Development of biosensors containing laccase and imidazolium bis(trifluoromethylsulfonyl)imide ionic liquid for the determination of rutin.

Biosensors based on hydrophobic ionic liquids (ILs) derived from the bis(trifluoromethylsulfonyl)imide [(CF(3)SO(2))(2)N(-) = Tf(2)N(-)] anion associated with three different imidazolium cations: 1-butyl-3-methylimidazolium (BMI x Tf(2)N), 1-decyl-3-methylimidazolium (DMI x Tf(2)N) and 1-tetradecyl-3-methylimidazolium (TDMI x Tf(2)N), along with laccase from Aspergillus oryzae, were constructed and optimized for determination of rutin. The laccase catalyzes the oxidation of rutin to the corresponding o-quinone, which is electrochemically reduced back to rutin. The best performance was obtained with 50:20:15:15% (w/w/w/w) as the graphite powder:laccase:Nujol:ILs composition in 0.1 mol L(-1) acetate buffer solution (pH 5.0). The parameters for the square-wave voltammetry experiments and scanning electron microscopy images of the biosensors were studied. Under the selected conditions, the cathodic peak current increased linearly in the rutin concentration ranges of 4.77x10(-6) to 4.62x10(-5) mol L(-1), 5.84x10(-6) to 5.36x10(-5) mol L(-1) and 5.84x10(-6) to 5.36x10(-5) mol L(-1) using the (I) BMI x Tf(2)N-laccase, (II) DMI x Tf(2)N-laccase and (III) TDMI x Tf(2)N-laccase, respectively. The rutin contents of commercial samples of pharmaceuticals were successfully determined by the biosensors and the results compared well with those obtained using the official method. The studies on rutin recovery from these samples gave values of 96.9-104.6%.

[1]  V. Villari,et al.  The rutin/beta-cyclodextrin interactions in fully aqueous solution: spectroscopic studies and biological assays. , 2005, Journal of pharmaceutical and biomedical analysis.

[2]  A. Mayer,et al.  Laccase: new functions for an old enzyme. , 2002, Phytochemistry.

[3]  A. Franzoi,et al.  Biomimetic sensor based on MnIIIMnII complex as manganese peroxidase mimetic for determination of rutin. , 2009, Talanta.

[4]  Murilo Santhiago,et al.  l-Cysteine determination in pharmaceutical formulations using a biosensor based on laccase from Aspergillus oryzae , 2007 .

[5]  Fabio Vianello,et al.  A high sensitivity amperometric biosensor using laccase as biorecognition element. , 2006, Biosensors & bioelectronics.

[6]  Joseph Wang,et al.  Sensitive and stable amperometric measurements at ionic liquid-carbon paste microelectrodes. , 2008, Analytica chimica acta.

[7]  P. Suarez,et al.  Physico-chemical processes in imidazolium ionic liquids. , 2006, Physical chemistry chemical physics : PCCP.

[8]  A. Franzoi,et al.  Biosensor based on laccase and an ionic liquid for determination of rosmarinic acid in plant extracts. , 2009, Talanta.

[9]  Yang Liu,et al.  An ionic liquid-type carbon paste electrode and its polyoxometalate-modified properties , 2005 .

[10]  J. Hao,et al.  Self-assembled structures and chemical reactions in room-temperature ionic liquids , 2007 .

[11]  Y. Kasuya,et al.  Determination of rutin in human plasma by high-performance liquid chromatography utilizing solid-phase extraction and ultraviolet detection. , 2001, Journal of chromatography. B, Biomedical sciences and applications.

[12]  R. Pilloton,et al.  Determination of phenolic acids using Trametes versicolor laccase. , 2007, Talanta.

[13]  M. Rebelo,et al.  A New Laccase Biosensor For Polyphenols Determination , 2003 .

[14]  Z. Song,et al.  Sensitive determination of sub-nanogram amounts of rutin by its inhibition on chemiluminescence with immobilized reagents. , 2002, Talanta.

[15]  J. Dupont,et al.  Synthesis and characterization of nickel nanoparticles dispersed in imidazolium ionic liquids. , 2007, Physical chemistry chemical physics : PCCP.

