Conducting Polymers for DNA Sensors and DNA Chips: from Fabrication to Molecular Detection

Perspectives in Bioanalysis

Volumn 1, Issue C, 2005, Pages 297-330

  Mailley, Pascal ^a   Roget, André ^a   Livache, Thierry ^a  

^a Departement de Recherches Fondamentales sur la Matiere Condensee CEA Grenoble   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77956977167     PISSN: 18710069     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1871-0069(05)01008-6     Document Type: Article

References (102)

1. Alfonta L., Singh A.K., and Willner I. Liposomes labeled with biotin and horseradish peroxidase: A probe for the enhanced amplification of antigen-antibody or oligonucleotide-DNA sensing processes by the precipitation of an insoluble product on electrodes. Anal. Chem. 73 (2001) 91-102
2. Armistead P.M., and Thorp H.H. Modification of indium tin oxide electrodes with nucleic acids: Detection of attomole quantities of immobilized DNA by electrocatalysis. Anal. Chem. 72 (2000) 3764-3770
3. Azek A., Grossiord C., Joannes M., Limoges B., and Brossier P. Hybridization assay at a disposable electrochemical biosensor for the attomole detection of amplified human cytomegalovirus DNA. Anal. Biochem. 284 (2000) 107-113
4. Bae A.H., Hatano T., Numata M., Takeuchi M., and Shinkai S. Higher-order conformations of DNA are useful templates to create various superstructural poly(pyrrole) morphologies. Chem. Lett. 33 (2004) 436-437
5. Bartlett P.N., and Cooper J.M. A review of the immobilization of enzymes in electropolymerized films. J. Electroanal. Chem. 362 (1993) 1-12
6. Brabec V. Nucleic acid analysis by voltammetry at carbon electrodes, Bioelectrochem. Bioenerg. 8 (1981) 437-449
7. Cai H., Xu Y., He P.-G., and Fang Y.-Z. Indicator free DNA hybridization detection by impedance measurement based on the DNA-doped conducting polymer film formed on the carbon nanotube modified electrode. Electroanalysis 15 (2003) 1864-1870
8. Cai H., Zhu N., Jiang Y., He P., and Fang Y. Cu@Au alloy nanoparticle as oligonucleotide labels for electrochemical stripping detection of DNA hybridization, Biosens. Bioelectron. 18 (2003) 1311-1319
9. Caillat, P., Cuzin, M., and Hofmeister, A., 2003. Wafer scale biomolecule grafting: The first step for low cost, high throughput active biochip manufacturing, Electron Devices Meeting, 2003. IEDM 03 Technical Digest, IEEE Int. 8-10(Dec.), 31.4.1-31.4.4
10. Calvoz-Muñoz M.-L., Dupont Filliard A., Billon M., Guillerez S., Bidan G., Marquette C., and Blum L. Detection of DNA hybridization by ABEI electrochemiluminescence in DNA-chip compatible assembly. Bioelectrochemistry 66 (2005) 139-143
11. Caruana D.J., and Heller A. Enzyme amplified amperometric detection of hybridization and of a single base pair mutation in a 18-base oligonucleotides on a 7-μm-diameter microelectrode. J. Am. Chem. Soc. 121 (1999) 769-774
12. Cha J., Han J.I., Choi Y., Yoon D.S., Oh K.W., and Lim G. DNA hybridization electrochemical sensor using conductive polymer. Biosens. Bioelectron. 18 (2003) 1241-1247
13. Cosnier S. Biomolecule immobilization on electrode surfaces by entrapment or attachment to electrochemically polymerized films. A review. Biosens. Bioelectron. 14 (1999) 443-456
