Hierarchical thin film architectures for enhanced sensor performance: Liquid crystal-mediated electrochemical synthesis of nanostructured imprinted polymer films for the selective recognition of bupivacaine

Biosensors

Volumn 4, Issue 2, 2014, Pages 90-110

  Suriyanarayanan, Subramanian ^a   Nawaz, Hazrat ^a   Ndizeye, Natacha ^a   Nicholls, Ian A ^a,b  

^a LINNAEUS UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

Bupivacaine; Electropolymerization; Liquid crystal; Molecularly imprinted polymer; Nanostructured polymer films; Piezoelectric sensor; Quartz crystal microbalance

Indexed keywords

BIOMATERIALS; ELECTROPOLYMERIZATION; FILM PREPARATION; GOLD COATINGS; LIQUID CRYSTALS; NANOFIBERS; QUARTZ; QUARTZ CRYSTAL MICROBALANCES; SPECTROSCOPIC ANALYSIS; THIN FILMS;

BUPIVACAINE; ELECTROCHEMICAL SYNTHESIS; ELECTROPOLYMERISATION; LIQUID CRYSTALLINE; LIQUID-CRYSTALS; MOLECULARLY IMPRINTED POLYMER; NANO-STRUCTURED; NANOSTRUCTURED POLYMER FILM; NANOSTRUCTURED POLYMERS; PIEZOELECTRIC SENSORS;

POLYMER FILMS;

BUPIVACAINE; MOLECULARLY IMPRINTED POLYMER; NANOFIBER; NANOFILM;

ARCHITECTURE; ARTICLE; CHEMICAL COMPOSITION; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; ELECTROCHEMICAL ANALYSIS; FILM; FILM COATING; FLOW INJECTION ANALYSIS; LIQUID CRYSTAL; MOLECULAR IMPRINTING; MOLECULAR RECOGNITION; POLYMERIZATION; QUARTZ CRYSTAL MICROBALANCE; SCANNING ELECTRON MICROSCOPE; SCANNING ELECTRON MICROSCOPY; TASK PERFORMANCE; X RAY DIFFRACTION;

EID: 84902329632     PISSN: None     EISSN: 20796374     Source Type: Journal    
DOI: 10.3390/bios4020090     Document Type: Article

References (67)

