Molecularly imprinted poly[bis(2,2'-bithienyl)methane] film with built-in molecular recognition sites for a piezoelectric microgravimetry chemosensor for selective determination of dopamine

Bioelectrochemistry

Volumn 80, Issue 1, 2010, Pages 62-72

  Pietrzyk Le, Agnieszka ^a   Suriyanarayanan, Subramanian ^a   Kutner, Wlodzimierz ^a,b   Maligaspe, Eranda ^c   Zandler, Melvin E ^c   D'Souza, Francis ^c  

^a INSTITUTE OF PHYSICAL CHEMISTRY   (Poland)

^b CARDINAL STEFAN WYSZY SKI UNIVERSITY   (Poland)

^c WICHITA STATE UNIVERSITY   (United States)

Author keywords

Barrier layer; Bis(2,2' bithienyl)methane Electropolymerization; Dopamine piezoelectric microgravimetry chemosensor; Molecularly imprinted polymers; Poly(bithiophene)

Indexed keywords

ASCORBIC ACID; BINDING SITES; ELECTRODES; ELECTROPOLYMERIZATION; EXTRACTION; METHANE; NEUROPHYSIOLOGY; PHYSIOLOGY; PIEZOELECTRICITY; PLATINUM; POLYMERS;

BARRIER LAYERS; BITHIOPHENES; CHEMOSENSOR; ELECTROCHEMICAL MEASUREMENTS; LOWER LIMIT OF DETECTIONS; MOLECULARLY IMPRINTED POLYMER; PERMEABILITY CHARACTERISTICS; SELECTIVE DETERMINATION;

AMINES;

ASCORBIC ACID; CROWN ETHER DERIVATIVE; DOPAMINE; HISTAMINE; PHENETHYLAMINE; PLATINUM; POLY(BITHIOPHENE); POLY[BIS(2,2' BITHIENYL)METHANE]; SILICON DIOXIDE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIFFERENTIAL PULSE VOLTAMMETRY; ELECTROCHEMICAL IMPEDANCE SPECTROSCOPY; ELECTROCHEMISTRY; ELECTRODE; FILM; FLOW INJECTION ANALYSIS; GRAVIMETRY; MOLECULAR IMPRINTING; MOLECULAR RECOGNITION; PIEZOELECTRICITY; POLYMERIZATION; SCANNING ELECTROCHEMICAL MICROSCOPY; SENSOR; THICKNESS; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 77957919990     PISSN: 15675394     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bioelechem.2010.03.004     Document Type: Article

References (70)

