Electrochemistry of methylene blue bound to a DNA-modified electrode

Bioconjugate Chemistry

Volumn 8, Issue 1, 1997, Pages 31-37

  Kelley, Shana O ^a   Barton, Jacqueline K ^a   Jackson, Nicole M ^b   Hill, Michael G ^b  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b OCCIDENTAL COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CYCLIC VOLTAMMETRY; ELECTRODES; OLIGONUCLEOTIDES; REDOX REACTIONS; SOLUTIONS; SURFACE WAVES;

BASE PAIRS; CHRONOCOULOMETRY; DNA DUPLEXES; DNA-MODIFIED ELECTRODES; DNA-OLIGONUCLEOTIDES; GOLD SURFACES; LABELINGS; METHYLENE BLUE; MODIFIED ELECTRODES; SURFACE COVERAGES;

DNA;

EID: 0031041964     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc960070o     Document Type: Article

References (73)

1. Stemp, E. D. A., and Barton, J. K. (1996) Electron transfer between metal complexes bound to DNA: Is DNA a molecular wire? Met. Ions Biol. Syst. 33, 325.
2. (a) Szent-Györgyi, A., Isenberg, I., and Baird, S. L. (1960) On the electron donating properties of carcinogens. Proc. Natl. Acad. Sci. U.S.A. 46, 1444.
3. (b) Snart, R. S. (1968) Photoelectric effects of deoxyribonucleic acid. Biopolymers 6, 293.
4. (c) Dee, D., and Baur, M. E. (1974) Charge and excitation migration in DNA chains. J. Chem. Phys. 60, 541.
5. (a) Magan, J. D., Blau, W., Croke, D. T., McConnell, D. J., and Kelly, J. M. (1987) One-dimensional photoconductivity in DNA. Chem. Phys. Lett. 141, 489.
6. (b) Cullis, P. M., McClymont, J. D., and Symons, M. C. R. (1990) Electron conduction and trapping in DNA: an electron spin resonance study. J. Chem. Soc., Faraday Trans. 86, 591.
7. (c) Houee-Levin, C., Gardes-Albert, M., Rouscilles, A., Ferradini, C., and Hickel, B. (1991) Intramolecular semiquinone disproportionation in DNA. Pulse radioylsis study of the one-electron reduction of daunorubicin intercalated in DNA. Biochemistry 30, 8216.
8. (d) Anderson, R. F., Patel, K. B., and Wilson, W. R. (1991) Determination of the one-electron reduction potential of electron-affinic compounds intercalated into DNA. J. Chem. Soc., Faraday Trans. 87, 3739.
9. Hall, D. B., Holmlin, R. E., and Barton, J. K. (1996) Oxidative DNA damage through long range electron transfer. Nature 382, 731.
10. (a) Palecek, E., Kolar, V., Jelen, F., and Heinemann, U. (1990) Electrochemical analysis of the self-complementary B-DNA decamer d(CCAGGGCTGG). Bioelectrochem. Bioenerg. 23, 285.
11. (b) Brett, C. M. A., Brett, A. M. O., and Serrano, S. H. P. (1994) On the adsorption and electrochemical oxidation of DNA at glassy carbon electrodes. J. Electroanal. Chem. 366, 225.
12. (a) Jovanovic, S. V., and Simic, M. G. (1986) One-electron redox potentials of purines and pyrimidines. J. Phys. Chem. 90, 974.
13. (b) Colson, A.-O., Besler, B., Close, D. M., and Sevilla, M. D. (1992) Ab initio molecular-orbital calculations of DNA bases and their radical ions in various protonation states: evidence for proton-transfer in GC base pair radical anions. J. Phys. Chem. 96, 661.
14. Armitage, B., Yu, C., Devadoss, C., and Schuster, G. B. (1994) Cationic anthraquinone derivatives as catalytic DNA photonucleases: mechanisms for DNA-damage and quinone recycling. J. Am. Chem. Soc. 116, 9847.
15. (a) Johnston, D. H., Cheng, C. C., Campbell, K. J., and Thorp, H. H. (1994) Trans-dioxorhenium(V)-mediated electrocatalytic oxidation of DNA at indium tin oxide electrodes: voltammetric detection of DNA cleavage in solution. Inorg. Chem. 33, 6388.
16. (b) Cheng, C. C., Goll, J. G., Neyhart, G. A., Welch, T. W., Singh, P., and Thorp, H. H. (1995) Relative rates and potentials of competing redox processes during DNA cleavage: oxidation mechanisms and sequence-specific catalysis of the self-inactivation of oxometal oxidants by DNA. J. Am. Chem. Soc. 117, 2970.