1. Daikhin, L.; Urbakh, M. Effect of surface film structure on the quartz crystal microbalance response in liquids. Langmuir 1996, 12, 6354-6360.
2. Zhang, Z.; Lu, D.-F.; Liu, Q.; Qi, Z.-M.; Yang, L.; Liu, J. Wavelength-interrogated surface plasmon resonance sensor with mesoporous-silica-film-enhanced sensitivity to small molecules. Analyst 2012, 137, 4822-4828.
3. Hotta, K.; Yamaguchi, A.; Teramae, N. Nanoporous waveguide sensor with optimized nanoarchitectures for highly sensitive label-free biosensing. ACS Nano 2012, 6, 1541-1547.
4. Berrier, A.; Offermans, P.; Cools, R.; van Megen, B.; Knoben, W.; Vecchi, G.; Rivas, J.G.; Crego-Calama, M.; Brongersma, S.H. Enhancing the gas sensitivity of surface plasmon resonance with a nanoporous silica matrix. Sens. Actuator B Chem. 2011, 160, 181-188.
5. Gaur, G.; Koktysh, D.S.; Weiss, S.M. Immobilization of quantum dots in nanostructured porous silicon films: Characterizations and signal amplification for dual-mode optical biosensing. Adv. Funct. Mater. 2013, 23, 3604-3614.
6. Niu, X.; Li, Y.; Tang, J.; Hu, Y.; Zhao, H.; Lan, M. Electrochemical sensing interfaces with tunable porosity for nonenzymatic glucose detection: A Cu foam case. Biosens. Bioelectron. 2014, 51, 22-28.
7. Ates, M. A review study of (bio)sensor systems based on conducting polymers. Mater. Sci. Eng. C 2013, 33, 1853-1859.
8. Anraku, Y.; Takahashi, Y.; Kitano, H.; Hakari, M. Recognition of sugars on surface-bound cap-shaped gold particles modified with a polymer brush. Colloids Surf. B 2007, 57, 61-68.
9. Suriyanarayanan, S.; Lee, H.-H.; Liedberg, B.; Aastrup, T.; Nicholls, I.A. Protein-resistant hyperbranched polyethyleneimine brush surfaces. J. Colloid Interface Sci. 2013, 396, 307-315.
10. Whitcombe, M.J.; Chianella, I.; Larcombe, L.; Piletsky, S.A.; Noble, J.; Porter, R.; Horgan, A. The rational development of molecularly imprinted polymer-based sensors for protein detection. Chem. Soc. Rev. 2011, 40, 1547-1571.
11. Mayes, A.G.; Whitcombe, M.J. Synthetic strategies for the generation of molecularly imprinted organic polymers. Adv. Drug Deliv. Rev. 2005, 57, 1742-1778.
12. Alexander, C.; Andersson, H.S.; Andersson, L.I.; Ansell, R.J.; Kirsch, N.; Nicholls, I.A.; O'Mahony, J.; Whitcombe, M.J. Molecular imprinting science and technology: A survey of the literature for the years up to and including 2003. J. Mol. Recognit. 2006, 19, 106-180.
13. Olsson, G.D.; Karlsson, B.C.G.; Shoravi, S.; Wiklander, J.G.; Nicholls, I.A. Mechanisms underlying molecularly imprinted polymer molecular memory and the role of crosslinker: Resolving debate on the nature of template recognition in phenylalanine anilide imprinted polymers. J. Mol. Recognit. 2012, 25, 69-73.
14. Suriyanarayanan, S.; Cywinski, P.J.; Moro, A.J.; Mohr, G.J.; Kutner, W. Chemosensors based on molecularly imprinted polymers. Mol. Imprint. 2012, 325, 165-265.
15. 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.
16. Azevedo, S.D.; Lakshmi, D.; Chianella, I.; Whitcombe, M.J.; Karim, K.; Ivanova-Mitseva, P.K.; Subrahmanyam, S.; Piletsky, S.A. Molecularly imprinted polymer-hybrid electrochemical sensor for the detection of beta-estradiol. Ind. Eng. Chem. Res. 2013, 52, 13917-13923.
17. Akbulut, M.; Lakshmi, D.; Whitcombe, M.J.; Piletska, E.V.; Chianella, I.; Guven, O.; Piletsky, S.A. Microplates with adaptive surfaces. ACS Comb. Sci. 2011, 13, 646-652.
18. Pietrzyk, A.; Suriyanarayanan, S.; Kutner, W.; Maligaspe, E.; Zandler, M.E.; D'Souza, F. 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 2010, 80, 62-72.
19. 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.
20. Li, J.; Zhang, X.; Liu, Y.; Tong, H.; Xu, Y.; Liu, S. Preparation of a hollow porous molecularly imprinted polymer using tetrabromobisphenol A as a dummy template and its application as SPE sorbent for determination of bisphenol a in tap water. Talanta 2013, 117, 281-287.
21. Carter, S.R.; Rimmer, S. Surface molecularly imprinted polymer core-shell particles. Adv. Funct. Mater. 2004, 14, 553-561.
22. Diaz-Garcia, M.E.; Laino, R.B. Molecular imprinting in sol-gel materials: Recent developments and applications. Microchim. Acta 2005, 149, 19-36.
23. Lofgreen, J.E.; Moudrakovski, I.L.; Ozin, G.A. Molecularly imprinted mesoporous organosilica. ACS Nano 2011, 5, 2277-2287.
