Catalytic electrooxidation of NADH for dehydrogenase amperometric biosensors

The developments in the techniques of NADH catalytic oxidation relevant for incorporation in amperometric biosensors with dehydrogenase enzymes are reviewed with special emphasis in the years following 1990. The review stresses the direct electro-catalytic methods of NAD+ recycling as opposed to enzymatic regeneration of the coenzyme. These developments are viewed and evaluated from a mechanistic perspective of recycling of NADH to enzymatically active NAD+, and from the point of view of development of technologically useful reagentless dehydrogenase biosensors. An effort is made to propose a method for the standardization of evaluation of new mediating and direct coenzyme recycling schemes. A perspective is given for the requirements that have to be met for successful biosensor development incorporating dehydrogenase enzymes that open the analytical possibilities to a number of new analytes. The intrinsic limitations of the system are finally discussed and a view of the future of the field is presented.

[1]  J. V. Bannister,et al.  Amperometric NADH determination via both direct and mediated electron transfer by NADH oxidase from Thermus aquaticus YT-1 , 1994 .

[2]  C. Wandrey,et al.  Continuous Generation of NADH from NAD⊕ and Formate Using a Homogeneous Catalyst with Enhanced Molecular Weight in a Membrane Reactor , 1990 .

[3]  K. Mosbach,et al.  The application of immobilized NAD+ in an enzyme electrode and in model enzyme reactors. , 1974, Biochimica et biophysica acta.

[4]  L. Gorton,et al.  Electrochemical and SERS studies of chemically modified electrodes: Nile Blue A, a mediator for NADH oxidation , 1990 .

[5]  Joseph Wang,et al.  Fumed-silica containing carbon-paste dehydrogenase biosensors , 1993 .

[6]  R. Nicholson,et al.  Double potential step method for measuring rate constants of dimerization reactions , 1969 .

[7]  L. Miller,et al.  An electrode modified with polymer-bound dopamine which catalyzes NADH oxidation , 1980 .

[8]  J. Savéant,et al.  Electrochemistry of NADH/NAD+ analogs. A detailed mechanistic kinetic and thermodynamic analysis of the 10-methylacridan/10-methylacridinium couple in acetonitrile , 1990 .

[9]  L. Gorton,et al.  Redox polymers for electrocatalytic oxidation of NADH – Cationic styrene and ethylenimine polymers , 1996 .

[10]  K. Rhee,et al.  Classical Raman spectroscopic studies of NADH and NAD+ bound to liver alcohol dehydrogenase by difference techniques. , 1987, Biochemistry.

[11]  M. Senda,et al.  Amperometric Biosensors Based on a Biocatalyst Electrode with Entrapped Mediator , 1986 .

[12]  Lo Gorton,et al.  Chemically modified electrodes for the electrocatalytic oxidation of nicotinamide coenzymes , 1986 .

[13]  J. Savéant,et al.  Homogeneous redox catalysis of electrochemical reactions: Part V. Cyclic voltammetry , 1980 .

[14]  R. Uppu Novel kinetics in a biomimetic redox reaction involving NADH and tetrazolium salts in aqueous micellar solutions. , 1995, Journal of inorganic biochemistry.

[15]  Björn Persson,et al.  A chemically modified graphite electrode for electrocatalytic oxidation of reduced nicotinamide adenine dinucleotide based on a phenothiazine derivative, 3-β-naphthoyl-toluidine blue O , 1990 .

[16]  G. Whitesides,et al.  Enzyme-catalyzed organic synthesis: a comparison of strategies for in situ regeneration of NAD from NADH , 1985 .

[17]  S. Dong,et al.  ELECTROCATALYTIC OXIDATION OF REDUCED NICOTINAMIDE COENZYMES AT METHYLENE GREEN-MODIFIED ELECTRODES AND FABRICATION OF AMPEROMETRIC ALCOHOL BIOSENSORS , 1994 .

[18]  John P. Hart,et al.  A reagentless, disposable biosensor for lactic acid based on a screen-printed carbon electrode containing Meldola's Blue and coated with lactate dehydrogenase, NAD+ and cellulose acetate , 1995 .

[19]  J. Verhoeven,et al.  Mechanism and transition-state structure of hydride-transfer reactions mediated by nad(p)h-models , 1986 .

[20]  A. Skillen,et al.  Amperometric enzyme electrode for NADH detection employing co-immobilized lactate dehydrogenase and lactate oxidase , 1992 .

[21]  R. Humphry-Baker,et al.  Luminescence, charge-transfer complexes, and photoredox processes involving N-alkyl nicotinamide/dihydronicotinamide surfactants , 1989 .