17. (a) Baguley, B. C., and LeBret, M. (1984) Quenching of DNA-ethidium fluorescence by amsacrine and other antitumor agents: a possible electron transfer effect. Biochemistry 23, 937.
18. (b) Fromhertz, P., and Rieger, B. (1986) Photoinduced electron transfer in DNA matrix from intercalated ethidium to condensed methylviologen. J. Am. Chem. Soc. 108, 5361.
19. (a) Brun, A. M., and Harriman, A. (1992) Dynamics of electron transfer between intercalated polycyclic molecules: effect of interspersed bases. J. Am. Chem. Soc. 114, 3656.
20. (b) Brun, A. M., and Harriman, A. (1994) Energy-transfer and electron-transfer processes involving palladium porphyrins bound to DNA. J. Am. Chem. Soc. 116, 10383.
21. Meade, T. J., and Kayyem, J. F. (1995) Electron-transfer through DNA: site-specific modification of duplex DNA with ruthenium donors and accepters. Angew. Chem., Int. Ed. Engl. 34, 352.
22. (a) Barton, J. K., Kumar, C. V., and Turro, N. J. (1986) DNA-mediated photoelectron transfer reactions. J. Am. Chem. Soc. 108, 6391.
23. (b) Purugganan, D., Kumar, C. V., Turro, N. J., and Barton, J. K. (1988) Accelerated electron-transfer between metal complexes mediated by DNA. Science 241, 1645.
24. Murphy, C. J., Arkin, M. A., Ghatlia, N. D., Bossman, S., Turro, N. J., and Barton, J. K. (1993) Long-range photoinduced electron transfer through a DNA helix. Science 262, 1025.
25. Murphy, C. J., Arkin, M. A., Ghatlia, N. D., Bossman, S., Turro, N. J., and Barton, J. K. (1994) Fast photoinduced electron transfer through DNA intercalation. Proc. Natl. Acad. Sci. U.S.A. 91, 5315.
26. (a) Stemp, E. D. A., Arkin, M. R., and Barton, J. K. (1995) Electron-transfer between metallointercalators bound to DNA: spectral identification of the transient intermediate. J. Am. Chem. Soc. 117, 2375.
27. (b) Arkin, M. R., Stemp, E. D. A., Turro, C., Turro, N., and Barton, J. K. (1996) Luminescence quenching in supramolecular systems: a comparison of DNA-mediated and SDS micelle-mediated photoinduced electron transfer between metal complexes. J. Am. Chem. Soc. 118, 2267.
28. (c) Arkin, M. R., Stemp, E. D. A., Holmlin, R. E., Barton, J. K., Hörmann, A., Olson, E. J. C., and Barbara, P. A. (1996) Rates of DNA-mediated electron transfer between metallointercalators. Science 273, 475.
29. 2+ in photoinduced DNA-mediated electron transfer reactions. J. Am. Chem. Soc. 118, 5236.
30. (a) Carter, M. T., Rodriguez, M., and Bard, A. J. (1989) Voltammetric Studies of the interaction of metal chelates with DNA. 2. Tris-chelated complexes of cobalt(III) and iron(II) with 1,10-phenanthroline and 2,2′-bipyridine. J. Am. Chem. Soc. 111, 8901.
31. (b) Carter, M. T., and Bard, A. J. (1990) Electrochemical investigations of the interaction of metal chelates with DNA. 3. Electrogenerated chemiluminescent investigation of the interaction of tris(1,10-phenanthroline)-ruthenium(II) with DNA. Bioconjugate Chem. 1, 257.
32. (c) Rodriguez, M., and Bard, A. J. (1990) Electrochemical studies of the interaction of metal chelates with DNA. 4. Voltammetric and electrogenerated chemiluminescent studies of the interaction of tris(2,2′-bipyridine)osmium(II) with DNA. Anal. Chem. 62, 2658-2662.
33. (a) Welch, T. W., Corbett, A. H., and Thorp, H. H. (1995) Electrochemical determination of nucleic acid diffusion coefficients through noncovalent association of a redox-active probe. J. Phys. Chem. 99, 11757.
