Poly(methyl vinyl ether‐alt‐maleic anhydride) functionalized with 3‐aminophenylboronic acid: A new boronic acid polymer for sensing diols in neutral water

Amidation of poly(methyl vinyl ether-alt-maleic anhydride) with 3-aminophenylboronic acid was used to prepare a new boronic acid polymer. The binding of catechol dye, Alizarin Red S to the polymer obtained resulted in getting a stable, colored sensor which was used to establish association constants with different diols in competitive assay. The binding of different diols was readily detected by color change and absorbance values measured at 450 nm were used to calculate the association constants. The polymer obtained formed high-affinity complexes with ribonucleosides, particularly cytidine and uridine. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40778.

[1]  Hiroki Yamamoto,et al.  Multicolor saccharide-sensing chips created via layer-by-layer adsorption of boronic acid-containing polymers , 2014 .

[2]  Kun Xu,et al.  Micro‐gels for impact protection , 2013 .

[3]  N. Kızılcan,et al.  In Situ Modification of Cyclohexanone Formaldehyde Resin with Boric Acid for High-Performance Applications , 2013 .

[4]  M. Smietana,et al.  Boron and nucleic acid chemistries: merging the best of both worlds. , 2013, Chemical Society reviews.

[5]  F. Ahmad,et al.  Effect of boric acid and melamine on the intumescent fire-retardant coating composition for the fire protection of structural steel substrates , 2013 .

[6]  T. Zhao,et al.  Thermal stability of novolac cured with polyborosilazane , 2013 .

[7]  P. Jankowski,et al.  Influence of the diol structure on the Lewis acidity of phenylboronates , 2013 .

[8]  N. Pleşu,et al.  Impedimetric detection of dopamine on poly(3-aminophenylboronic acid) modified skeleton nickel electrodes , 2013 .

[9]  B. Gierczyk,et al.  17 O NMR studies of boronic acids and their derivatives , 2013 .

[10]  J. Lubczak,et al.  Synthesis and applications of oligoetherols with perhydro-1,3,5-triazine ring and boron , 2013 .

[11]  L. Ye,et al.  Boronic Acid Terminated Thermo-Responsive and Fluorogenic Polymer: Controlling Polymer Architecture for Chemical Sensing and Affinity Separation , 2012 .

[12]  L. Ye,et al.  Fluorogenic affinity gels constructed from clickable boronic acids , 2012 .

[13]  T. James,et al.  Well-controlled synthesis of boronic-acid functionalised poly(lactide)s: a versatile platform for biocompatible polymer conjugates and sensors , 2012 .

[14]  K. Scott,et al.  The synthesis and characteristic of an anion conductive polymer membrane for alkaline anion exchange fuel cells , 2012 .

[15]  B. Sumerlin,et al.  Biomedical applications of boronic acid polymers , 2011 .

[16]  Mingzhu Liu,et al.  A novel triple-responsive poly(3-acrylamidephenylboronic acid-co-2-(dimethylamino) ethyl methacrylate)/(β-cyclodextrin-epichlorohydrin)hydrogels: Synthesis and controlled drug delivery , 2011 .

[17]  Yu Okasaka,et al.  Direct spectroscopic observation of binding of sugars to polymers having phenylboronic acids substituted with an ortho-phenylazo group. , 2010, Colloids and surfaces. B, Biointerfaces.

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

[19]  Z. Rzayev,et al.  Bioengineering functional copolymers. XII. Interaction of boron-containing and PEO branched derivatives of poly(MA-alt-MVE) with HeLa cells , 2010 .

[20]  H. Zou,et al.  Synthesis and characterization of a new boronate affinity monolithic capillary for specific capture of cis-diol-containing compounds. , 2009, Journal of chromatography. A.

[21]  L. Mikhalovska,et al.  Glucose sensors with increased sensitivity based on composite gels containing immobilized boronic acid , 2008 .

[22]  Pengyuan Yang,et al.  Facile synthesis of aminophenylboronic acid-functionalized magnetic nanoparticles for selective separation of glycopeptides and glycoproteins. , 2008, Chemical communications.

