REDUCTION;

ANALYTES; CHITOSAN LAYERS; CYTOCHROME C; GOLD NANOPARTICLE-MODIFIED ELECTRODES; HEME PEPTIDE; HEMIN; MICROPEROXIDASE-11; P-AMINOPHENOL; PEROXIDE DEPENDENT CATALYSE; PROSTHETIC GROUPS;

SUBSTRATES;

4 AMINOPHENOL; ANILINE; ANILINE DERIVATIVE; AROMATIC COMPOUND; CATECHOL; CHITOSAN; CYTOCHROME C; GOLD NANOPARTICLE; HEME; HYDROGEN PEROXIDE; IMMOBILIZED ENZYME; MICROPEROXIDASE 11; PARACETAMOL; PEPTIDE DERIVATIVE; PEROXIDASE; PEROXIDE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; BIOCATALYST; BIOCOMPATIBILITY; BIOSENSOR; CYCLIC POTENTIOMETRY; DEGRADATION; DEHALOGENATION; ELECTROCHEMISTRY; ELECTRODE; ELECTRON TRANSPORT; ENZYME ACTIVITY; ENZYME IMMOBILIZATION; ENZYME MECHANISM; ENZYME SUBSTRATE COMPLEX; HYDROXYLATION; MOLECULAR INTERACTION; OXIDATION; OXIDATION REDUCTION REACTION; PEROXIDATION; REDUCTION;

EID: 84879192486     PISSN: None     EISSN: 20796374     Source Type: Journal    
DOI: 10.3390/bios2020189     Document Type: Article

References (51)