24. Suriyanarayanan, S.; Petrone, L.; Ederth, T.; Nicholls, I.A. Biotinyl moiety-selective polymer films with highly ordered macropores. Chem. Commun. 2013, 49, 5274-5276.
25. Yilmaz, E.; Ramstrom, O.; Moller, P.; Sanchez, D.; Mosbach, K. A facile method for preparing molecularly imprinted polymer spheres using spherical silica templates. J. Mater. Chem. 2002, 12, 1577-1581.
26. Giovannoli, C.; Anfossi, L.; Biagioli, F.; Passini, C.; Baggiani, C. Solid phase extraction of penicillins from milk by using sacrificial silica beads as a support for a molecular imprint. Microchim. Acta 2013, 180, 1371-1377.
27. Yilmaz, E.; Haupt, K.; Mosbach, K. The use of immobilized templates-A new approach in molecular imprinting. Angew. Chem. Int. Ed. 2000, 39, 2115-2118.
28. Ahir, S.V.; Petrov, P.G.; Terentjev, E.M. Rheology at the phase transition boundary: 2. Hexagonal phase of Triton X-100 surfactant solution. Langmuir 2002, 18, 9140-9148.
29. Liu, S.Q.; Bakovic, L.; Chen, A.C. Specific binding of glycoproteins with poly(aniline boronic acid) thin film. J. Electroanal. Chem. 2006, 591, 210-216.
30. Shoji, E.; Freund, M.S. Potentiometric saccharide detection based on the pKa changes of poly(aniline boronic acid). J. Am. Chem. Soc. 2002, 124, 12486-12493.
31. Feng, L.; Liu, Y.; Tan, Y.; Hu, J. Biosensor for the determination of sorbitol based on molecularly imprinted electro synthesized polymers. Biosens. Bioelectron. 2004, 19, 1513-1519.
32. Cheng, Z.L.; Wang, E.K.; Yang, X.R. Capacitive detection of glucose using molecularly imprinted polymers. Biosens. Bioelectron. 2001, 16, 179-185.
33. Sayyah, S.M.; Abd El-Rehim, S.S.; El-Deeb, M.M.; Kamal, S.M.; Azooz, R.E. Electropolymerization of p-phenylenediamine on Pt-electrode from aqueous acidic solution: Kinetics, mechanism, electrochemical studies, and characterization of the polymer obtained. J. Appl. Polym. Sci. 2010, 117, 943-952.
34. Sayyah, S.M.; Ei-Rabiey, M.M.; El-Rehim, S.S.A.; Azooz, R.E. Electropolymerization kinetics of a binary mixture of pyrrole and o-aminobenzoic acid and characterization of the obtained polymer films. J. Appl. Polym. Sci. 2008, 109, 1643-1653.
35. Mackay, R.A.; Texter, J. Electrochemistry in colloids and dispersions. J. Chem. Educ. 1993, 70, doi:10.1021/ed070pA146.3.
36. Raoof, J.-B.; Ojani, R.; Hosseini, S.R. Electrochemical fabrication of novel Pt/poly (m-toluidine)/Triton X-100 composite catalyst at the surface of carbon nanotube paste electrode and its application for methanol oxidation. Int. J. Hydrogen Energy 2011, 36, 52-63.
37. Girija, T.C.; Sangaranarayanan, M.V. Polyaniline-based nickel electrodes for electrochemical supercapacitors-Influence of Triton X-100. J. Power Sources 2006, 159, 1519-1526.
38. Kupila, E.L.; Kankare, J. Electropolymerization of pyrrole-Effects of pH and anions on the conductivity and growth-kinetics of polypyrrole. Synth. Met. 1993, 55, 1402-1405.
39. Boogaerts, J.G.; Lafont, N.D.; Carlino, S.; Noel, E.; Raynal, P.; Goffinet, G.; Legros, F.J. Biodistribution of liposome-associated bupivacaine after extradural administration to rabbits. Br. J. Anaesth. 1995, 75, 319-325.
40. Corciova, A. Spectrophotometric method for determination of bupivacaine hydrochloride in pharmaceutical preparations. Eur. Chem. Bull. 2013, 2, 554-557.
41. Siva Rama Krishna, V.; Bhat, N.; Amrutur, B.; Chakrapani, K.; Sampath, S. Detection of Glycated Hemoglobin Using 3-Aminophenylboronic Acid Modified Graphene Oxide. In Proceedings of 2011 IEEE/NIH Life Science Systems and Applications Workshop (LiSSA), Bethesda, MD, USA, 7-8 April 2011; pp. 1-4.
42. Zhang, Y.-P.; Lee, S.-H.; Reddy, K.R.; Gopalan, A.I.; Lee, K.-P. Synthesis and characterization of core-shell SiO2 nanoparticles/poly(3-aminophenylboronic acid) composites. J. Appl. Polym. Sci. 2007, 104, 2743-2750.
43. Pham, Q.L.; Haldorai, Y.; van Hoa, N.; Tuma, D.; Shim, J.-J. Facile synthesis of poly(p-phenylenediamine)/MWCNT nanocomposites and characterization for investigation of structural effects of carbon nanotubes. Bull. Mater. Sci. 2011, 34, 37-43.
44. Li, X.G.; Huang, M.R.; Chen, R.F.; Jin, Y.; Yang, Y.L. Preparation and characterization of poly(p-phenylenediamine-co-xylidine). J. Appl. Polym. Sci. 2001, 81, 3107-3116.
45. Brewer, S.H.; Allen, A.M.; Lappi, S.E.; Chasse, T.L.; Briggman, K.A.; Gorman, C.B.; Franzen, S. Infrared detection of a phenylboronic acid terminated alkane thiol monolayer on gold surfaces. Langmuir 2004, 20, 5512-5520.