14. Cosnier S. Biosensors based on electropolymerised films: New trends. Anal. Bioanal. Chem. 377 (2003) 507-520
15. Cosnier S., and Le Pellec A. Poly(pyrrole-biotin): A new polymer for biomolecule grafting on electrode surfaces. Electrochim. Acta 44 (1999) 1833-1836
16. Cuzin M. DNA chips: A new tool for genetic analysis and diagnostics, Transfus. Clin. Biol. 8 (2001) 291-296
17. Deshpande M.V., and Hall E.A.H. An electrochemically grown polymer as an immobilization matrix for whole cells: Application in an amperometric dopamine sensor. Biosens. Bioelectron. 5 (1990) 431-448
18. Dryhurst G. Electrochemical determination of adenine and adenosine: Adsorption of adenine and adenosine at the pyrolytic graphite electrode. Talanta 18 (1972) 769-787
19. Dryhurst G., and Pace G.F. Electrochemical oxidation of guanine at the pyrolytic graphite electrode. J. Electrochem. Soc. 117 (1970) 1259-1264
20. Dupont-Filliard A., Roget A., Livache T., and Billon M. Reversible oligonucleotide immobilization based on biotinylated polypyrrole film. Anal. Chim. Acta 449 (2001) 45-50
21. Emge A., and Bäuerle P. Synthesis and molecular recognition properties of DNA- and RNA-base-functionalized oligo- and polythiophenes, Synth. Met. 84 (1997) 213-214
22. Emr S.A., and Yacynych A.M. Use of polymer films in amperometric biosensors. Electroanalysis 7 (1995) 913-923
23. Faïd, K. and M. Leclerc, 1996, Functionalized regioregular polythiophenes: Towards the development of biochromic sensors, Chem. Commun. 1761-1762.
24. Farace G., Lillie G., Hianik T., Payne P., and Vadgama P. Reagentless biosensing using electrochemical impedance spectroscopy. Bioelectrochemistry 55 (2002) 1-3
25. Fiaccabrino G.C., Koudelka-Hep M., Jeannret M., Van den Berg A., and de Rooij N.F. Array of individually addressable microelectrodes. Sens. Actuat. B 18-19 (1994) 675-677
26. Fodor S.P.A., Read J.L., Pirrung M.C., Stryer L., Lu A.T., and Solas D. Light-directed, spatially addressable parallel chemical synthesis. Science 251 (1991) 767-773
27. Fortin E., Defontaine Y., Mailley P., Livache T., and Szunerits S. Micro-imprinting of oligonucleotides and oligonucleotide gradients on gold surface: A new approach based on the combination of Scanning Electrochemical Microscopy and Surface Plasmon Resonance imaging (SECM/SPR-i). Electroanalysis 17 (2005) 495-503
28. Foulds N.C., and Lowe C.R. Enzyme entrapment in electrically conducting polymers. J. Chem. Soc. Faraday Trans. 1 82 (1986) 1259-1264
29. Furtado L.M., and Thompson M. Hybridization of complementary strands and single-base mutated oligonucleotides detected with an on-line acoustic wave sensor. Analyst 123 (1998) 1937-1945
30. Galasso K., Livache T., Roget A., and Vieil E. Electrogravimetric detection of DNA hybridization on polypyrrole copolymer. J. Chim. Phys. 95 (1998) 1514-1517
31. Gambhir A., Gerard M., Jain K.S., and Malhotra B.D. Characterization of DNA immobilized on electrochemically prepared conducting polypyrrole-polyvinyl sulfonate films. Appl. Biochem. Biotech. 96 (2001) 303-309
32. Garnier F.P., Korri-Youssoufi H., Strivastava P., Mandrand B., and Delair T. Toward intelligent polymers: DNA sensors based on oligonucleotide-functionalized polypyrroles. Synth. Met. 100 (1999) 89-94