34. (b) Kelly, J. M., Lyons, M. E. G., and Van Der Putten, W. J. M. (1986) In Electrochemistry, Sensors and Analysis (M. R. Smyth and J. G. Vos, Eds.) pp 205-213, Elsevier, Amsterdam.
35. (c) Molinier-Jumel, C., Malfoy, B., Raymond, J., Reynaud, J. A., and Aubel-Sadron, G. (1978) Electrochemical study of DNA-anthracyclines interaction. Biochem. Biophys. Res. Commun. 84, 441.
36. (d) Berg, H., Horn, G., Luthardt, U., and Ihn, W. (1981) Interaction of anthracycline antibiotics with biopolymers. Part V. Polarographic behavior and complexes with DNA. Bioelectrochem. Bioenerg. 8, 537.
37. (e) Plambeck, J., and Lown, J. W. (1984) Electrochemical studies of antitumor antibiotics. 5. An electrochemical method of measurement of the binding of doxorubicin and daunorubicin derivatives to DNA. J. Electrochem. Soc. 131, 2556.
38. Johnston, D. H., Glasgow, K. C., and Thorp, H. H. (1995) Electrochemical measurement of the solvent accessibility of nucleobases using electron transfer between DNA and metal complexes. J. Am. Chem. Soc. 117, 8933.
39. (a) Hashimoto, K., Ito, K., and Ishimori, Y. (1994) Sequence-specific gene detection with a gold electrode modified with DNA probes and an electrochemically active dye. Anal. Chem. 66, 3830.
40. (b) Hashimoto, K., Ito, K., and Ishimori, Y. (1994) Novel DNA sensor for electrochemical gene detection. Anal. Chim. Acta 286, 219.
41. Okahata, Y., Matsunobu, Y., Ijiro, K., Mukae, M., Murakami, A., and Makino, K. (1992) Hybridization of nucleic acids immobilized on a quartz crystal microbalance. J. Am. Chem. Soc. 114, 8300.
42. Millan, K. M., and Mikkelsen, S. R. (1993) Sequence-selective biosensor for DNA based on electroactive hybridization indicators. Anal. Chem. 65, 2317-2323.
43. (a) Xu, X.-H., Yang, H. C., Mallouk, T. E., and Bard, A. J. (1994) Immobilization of DNA on an aluminum(III) alkanebisphosphonate thin film with electrogenerated chemiluminsecent detection. J. Am. Chem. Soc. 116, 8386.
44. (b) Xu, X.-H., and Bard, A. J. (1995) Immobilization and hybridization of DNA on an aluminum(III) alkanebisphosphonate thin film with electrogenerated chemiluminescent detection. J. Am. Chem. Soc. 117, 2627.
45. (a) Maeda, M., Mitsuhashi, Y., Nakano, K., and Takagi, M. (1992) DNA-immobilized gold electrode for DNA-binding sensor. Anal. Sci. 8, 83.
46. 2+-selective electrode comprising double-helical DNA as receptive entity. Chem. Lett. 1805.
47. Ulman, A. (1991) An Introduction to Ultrathin Organic Films: from Langmuir-Blodgett to Self-Assembly, Academic Press, Boston.
48. (a) Zutic, V., Svetlicic, V., Lovric, M., Ruzic, I., and Chevalet, J. (1984) Electron-transfer kinetics of an adsorbed redox couple by double potential-step chronocoulometry: methylene blue leucomethylene blue. J. Electroanal. Chem. 177, 253.
49. (b) Svetlicic, V., Clavilier, J., Zutic, V., and Chevalet, J. (1991) Electrochemical evidence of 2-dimensional surface compounds of heterocyclic molecules at sulfur-covered gold and platinum. 1. Methylene blue. J. Electroanal. Chem. 312, 205.
50. (c) Ju, H., Zhou, J., Cai, C., and Chen, H. (1995) The electrochemical behavior of methylene blue at a microcylinder carbon-fiber electrode. Electroanalysis 7, 1165.
51. (a) Bradley, D. F., Stellwagen, N. C., O'Konski, C. T., and Paulson, C. M. (1972) Electric birefringence and dichroism of acridine orange and methylene blue complexes with polynucleotides. Biopolymers 11, 645.
52. (b) Nordén, B., and Tjerneld, F. (1982) Structure of methylene blue-DNA complexes studied by linear and circular dichrism spectroscopy. Biopolymers 21, 1713.
53. (c) Tuite, E., and Nordén, B. (1994) Sequence-specific interactions of methylene blue with polynucleotides and DNA: a spectroscopic study. J. Am. Chem. Soc. 116, 7548.