46. DrugBank: Bupivacaine (DB00297). Available online: http://www.drugbank.ca/drugs/DB00297 (accessed on 14 March 2014).
47. DrugBank: M-Aminophenylboronic Acid (DB01896). Available online: http://www.drugbank.ca/ drugs/DB01896 (accessed on 14 March 2014).
48. O'Shannessy, D.J.; Brighma-Burke, M.; Soneson, K.K.; Hensley, P.; Brooks, I. Determination of rate and equilibrium binding constants for macromolecular interactions using surface plasmon resonance: Use of nonlinear least squares analysis methods. Anal. Biochem. 1993, 212, 457-468.
49. Morton, T.A.; Myszka, D.G.; Chaiken, I.M. Interpreting complex binding-kinetics from optical biosensors-A comparison of analysis by linearization, the integrated rate-equation, and numerical-integration. Anal. Biochem. 1995, 227, 176-185.
50. Navratilova, I.; Skladal, P.; Viklicky, V. Development of piezoelectric immunosensors for measurement of albuminuria. Talanta 2001, 55, 831-839.
51. Skladal, P.; Horacek, J. Kinetic studies of affinity interactions: Comparison of piezoelectric and resonant mirror-based biosensors. Anal. Lett. 1999, 32, 1519-1529.
52. Pribyl, J.; Hepel, M.; Skladal, P. Piezoelectric immunosensors for polychlorinated biphenyls operating in aqueous and organic phases. Sens. Actuator B Chem. 2006, 113, 900-910.
53. Halamek, J.; Hepel, M.; Skladal, P. Investigation of highly sensitive piezoelectric immunosensors for 2,4-dichlorophenoxyacetic acid. Biosens. Bioelectron. 2001, 16, 253-260.
54. Pietrzyk, A.; Suriyanarayanan, S.; Kutner, W.; Chitta, R.; Zandler, M.E.; D'Souza, F. Molecularly imprinted polymer (MIP) based piezoelectric microgravimetry chemosensor for selective determination of adenine. Biosens. Bioelectron. 2010, 25, 2522-2529.
55. Horacek, J.; Skladal, P. Effect of organic solvents on immunoassays of environmental pollutants studied using a piezoelectric biosensor. Anal. Chim. Acta 2000, 412, 37-45.
56. Skladal, P. Piezoelectric quartz crystal sensors applied for bioanalytical assays and characterization of affinity interactions. J. Braz. Chem. Soc. 2003, 14, 491-502.
57. Dincel, A.; Basci, N.E. An experimental design approach to selecting the optimum LC conditions for the determination of local anaesthetics. Chromatographia 2007, 66, S81-S85.
58. Venkateshwaran, T.G.; Stewart, J.T. HPLC determination of morphine-hydromorphone-bupivacaine and morphine-hydromorphone-tetracaine mixtures in 0.9% sodium chloride injection. J. Liq. Chromatogr. 1995, 18, 565-578.
59. Fijalek, Z.; Baczynski, E.; Piwonska, A.; Warowna-Grzeskiewicz, M. Determination of local anaesthetics and their impurities in pharmaceutical preparations using HPLC method with amperometric detection. J. Pharm. Biomed. Anal. 2005, 37, 913-918.
60. Lindberg, R.L.P.; Pihlajamaki, K.K. High-performance liquid-chromatographic determination of bupivacaine in human-serum. J. Chromatogr. A 1984, 309, 369-374.
61. Shoukry, A.F.; Issa, Y.M.; Elshiekh, R.; Zareh, M. New ion-selective electrodes for determination of bupivacaine and oxybuprocaine. Anal. Lett. 1991, 24, 1581-1590.
62. Wang, C.; Chen, D.; Jiao, X. Lyotropic liquid crystal directed synthesis of nanostructured materials. Sci. Tech. Adv. Mater. 2009, 10, doi:10.1088/1468-6996/10/2/023001.
63. Agha, H.; Fleury, J.B.; Galerne, Y. Micro-wires self-assembled and 3D-connected with the help of a nematic liquid crystal. Eur. Phys. J. E Soft Matter 2012, 35, doi:10.1140/epje/i2012-12082-1.
64. Haegel, F.H.; Schlupen, J.; Schultze, J.W.; Winkels, S.; Stromberg, C. Anodic polymerization of thiophene derivatives from microemulsions and liquid crystals. Electrochim. Acta 2001, 46, 3973-3984.
65. Song, G.; Han, J.; Bo, J.; Guo, R. Synthesis of polyaniline nanostructures in different lamellar liquid crystals and application to lubrication. J. Mater. Sci. 2009, 44, 715-720.
66. Kawabata, K.; Yoneyama, H.; Goto, H. Uniaxially ordered conjugated polymer film prepared by electrochemical polymerization in a nematic liquid crystal with rubbing orientation method showing redox-driven tunable dichroism. Polym. Chem. 2010, 1, 1606-1608.
67. Yu, Z.X.; Westerlund, D. Direct injection of large volumes of plasma in a column-switching system for the analysis of local anaesthetics. II. Determination of bupivacaine in human plasma with an alkyl-diol silica precolumn. J. Chromatogr. A 1996, 725, 149-155.