Electrochemical and solid-phase synthetic modification of glassy carbon electrodes with dihydroxybenzene compounds and the electrocatalytic oxidation of NADH

Bioelectrochemistry

Volumn 76, Issue 1-2, 2009, Pages 115-125

  Ghanem, Mohamed A ^a,b   Chrétien, Jean Mathieu ^a   Kilburn, Jeremy D ^a   Bartlett, Philip N ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b SUEZ CANAL UNIVERSITY   (Egypt)

Author keywords

Dihydroxybenzene; Library; Modified electrode; NADH oxidation; Solid phase synthesis

Indexed keywords

CATALYTIC ACTIVITY; CHARACTERISATION; DEPROTECTION; DIHYDROXYBENZENE; DIHYDROXYBENZENES; ELECTRO-CATALYTIC OXIDATION; ELECTROCATALYTIC ACTIVITY; ELECTROCHEMICAL PARAMETERS; ETHYLENE DIAMINE; GLASSY CARBON; GLASSY CARBON ELECTRODES; METHOXY GROUP; MODIFIED ELECTRODE; MODIFIED ELECTRODES; NADH OXIDATION; PATTERN OF SUBSTITUTION; PEAK POTENTIALS; SINGLE BOND; SOLID-PHASE; SOLID-PHASE SYNTHESIS; SURFACE COVERAGES; SYNTHETIC MODIFICATIONS;

CATALYST ACTIVITY; CATALYTIC OXIDATION; CHLORINE COMPOUNDS; CYCLIC VOLTAMMETRY; ELECTROCATALYSIS; ELECTROCHEMICAL SENSORS; ELECTRODES; GLASS MEMBRANE ELECTRODES; OXIDATION;

COMPLEXATION;

CARBON; ETHYLENEDIAMINE; PHENOL DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE;

ARTICLE; CATALYSIS; CYCLIC POTENTIOMETRY; DEPROTECTION REACTION; ELECTROCHEMISTRY; ELECTRODE; IMMOBILIZATION; OXIDATION; SOLID PHASE SYNTHESIS; SURFACE PROPERTY;

ASCORBIC ACID; CARBON; CATALYSIS; ELECTROCHEMISTRY; ELECTRODES; GLASS; HYDRAZINES; HYDROGEN-ION CONCENTRATION; NAD; OXIDATION-REDUCTION; PHENOLS;

EID: 68549087225     PISSN: 15675394     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bioelechem.2009.02.008     Document Type: Article

References (45)