54. (d) Tuite, E., and Kelly, J. M. (1995) The interaction of methylene blue, azure B, and thionine with DNA: formation of complexes with polynucleotides and mononucleotides as model systems. Biopolymers 35, 419.
55. Beaucage, S. L., and Caruthers, M. H. (1981) Deoxynucleoside phosphoramidites: a new class of key intermediates for deoxypolynucleotide synthesis. Tetrahedron Lett. 22, 1859.
56. (a) Widrig, C. A., Alves, C. A., and Porter, M. D. (1991) Scanning tunneling microscopy of ethanethiolate and normal-octadecanethiolate monolayers spontaneously adsorbed at gold surfaces. J. Am. Chem. Soc. 113, 2805.
57. (b) Zei, M. S., Nakai, Y., Lehmpfuhl, G., and Kolb, D. M. (1983) The structure of gold and silver films evaporated on glass: a LEED and RHEED study. J. Electroanal. Chem. 150, 201.
58. (a) Nahir, T. M., Clark, R. A., and Bowden, E. F. (1994) Linear-sweep voltammetry of irreversible electron transfer in surface-confined species using Marcus theory. Anal. Chem. 66, 2595.
59. (b) Weber, K., and Creager, S. E. (1994) Voltammetry of redox-active grouops irreversibly adsorbed onto electrodes: treatment using the Marcus relation between rate and overpotential. Anal. Chem. 66, 3164.
60. (c) Tender, L., Carter, M. T., and Murray, R. W. (1994) Cyclic voltammetric analysis of ferrocene alkanethiol monolayer electrode kinetics based on Marcus theory. Anal. Chem. 66, 3173.
61. Laviron, E. (1975) A critical study of the factors causing the appearance of Brdicka's adsorption currents. Influence of the interactions between adsorbed molecules. J. Electroanal. Chem. 63, 254.
62. Sabatini, E., Rubinstein, I., Maoz, R., and Sagiv, J. (1987) Oraganized self-assembling monolayers on electrodes. 1. Octadecyl derivatives on gold. J. Electroanal. Chem. 219, 365.
63. Finklea, H. O., Snider, D. A., and Fedyk, J. (1990) Passivation of pinholes in octadecanethiol monolayers on gold electrodes by electrochemical polymerization of phenol. Langmuir 6, 371.
64. Widrig, C. A., Chung, C., and Porter, M. D. (1991) The electrochemical desorption of n-alkanethiol monolayers from polycrystalline Au and Ag electrodes. J. Electroanal. Chem. 310, 335.
65. Matthews, C. K., and Van Holde, K. E. (1990) Biochemistry, Benjamin Cummings, Redwood City, CA.
66. Bard, A. J., and Faulkner, L. R. (1980) Electrochemical Methods, Wiley and Sons, New York.
67. Christie, J. H., Anson, F. C., Lauer, G., and Osteryoung, R. A. (1963) Determination of charge passed following application of potential step in study of electrode processes. Anal. Chem. 35, 1979.
68. Connors, K. A. (1987) Binding Constants: The Measurement of Molecular Complex Stability, Wiley-Interscience, New York.
69. Crothers, D. M. (1968) Calculation of binding isotherms for heterogeneous polymers. Biopolymers 6, 575.
70. Chidsey, C. E. D., Bertozzi, C. R., Putvinski, T. M., and Mujsce, A. M. (1990) Coadsorption of ferrocene-terminated and unsubstituted alkanethiols on gold: electroactive self-assembled monolayers. J. Am. Chem. Soc. 112, 4301.
71. (a) Smalley, J. F., Feldberg, S. W., Chidsey, C. E. D., Linford, M. R., Newton, M. D., and Liu, Y. (1995) The kinetics of electron transfer through ferrocene-terminated alkanethiol monolayers on gold. J. Phys. Chem. 99, 13141.
72. (b) Finklea, H. O., and Hanshew, D. D. (1992) Electron-transfer kinetics in organized hiol monolayers with attached pentaammine-(pyridine)ruthenium redox centers. J. Am. Chem. Soc. 114, 3173.
73. Marcus, R. A., Sutin, N. (1985) Electron transfers in chemistry and biology. Biochim. Biophys. Acta 811, 265.