[22]  J. Leprêtre,et al.  Electrochemical behaviour of 1-alkyl-3,5-di(alkylcarbamoyl)pyridinium ions as a model of the NAD+/NADH system in aqueous solution , 1990 .

[23]  P. Elving,et al.  Mechanistic aspects of the electrochemical oxidation of dihydronicotinamide adenine dinucleotide (NADH) , 1980 .

[24]  T. Kuwana,et al.  Electrochemical stability of catechols with a pyrene side chain strongly adsorbed on graphite electrodes for catalytic oxidation of dihydronicotinamide adenine dinucleotide , 1983 .

[25]  Jenny Emnéus,et al.  Electrochemical characterization of carbon pastes modified with proteins and polycations , 1994 .

[26]  N. Oppenheimer,et al.  Stereospecificity for nicotinamide nucleotides in enzymatic and chemical hydride transfer reactions. , 1985, CRC critical reviews in biochemistry.

[27]  Soichi Yabuki,et al.  Amperometric enzyme electrode with the use of dehydrogenase and NAD(P)H oxidase , 1993 .

[28]  H. B.F.,et al.  Catalytic oxidation of reduced nicotinamide adenine dinucleotide at hexacyanoferrate-modified nickel electrodes , 1987 .

[29]  S. Itoh,et al.  Heterocyclic o-quinones. Mediator for electrochemical oxidation of NADH , 1992 .

[30]  A. Anne,et al.  Redox potentials and acid-base equilibria of NADH/NAD+ analogs in acetonitrile , 1990 .

[31]  L. Gorton,et al.  A carbon paste electrode chemically modified with a phenothiazine polymer derivative for electrocatalytic oxidation of NADH: Preliminary study , 1993 .

[32]  H. Jägfeldt A study of the products formed in the electrochemical reduction of nicotinamide-adenine-dinucleotide , 1981 .

[33]  P. Elving,et al.  Anodic oxidation of dihydronicotinamide adenine dinucleotide at solid electrodes; mediation by surface species , 1983 .

[34]  Björn Persson,et al.  Amperometric glucose sensors based on immobilized glucose-oxidizing enzymes and chemically modified electrodes , 1991 .

[35]  F. Toda,et al.  Calatytic Mechanism and Activity of Bis(2,2':6',2"-terpyridine) rhodium(III) for the Reduction of NAD+ into NADH in a Photosensitized Reaction System. , 1993 .

[36]  A. Yu,et al.  Catalytic oxidation of NADH at a methylene-green chemically modified electrode and FIA applications , 1995 .

[37]  E. Katz,et al.  Surface‐modified gold electrodes for electrocatalytic oxidation of NADH based on the immobilization of phenoxazine and phenothiazine derivatives on self‐assembled monolayers , 1995 .

[38]  S. Fukuzumi,et al.  Mechanism of hydride transfer from an NADH model compound to p-benzoquinone derivatives , 1984 .

[39]  L. Miller,et al.  Mechanism of the oxidation of NADH by quinones. Energetics of one-electron and hydride routes , 1985 .

[40]  J. Savéant,et al.  Oxidation of 10-methylacridan, a synthetic analog of NADH and deprotonation of its cation radical: convergent application of laser flash photolysis, and direct and redox catalyzed electrochemistry to the kinetics of deprotonation of the cation radical , 1991 .

[41]  J. Kulys,et al.  Chronoamperometric and cyclic voltammetric study of carbon paste electrodes using ferricyanide and ferrocenemonocarboxylic acid , 1994 .

[42]  S. Dong,et al.  Study on electrocatalytic oxidation of NADH by ferrocene derivatives and determination of catalytic rate constant at microdisk electrode , 1995 .

[43]  Theodore Kuwana,et al.  Electrocatalysis of dihydronicotinamide adenosine diphosphate with quinones and modified quinone electrodes , 1978 .

[44]  W. Kuhr,et al.  Electrocatalytic surface for the oxidation of NADH and other anionic molecules of biological significance. , 1995, Analytical chemistry.

[45]  H. Maeda,et al.  The Co-immobilization of NAD and Dehydrogenases and Its Application to Bioreactors for Synthesis and Analysis , 1982 .

[46]  A. Fry,et al.  Cross-Linked LDH Crystals for Lactate Synthesis Coupled to Electroenzymatic Regeneration of NADH , 1996 .

[47]  Joseph Wang,et al.  Improved alcohol biosensor based on ruthenium-dispersed carbon paste enzyme electrodes , 1993 .

