Multivalent interaction-based carbohydrate biosensors for signal amplification.

Multivalent interaction between boronic acids immobilized on quartz crystal microbalance (QCM) sensor surface and the carbohydrates modified Au-nanoparticle (AuNP) has been demonstrated for the development of a sensitive carbohydrate biosensor. Briefly, a boronic acid-containing polymer (boropolymer) as multivalent carbohydrate receptor was oriented immobilized on the cysteamine coated electrode through isourea bond formation. Carbohydrates were conjugated to AuNPs to generate a multivalent carbohydrates moiety to amplify the response signal. Thus, the binding of the carbohydrate conjugated AuNPs to the boropolymer surface are multivalent which could simultaneously increase the binding affinity and specificity. We systematically studied the binding between five carbohydrates conjugated AuNPs and the boropolymer. Our studies show that the associate constant (K(a)) was in the order of fucose<glucose<mannose<galactose<maltose. A linear response in the range from 23 μM to 3.83 mM was observed for mannose conjugated AuNPs and the boropolymer recognition elements, with the lower detection limit of 1.5 μM for the carbohydrate analytes. Furthermore, the multivalent binding between carbohydrates and boronic acids are reversible and allow the regeneration of boropolymer surface by using 1M acetic acid so as to sequentially capture and release the carbohydrate analytes.

[1]  H. Kitano,et al.  Interfacial Recognition of Sugars by Boronic Acid-Carrying Self-Assembled Monolayer† , 2000 .

[2]  M. Ding,et al.  Analysis of carbohydrates in drinks by high-performance liquid chromatography with a dynamically modified amino column and evaporative light scattering detection. , 2000, Journal of chromatography. A.

[3]  Wolfgang Schuhmann,et al.  Microbial biosensor array with transport mutants of Escherichia coli K12 for the simultaneous determination of mono-and disaccharides. , 2002, Biosensors & bioelectronics.

[4]  E. Anslyn,et al.  Creative Chemical Sensor Systems , 2007 .

[5]  S. Shuman,et al.  Structure, mechanism, and evolution of the mRNA capping apparatus. , 2001, Progress in nucleic acid research and molecular biology.

[6]  I. Willner,et al.  Electrical contacting of flavoenzymes and NAD(P)+-dependent enzymes by reconstitution and affinity interactions on phenylboronic acid monolayers associated with Au-electrodes. , 2002, Journal of the American Chemical Society.

[7]  B. Wang,et al.  Water-soluble fluorescent boronic acid compounds for saccharide sensing: substituent effects on their fluorescence properties. , 2006, Chemistry.

[8]  M. Gazouli,et al.  Characterization of Mycobacterium tuberculosis Complex Isolates from Greek Patients with Sarcoidosis by Spoligotyping , 2005, Journal of Clinical Microbiology.

[9]  F. Diederich,et al.  Optically Active Cyclophane Receptors for Mono- and Disaccharides: The Role of Bidentate Ionic Hydrogen Bonding in Carbohydrate Recognition , 2001 .

[10]  L. Gorton,et al.  Selective post-column liquid chromatographic determination of sugars in spent sulphite liquor with two enzymatic electrochemical detectors in parallel , 1990 .

[11]  A. Kubba,et al.  Identification of mycobacterial DNA in cutaneous lesions of sarcoidosis , 1998, Journal of cutaneous pathology.

[12]  R. Baldwin Electrochemical determination of carbohydrates: enzyme electrodes and amperometric detection in liquid chromatography and capillary electrophoresis. , 1999, Journal of pharmaceutical and biomedical analysis.

[13]  Catherine J. Murphy,et al.  An Improved Synthesis of High‐Aspect‐Ratio Gold Nanorods , 2003 .

[14]  Xue-Long Sun,et al.  Synthesis and characterization of biotin chain-end functionalized boronic acid-containing polymer (boropolymer) as functional glyco-affinity macroligand , 2010 .

[15]  George C Schatz,et al.  What controls the melting properties of DNA-linked gold nanoparticle assemblies? , 2000, Journal of the American Chemical Society.