33. Gaskin, M., V.-E. Choong, S. Gallagher, C. Li, G. Maracas and S. Si, 2001, Worldwide Patent WO014258, Motorola Inc.
34. Gerard M., Chaubey A., and Malhotra B.D. Application of conducting polymers to biosensors. Biosens. Bioelectron. 17 (2001) 345-359
35. Gheorghe M., Lei C., and Guiseppi-Elie A. Low-density arrays of DNA-doped polypyrrole. Polym. Mat. Sci. Eng. 83 (2000) 551-552
36. Godillot P., Korri-Youssoufi H., Strivastava P., El Kassmi A., and Garnier F. Direct chemical functionalization of as-grown electroactive polypyrrole film containing leaving groups. Synth Met. 83 (1996) 117-123
37. Gu H., Su G., and Loh K.P. Conductive polymer-modified boron doped diamond for DNA hybridization analysis. Chem. Phys. Lett. 388 (2004) 483-487
38. Guedon P., Livache T., Roget A., Martin F., Lesbre F., Bidan G., and Levy Y. Characterization and optimization of a real time, parallel, label free, polypyrrole-based DNA sensor by surface plasmon resonance imaging. Anal. Chem. 72 24 (2000) 6003-6006
39. Ho H.-A., Boissinot M., Bergeron M.B., Corbeil G., Doré K., Boudreau D., and Leclerc M. Colorimetric and fluorimetric detection of nucleic acids using cationic polythiophene derivatives. Angew. Chem. Int. Ed. 41 (2002) 1548-1551
40. Ho H.-A., and Leclerc M. Optical sensors based on hybrid aptamer/conjugated polymer complexes. J. Am. Chem. Soc. 126 (2004) 1384-1387
41. Ihara, T., M. Nakayama, M. Murata, K. Nakano, and M. Maeda, 1997, Gene sensor using ferrocenyl oligonucleotides, Chem. Commun. 1609-1610.
42. Jelen F., Yosypchuk B., Kourilova A., Novotny L., and Palecek E. Label-free determination of picogram quantities of DNA by stripping voltammetry with solid copper amalgam or mercury electrodes in the presence of copper. Anal. Chem. 74 (2002) 4788-4793
43. Katz E., Willner I., and Wang J. Electroanalytical and bioelectroanalytical systems based on metal and semiconductor nanoparticles. Electroanalysis 16 (2004) 19-44
44. Korri-Youssoufi H., Garnier F., Srivastava P., Godillot P., and Yassar A. Toward bioelectronics: Specific DNA recognition based on an oligonucleotide-functionalized polypyrrole. J. Am. Chem. Soc. 119 (1997) 7388-7389
45. Korri-Youssoufi H., and Makrouf B. Electrochemical biosensing of DNA hybridization by ferrocenyl groups functionalized polypyrrole. Anal. Chim. Acta 469 (2002) 85-92
46. Kranz C., Gaub H.E., and Schuhmann W. Polypyrrole towers grown with the scanning electrochemical microscope. Adv. Mater. 8 (1996) 634-637
47. Krishnamoorty, K., R.S. Gokhale, A.Q. Contractor and A. Kumar, 2004, Novel label-free DNA sensors based on poly(3,4-ethylenedioxythiophene), Chem. Commun. 820-821.