[48]  T. Yagi,et al.  The bacterial energy-transducing NADH-quinone oxidoreductases. , 1993, Biochimica et biophysica acta.

[49]  Hongyuan Chen,et al.  Cobalt hexacyanoferrate modified microband gold electrode and its electrocatalytic activity for oxidation of NADH , 1995 .

[50]  Harry B. Mark,et al.  Voltammetric studies of the oxidation of reduced nicotinamide adenine dinucleotide at a conducting polymer electrode , 1990 .

[51]  R. Engstrom,et al.  Reagentless enzyme electrodes for ethanol, lactate, and malate , 1980 .

[52]  Qiang Chen,et al.  Lactate biosensor based on a lactate dehydrogenase/nicotinamide adenine dinucleotide biocomposite , 1994 .

[53]  T. Yao,et al.  Specific detection of nicotinamide coenzymes by liquid chromatography and amperometric detection with immobilized glucose-6-phosphate dehydrogenase , 1989 .

[54]  G. Whitesides,et al.  Enzyme-catalyzed organic synthesis: NAD(P)H cofactor regeneration by using glucose-6-phosphate and the glucose-5-phosphate dehydrogenase from Leuconostoc mesenteroides , 1981 .

[55]  M. Comtat,et al.  Reduction of NAD(P)+ by electrochemically driven FADH2 and FMNH2 , 1992 .

[56]  E. Katz,et al.  Toluidine blue covalently immobilized onto gold electrode surfaces: An electrocatalytic system for nadh oxidation , 1994 .

[57]  K. W. Sim Steady-state model for an organic conducting salt NADH enzyme electrode , 1993 .

[58]  Arne Torstensson,et al.  Electrocatalytic oxidation of reduced nicotinamide coenzymes by graphite electrodes modified with an adsorbed phenoxazinium salt, meldola blue , 1984 .

[59]  M. Schulz,et al.  Direct Electron Transfer between Carbon Electrodes, Immobilized Mediator and an Immobilized Viologen‐accepting Pyridine Nucleotide Oxidoreductase , 1990 .

[60]  L. Gorton,et al.  Effect of surface-active agents on amperometric NADH measurements with chemically modified electrodes , 1995 .

[61]  B. Strehlitz,et al.  Mediator-modified electrodes for electrocatalytic oxidation of NADH , 1995 .

[62]  Kiyoshi Matsumoto,et al.  Co-immobilization of Alcohol Dehydrogenase, Diaphorase and NAD and Its Application to Flow Injection Analytical System for Ethanol , 1989 .

[63]  S. Fukuzumi,et al.  Energetic comparison between photoinduced electron-transfer reactions from NADH model compounds to organic and inorganic oxidants and hydride-transfer reactions from NADH model compounds to p-benzoquinone derivatives , 1987 .

[64]  Björn Persson,et al.  Selective detection in flow analysis based on the combination of immobilized enzymes and chemically modified electrodes , 1991 .

[65]  Theodore Kuwana,et al.  Stability of catechol modified carbon electrodes for electrocatalysis of dihydronicotinamide adenine dinucleotide and ascorbic acid , 1982 .

[66]  B. Keita,et al.  Oxidation of NADH by oxometalates , 1994 .

[67]  K. Cundy,et al.  Amperometric high-performance liquid chromatographic detection of NADH at a base-activated glassy carbon electrode , 1991 .

[68]  C. J. Murray,et al.  General acid catalysis of the reduction of p-benzoquinone by an NADH analog. Evidence for concerted hydride and hydron transfer , 1992 .

[69]  P. Bartlett,et al.  Amperometric enzyme electrodes: Part IV. An enzyme electrode for ethanol , 1987 .

[70]  L. Gorton,et al.  An amperometric glucose electrode based on carbon paste, chemically modified with glucose dehydrogenase, nicotinamide adenine dinucleotide, and a phenoxazine mediator, coated with a poly(ester sulfonic acid) cation exchanger , 1991 .

[71]  P. Neta,et al.  Oxidation of NADH involving rate-limiting one-electron transfer , 1984 .

[72]  T. Matsue,et al.  Electron-transfer from NADH dehydrogenase to polypyrrole and its applicability to electrochemical oxidation of NADH , 1991 .

[73]  T. Osa,et al.  Electrocatalytic Oxidation of NADH on Thin Poly(acrylic acid) Film Coated Graphite Felt Electrode Coimmobilizing Ferrocene and Diaphorase , 1993 .

[74]  H. Jägfeldt,et al.  Adsorption and electrochemical oxidation behaviour of NADH at a clean platinum electrode , 1980 .