1. Diederix, R.E.M.; Ubbink, M.; Canters, G.W. Effect of the protein matrix of cytochrome c in suppressing the inherent peroxidase activity of its heme prosthetic group. ChemBioChem 2002, 3, 110-112.
2. Lohmann, W.; Karst, U. Biomimetic modelling of oxidative drug metabolism. Anal. Bioanal. Chem. 2011, 391, 79-96.
3. Ahluwalia, U.; Nayeem, S.M.; Deep, S. The non-native conformations of cytochrome c in sodium dodecyl sulfate and their modulation by ATP. Eur. Biophys. J. 2011, 40, 259-271.
4. Vazquez-Duhalt, R. Cytochrome c as a biocatalyst. J. Mol. Catal. B Enzym. 1999, 7, 241-249.
5. Laszlo, J.A.; Compton, D.L. Comparison of peroxidase activities of hemin, cytochrome c, and microperoxidase-11 in molecular solvents and imidazolium-based ionic liquids. J. Mol. Catal. B Enzym. 2002, 18, 109-120.
6. Everse, J.; Liu, C.-J.J.; Coates, P.W. Physical and catalytic properties of a peroxidase derived from cytochrome c. Biochim. Biophys. Acta 2011, 1812, 1138-1145.
7. Kluck, R.M.; Ellerby, L.M.; Ellerby, H.M.; Naiem, S.; Yaffe, M.P.; Margoliash, E.; Bredesen, D.; Mauk, A.G.; Sherman, F.; Newmeyer, D.D. Determinants of cytochrome c pro-apoptotic activity. J. Biol. Chem. 2000, 275, 16127-16133.
8. Cai, J.; Yang, J.; Jones, D.P. Mitochondrial control of Apoptosis: The role of the cytochrome c. Biochim. Biophys. Acta 1998, 1366, 139-149.
9. Yarman, A.; Badalyan, A.; Gajovic-Eichelmann, N.; Wollenberger, U.; Scheller, F.W. Enzyme electrode for aromatic compounds exploiting the catalytic activities of microperoxidase-11. Biosens. Bioelectron. 2011, 30, 320-323.
10. Bonnard, C.; Papermaster, D.S.; Kiraehenbuhl, J.-P. The streptavidin-biotin bridge technique: Applications in light and electron microscope immunocytochemistry. In Immunolabeling for Electron Microscopy; Elsevier: New York, NY, USA, 1984.
11. Peng, L.; Wollenberger, U.; Hofrichter, M.; Ullrich, R.; Scheibner, K.; Scheller, F.W. Bioelectrocatalytic properties of Agrocybe aegerita peroxygenase. Electrochim. Acta 2010, 55, 7809-7813.
12. Marcus, R.A.; Sutin, N. Electron transfer in chemistry and biology. Biochim. Biophys. Acta 1985, 811, 265-322.
13. Lötzbeyer, T.; Schuhmann, W.; Schmidt, H.-L. Minienzymes: A review for the development of reagentless amperometric biosensors based on direct electron-transfer process. Bioelectrochem. Bioenerg. 1997, 42, 1-6.
14. Yarman, A.; Nagel, T.; Gajovic-Eichelmann, N.; Fischer, A.; Wollenberger, U.; Scheller, F.W. Bioelectrocatalysis by microperoxidase-11 in a multilayer architecture of chitosan embedded gold nanoparticles. Electroanalysis 2011, 23, 611-618.
15. Liu, J.; Qiu, J.; Sun, K.; Chen, J.; Miao, Y. Electrochemistry of hemin self-assembled from aqueous hexadecyltrimethylammonium bromide (CTAB) solution on single-wall-carbon-nanotube-modified glassy carbon electrodes. Helv. Chim. Acta 2009, 92, 462-469.
16. Feng, Z.Q.; Sagara, T.; Niki, K. Electroreflectance study of hemin adsorbed on pyrolytic graphite electrode surface and its coadsorption with with methylene blue. J. Electroanal. Chem. 1993, 349, 159-171.
17. Chen, J.; Wollenberger, U.; Lisdat, F.; Ge, B.; Scheller, F.W. Superoxide sensor based on hemin modified electrode. Sens. Actuat. B 2000, 70, 115-120.
18. Zheng, N.; Zeng, Y.; Osborne, P.G.; Li, Y.; Chang, W.; Wang, Z. Electrocatalytic reduction of dioxygen on hemin based carbon paste electrode. J. Appl. Electrochem. 2002, 32, 129-133.
19. Feng, J.-J.; Li, Z.-H.; Li, Y.-F.; Wang, A.-J.; Zhang, P.-P. Electrochemical determination of dioxygen and hydrogen peroxide using Fe3O4@SiO2@hemin microparticles. Microchim. Acta 2002, 32, 129-133.
20. Laviron, E. General expression of the linear potential sweep voltammogram in the case of diffusionless electrochemical systems. J. Electroanal. Chem. 1979, 101, 19-28.
21. Gorton, L.; Lindgren, A.; Larsson, T.; Munteanu, F.D.; Ruzgas, T.; Gazaryan, I. Direct electron transfer between heme-containing enzymes and electrodes as basis for third generation biosensors. Anal. Chim. Acta 1999, 400, 91-108.
22. Marques, M.H. Insights into porphyrin chemistry provided by the microperoxidases, the haempeptides derived from cytochrome c. Dalton Trans. 2007, 39, 4371-4385.
23. Ruzgas, T.; Gaigalas, A.; Gorton, L. Diffusionless electron transfer of microperoxidase-11 on gold electrodes. J. Electroanal. Chem. 1999, 469, 123-131.
24. Zhou, Y.; Liu, S.; Jiang, H.-J.; Yang, H.; Chen, H.Y. Direct electrochemistry and bioelectrocatalysis of microperoxidase-11 immobilized on chitosan-graphene nanocomposite. Electroanalysis 2010, 22, 1323-1328.
25. Feng, J.-J.; Zhao, G.; Xu, J.-J.; Chen, H.-Y.; Direct electrochemistry and electrocatalysis of heme proteins immobilized on gold nanoparticles stabilized by chitosan. Anal. Biochem. 2005, 342, 280-286.
26. Dallacosta, C.; Casella, L.; Monzani, E. Modified microperoxidases exhibit different reactivity towards phenolic substrates. ChemBioChem 2004, 5, 1692-1699.
27. Csöregi, E.; Jönsson-Petterson, G.; Gorton, L. Mediatorless electrocatalytic reduction of hydrogen peroxide at graphite electrodes chemically modified with peroxidases. J. Biotechnol. 1993, 30, 315-337.