1. Downard A.J. Electrochemically assisted covalent modification of carbon electrodes. Electroanalysis 12 (2000) 1085-1096
2. Pinson J., and Podvorica F. Attachment of organic layers to conductive or semiconductive surfaces by reduction of diazonium salts. Chem. Soc. Rev. 34 (2005) 429-439
3. Adenier A., Chehimi M.M., Gallardo I., Pinson J., and Vilà N. Electrochemical oxidation of aliphatic amines and their attachment to carbon and metal surfaces. Langmuir 20 (2004) 8243-8253
4. Barbier B., Pinson J., Desarmot G., and Sanchez M. Electrochemical bonding of amines to carbon fiber surfaces toward improved carbon-epoxy composites. J. Electroanal. Chem. 137 (1990) 1757-1764
5. Deinhammer R.S., Ho M., Anderegg J.W., and Porter M.D. Electrochemical oxidation of amine-containing compounds: a route to the surface modification of glassy carbon electrodes. Langmuir 10 (1994) 1306-1313
6. Gallardo I., Pinson J., and Vilà N. Spontaneous attachment of amines to carbon and metallic surfaces. J. Phys. Chem. B 110 (2006) 19521-19529
7. Hoekstra K.J., and Bein T. Adsorption of zirconium-phosphonate multilayers onto phosphate-derivatized glassy carbon substrates. Chem. Mater. 8 (1996) 1865-1870
8. 2 electroreduction. J. Electroanal. Chem. 437 (1997) 29-35
9. Bourdillon C., Delamar M., Demaille C., Hitmi R., Moiroux J., and Pinson J. Immobilization of glucose oxidase on a carbon surface derivatized by electrochemical reduction of diazonium salts. J. Electroanal. Chem. 336 (1992) 113-123
10. Delamar M., Hitmi R., Pinson J., and Savéant J.-M. Covalent modification of carbon surfaces by grafting of functionalized aryl radicals produced from electrochemical reduction of diazonium salts. J. Amer. Chem. Soc. 114 (1992) 5883-5884
11. Pinson J., Savéant J.-M., and Hitmi R. Process for modifying the surface of carbon-containing materials by electrochemical reduction of diazonium salts, applicable in particular to carbon fibres for composite materials, carbon-containing so modified. International Patent WO9213983 (1992)
12. Downard A.J., and Roddick A.D. Protein adsorption at glassy carbon electrodes: the effect of covalently bound surface groups. Electroanalysis 7 (1995) 376-378
13. Kariuki J.K., and McDermott M.T. Nucleation and growth of functionalized aryl films on graphite electrodes. Langmuir 15 (1999) 6534-6540
14. Liu Y.-C., and McGreery R.L. Reactions of organic monolayers on carbon surfaces observed with unenhanced Raman spectroscopy. J. Amer. Chem. Soc. 117 (1995) 11254-11259
15. Saby C., Ortiz B., Champagne G.Y., and Bélanger D. Electrochemical modification of glassy carbon electrode using aromatic diazonium salts. 1. Blocking effect of 4-nitrophenyl and 4-carboxyphenyl groups. Langmuir 13 (1997) 6805-6813
16. Allongue P., Delamar M., Desbat B., Fagebaume O., Hitmi R., Pinson J., and Savéant J.-M. Covalent modification of carbon surfaces by aryl radicals generated from the electrochemical reduction of diazonium salts. J. Amer. Chem. Soc. 119 (1997) 201-207
17. Bath B.D., Martin H.B., Wightman R.M., and Anderson M.R. Dopamine adsorption at surface modified carbon-fiber electrodes. Langmuir 17 (2001) 7032-7039
18. Fagebaume O., Pinson J., and Savéant J.-M. Method for producing by electrochemical process a carbon-containing material with its surface modified by organic groups, use of modified material. International Patent WO9844172 (1998)
19. Masheter A.T., Wildgoose G.G., Crossley A., Jones J.H., and Compton R.G. A facile method of modifying graphite powder with aminophenyl groups in bulk quantities. J. Mater. Chem. 17 (2007) 3008-3014
20. Liu G., Liu J., Böcking T., Eggers P.K., and Gooding J.J. The modification of glassy carbon and gold electrodes with aryl diazonium salt: the impact of the electrode materials on the rate of heterogeneous electron transfer. Chem. Phys. 319 (2005) 136-146
21. Coulon E., Pinson J., Bourzat J.D., Commerçon A., and Pulicani J.P. Surface-modified carbon felts: possible supports for combinatorial chemistry. J. Org. Chem. 67 (2002) 8513-8518
22. Griveau S., Mercier D., Vautrin-Ul C., and Chaussé A. Electrochemical grafting by reduction of 4-aminoethylbenzenediazonium salt: application to the immobilization of (bio)molecules. Electrochem. Commun. 9 (2007) 2768-2773