[75]  G. Johansson,et al.  Electrochemical oxidation of reduced nicotinamide adenine dinucleotide directly and after reduction in an enzyme reactor , 1978 .

[76]  H. Abruña,et al.  Spectral, electrochemical and electrocatalytic properties of 1,10-phenanthroline-5,6-dione complexes of transition metals , 1985 .

[77]  M. Senda,et al.  Bioelectrocatalysis at NAD-Dependent Dehydrogenase and Diaphorase-Modified Carbon Paste Electrodes Containing Mediators , 1989 .

[78]  L. Miller,et al.  Electrochemical study of the kinetics of NADH being oxidized by diimines derived from diaminobenzenes and diaminopyrimidines , 1981 .

[79]  I. Katakis,et al.  Reagentless amperometric glucose dehydrogenase biosensor based on electrocatalytic oxidation of NADH by osmium phenanthrolinedione mediator , 1996 .

[80]  I. Okura,et al.  Photochemical reduction of NADP to NADPH and hydrogenation of 2-butanone using 2,2'-bipyridinium salts as electron carriers , 1988 .

[81]  H. Abruña,et al.  Thermodynamics and kinetics of adsorption and electrocatalysis of NADH oxidation with a self-assembling quinone derivative , 1995 .

[82]  Fuqiang Xu,et al.  Electrocatalytic oxidation of NADH at poly(metallophthalocyanine)-modified electrodes , 1994 .

[83]  A. Karyakin,et al.  Electroreduction of NAD+ to enzymatically active NADH at poly(neutral red) modified electrodes , 1995 .

[84]  M. Ishikawa,et al.  Mechanisms of photo-oxidation of NADH model compounds by oxygen , 1989 .

[85]  L. Gorton,et al.  Redox polymers for electrocatalytic oxidation of NADH – A random block methyl‐siloxane polymer containing meldola blue , 1995 .

[86]  N. Hampp,et al.  Electrocatalytic oxidation of reduced nicotinamide adenine dinucleotide (NADH) at thick-film gold electrodes , 1995 .

[87]  J. Marty,et al.  Bi-enzyme amperometric d-lactate sensor using macromolecular NAD+ , 1995 .

[88]  I. Katakis,et al.  Characterization and stabilization of enzyme biosensors , 1995 .

[89]  Richard S. Nicholson,et al.  Some Examples of the Numerical Solution of Nonlinear Integral Equations , 1965 .

[90]  W. Blaedel,et al.  Study of the electrochemical oxidation of reduced nicotinamide adenine dinucleotide. , 1975, Analytical chemistry.

[91]  K. Kano,et al.  Reactions between diaphorase and quinone compounds in bioelectrocatalytic redox reactions of NADH and NAD , 1995 .

[92]  A. Fry,et al.  Electroenzymatic synthesis (regeneration of NADH coenzyme) : use of nafion ion exchange films for immobilization of enzyme and redox mediator , 1994 .

[93]  J. V. Bannister,et al.  Mediatorless electrocatalysis at a conducting polymer electrode: application to ascorbate and NADH measurement , 1993 .

[94]  A. Hillman,et al.  Transport and kinetics in modified electrodes , 1984 .

[95]  J. Kulys,et al.  Reagentless Biosensors for Substrates of Dehydrogenases , 1991 .

[96]  M. Aizawa,et al.  Immobilized‐enzyme continuous‐flow reactor incorporating continuous electrochemical regeneration of NAD , 1975 .

[97]  Tetracyanoquinodimethane-mediated flow injection analysis electrochemical sensor for NADH coupled with dehydrogenase enzymes. , 1994, Analytical biochemistry.

[98]  J. Moiroux,et al.  Electrochemical regeneration of NAD in a plug‐flow reactor , 1990, Biotechnology and bioengineering.

[99]  T. Matsue,et al.  Electron transferase activity of diaphorase (NADH: acceptor oxidoreductase) from Bacillus stearothermophilus. , 1990, Biochimica et biophysica acta.

[100]  W. Schuhmann,et al.  Electrocatalytic oxidation of NADH at mediator-modified electrode surfaces , 1993 .

[101]  M. Ozsoz,et al.  Renewable alcohol biosensors based on alcohol‐dehydrogenase/nicotinamide‐adenine‐dinucleotide graphite epoxy electrodes , 1992 .

[102]  T. Yao,et al.  Electrochemical enzymatic determinations of ethanol and l-lactic acid with a carbon paste electrode modified chemically with nicotinamide adenine dinucleotide , 1979 .

