Synthesis and characterization of biotin chain-end functionalized boronic acid-containing polymer (boropolymer) as functional glyco-affinity macroligand

Chalagalla, Srinivas; Sun, Xue‐Long

doi:10.1016/j.reactfunctpolym.2010.03.005

Cited by 9 publications

(6 citation statements)

References 27 publications

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“…Briefly, the boropolymer was synthesized by a copolymerization between acrylated phenylboronic acid and acrylamide initiated by cyanoxyl radicals, which was generated by reaction between cyanate anions from a sodium cyanate aqueous solution and aryl - diazonium salts prepared in situ through a diazotization reaction of arylamine in water. Detail synthesis has been described in another paper (Chalagalla et al 2010). Structure of boropolymer is shown in figure 2.…”

Section: Methodsmentioning

confidence: 99%

Multivalent interaction-based carbohydrate biosensors for signal amplification

Wang

Chalagalla

et al. 2010

Biosensors and Bioelectronics

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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 acidcontaining 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 carbohydrate 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.

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Section: Methodsmentioning

confidence: 99%

Multivalent interaction-based carbohydrate biosensors for signal amplification

Wang

Chalagalla

et al. 2010

Biosensors and Bioelectronics

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“…Boronic acid functionalized nanoparticles have also been used to concentrate antibodies by capturing the carbohydrates attached to the Fc region of IgG (Lin et al, ). Chalagalla and Sun () have prepared a boronic acid‐containing polymer capped with biotin ( 57 ) for linkage to a magnetic bead and used the product for glycan capture and Lin et al () have constructed magnetic nanoparticles with immobilized APB acid for glycoprotein capture. “SnO 2 @Poly(HEMA‐co‐St‐co‐VPBA)” Core‐shell nanoparticles containing boronic acid groups have been prepared by of copolymerization between 2‐hydroxyethyl methacrylate grafted ( 58 ) on SnO 2 nanoparticles, styrene, and 4‐vinylphenylboronic acid (VPBA, 59 ).…”

Section: Studies On Specific Carbohydrate Typesmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2009–2010

Harvey

2014

Mass Spectrometry Reviews

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This review is the sixth update of the original article published in 1999 on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2010. General aspects such as theory of the MALDI process, matrices, derivatization, MALDI imaging, arrays and fragmentation are covered in the first part of the review and applications to various structural typed constitutes the remainder. The main groups of compound that are discussed in this section are oligo and polysaccharides, glycoproteins, glycolipids, glycosides and biopharmaceuticals. Many of these applications are presented in tabular form. Also discussed are medical and industrial applications of the technique, studies of enzyme reactions and applications to chemical synthesis.

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“…Supramolecular chemistry was widely investigated to generate such "smart" block copolymers employing non-covalent junction 24 based on host-guest interactions or van der Waals force, [25][26][27][28][29][30] hydrogen bonding 31 and coordinative interactions. In this context, most reports concern the synthesis of well-defined polymers containing pendant boronic acid groups [45][46][47][48][49] for the conception of stimuli responsive macromolecular assemblies (hydrogels, nanoparticles, etc). Among the few reported examples in literature, the hetero Diels-Alder reaction between diene endfunctionalized polymers and the complementary thiocarbonyl end-functionalized polymer leds to block copolymers with a thermoreversible covalent junction.…”

Section: Introductionmentioning

confidence: 99%

“…Thus, the incorporation of boronic acid moieties within polymeric structures has opened the door to various reversible macromolecular architectures featuring a dynamic character close to that observed for supramolecular systems. In this context, most reports concern the synthesis of well-defined polymers containing pendant boronic acid groups [45][46][47][48][49] for the conception of stimuli responsive macromolecular assemblies (hydrogels, nanoparticles, etc.). 46,[50][51][52][53][54][55] In this publication, we report on the synthesis and the coupling of different complementary end-functionalized homopolymers bearing a nitrocatechol group and a boronic acid entity.…”

Section: Introductionmentioning

confidence: 99%

Catechol/boronic acid chemistry for the creation of block copolymers with a multi-stimuli responsive junction

et al. 2016

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Two original Chain Transfer Agents (CTAs) integrating either a nitrocatechol or a boronic acid moiety were synthesized allowing the conception of a wide library of end-functionalized well-defined homopolymers via the Reversible Addition-Fragmentation chain Transfer (RAFT) process. Kinetic studies using NMR spectroscopy and Size Exclusion Chromatography (SEC) were carried out, revealing a good control of polymerizations for various monomers. Then, a coupling reaction between the complementary nitrocatechol and boronic acid end-chain polymers was optimized to create a dynamic boronate ester junction between polymer blocks. The effectiveness of the reaction was demonstrated by means of NMR ( 1 H, DOSY), SEC and cyclic voltammetry. The ability of the covalent bond, and thus the block copolymers, to be disrupted on demand was assessed using a competitive molecule (2-naphthylboronic acid) and UV irradiation as stimuli. Figure 3. A) Kinetic plots and B) dependence of the molar mass and polydispersity index on monomer conversion for the RAFT polymerization involving ND-CTA (see Table 1 for experimental conditions).After the obtention of well-defined homopolymers bearing either a nitrocatechol moiety (ND-Polymer) or a boronic acid group (Boro-Polymer) at their extremity, we next turned our attention to whether they can be readily connected through the boronate ester formation to furnish diblock copolymer architectures. This was exemplified by mixing two complementary end-functionalized homopolymers, ND-PDMAc (M n,NMR =1700 g.mol -1 , Ð=1.2) and Boro-PnBuA (M n,NMR =2000 g.mol -1 , Ð=1.1), in acetonitrile under reflux for 24 hours. The block copolymer PDMAc-b-PnBuA was recovered after purification through dialysis (MWCO = 3500 g/mol) in acetonitrile and then characterized by 1 H NMR spectroscopy. First, we tried to perform the coupling reaction from an equimolar amount of each polymer in acetonitrile for 24h. After dialysis, 1 H NMR analysis revealed the presence of the pure block copolymer in the dialysis bag and traces of both starting homopolymers in the filtrate, suggesting that the reaction was not quantitative. Thus, to ensure a complete reaction, 2 equivalents of Boro-PnBuA and 1 equivalent of ND-PDMAc were next reacted in similar reaction conditions. In that case, no trace of unreacted ND-PDMAc was detected in the filtrate after purification. linked block copolymer (1 equivalent). Indeed, it has already been demonstrated that NBA displays a much lower fluorescence intensity in organic medium once bounded to diols. 65 Thus, this trend has been exploited to monitor the disassembly of a block copolymer PDMAcb-PnBuA (Scheme 3). Scheme 3. Reaction between NBA and ND-PDMAc (Pathway 1) and PDMAc-b-PnBuA (Pathway 2).On Figure 8, the typical emission spectrum of NBA is presented while the block copolymer PDMAc-b-PnBuA exhibits no fluorescence. On the other hand, when the homopolymer ND-PDMAc is directly coupled with NBA (pathway 1, Scheme 3), the resulting functionalized NBA-PDMAc is less fluorescent than NBA alone, as d...

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Synthesis and characterization of biotin chain-end functionalized boronic acid-containing polymer (boropolymer) as functional glyco-affinity macroligand

Cited by 9 publications

References 27 publications

Multivalent interaction-based carbohydrate biosensors for signal amplification

Multivalent interaction-based carbohydrate biosensors for signal amplification

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2009–2010

Catechol/boronic acid chemistry for the creation of block copolymers with a multi-stimuli responsive junction

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