[16]  O. Fatibello‐Filho,et al.  Biosensor based on laccase immobilized on microspheres of chitosan crosslinked with tripolyphosphate , 2008 .

[17]  J. Dupont,et al.  A Simple and Practical Method for the Preparation and Purity Determination of Halide‐Free Imidazolium Ionic Liquids , 2006 .

[18]  Wei Sun,et al.  Application of carbon ionic liquid electrode for the electrooxidative determination of catechol , 2008 .

[19]  R. G. Evans,et al.  Non-haloaluminate room-temperature ionic liquids in electrochemistry--a review. , 2004, Chemphyschem : a European journal of chemical physics and physical chemistry.

[20]  Shaojun Dong,et al.  A biofuel cell harvesting energy from glucose-air and fruit juice-air. , 2007, Biosensors & bioelectronics.

[21]  S. Dong,et al.  Electrochemical catalysis and thermal stability characterization of laccase-carbon nanotubes-ionic liquid nanocomposite modified graphite electrode. , 2007, Biosensors & bioelectronics.

[22]  I. Vieira,et al.  Development of a biosensor based on gilo peroxidase immobilized on chitosan chemically crosslinked with epichlorohydrin for determination of rutin. , 2006, Journal of pharmaceutical and biomedical analysis.

[23]  Zebao Rui,et al.  Electrochemical behavior and adsorptive stripping voltammetric determination of quercetin at multi-wall carbon nanotubes-modified paraffin-impregnated graphite disk electrode , 2006 .

[24]  S. Dong,et al.  A biofuel cell with enhanced power output by grape juice , 2007 .

[25]  D. Pang,et al.  Activity and stability of horseradish peroxidase in hydrophilic room temperature ionic liquid and its application in non-aqueous biosensing , 2007 .

[26]  Gang Chen,et al.  Determination of rutin and quercetin in plants by capillary electrophoresis with electrochemical detection. , 2000 .

[27]  A. Ensafi,et al.  Determination of Rutin in Pharmaceutical Compounds and Tea Using Cathodic Adsorptive Stripping Voltammetry , 2006 .

[28]  L. Gorton,et al.  Amperometric detection of mono- and diphenols at Cerrena unicolor laccase-modified graphite electrode: correlation between sensitivity and substrate structure. , 2005, Talanta.

[29]  Marta Sánchez-Paniagua López,et al.  Rutin Determination at an Amperometric Biosensor , 2007 .

[30]  S. Cosnier,et al.  Laccase immobilization in redox active layered double hydroxides: a reagentless amperometric biosensor. , 2007, Biosensors & bioelectronics.

[31]  A. Ivaska,et al.  Applications of ionic liquids in electrochemical sensors. , 2008, Analytica chimica acta.

[32]  P. Suarez,et al.  Ionic liquid (molten salt) phase organometallic catalysis. , 2002, Chemical reviews.

[33]  S. R. Couto,et al.  Industrial and biotechnological applications of laccases: a review. , 2006, Biotechnology advances.

[34]  Wei Sun,et al.  Electrocatalytic oxidation of dopamine at an ionic liquid modified carbon paste electrode and its analytical application , 2007, Analytical and bioanalytical chemistry.

[35]  A. Franzoi,et al.  Rutin determination in pharmaceutical formulations using a carbon paste electrode modified with poly(vinylpyrrolidone). , 2008, Journal of pharmaceutical and biomedical analysis.

[36]  G. Shen,et al.  β-Cyclodextrin incorporated carbon nanotube-modified electrode as an electrochemical sensor for rutin , 2006 .

[37]  F. Tajabadi,et al.  High-performance carbon composite electrode based on an ionic liquid as a binder. , 2006, Analytical chemistry.

[38]  R. Adams Carbon Paste Electrodes , 1958 .

[39]  Richard G Compton,et al.  Ionic liquid-carbon composite glucose biosensor. , 2008, Biosensors & bioelectronics.

[40]  Jianbin Zheng,et al.  Comparative investigation on electrochemical behavior of hydroquinone at carbon ionic liquid electrode, ionic liquid modified carbon paste electrode and carbon paste electrode , 2007 .