Information processing through a bio-based redox capacitor: Signatures for redox-cycling

Bioelectrochemistry

Volumn 98, Issue , 2014, Pages 94-102

  Liu, Yi ^a,b   Kim, Eunkyoung ^a,b   White, Ian M ^b   Bentley, William E ^a,b   Payne, Gregory F ^a,b  

^a UNIVERSITY OF MARYLAND   (United States)

^b UNIVERSITY OF MARYLAND   (United States)

Author keywords

Biofabrication; Chitosan; Electrodeposition; Redox cycling; Signal processing

Indexed keywords

CAPACITORS; CHITOSAN; DATA PROCESSING; DRUG PRODUCTS; ELECTROCHEMISTRY; ELECTRODEPOSITION; ELECTRODES; ELECTRONIC PROPERTIES; ORGANOMETALLICS; SIGNAL PROCESSING;

BIOFABRICATION; CHEMICAL ACTIVITIES; ELECTROCHEMICAL MEDIATORS; POLYSACCHARIDE HYDROGELS; REACTIVE OXYGEN SPECIES; REDOX-ACTIVE COMPOUNDS; REDOX-CYCLING; SIGNAL AMPLIFICATIONS;

REDOX REACTIONS;

ASCORBIC ACID; CATECHOL; FERROCENE; METHANOL; PARACETAMOL; POLYSACCHARIDE; PYOCYANINE; FERROCENEMETHANOL; FERROUS ION; REACTIVE OXYGEN METABOLITE; RUTHENIUM DERIVATIVE;

ARTICLE; CONTROLLED STUDY; ELECTROCHEMISTRY; ELECTRODE; HYDROGEL; INFORMATION PROCESSING; OXIDATION REDUCTION REACTION; SENSITIVITY ANALYSIS; VELOCITY; CHEMISTRY; ELECTROCHEMICAL ANALYSIS; GENETIC PROCEDURES; THERMODYNAMICS;

ACETAMINOPHEN; ASCORBIC ACID; BIOSENSING TECHNIQUES; ELECTROCHEMICAL TECHNIQUES; ELECTRODES; FERROUS COMPOUNDS; OXIDATION-REDUCTION; PYOCYANINE; REACTIVE OXYGEN SPECIES; RUTHENIUM COMPOUNDS; THERMODYNAMICS;

EID: 84899151760     PISSN: 15675394     EISSN: 1878562X     Source Type: Journal    
DOI: 10.1016/j.bioelechem.2014.03.012     Document Type: Article

References (71)

