Bile Acid Imprinting Polymers Prepared by Covalent-Ester Monomer-Template Technique: Synthesis, Characterization and Fluorescence Application for BA Recognition

Kobayashi, Taishi; Kusunoki, Takayuki; Zhang, Quanqiu; Takeda, Kohei

doi:10.1252/jcej.40.516

Cited by 3 publications

(5 citation statements)

References 16 publications

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“…It could be argued that the increased use of MIPs in sensor development has been in part driven by developments in MIP formats, not least by the establishment of reproducible strategies for thin film, fiber and (nano)particle preparation. Optical,…”

Section: Applicationsmentioning

confidence: 99%

Molecular imprinting science and technology: a survey of the literature for the years 2004-2011

2014

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SummaryHerein we present a survey of the literature covering the development of molecular imprinting science and technology over the years 2004 to 2011. In total, 3779 references to the original papers, reviews, edited volumes and monographs from this period are included, along with recently identified uncited materials from prior to 2004 which were omitted in the first instalment of this series covering the years 1930 to 2003. 1 In the presentation of the assembled references, a section presenting reviews and monographs covering the area is followed by sections describing fundamental aspects of molecular imprinting including the development of novel polymer formats. Thereafter, literature describing efforts to apply these polymeric materials to a range of application areas is presented. Current trends and areas of rapid development are discussed.2

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Section: Applicationsmentioning

confidence: 99%

Molecular imprinting science and technology: a survey of the literature for the years 2004-2011

2014

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“…The results obtained with natural and synthetic polymers indicate that a bile acid sequestrant should meet the following features [12][13][14][15]: i) to posses cationic groups that enable a fast interaction with bile salts; ii) to contain hydrophobic groups to enhance the stability of the complexes; and iii) to swell to a certain extent to make the network accessible to the bile salt. Molecular imprinting technology has been tested as tool to optimize performances of selective traps [16][17][18]. This technology consists in adding the target molecule to a monomers solution for enabling the arrangement of the monomers around the target analyte according to their interaction capability.…”

Section: Introductionmentioning

confidence: 99%

“…After extraction of the template molecules, the resultant polymeric networks exhibit pockets with size and shape specific for the template and with the most favorable chemical groups for the reuptake once in contact again with the template molecules [19][20][21]. Both non-covalent and covalent imprinting have been applied for creating bile acids traps using vinyl or acrylic monomers [16][17][18]. Although the imprinting effect in aqueous environment is harder to achieve than in organic media, imprinted networks have shown a greater uptake of sodium cholate, both in vitro and in vivo, than the non imprinted networks [16][17][18].…”

Section: Introductionmentioning

confidence: 99%

“…Both non-covalent and covalent imprinting have been applied for creating bile acids traps using vinyl or acrylic monomers [16][17][18]. Although the imprinting effect in aqueous environment is harder to achieve than in organic media, imprinted networks have shown a greater uptake of sodium cholate, both in vitro and in vivo, than the non imprinted networks [16][17][18].…”

Section: Introductionmentioning

confidence: 99%

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Computational modeling and molecular imprinting for the development of acrylic polymers with high affinity for bile salts

Yáñez

Chianella

Piletsky

et al. 2010

Analytica Chimica Acta

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This work has focused on the rational development of polymers capable of acting as traps of bile salts. Computational modeling was combined with molecular imprinting technology to obtain networks with high affinity for cholate salts in aqueous medium. The screening of a virtual library of 18 monomers, which are commonly used for imprinted networks, identified N-(3-aminopropyl)-methacrylate hydrochloride (APMA.HCl), N,N-diethylamino ethyl methacrylate (DEAEM) and ethyleneglycol methacrylate phosphate (EGMP) as suitable functional monomers with medium-to-high affinity for cholic acid. The polymers were prepared with a fix cholic acid:functional monomer mole ratio of 1:4, but with various cross-linking densities. Compared to polymers prepared without functional monomer, both imprinted and non-imprinted microparticles showed a high capability to remove sodium cholate from aqueous medium. High affinity APMA-based particles even resembled the performance of commercially available cholesterol-lowering granules. The imprinting effect was evident in most of the networks prepared, showing that computational modeling and molecular imprinting can act synergistically to improve the performance of certain polymers. Nevertheless, both the imprinted and non-imprinted networks prepared with the best monomer (APMA.HCl) identified by the modeling demonstrated such high affinity for the template that the imprinting effect was less important. The fitting of adsorption isotherms to the Freundlich model indicated that, in general, imprinting increases the population of high affinity binding sites, except when the affinity of the functional monomer for the target molecule is already very high. The cross-linking density was confirmed as a key parameter that determines the accessibility of the binding points to sodium cholate. Materials prepared with 9% mol APMA and 91% mol cross-linker showed enough affinity to achieve binding levels of up to 0.4 mmol g(-1) (i.e., 170 mg g(-1)) under flow (1 mL min(-1)) of 0.2 mM sodium cholate solution.

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“…MIPs prepared via covalent bonding have the disadvantage of a difficult template molecule elution and poor specific recognition. Thus, the number of MIPs prepared by this method is limited [ 24 ]. In contrast, non-covalent MIPs facilitate template elution and can rapidly recognize template molecules, achieving high affinities and distinct selectivities.…”

Section: Resultsmentioning

confidence: 99%

Preparation of Molecularly Imprinted Polymer Microspheres for Selective Solid-Phase Extraction of Capecitabine in Urine Samples

Song

Xie

et al. 2022

Polymers

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Molecularly imprinted solid-phase extraction to treat biological samples has attracted considerable attention. Herein, molecularly imprinted polymer (MIP) microspheres with porous structures were prepared by a combined suspension-iniferter polymerization method using capecitabine (CAP) as a template molecule. This material was subsequently used as a solid-phase extraction agent to separate and enrich drug molecules in urine samples. UV analysis revealed that methacrylate (MAA) was an ideal functional monomer, and 1H Nuclear Magnetic Resonance (1H NMR), Ultraviolet (UV), and Fourier transform-infrared (FT-IR) spectroscopic analyses were used to study the interaction forces between MAA and CAP, demonstrating that hydrogen bonding was the primary interaction force. MIPs with outstanding selectivity were successfully prepared, and the analysis of their surface morphology and chemical structure revealed a spherical morphology with small holes distributed across a rough surface. This surface morphology significantly reduced the mass transfer resistance of template molecules, providing an ideal template recognition effect. Using the molecularly imprinted solid-phase extraction method, CAP and the structural analog cytidine (CYT) were pretreated in urine samples and quantified by HPLC. The results showed that CAP and CYT recoveries reached 97.2% and 39.8%, respectively, with a limit of detection of 10.0–50.0 µg·mL−1. This study provides a novel approach to drug molecule pretreatment that can be applied in drug separation and functional materials science fields.

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Bile Acid Imprinting Polymers Prepared by Covalent-Ester Monomer-Template Technique: Synthesis, Characterization and Fluorescence Application for BA Recognition

Cited by 3 publications

References 16 publications

Molecular imprinting science and technology: a survey of the literature for the years 2004-2011

Molecular imprinting science and technology: a survey of the literature for the years 2004-2011

Computational modeling and molecular imprinting for the development of acrylic polymers with high affinity for bile salts

Preparation of Molecularly Imprinted Polymer Microspheres for Selective Solid-Phase Extraction of Capecitabine in Urine Samples

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