28. Ranieri, A.; Battistuzzi, G.; Borsari, M.; Bortolotti, C.A.; Di Rocco, G.; Monari, S.; Sola, M. A bis-histidine-ligated unfolded cytochrome c immobilized on anionic SAM shows pseudo-peroxidase activity. Electrochem. Commun. 2012, 14, 29-31.
29. Dunford, H.B. Oxidations of iron(II)/(III) by hydrogen peroxide: From aquo to enzyme. Coord. Chem. Rev. 2002, 311, 233-234.
30. Astuti, Y.; Topoglidis, E.; Durrant, J.R. Use of microperoxidase-11 to functionalize tin dioxide electrodes for the optical and electrochemical sensing of hydrogen peroxide. Anal. Chim. Acta 2011, 686, 126-132.
31. Razumas, V.; Kazlauskaitė, J.; Vidžiūnaitė, R. Electrocatalytic reduction of hydrogen peroxide on the microperoxidase-11 modified carbon paste and graphite electrodes. Bioelectrochem. Bioenerg. 1996, 39, 139-143.
32. Youssoufi-Korri, H.; Desbenoit, N.; Ricoux, R.; Mahy, J.P.; Lecomte, S. Eleboration of a new hydrogen peroxide biosensor using microperoxidase 8 (MP8) immobilised on a polypyyrole coated electrode. Mater. Sci. Eng. C 2008, 28, 855-860.
33. Wang, M.; Shen, Y.; Liu, Y.; Wang, T.; Zhao, F.; Liu, F.; Dong, S. Direct electrochemistry of microperoxidase-11 using carbon nanotube modified electrodes. J. Electroanal. Chem. 2005, 578, 121-127.
34. Liu, Y.; Wang, M.; Zhao, F.; Guo, Z.; Chen, H.; Dong, S. Direct electron transfer and electrocatalysis of microperoxidase immobilised on nanohybrid film. J. Electroanal. Chem. 2005, 581, 1-10.
35. Zhu, X.; Yuri, I.; Gan, X.; Suzuki, I.; Li, G. Electrochemical study of the effect of nano-zinc oxide on microperoxidase and its application to more sensitive hydrogen peroxide biosensor preparation. Biosens. Bioelectron. 2007, 22, 1600-1604.
36. Huang, W.; Jia, J.; Zhang, Z.; Han, X.; Tang, J.; Wang, J.; Dong, S.; Wang, E. Hydrogen peroxide biosensor based on microperoxidase-11 entrapped in lipid membrane. Biosens. Bioelectron. 2003, 18, 1225-1230.
37. Cipriano, T.C.; Takahashi, P.M.; de Lima, D.; Oliveira, V.X.; Souza, J.A.; Martinho, H.; Alves, W.A. Spatial organization of peptide nanotubes for electrochemical devices. J. Mater. Sci. 2010, 45, 5101-5108.
38. Wan, J.; Bi, J.; Du, P.; Zhang, S. Biosensor based on the biocatalysis of microperoxidase-11 in nanocomposite material of multiwalled carbon nanotubes/room temperature ionic liquid for amperometric determination of hydrogen peroxide. Anal. Biochem. 2009, 386, 256-261.
39. Chen, Z.; Sun, D.; Zhou, Y.; Zhao, J.; Lu, T.; Huang, X.; Cai, C.; Shen, J. Nano polyurethane-assisted ultrasensitive biodetection of hydrogen peroxide over immobilized Microperoxidase-11. Biosens. Bioelectron. 2011, 29, 53-59.
40. Ju, H.; Liu, S. Ge, B.; Lisdat, F.; Scheller, F.W. Electrochemistry of cytochrome c immobilized on colloidal gold modified carbon paste electrodes and its electrocatalytic activity. Electroanalysis 2002, 14, 141-147.
41. Wang, L.; Waldeck, D.H. Denaturation of cytochrome c and its peroxidase activity when immobilized on SAM films. J. Phys. Chem. C 2008, 112, 1351-1356.
42. Jänchen, M.; Scheller, F.; Prümke, H.-J.; Mohr, P. Polarographische untersuchungen zur peroxidaseaktivität von ligandiertem deuterohämin. Acta Biol. Medica Ger. 1975, 34, 319-324.
43. Yang, S.; Li, Y.; Jiang, X.; Chen, Z.; Lin, X. Horseradish peroxidase biosensor based on layer-by-layer technique for the determination of phenolic compounds. Sens. Actuat. B 2006, 114, 774-780.
44. Veeger, C. Does P450-type catalysis proceed through a peroxo-iron intermediate? A review of studies with microperoxidase. J. Inorg. Biochem. 2002, 91, 35-45.
45. Lin, M.S.; Jan, B.I.; Chen, P.Y.; Cheng, W.C.; Chen, C.H. New determination scheme of p-aminophenol by MnO2 modified electrode coupled with flow injection analysis. Electroanalysis 2010, 22, 1278-1281.
46. Wollenberger, U.; Lisdat, F.; Rose, A.; Streffer, K. Bioelectrochemistry: Fundamentals, Experimental Techniques and Applications; Bartlett, P., Ed.; John Wiley & Sons: Hoboken, NJ, USA, 2008.
47. Wollenberger, U.; Neumann, B. Quinoprotein glucose dehydrogenase modified carbon paste electrode for the detection of phenolic compounds. Electroanalysis 1997, 9, 366-371.
48. Mie, Y.; Kowata, K.; Hirano, Y.; Niwa, O.; Mizutani, F. Comparison of enzymatic recycling electrodes for measuring aminophenol: Development of a highly sensitive natriuretic peptide assay system. Anal. Sci. 2008, 24, 577-582.
49. Solná, R.; Skládal, P. Amperometric flow-injection determination of phenolic compounds using a biosensor with immobilized laccase, peroxidase and tyrosinase. Electroanalysis 2005, 17, 2137-2146.
50. Zhu, Y.; Li, J.; Dong, S. Dimerization of hydroxylated species of m-aminophenolby cytochrome c with hydrogen peroxide. J. Mol. Catal. B Enzym. 1998, 5, 475-482.
51. Kawakami, M.; Akamatsu, N.; Koya, H.; Amada, K. Amperometric detection of phenol with cytochrome c-modified gold electrode using dual working electrode system. Anal. Lett. 2005, 38, 549-561.