48. Lassalle N., Mailley P., Vieil E., Livache T., Roget A., Correia J.P., and Abrantes L.M. Electronically conductive polymer grafted with oligonucleotides as electrosensors of DNA - Preliminary study of real time monitoring by in situ techniques. J. Electroanal. Chem. 509 (2001) 48-57
49. Lassalle N., Roget A., Livache T., Mailley P., and Vieil E. Electropolymerisable pyrrole-oligonucleotide: Synthesis and analysis of ODN hybridization by fluorescence and QCM. Talanta 55 (2001) 993-1004
50. Lassalle N., Vieil E.A., Correia J.P., and Abrantes L.M. Study of DNA hybridization on polypyrrole grafted with oligonucleotides by photocurrent spectroscopy. Biosens. Bioelectron. 16 (2001) 295-303
51. Lassalle N., Vieil E., Correia J.P., and Abrantes L.M. Study of DNA hybridization by photocurrent spectroscopy. Synth. Met. 119 (2001) 407-408
52. Lee T.-Y., and Shim Y.-B. Direct hybridization detection based on oligonucleotides-functionalized conductive polymer. Anal. Chem. 73 (2003) 5629-5632
53. Lei C., Gheorghe M., and Guiseppi-Elie A. DNA immobilization and bioelectronic detection based on conducting polymers. Polym. Mat. Sci. Eng. 83 (2000) 552-553
54. Li L.-L., Cai H., Lee T.M.-H., Barford J., and Hsing I.-M. Electrochemical detection of PCR amplicons using electroconductive polymer modified electrode and multiple nanoparticles labels. Electroanalysis 16 (2004) 81-87
55. Li C.M., Sun C.Q., Song S., Choong V.E., Maracas G., and Zhang X.J. Impedance labelless detection-based polypyrrole DNA biosensor. Front. Biosci. 10 (2005) 180-186
56. Lim J.-H., and Mirkin C.A. Electrostatically driven dip-pen nanolithography of conducting polymers. Adv. Mater. 14 (2002) 1474-1477
57. Livache T., Bazin H., Caillat P., and Roget A. Electroconducting polymers for the construction of DNA or peptide arrays on silicon chip. Biosens. Bioelectron. 13 (1998) 629-634
58. Livache T., Fouque B., Roget A., Marchand J., Bidan G., Teoule R., and Mathis G. Polypyrrole DNA chip on silicon device; example of Hepatitis C virus genotyping. Anal. Biochem. 255 (1998) 188-194
59. Livache T., Guedon P., Brakha C., Roget A., Levy Y., and Bidan G. Polypyrrole electrospotting for the construction of oligonucleotide arrays compatible with a surface plasmon resonance hybridization detection. Synth. Met. 121 (2001) 1443-1444
60. Livache T., Maillart E., Lassalle N., Mailley P., Corso B., Guedon P., Roget A., and Levy Y. Polypyrrole based DNA hybridization assays: Study of label free detection processes versus fluorescence on microchips. J. Pharm. Biomed. Anal. 32 (2003) 687-696
61. Livache T., Roget A., Dejean E., Barthet C., Bidan G., and Teoule R. Preparation of a DNA matrix via an electrochemically directed copolymerization of pyrrole and oligonucleotides bearing a pyrrole group. Nucleic Acids Res. 22 (1994) 2915-2921
62. Lofas S.M., Malmqvist M., Roennberg I., Stenberg E., Liedberg B., and Lundstroem I. Bioanalysis with surface plasmon resonance. Sens. Actuat. B 5 (1991) 79-84
63. Lopez-Crapez E., Livache T., Marchand J., and Grenier J. K-ras mutation detection by hybridization to a polypyrrole DNA chip. Clin. Chem. 47 2 (2001) 186-194
64. Ma Y., Zhang J., Zhang G., and He H. Polyaniline nanowires on Si surfaces fabricated with DNA templates. J. Am. Chem. Soc. 126 (2004) 7097-7101
65. Maillart E., Brengel-Pesce K., Capela D., Roget A., Livache T., Canva M., Levy Y., and Soussi T. Versatile analysis of multiple macromolecular interactions by SPR imaging: Application to p53 and DNA interaction. Oncogene 23 32 (2004) 5543-5550
66. Marx K.A., Lim J.O., Minehan D.S., Pande R., Kamath M., Tripathy S., and Kaplan D.L. Intelligent biomaterials properties of DNA and strategies for its incorporation into electroactive polymeric thin film systems. J. Intel. Mater. Syst. Struct. 5 (1994) 447-454
67. McQuade D.T., Pullen A.E., and Swager T.M. Conjugated polymer-based chemical sensors. Chem. Rev. 100 (2000) 2537-2574
68. Minehan D.S., Marx K.A., and Tripathy S. Kinetics of DNA binding to electrically conducting polypyrrole films. Macromolecules 27 (1994) 777-783