1. Stamford J.A., Justice J.B.J. Probing brain chemistry: voltammetry comes of age. Anal. Chem. 1996, 68:359A-363A.
2. Thorner M.O. Dopamine is an important neurotransmitter in the autonomic nervous system. Lancet 1975, 1:662-665.
3. Goodall M., Alton H. Dopamine (3-hydroxytyramine) metabolism in parkinsonism. J. Clin. Invest. 1969, 48:2300-2308.
4. Fischer J.E. False neurotransmitters and hepatic coma. Res. Pub. Assoc. Res. Nerv. Ment. Dis. 1974, 53:53-73.
5. Sever B.O.P.S., Birch M. Plasma-noradrenaline in essential hypertension. Lancet 1977, 1:1078-1081.
6. Goldberg L. Use of sympathomimetic amines in heart failure. Amer. J. Cardiol. 1968, 22:177-182.
7. Muskiet F.A., Fremouv-Ottevangers D.C., Meulen J. Determination of some l-3,4-dihydroxyphenylalanine and dopamine metabolites in urine by means of mass fragmentography. Clin. Chem. 1978, 24:122-127.
8. Holdiness M.R., Rosen M.T., Justice J.B., Neill D.B. Gas chromatographic-mass spectrometric determination of dopamine in subregions of rat brain. J. Chromatogr. 1980, 198:329-336.
9. Loutelier-Bourhis C., Legros H., Bonnet J.-J., Costentin J., Lange C.M. Gas chromatography/mass spectrometric identification of dopaminergic metabolites in striata of rats treated with L-DOPA. Rapid Commun. Mass Spectrom. 2004, 18:571-576.
10. Takeuchi T., Murase N., Maki H., Mukawa T., Shinmori H. Dopamine selective molecularly imprinted polymers via post-imprinting modification. Org. Biomol. Chem. 2006, 4:565-568.
11. King W.P., Joseph K.T., Kissinger P.T. Liquid chromatography with amperometric detection for determining phenolic preservatives. J. Assoc. Off. Anal. Chem. 1980, 63:137-142.
12. Shang F., Liu Y., Hrapovic S., Glennona J.D., Luong J.H.T. Selective detection of dopamine using a combined permselective film of electropolymerized (poly-tyramine and poly-pyrrole-1-propionic acid) on a boron-doped diamond electrode. Analyst 2009, 134:519-527.
13. Xu G.-R., Zhang Y.P., Tao J.Z., Kim S., Bae Z.-U. Doubly modified electrodes for the selective determination of dopamine in the presence of interfering species. Electroanalysis 2007, 19:1085-1092.
14. Xiao Y., Guo C., Li C.M., Li Y., Zhang J., Xue R., Zhang S. Highly sensitive and selective method to detect dopamine in the presence of ascorbic acid by a new polymeric composite film. Anal. Biochem. 2007, 371:229-237.
15. Xu H.T., Kitamura F., Ohsaka T., Tokuda K. Simultaneous determination of dopamine and ascorbic acid with poly(3-methylthiophene)/polypyrrole bilayer-coated carbon fiber electrodes. Anal. Sci. 1994, 10:399-404.
16. Deftereos N.T., Calokerinos A., Efstathiou C.E. Flow injection chemiluminometric determination of epinephrine, norepinephrine, dopamine and L-dopa. Analyst 1993, 118:627-632.
17. Wang H.Y., Sun Y., Tang B. Study on fluorescence property of dopamine and determination of dopamine by fluorimetry. Talanta 2002, 57:899-907.
18. Wang H.Y., Hui Q.S., Xu L.X., Jiang J.G., Sun Y. Fluorimetric determination of dopamine in pharmaceutical products and urine using ethylene diamine as the fluorigenic age. Anal. Chim. Acta 2003, 497:93-99.
19. Maminski M., Olejniczak M., Chudy M., Dybko A., Brzózka Z. Spectrophotometric determination of dopamine in microliter scale using microfluidic system based on polymeric technology. Anal. Chim. Acta 2005, 540:153-157.
20. Peng W.F., Wang E.K. Preparation and characterization of a multi-cylinder microelectrode coupled with a conventional glassy carbon electrode and its application to the detection of dopamine. Anal. Chim. Acta 1993, 281:663-671.
21. da Silva R.P., Lima A.W.O., Serrano S.H.P. Simultaneous voltammetric detection of ascorbic acid, dopamine, and uric acid using a pyrolytic graphite electrode modified into dopamine solution. Anal. Chim. Acta 2008, 612:89-98.
22. Forzani E.S., Rivas G.A., Solís V.M. Amperometric determination of dopamine on an enzymatically modified carbon paste electrode. J. Electroanal. Chem. 1995, 382:33-40.
23. Tokonami S., Shiigi H., Nagaoka T. Review: micro- and nanosized molecularly imprinted polymers for high-throughput analytical applications. Anal. Chim. Acta 2009, 641:7-13.
24. Ye L., Mosbach K. Molecular imprinting: synthetic materials as substitutes for biological antibodies and receptors. Chem. Mater. 2008, 20:859-868.
25. Kloskowski A., Pilarczyk M., Przyjazny J., Namieśnik A. Progress in development of molecularly imprinted polymers as sorbents for sample preparation. Crit. Rev. Anal. Chem. 2009, 39:43-58.