1. Wlodzimirow K.A., Abu-Hanna A., Schultz M.J., Maas M.A.W., Bos L.D.J., Sterk P.J., Knobel H.H., Soers R.J.T., Chamuleau R.A.F.M. Exhaled breath analysis with electronic nose technology for detection of acute liver failure in rats. Biosens. Bioelectron. 2014, 53:129-134.
2. van de Kant K.D.G., van der Sande L., Jobsis Q., van Schayck O.C.P., Dompeling E. Clinical use of exhaled volatile organic compounds in pulmonary diseases: a systematic review. Respir. Res. 2012, 13:117.
3. Tisch U., Schlesinger I., Ionescu R., Nassar M., Axelrod N., Robertman D., Tessler Y., Azar F., Marmur A., Aharon-Peretz J., Haick H. Detection of Alzheimer's and Parkinson's disease from exhaled breath using nanomaterial-based sensors. Nanomedicine 2012, 8:43-56.
4. Santonico M., Pennazza G., Capuano R., Falconi C., Vink T.J., Knobel H.H., Van der Schee M.P., Sterk P.J., Montuschi P., D'Amico A. Electronic noses calibration procedure in the context of a multicentre medical study. Sensors Actuators B Chem. 2012, 173:555-561.
5. Espey M.G. Role of oxygen gradients in shaping redox relationships between the human intestine and its microbiota. Free Radic. Biol. Med. 2013, 55:130-140.
6. Okegbe C., Sakhtah H., Sekedat M.D., Price-Whelan A., Dietrich L.E.P. Redox eustress: roles for redox-active metabolites in bacterial signaling and behavior. Antioxid. Redox Signal. 2012, 16:658-667.
7. Jacob C., Jamier V., Ba L.A. Redox active secondary metabolites. Curr. Opin. Chem. Biol. 2011, 15:149-155.
8. Lau G.W., Hassett D.J., Ran H.M., Kong F.S. The role of pyocyanin in Pseudomonas aeruginosa infection. Trends Mol. Med. 2004, 10:599-606.
9. Graham G.G., Davies M.J., Day R.O., Mohamudally A., Scott K.F. The modern pharmacology of paracetamol: therapeutic actions, mechanism of action, metabolism, toxicity and recent pharmacological findings. Inflammopharmacology 2013, 21:201-232.
10. Boutaud O., Moore K.P., Reeder B.J., Harry D., Howie A.J., Wang S., Carney C.K., Masterson T.S., Amin T., Wright D.W., Wilson M.T., Oates J.A., Roberts L.J. Acetaminophen inhibits hemoprotein-catalyzed lipid peroxidation and attenuates rhabdomyolysis-induced renal failure. Proc. Natl. Acad. Sci. U. S. A. 2010, 107:2699-2704.
11. Uzi D., Barda L., Scaiewicz V., Mills M., Mueller T., Gonzalez-Rodriguez A., Valverde A.M., Iwawaki T., Nahmias Y., Xavier R., Chung R.T., Tirosh B., Shibolet O. CHOP is a critical regulator of acetaminophen-induced hepatotoxicity. J. Hepatol. 2013, 59:495-503.
12. Shchepin R.V., Liu W., Yin H., Zagol-Ikapitte I., Amin T., Jeong B.-S., Roberts L.J., Oates J.A., Porter N.A., Boutaud O. Rational design of novel pyridinol-fused ring acetaminophen analogues. ACS Med. Chem. Lett. 2013, 4:710-714.
13. Johnston P.A., Soares K.M., Shinde S.N., Foster C.A., Shun T.Y., Takyi H.K., Wipf P., Lazo J.S. Development of a 384-well colorimetric assay to quantify hydrogen peroxide generated by the redox cycling of compounds in the presence of reducing agents. Assay Drug Dev. Technol. 2008, 6:505-518.
14. Kishikawa N., Higuchi S., Ohyama K., Nakashima K., Kuroda N. A simple and rapid chemiluminescence assay for on-site analysis of paraquat using a portable luminometer. Forensic Toxicol. 2013, 31:301-306.
15. Kishikawa N., Ohkubo N., Ohyama K., Nakashima K., Kuroda N. Selective determination of ubiquinone in human plasma by HPLC with chemiluminescence reaction based on the redox cycle of quinone. Anal. Bioanal. Chem. 2011, 400:381-385.