69. Minehan D.S., Marx K.A., and Tripathy S. DNA binding to electropolymerized polypyrrole: The dependence on film characteristics. J. Macromol. Sci. Pure Appl. Chem. A 38 (2001) 1245-1258
70. Misoska V., Price W.E., Ralph S.F., Wallace G.G., and Ogata N. Synthesis, characterization and ion transport studies on polypyrrole/deoxyribonucleic acid conducting polymer membranes. Synth. Met. 123 (2001) 279-286
71. Nagarajan R., Liu W., Kumar J., Tripathy S.K., Bruno F.F., and Samuelson L.A. DNA conformation switching using a templated conducting polymer. Polym. Mat. Sci. Eng. 83 (2000) 546-547
72. Nagarajan R., Tripathy S.K., Kumar J., Bruno F.F., and Samuelson L.A. Manipulating DNA conformation using intertwined conducting polymer chains. Macromolecules 34 (2001) 3921-3927
73. Nilsson K.P.R., and Inganäs O. Chip and solution detection of DNA hybridization using a luminescent zwitterionic polythiophene derivative. Nat. Mater. 2 (2003) 419-421
74. Nilsson K.P.R., Rydberg J., Baltzer L., and Inganäs O. Self-assembly of synthetic peptides control conformation and optical properties of a zwitterionic polythiophene derivative. Proc. Natl. Acad. Sci. USA 100 (2003) 10171-10174
75. Okahata Y., Kawase M., Niikura K., Ohtake F., Furusawa H., and Ebara Y. Kinetic measurements of DNA hybridization on an oligonucleotide-immobilized 27-MHz quartz crystal microbalance. Anal. Chem. 70 (1998) 1288-1296
76. Pande R., Ruben G.C., Lim J.O., Tripathy S., and Marx K.A. DNA bound to polypyrrole films: High-resolution imaging, DNA binding kinetics and internal migration. Biomaterials 19 (1998) 1657-1667
77. Peng, H., Soeller, C. Vigar, N. Kilmartin, P.A. Cannell, M.B., Bowmaker, G.A., Cooney, R.P., Travas-Sejdic, J., 2005. Label-free electrochemical DNA sensor based on functionalised conducting copolymer, 20, 1821-1828.
78. Pham, M.-C., Piro, Tran L.D., B., Ledoan, T. Dao, L.H., 2003. Direct electrochemical detection of oligonucleotides hybridization on poly (5-hydroxy-1,4- naphtoquinone-co-5hydroxy-3-thioacetic acid-1,4- naphtoquinone) film, Anal. Chem. 75, 6748-6752.
79. Pike A.R., Patole S.N., Murray N.C., Ilyas T., Connolly B.A., Horrocks B.R., and Houlton A. Covalent and non covalent attachment and patterning of polypyrrole at silicon surfaces. Adv. Mater. 15 (2003) 254-257
80. Piro B., Haccoun J., Tran L.D., Rubin A., Perrot H., and Gabrielli C. Characterization of a quinine-containing électroactive polymer film used as DNA sensor. Study of the hybridization mechanism by cyclic voltammetry and electrochemical impedance spectroscopy. J. Electroanal. Chem. 577 (2005) 155-165
81. Piro B., Pham M.-C., and Ledoan T. Electrochemical method for entrapment of oligonucleotides in polymer-coated electrodes. J. Biomed. Mater. Res. 46 (1999) 566-572
82. Pirrung M.C. How to make a DNA chip, Angew. Chem. Int. Ed. 41 (2002) 1276-1289
83. Purvis D., Leonardova O., Farmakovsky D., and Cherkasov V. An ultrasensitive and stable potentiometric immunosensor. Biosens. Bioelectron. 18 (2003) 1385-1390
84. Ramanaviciene A., and Ramanavicius A. Pulsed amperometric detection of DNA with an ssDNA/polypyrrole-modified electrode. Anal. Bioanal. Chem. 379 (2004) 287-293
85. Roget A., and Livache T. In situ synthesis and copolymerization of oligonucleotides on conducting polymers. Mikrochim. Acta 131 (1999) 3-8
86. Saoudi B., Despas C., Chehimi M.M., Jammul N., Delamar M., Bessiere J., and Walcarius A. Study of DNA adsorption on polypyrrole: Interest of dielectric monitoring. Sens. Actuat. B 62 (2000) 35-42
87. Saoudi B., Jammul N., Abel M.-L., Chehimi M.M., and Dodin G. DNA adsorption onto conducting polypyrrole. Synth. Met. 87 (1997) 97-103
88. Shimidzu T. Functionalized conducting polymers for development of new polymeric reagents. React. Polym. 6 (1987) 221-227
89. Szunerits, S., L. Bouffier, B. Corso, K. Brakha, Y. Defontaine, M. Demeunynck, E. Descamps, J.-B. Fiche, E. Fortin, N. Lassalle, T. Livache, P. Mailley, A. Roget, E. Vieil, and B. Wang, 2005, Review on different strategies on DNA chip fabrication as well as DNA-sensing: Optical and electrochemical approaches, Submitted paper.