26. Suedee R., Seechamnanturakit V., Canyuk B., Ovatlarnporn C., Martin G.P. Temperature sensitive dopamine-imprinted (N, N-methylene-bis-acrylamide cross-linked) polymer and its potential application to the selective extraction of adrenergic drugs from urine. J. Chromatogr. A 2006, 1114:239-249.
27. Lulinski P., Maciejewska D., Bamburowicz-Klimkowska M., Szutowski M. Dopamine-imprinted polymers: template-monomer interactions, analysis of template removal and application to solid phase extraction. Molecules 2007, 12:2434-2449.
28. Ling T.-R., Syu Y.Z., Tasi Y.-C., Chou T.-C., Liu C.-C. Size-selective recognition of catecholoamines by molecular imprinting on silica-alumina gel. Biosens. Bioelectron. 2005, 21:901-907.
29. Makote R., Collinson M.M. Dopamine recognition in templated silicate films. Chem. Commun. 1998, 425-426.
30. Suedee R., Seechamnanturakit V., Suksuwan A., Canyuk B. Recognition properties and competitive assays of a dual dopamine/serotonin selective molecularly imprinted polymer. Int. J. Mol. Sci. 2008, 9:2333-2356.
31. Haupt K. Imprinted polymers - tailor-made mimics of antibodies and receptors. Chem. Commun. 2003, 171-178.
32. Petcu M., Karlsson J.G., Whitcombe M.J., Nicholls I.A. Probing the limits of molecular imprinting: strategies with a template of limited size and functionality. J. Mol. Recogn. 2009, 8:18-25.
33. Öpik A., Menaker A., Reut J., Syritski V. Molecularly imprinted polymers: a new approach to the preparation of functional materials. Proc. Est. Acad. Sci. 2009, 58:3-11.
34. Lakshmi D., Bossi A., Whitcombe A.J., Chianella I., Fowler S.A., Subrahmanyam S., Piletska E.V., Piletsky S.A. Electrochemical sensor for catechol and dopamine based on a catalytic molecularly imprinted polymer-conducting polymer hybrid recognition element. Anal. Chem. 2008, 81:3576-3584.
35. Haupt K., Mosbach K. Molecularly imprinted polymers and their use in biomimetic sensors. Chem. Rev. 2000, 100:2495-2504.
36. Alexander C., Andersson H.S., Andersson L.I., Ansell R.J., Kirsch N., Nicholls I.A., O'Mahoney J., Whitcombe M.J. Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003. J. Mol. Recogn. 2006, 19:106-180.
37. Stobiecka M., Deeb J., Hepel M. Molecularly templated polymer matrix films for biorecognition processes: sensors for evaluating oxidative stress and redox buffering capacity. ECS Trans. 2009, 19:15-32.
38. Marx K.A. Quartz crystal microbalance: a useful tool for studying thin polymer films and complex biomolecular systems at the solution-surface interface. Biomacromolecules 2003, 4:1099-1120.
39. Pietrzyk A., Suriyanarayanan S., Kutner W., Chitta R., D'Souza F. Selective histamine piezoelectric chemosensor using a recognition film of the molecularly imprinted polymer of bis(bithiophene) derivatives. Anal. Chem. 2009, 81:2633-2643.
40. Pietrzyk A., Kutner W., Chitta R., Zandler M.E., D'Souza F., Sannicolo F., Mussini P.R. Melamine acoustic chemosensor based on molecularly imprinted polymer film. Anal. Chem. 2009, 81:10061-10070.
41. Kröger S., Turner A.P.F., Mosbach K., Haupt K. Imprinted polymer-based sensor system for herbicides using differential-pulse voltammetry on screen-printed electrodes. Anal. Chem. 1999, 71:3698-3702.
42. Kriz D., Mosbach K. Competitive amperometric morphine sensor based on an agarose immobilised molecularly imprinted polymer. Anal. Chim. Acta 1995, 300:71-75.
43. Pizzariello A., Stredansky M., Stredanska S., Miertus S. A solid binding matrix/molecularly imprinted polymer-based sensor system for the determination of clenbuterol in bovine liver using differential-pulse voltammetry. Sens. Actuators, B 2001, 76:286-294.
44. Yasuo Y., Ryo O., Chiaki I., Kiyotaka S. "Gate effect" of thin layer of molecularly-imprinted poly(methacrylic acid-co-ethyleneglycol dimethacrylate). Sens. Actuators, B 2001, 73:49-53.
45. Dayton M.A., Ewing A.G., Wightman R.M. Response of microvoltammetric electrodes to homogeneous catalytic and slow heterogeneous charge-transfer reactions. Anal. Chem. 1980, 52:2392-2396.
46. Gonon F.G., Navarre F., Buda M.J. In vivo monitoring of dopamine release in the rat brain with differential normal pulse voltammetry. Anal. Chem. 1984, 56:573-575.
47. Biancardo M., Krebs F.C. Battery effects in organic photovoltaics based on polybithiophene. Sol. Energy Mater. Sol. Cells 2008, 92:353-356.
48. 2bilayers by electrochemical impedance spectroscopy and photoelectrochemistry. Electrochim. Acta 2001, 46:2363-2371.