16. Kishikawa N., Ohkubo N., Ohyama K., Nakashima K., Kuroda N. Chemiluminescence assay for quinones based on generation of reactive oxygen species through the redox cycle of quinone. Anal. Bioanal. Chem. 2009, 393:1337-1343.
17. Martin K.R., Narang P., Medina-Franco J.L., Meurice N., MacKeigan J.P. Integrating virtual and biochemical screening for protein tyrosine phosphatase inhibitor discovery. Methods 2014, 65:219-228.
18. Johnston P.A. Redox cycling compounds generate H2O2 in HTS buffers containing strong reducing reagents-real hits or promiscuous artifacts?. Curr. Opin. Chem. Biol. 2011, 15:174-182.
19. Baell J.B. Redox-active nuisance screening compounds and their classification. Drug Discov. Today 2011, 16:840-841.
20. 2 by redox cycling in reducing environments. Assay Drug Dev. Technol. 2010, 8:152-174.
21. Rana P., Naven R., Narayanan A., Will Y., Jones L.H. Chemical motifs that redox cycle and their associated toxicity. MedChemComm 2013, 4:1175-1180.
22. Yang H. Enzyme-based ultrasensitive electrochemical biosensors. Curr. Opin. Chem. Biol. 2012, 16:422-428.
23. Walter A., Wu J., Flechsig G.-U., Haake D.A., Wang J. Redox cycling amplified electrochemical detection of DNA hybridization: application to pathogen E. coli bacterial RNA. Anal. Chim. Acta. 2011, 689:29-33.
24. Kim E., Liu Y., Shi X.-W., Yang X., Bentley W.E., Payne G.F. Biomimetic approach to confer redox activity to thin chitosan films. Adv. Funct. Mater. 2010, 20:2683-2694.
25. Kim E., Leverage W.T., Liu Y., White I.M., Bentley W.E., Payne G.F. Redox-capacitor to connect electrochemistry to redox-biology. Analyst 2014, 139:32-43.
26. Gray K.M., Kim E., Wu L.Q., Liu Y., Bentley W.E., Payne G.F. Biomimetic fabrication of information-rich phenolic-chitosan films. Soft Matter 2011, 7:9601-9615.
27. Kim E., Gordonov T., Bentley W.E., Payne G.F. Amplified and in situ detection of redox-active metabolite using a biobased redox capacitor. Anal. Chem. 2013, 85:2102-2108.
28. Kim E., Gordonov T., Liu Y., Bentley W.E., Payne G.F. Reverse engineering to suggest biologically relevant redox activities of phenolic materials. ACS Chem. Biol. 2013, 8:716-724.
29. 2 generation by fabricated catecholic films in the absence of enzymes. Biomacromolecules 2011, 12:880-888.
30. Kim E., Liu Y., Bentley W.E., Payne G.F. Redox capacitor to establish bio-device redox-connectivity. Adv. Funct. Mater. 2012, 22:1409-1416.
31. Suginta W., Khunkaewla P., Schulte A. Electrochemical biosensor applications of polysaccharides chitin and chitosan. Chem. Rev. 2013, 113:5458-5479.
32. Koev S.T., Dykstra P.H., Luo X., Rubloff G.W., Bentley W.E., Payne G.F., Ghodssi R. Chitosan: an integrative biomaterial for lab-on-a-chip devices. Lab Chip 2010, 10:3026-3042.
33. Wu L.Q., Gadre A.P., Yi H.M., Kastantin M.J., Rubloff G.W., Bentley W.E., Payne G.F., Ghodssi R. Voltage-dependent assembly of the polysaccharide chitosan onto an electrode surface. Langmuir 2002, 18:8620-8625.
34. Liu Y., Zhang B., Gray K.M., Cheng Y., Kim E., Rubloff G.W., Bentley W.E., Wang Q., Payne G.F. Electrodeposition of a weak polyelectrolyte hydrogel: remarkable effects of salt on kinetics, structure and properties. Soft Matter 2013, 9:2703-2710.
35. Liu Y., Kim E., Lee M.E., Zhang B., Elabd Y.A., Wang Q., White I.M., Bentley W.E., Payne G.F. Enzymatic writing to soft films: potential to filter, store, and analyze biologically relevant chemical information. Adv. Funct. Mater. 2014, 24:480-491.
36. Kviecinski M.R., Pedrosa R.C., Felipe K.B., Farias M.S., Glorieux C., Valenzuela M., Sid B., Benites J., Valderrama J.A., Verrax J., Buc Calderon P. Inhibition of cell proliferation and migration by oxidative stress from ascorbate-driven juglone redox cycling in human bladder-derived T24 cells. Biochem. Biophys. Res. Commun. 2012, 421:268-273.