90. Szunerits S., Knorr N., Calemczuk R., and Livache T. New approach to writing and simultaneous reading of micropatterns: Combining surface plasmon resonance imaging with scanning electrochemical microscopy (SECM). Langmuir 20 21 (2004) 9236-9241
91. Takenaka, S., 2003, Electrochemical detection of DNA with small molecules, 'DNA and RNA Binders: From Small Molecules to Drugs', Eds. M. Demeunynck, C. Bailly and W.D. Wilson, Wiley-VCH, Weinheim, pp. 224-246.
92. Thompson L.A., Kowalik J., Josowicz M., and Janata J. Label-free DNA hybridization probe based on a conducting polymer. J. Am. Chem. Soc. 125 (2003) 324-325
93. Torres-Rodriguez, L.M., Roget, A. Billon, M. Livache T. and Bidan G. 1998, Synthesis of a biotin functionalized pyrrole and its electropolymerization: Toward a versatile avidin biosensor, Chem. Commun. 1993-1994.
94. Umana M., and Waller J. Protein-modified electrodes. The glucose oxidase/polypyrrole system. Anal. Chem. 58 (1986) 2979-2983
95. Wang B., Bouffier L., Demeunynck M., Mailley P., Roget A., Livache T., and Dumy P. New acridone derivatives for the electrochemical DNA-hybridization labelling. Bioelectrochemistry 63 (2004) 233-237
96. Wang J., Cai X., Rivas G., Shiraishi H., and Dontha N. Nucleic-acid immobilization, recognition and detection at chronopotentiometric DNA chips. Biosens. Bioelectron. 12 (1997) 587-599
97. Wang J., and Jiang M. Toward genoelectronics: Nucleic acid doped conducting polymers. Langmuir 16 (2000) 2269-2274
98. Wang J., Jiang M., Fortes A., and Mukherjee B. New label-free DNA recognition based on doping nucleic-acid probes within conducting polymer films. Anal. Chim. Acta 402 (1999) 7-12
99. Wang J., and Mukherjee B. Recognition and detection of oligonucleotides in the presence of chromosomal DNA based on entrapment within conducting polymer network. J. Electroanal. Chem. 500 (2001) 584-589
100. Wu J., Zou Y., Liu H., Shen G., and Yu R. A biosensor monitoring DNA hybridization based on polyaniline intercalated graphite oxide nanocomposite. Sens. Actuat. B 104 (2005) 43-49
101. Xu Y., Jiang Y., Cai H., He P.-G., and Fang Y.-Z. Electrochemical impedance detection of DNA hybridization based on the formation of M-DNA on polypyrrole/carbon nanotube modified electrode, Anal. Chim. Acta 516 (2004) 19-27
102. Yamamoto T., Shimizu T., and Kurokawa E. Doping behaviour of water-soluble π-conjugated polythiophenes depending on pH and interaction of the polymer with DNA. React. Funct. Polym. 43 (2000) 79-84