23. Evrard D., Lambert F., Policar C., Balland V., and Limoges B. Electrochemical functionalization of carbon surfaces by aromatic azide or alkyne molecules: a versatile platform for click chemistry. Chem. Eur. J. 14 (2008) 9286-9291
24. Chrétien J.-M., Ghanem M.A., Bartlett P.N., and Kilburn J.D. Covalent tethering of organic functionality to the surface of glassy carbon electrodes using electrochemical and solid-phase synthesis methodologies. Chem. Eur. J. 14 (2008) 2548-2556
25. Ghanem M.A., Chrétien J.-M., Pinczewska A., Kilburn J.D., and Bartlett P.N. Covalent modification of glassy carbon surface with organic redox probes through diamine linkers using electrochemical and solid-phase synthesis methodologies. J. Mater. Chem. 18 (2008) 4917-4927
26. Hall S.B., Yang X., Officer D.L., Belcher W.J., and Burrell A.K. Glassy carbon based sensors. Synth. Met. 137 (2003) 1429-1430
27. Yang X., Hall S.B., Burrell A.K., and Officer D.L. A pH-responsive hydroquinone-functionalised glassy carbon electrode. Chem. Commun. (2001) 2628-2629
28. Dixon M., and Webb E.C. Enzymes (1979), Longman, London
29. Lodish H., Baltimore D., Berk A., Zipursky S.L., Matsudaira P., and Darnell J. Molecular Cell Biology, Scientific American Books, New York (1995)
30. Bartlett P.N., Tebbutt P., and Whitaker R.G. Kinetics aspects of the use of modified electrodes and mediators in bioelectrochemistry. Prog. React. Kinet. 16 (1991) 55-156
31. Gorton L. Chemically modified electrodes for the electrocatalytic oxidation of nicotinamide coenzymes. J. Chem. Soc., Faraday Trans. 1 82 (1986) 1245-1258
32. Gorton L., and Bartlett P.N. NAD(P)-based biosensors. In: Bartlett P.N. (Ed). Bioelectrochemistry: Fundamentals, Experimental Techniques and Applications (2008), John Wiley & Sons, Chichester 157-198
33. Simon E., and Bartlett P.N. Modified electrodes for the oxidation of NADH. In: Rusling J.F. (Ed). Biomolecular Films: Design, Function, and Applications (2003), Marcel Dekker, New York 499-544
34. Gorton L., and Domi{dotless}nguez E. Electrocatalytic oxidation of NAD(P)/H at mediator-modified electrodes. Rev. Mol. Biotech. 82 (2002) 371-392
35. Carlson B.W., and Miller L.L. Mechanism of the oxidation of NADH by quinones, energetics of one-electron and hydride routes. J. Amer. Chem. Soc. 107 (1985) 479-485
36. Fukui M., Kitani A., Degrand C., and Miller L.L. Propagation of a redox reaction through a quinoid polymer film on an electrode. J. Amer. Chem. Soc. 104 (1982) 28-33
37. Jaegfeldt H., Kuwana T., and Johansson G. Electrochemical stability of catechols with a pyrene side chain strongly adsorbed on graphite electrodes for catalytic oxidation of dihydronicotinamide adenine dinucleotide. J. Amer. Chem. Soc. 105 (1983) 1805-1814
38. Tse D.C.-S., and Kuwana T. Electrocatalysis of dihydronicotinamide adenosine diphosphate with quinones and modified quinone electrodes. Anal. Chem. 50 (1978) 1315-1318
39. Ueda C., Tse D.C., and Kuwana T. Stability of catechol modified carbon electrodes for electrocatalysis of dihydronicotinamide adenine dinucleotide and ascorbic acid. Anal. Chem. 54 (1982) 850-856
40. Jaegfeldt H., Torstensson A.B.C., Gorton L.G.O., and Johansson G. Catalytic oxidation of reduced nicotinamide adenine dinucleotide by graphite electrodes modified with adsorbed aromatics containing catechol functionalities. Anal. Chem. 53 (1981) 1979-1982
41. Moreno G., Pariente F., and Lorenzo E. Electrocatalytic oxidation of ascorbate at glassy carbon electrodes modified with electrodeposited films derived from dihydroxybenzaldehyde isomers. Anal. Chim. Acta 420 (2000) 29-37
42. Nassef H.M., Radi A.-E., and O'Sullivan C.K. Electrocatalytic oxidation of hydrazine at o-aminophenol grafted modified glassy carbon electrode: reusable hydrazine amperometric sensor. J. Electroanal. Chem. 592 (2006) 139-146
43. Wildgoose G.G., Pandurangappa M., Lawrence N.S., Jiang L., Jones T.G.J., and Compton R.G. Anthraquinone-derivatised carbon powder: reagentless voltammetric pH electrodes. Talanta 60 (2004) 887-893
44. Clark W.M. Oxidation-Reduction Potentials of Organic Systems (1972), Robert E. Krieger Publishing Corp., Huntingdon
45. Jensen K.B., Braxmeier T.B., Demarcus M., Frey J.G., and Kilburn J.D. Synthesis of guanidinium-derived receptor libraries and screening for selective peptide receptors in water. Chem. Eur. J. 8 (2002) 1300-1309