[16]  N. Siafakas,et al.  Miliary Sarcoidosis following Miliary Tuberculosis , 2000, Respiration.

[17]  Marisela Vélez,et al.  Immobilization of peroxidase glycoprotein on gold electrodes modified with mixed epoxy-boronic Acid monolayers. , 2002, Journal of the American Chemical Society.

[18]  P. Chomczyński,et al.  Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction. , 1987, Analytical biochemistry.

[19]  D. Harvey,et al.  Matrix-assisted laser desorption/ionization mass spectrometry of carbohydrates. , 1999, Mass spectrometry reviews.

[20]  W. Tan,et al.  Conjugation of biomolecules with luminophore-doped silica nanoparticles for photostable biomarkers. , 2001, Analytical chemistry.

[21]  A. J. Mello,et al.  Chip-based refractive index detection using a single point evanescent wave probe , 2001 .

[22]  E. Chaikof,et al.  Facile synthesis of chain-end functionalized glycopolymers for site-specific bioconjugation. , 2004, Bioconjugate chemistry.

[23]  D. Fink,et al.  Glucose determination using a re-usable enzyme-modified ion track membrane sensor. , 2009, Biosensors & bioelectronics.

[24]  Ashutosh Chilkoti,et al.  A colorimetric gold nanoparticle sensor to interrogate biomolecular interactions in real time on a surface. , 2002, Analytical chemistry.

[25]  S. Honda Postcolumn derivatization for chromatographic analysis of carbohydrates , 1996 .

[26]  F. Wood,et al.  Peer Review of Grant Applications: A Systematic Review , 2003 .

[27]  N. Puizina-Ivic,et al.  A rare case of pulmonary tuberculosis with simultaneous pulmonary and skin sarcoidosis: a case report , 2010, Cases journal.

[28]  John O. Edwards,et al.  Polyol Complexes and Structure of the Benzeneboronate Ion , 1959 .

[29]  Xiangqun Zeng,et al.  Single chain fragment variable recombinant antibody functionalized gold nanoparticles for a highly sensitive colorimetric immunoassay. , 2009, Biosensors & bioelectronics.

[30]  A. Morell,et al.  The role of surface carbohydrates in the hepatic recognition and transport of circulating glycoproteins. , 2006, Advances in enzymology and related areas of molecular biology.

[31]  C. Mirkin,et al.  A fluorescence-based method for determining the surface coverage and hybridization efficiency of thiol-capped oligonucleotides bound to gold thin films and nanoparticles. , 2000, Analytical chemistry.

[32]  K. M. Faucher,et al.  Design and synthesis of biotin chain-terminated glycopolymers for surface glycoengineering. , 2002, Journal of the American Chemical Society.

[33]  A. P. Davis,et al.  Carbohydrate recognition in water by a tricyclic polyamide receptor. , 2004, Angewandte Chemie.

[34]  Xiangqun Zeng,et al.  Nonlabeled quartz crystal microbalance biosensor for bacterial detection using carbohydrate and lectin recognitions. , 2007, Analytical chemistry.

[35]  S. Shinkai,et al.  Saccharide Sensing with Molecular Receptors Based on Boronic Acid , 1996 .

[36]  Xiangqun Zeng,et al.  Engineered recombinant single-chain fragment variable antibody for immunosensors. , 2005, Analytical chemistry.

[37]  A. Aggarwal,et al.  Molecular evidence for the role of mycobacteria in sarcoidosis: a meta-analysis , 2007, European Respiratory Journal.

[38]  H. Kawagishi,et al.  Analysis of the carbohydrate binding specificity of the mushroom Pleurotus ostreatus lectin by surface plasmon resonance. , 2005, Analytical biochemistry.

[39]  George M Whitesides,et al.  Polyvalent Interactions in Biological Systems: Implications for Design and Use of Multivalent Ligands and Inhibitors. , 1998, Angewandte Chemie.

[40]  M. Váradi,et al.  Application of biosensor for monitoring galactose content. , 1996, Biosensors & bioelectronics.

[41]  P. Wang,et al.  Studying the Interaction of α-Gal Carbohydrate Antigen and Proteins by Quartz-Crystal Microbalance , 2003 .