37. Kovacic P., Somanathan R. Recent developments in the mechanism of anticancer agents based on electron transfer, reactive oxygen species and oxidative stress. Anti Cancer Agents Med. Chem. 2011, 11:658-668.
38. Toyooka T., Shinmen T., Aarts J., Ibuki Y. Dual effects of N-acetyl-l-cysteine dependent on NQO1 activity: suppressive or promotive of 9,10-phenanthrenequinone-induced toxicity. Toxicol. Appl. Pharmacol. 2012, 264:404-412.
39. Shaaban S., Diestel R., Hinkelmann B., Muthukumar Y., Verma R.P., Sasse F., Jacob C. Novel peptidomimetic compounds containing redox active chalcogens and quinones as potential anticancer agents. Eur. J. Med. Chem. 2012, 58:192-205.
40. Bussy U., Delaforge M., El-Bekkali C., Ferchaud-Roucher V., Krempf M., Tea I., Galland N., Jacquemin D., Boujtita M. Acebutolol and alprenolol metabolism predictions: comparative study of electrochemical and cytochrome P450-catalyzed reactions using liquid chromatography coupled to high-resolution mass spectrometry. Anal. Bioanal. Chem. 2013, 405:6077-6085.
41. Baumann A., Pfeifer T., Melles D., Karst U. Investigation of the biotransformation of melarsoprol by electrochemistry coupled to complementary LC/ESI-MS and LC/ICP-MS analysis. Anal. Bioanal. Chem. 2013, 405:5249-5258.
42. Simon H., Melles D., Jacquoilleot S., Sanderson P., Zazzeroni R., Karst U. Combination of electrochemistry and nuclear magnetic resonance spectroscopy for metabolism studies. Anal. Chem. 2012, 84:8777-8782.
43. Jahn S., Baumann A., Roscher J., Hense K., Zazzeroni R., Karst U. Investigation of the biotransformation pathway of verapamil using electrochemistry/liquid chromatography/mass spectrometry-a comparative study with liver cell microsomes. J. Chromatogr. A 2011, 1218:9210-9220.
44. Odijk M., Baumann A., Olthuis W., van den Berg A., Karst U. Electrochemistry-on-chip for on-line conversions in drug metabolism studies. Biosens. Bioelectron. 2010, 26:1521-1527.
45. Mali'n T.J., Weidolf L., Castagnoli N., Jurva U. P450-catalyzed vs. electrochemical oxidation of haloperidol studied by ultra-performance liquid chromatography/electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2010, 24:1231-1240.
46. Baumann A., Karst U. Online electrochemistry/mass spectrometry in drug metabolism studies: principles and applications. Expert Opin. Drug Metab. Toxicol. 2010, 6:715-731.
47. Jurva U., Holmen A., Gronberg G., Masimirembwa C., Weidolf L. Electrochemical generation of electrophilic drug metabolites: characterization of amodiaquine quinoneimine and cysteinyl conjugates by MS, IR, and NMR. Chem. Res. Toxicol. 2008, 21:928-935.
48. Melles D., Vielhaber T., Baumann A., Zazzeroni R., Karst U. In chemico evaluation of skin metabolism: Investigation of eugenol and isoeugenol by electrochemistry coupled to liquid chromatography and mass spectrometry. J. Chromatogr. B 2013, 913:106-112.
49. Melles D., Vielhaber T., Baumann A., Zazzeroni R., Karst U. Electrochemical oxidation and protein adduct formation of aniline: a liquid chromatography/mass spectrometry study. Anal. Bioanal. Chem. 2012, 403:377-384.
50. Zaki M.E.A., Bettencourt A.P., Fernandes F.M., Proenca M.F. Synthesis and electrochemical evaluation of substituted imidazo 4,5-d pyrrolo 3,2-f 1,3 diazepine scaffolds. Tetrahedron 2012, 68:4628-4634.