[23]  Z. Brzózka,et al.  ortho-(Aminomethyl)phenylboronic acids—synthesis, structure and sugar receptor activity , 2008 .

[24]  M. Stenzel RAFT polymerization: an avenue to functional polymeric micelles for drug delivery. , 2008, Chemical communications.

[25]  Stephan M Levonis,et al.  Enhanced fructose, glucose and lactose transport promoted by a lipophilic 2-(aminomethyl)-phenylboronic acid , 2008 .

[26]  T. Sager,et al.  Boronic acid based peptidic receptors for pattern-based saccharide sensing in neutral aqueous media, an application in real-life samples. , 2007, Journal of the American Chemical Society.

[27]  V. Boyko,et al.  Influence of grafting on the solution properties and the dissociation behavior of ionic/nonionic grafted copolymers , 2007 .

[28]  A. Tuncel,et al.  A new thermosensitive fluorescent probe for diol sensing: Poly(N-isopropylacrylamide-co-vinylphenylboronic acid)-alizarin red S complex , 2007 .

[29]  D. Hall,et al.  An improved class of sugar-binding boronic acids, soluble and capable of complexing glycosides in neutral water. , 2006, Journal of the American Chemical Society.

[30]  A. Sporzyński,et al.  Evidence for strong heterodimeric interactions of phenylboronic acids with amino acids , 2006 .

[31]  C. Larpent,et al.  Boronic acid-functionalized nanoparticles: synthesis by microemulsion polymerization and application as a re-usable optical nanosensor for carbohydrates , 2005 .

[32]  E. Pişkin,et al.  Bioengineering functional copolymers: V. Synthesis, LCST, and thermal behavior of poly(N-isopropyl acrylamide-co-p-vinylphenylboronic acid) , 2005 .

[33]  K. Sreenivasan Imparting affinity sites for adenosine triphosphate on the surface of polyurethane through molecular imprinting , 2004 .

[34]  Akira Matsumoto,et al.  Glucose-responsive polymer gel bearing phenylborate derivative as a glucose-sensing moiety operating at the physiological pH. , 2004, Biomacromolecules.

[35]  K. Kataoka,et al.  Glucose-responsive polymer bearing a novel phenylborate derivative as a glucose-sensing moiety operating at physiological pH conditions. , 2003, Biomacromolecules.

[36]  S. Sershen,et al.  Implantable, polymeric systems for modulated drug delivery. , 2002, Advanced drug delivery reviews.

[37]  M. Sherburn,et al.  Cavitand boronic acids mediate highly selective fructose transport. , 2002, Organic letters.

[38]  Binghe Wang,et al.  A detailed examination of boronic acid–diol complexation , 2002 .

[39]  G. Springsteen,et al.  Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates. , 2001, Chemical communications.

[40]  A. Tuncel,et al.  Boronic acid–functionalized HEMA-based gels for nucleotide adsorption , 2000 .

[41]  O. Wolfbeis,et al.  A Polyaniline with Near-Infrared Optical Response to Saccharides , 1999 .

[42]  T. Okano,et al.  Selective adhesion of rat lymphocyte subpopulation on the polymer surface with phenylboronic acid moieties: evaluation by field-flow fractionation/adhesion chromatography (FFF/AC) method , 1998 .

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

[44]  T. Okano,et al.  Amine containing phenylboronic acid gel for glucose-responsive insulin release under physiological pH , 1995 .

[45]  J. Kopeček,et al.  Effect of molecular weight (Mw) of N-(2-hydroxypropyl)methacrylamide copolymers on body distribution and rate of excretion after subcutaneous, intraperitoneal, and intravenous administration to rats. , 1987, Journal of biomedical materials research.

[46]  Joel H. Hildebrand,et al.  A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons , 1949 .

[47]  J. Anzai,et al.  Sugar response of boronic acid-substituted azobenzene dye-modified polymer , 2009 .

[48]  T. Okano,et al.  Preparation and characterization of a glucose-responsive insulin-releasing polymer device. , 1994, Biomaterials.