[103]  W. Schuhmann,et al.  New amperometric dehydrogenase electrodes based on electrocatalytic NADH‐oxidation at poly (methylene blue)‐modified electrodes , 1994 .

[104]  T. Matsue,et al.  Immobilized-enzyme electrode for nicotinamide adenine dinucleotide (reduced form) (NADH) sensing and application to the kinetic studies of NADH dependent dehydrogenases. , 1991, The Analyst.

[105]  Héctor D. Abruña,et al.  Electrocatalysis of NADH Oxidation with Electropolymerized Films of 3,4-Dihydroxybenzaldehyde , 1994 .

[106]  Allen J. Bard,et al.  Electrochemical Methods: Fundamentals and Applications , 1980 .

[107]  P. Spedding,et al.  Regeneration of NADH in a bioreactor using yeast cells immobilized in alginate fiber: I. Method and effect of reactor variables , 1993, Biotechnology and bioengineering.

[108]  R G Whitaker,et al.  Strategies for the development of amperometric enzyme electrodes. , 1987, Biosensors.

[109]  M. Desmadril,et al.  Rate-limiting one-electron transfer in the oxidation of NADH by polyoxometalates , 1995 .

[110]  N. Oyama,et al.  Preparation of Poly(thionine)-Modified Electrode and Its Application to an Electrochemical Detector for the Flow-Injection Analysis of NADH , 1993 .

[111]  A. Murthy,et al.  NADH sensor with electrochemically modified TCNQ electrode , 1994 .

[112]  Wolfgang Schuhmann,et al.  Electrocatalytic oxidation of reduced nicotinamide coenzymes at gold and platinum electrode surfaces modified with a monolayer of pyrroloquinoline quinone. Effect of Ca2+ cations , 1994 .

[113]  E. Steckhan,et al.  Formate-Driven, Non-Enzymatic NAD(P)H Regeneration for the Alcohol Dehydrogenase Catalyzed Stereoselective Reduction of 4-Phenyl-2-butanone† , 1992 .

[114]  M. Tabata,et al.  Use of a biosensor consisting of an immobilized NADH oxidase column and a hydrogen peroxide electrode for the determination of serum lactate dehydrogenase activity , 1994 .

[115]  Jean-Louis Marty,et al.  Comparison of the performances of two bi-enzymatic sensors for the detection of D-lactate , 1995 .

[116]  L. Gorton,et al.  Reagentless chemically modified carbon paste electrode based on a phenothiazine polymer derivative and yeast alcohol dehydrogenase for the analysis of ethanol , 1993 .

[117]  G. McNally,et al.  Optimisation of the fibre production system used for the immobilisation of Saccharomyces cerevisiae employed in the production of NADH in a novel bioreactor , 1995 .

[118]  A. L. Lacey,et al.  Amperometric enzyme electrode for NADP+ based on a ferrodoxin-NADP+ reductase and viologen-modified glassy carbon electrode , 1995 .

[119]  W. Kuhr,et al.  Dehydrogenase-modified carbon-fiber microelectrodes for the measurement of neurotransmitter dynamics. 1. NADH voltammetry. , 1993, Analytical chemistry.

[120]  A. Heller,et al.  Hydrogen peroxide and .beta.-nicotinamide adenine dinucleotide sensing amperometric electrodes based on electrical connection of horseradish peroxidase redox centers to electrodes through a three-dimensional electron relaying polymer network , 1992 .

[121]  J. R. Mellado,et al.  On the electrochemical reduction of nicotinamide in an acid medium , 1989 .

[122]  Philip N. Bartlett,et al.  An organic conductor electrode for the oxidation of NADH , 1984 .

[123]  J. Kulys Development of new analytical systems based on biocatalysers , 1981 .

[124]  L. Miller,et al.  Electrochemical oxidation of NADH: Kinetic control by product inhibition and surface coating , 1984 .

[125]  L. Gorton,et al.  A comparative study of some 3,7-diaminophenoxazine derivatives and related compounds for electrocatalytic oxidation of NADH , 1990 .

[126]  B Mattiasson,et al.  A reagentless amperometric electrode based on carbon paste, chemically modified with D‐lactate dehydrogenase, NAD+, and mediator containing polymer for D‐lactic acid analysis. I. Construction, composition, and characterization , 1995, Biotechnology and bioengineering.

[127]  Anita,et al.  Tetracyanoquinodimethane (TCNQ) modified electrode for NADH oxidation , 1994 .

[128]  L. Gorton,et al.  Amperometric biosensors based on electrocatalytic regeneration of NAD+ at redox polymer-modified electrodes , 1993 .