49. Aeiyach S., Bazzaoui E.A., Lacaze P.C. Electropolymerization of thiophene on oxidizable metals in organic media. J. Electroanal. Chem. 1997, 434:153-162.
50. Wang G., Wong T.K.S., Hu X. Influence of thickness of electrochemically deposited hole-transport film on electroluminescent properties. Appl. Phys. A 2000, 71:117-120.
51. Trznadel M., Pron A., Zagorska M., Chrzaszcz R., Pielichowski J. Effect of molecular weight on spectroscopic and spectroelectrochemical properties of regioregular poly(3-hexylthiophene). Macromolecules 1998, 31:5051-5058.
52. Demadrille R., Divisia-Blohorn B., Zagorska M., Quillard S., Rannou P., Traversa J.P., Pron A. Preparation and spectroelectrochemical behaviour of a new alternate copolymer of 3, 3-di-n-octyl-2, 2-bithiophene and fluoren-9-one. New J. Chem. 2003, 27:1479-1484.
53. Pietrzyk A., Suriyanarayanan S., Kutner W., Chitta R., Zandler M., D'Souza F. Molecularly Imprinted Polymer (MIP) based piezoelectric microgravimetry chemosensor for selective determination of adenine. Biosens. Bioelectron 2010, 25:2522-2529.
54. Kochman A., Krupka A., Grissbach J., Kutner W., Gniewinska B., Nafalski L. Design and performance of a new thin-layer radial-flow holder for a quartz crystal resonator of an electrochemical quartz crystal microbalance. Electroanalysis 2006, 18:2168-2173.
55. Frisch M.J.T., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B.G., Chen W., Wong M.W., Andres J.L., Head-Gordon M., Replogle E.S., Pople J.A. Gaussian 03 2003, Gaussian, Inc, Pittsburgh PA.
56. Luczak T. Electrochemical oxidation of dopamine in the presence of secondary amine. An alternative way for quantitative dopamine determination at a gold electrode. Electroanalysis 2008, 20:1639-1646.
57. Razmi H., Azadbakht A. Electrochemical characteristics of dopamine oxidation at palladium hexacyanoferrate film, electroless plated on aluminum electrode. Electrochim. Acta 2005, 50:2193-2201.
58. Skompska M., Jackson A., Hillman A.R. Evolution from gravimetric to viscoelastic response of poly(3-methylthiophene)-loaded acoustic wave resonators. Phys. Chem. Chem. Phys. 2000, 2:4748-4757.
59. Liu A., Zhao L., Bai H., Zhao H., Xing X., Shi G. Polypyrrole actuator with a bioadhesive surface for accumulating bacteria from physiological media. ACS Appl. Mater. Interfaces 2009, 1:951-955.
60. Adenier A., Chehimi M.M., Gallardo I., Pinson J., Vila N. Electrochemical oxidation of aliphatic amines and their attachment to carbon and metal surfaces. Langmuir 2004, 20:8243-8253.
61. Zheng W.T., Xing K.Z., Hellgren N., Lögdlund M., Johansson Å., Gelivs U., Salaneck W.R., Sundgren J.-E. Nitrogen ls electron binding energy assignment in carbon nitride thin films with different structures. J. Electron Spectrosc. Relat. Phenom. 1997, 87:45-49.
62. Liu J., Li Q., Yu Y., Fang X. Spectroscopic and electrochemical studies of DNA breakage induced by dopamine and copper ion. Analyt. Sci. 2003, 19:1099-1102.
63. Madrakian T., Afkhami A., Khalafi L., Mohammadnejad M. Spectrophotometric determination of catecholamines based on their oxidation reaction followed by coupling with 4-aminobenzoic acid. J. Braz. Chem. Soc. 2006, 17:1259-1265.
64. A. Lasia, Modern Aspects of Electrochemistry, B. E. Conway, J. Bockris, R. E. White, Kluwer Academic/Plenum, 1999, 143 pp.
65. Williams M.E., Hupp J.T. Scanning electrochemical microscopy assessment of rates of molecular transport through mesoporous thin-films of porphyrinic "Molecular Squares". J. Phys. Chem. B 2001, 105:8944-8950.
66. Berfield J.L., Wang L.C., Reith M.E.A. Which form of dopamine is the substrate for the human dopamine transporter: the cationic or the uncharged species?. J. Biol. Chem. 1999, 274:4876-4882.
67. Skladal P. Piezoelectric quartz crystal sensors applied for bioanalytical assays and characterization of affinity interactions. J. Braz. Chem. Soc. 2003, 14:491-502.
68. Halamek J., Hepel M., Skladal P. Investigation of highly sensitive piezoelectric immunosensors for 2, 4-dichlorophenoxyacetic acid. Biosen. Bioelectron. 2001, 16:253-260.
69. Pribyl J., Hepel M., Skladal P. Piezoelectric immunosensors for polychlorinated biphenyls operating in aqueous and organic phases. Sens. Actuators B 2006, 113:900-910.
70. Liu Z., Zhang J., Fei J., Guo L. A novel mechanism of dopamine neurotoxicity involving the peripheral extracellular and the plasma membrane dopamine transporter. Neuropharmacol. Neurotoxicol. 2001, 12:3293-3297.