51. Lavaggi M.L., Nieves M., Cabrera M., Olea-Azar C., de Cerain A.L., Monge A., Cerecetto H., Gonzalez M. Structural modifications on the phenazine N, N'-dioxide-scaffold looking for new selective hypoxic cytotoxins. Eur. J. Med. Chem. 2010, 45:5362-5369.
52. Dietrich L.E.P., Teal T.K., Price-Whelan A., Newman D.K. Redox-active antibiotics control gene expression and community behavior in divergent bacteria. Science 2008, 321:1203-1206.
53. Price-Whelan A., Dietrich L.E.P., Newman D.K. Pyocyanin alters redox homeostasis and carbon flux through central metabolic pathways in Pseudomonas aeruginosa PA14. J. Bacteriol. 2007, 189:6372-6381.
54. Price-Whelan A., Dietrich L.E., Newman D.K. Rethinking 'secondary' metabolism: physiological roles for phenazine antibiotics. Nat. Chem. Biol. 2006, 2:71-78.
55. Hao Y.H., Kuang Z.H., Xu Y., Walling B.E., Lau G.W. Pyocyanin-induced mucin production is associated with redox modification of FOXA2. Respir. Res. 2013, 14:14.
56. Lau G.W., Ran H.M., Kong F.S., Hassett D.J., Mavrodi D. Pseudomonas aeruginosa pyocyanin is critical for lung infection in mice. Infect. Immun. 2004, 72:4275-4278.
57. Branski L.K., Al-Mousawi A., Rivero H., Jeschke M.G., Sanford A.P., Herndon D.N. Emerging infections in burns. Surg. Infect. (Larchmt) 2009, 10:389-397.
58. Tredget E.E., Shankowsky H.A., Rennie R., Burrell R.E., Logsetty S. Pseudomonas infections in the thermally injured patient. Burns 2004, 30:3-26.
59. Sheng L.L., Pu M.M., Hegde M., Zhang Y.X., Jayaraman A., Wood T.K. Interkingdom adenosine signal reduces Pseudomonas aeruginosa pathogenicity. Microb. Biotechnol. 2012, 5:560-572.
60. Shimizu K., Ogura H., Goto M., Asahara T., Nomoto K., Morotomi M., Yoshiya K., Matsushima A., Sumi Y., Kuwagata Y., Tanaka H., Shimazu T., Sugimoto H. Altered gut flora and environment in patients with severe SIRS. J. Trauma Inj. Infect. Crit. Care 2006, 60:126-133.
61. Foyer C.H., Noctor G. Ascorbate and glutathione: the heart of the redox hub. Plant Physiol. 2011, 155:2-18.
62. Roginsky V.A., Barsukova T.K., Stegmann H.B. Kinetics of redox interaction between substituted quinones and ascorbate under aerobic conditions. Chem. Biol. Interact. 1999, 121:177-197.
63. Paz M.M. Reductive activation of mitomycins A and C by vitamin C. Bioorg. Chem. 2013, 48:1-7.
64. Vasquez D.R., Verrax J., Valderrama J.A., Calderon P.B. Aminopyrimidoisoquinolinequinone (APIQ) redox cycling is potentiated by ascorbate and induces oxidative stress leading to necrotic-like cancer cell death. Invest. New Drugs 2012, 30:1003-1011.
65. Sanchez-Cruz P., Garcia C., Alegria A.E. Role of quinones in the ascorbate reduction rates of S-nitrosoglutathione. Free Radic. Biol. Med. 2010, 49:1387-1394.
66. Verrax J., Delvaux M., Beghein N., Taper H., Gallez B., Buc Calderon P. Enhancement of quinone redox cycling by ascorbate induces a caspase-3 independent cell death in human leukaemia cells. An in vitro comparative study. Free Radic. Res. 2005, 39:649-657.
67. Lodge J.K. Molecular actions of ascorbic acid. Curr. Top. Nutraceutical Res. 2008, 6:1-13.
68. Parkinson E.I., Bair J.S., Cismesia M., Hergenrother P.J. Efficient NQO1 substrates are potent and selective anticancer agents. ACS Chem. Biol. 2013, 8:2173-2183.
69. Madamanchi N.R., Vendrov A., Runge M.S. Oxidative stress and vascular disease. Arterioscler. Thromb. Vasc. Biol. 2005, 25:29-38.
70. Jones D.P. Redefining oxidative stress. Antioxid. Redox Signal. 2006, 8:1865-1879.
71. Woolley J.F., Stanicka J., Cotter T.G. Recent advances in reactive oxygen species measurement in biological systems. Trends Biochem. Sci. 2013, 38:556-565.