Effect of Reversible Cross-linker, <i>N</i>,<i>N</i>‘-Bis(acryloyl)cystamine, on Calcium Ion Adsorption by Imprinted Gels

Hiratani, Haruyuki; Alvarez‐Lorenzo, Carmen; Chuang, Jeffrey H.; Güney, Orhan; Grosberg, Alexander Y.; Tanaka, Toyoichi

doi:10.1021/la010056m

Cited by 69 publications

(38 citation statements)

References 19 publications

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“…[26][27][28] This kind of stimuli-sensitive recognition is very similar to the recognition of proteins in natural systems. [29][30][31] So far, to the best of our knowledge, the preparation of a thermosensitive polymer to imprint a protein has been limited to static formats, such as our previous study on the bulk polymerization of a macroporous thermosensitive imprinted hydrogel for the recognition of proteins, [32] and has not been applied to monolithic columns for proteins. [33][34][35][36] This study focuses on the combined merits of the monolithic column and the thermosensitive protein MIP to selectively separate a template protein in an on-line method.…”

Section: Introductionmentioning

confidence: 99%

A Thermosensitive Monolithic Column as an Artificial Antibody for the On‐line Selective Separation of the Protein

Qin

Man

et al. 2010

Chemistry A European J

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The main objective of this study was to develop a new methodology for the preparation of a protein (antigen) that is a molecularly imprinted polymer (MIP, an artificial antibody) modified onto the surface of a silica skeleton in which the resulting stationary phase is thermosensitive. The silica monolithic skeleton with vinyl groups was synthesized in a stainless‐steel column by using a mild one‐step sol–gel process with two types of precursor: methyltrimethoxysilane (MTMS) and γ‐methacryloxypropyltrimethoxysilane (γ‐MAPS). Subsequently, three types of the thermosensitive protein MIP were anchored onto the surface of the silica skeleton to prepare the MIP monoliths, which were systematically investigated for back pressure and separation ability at different temperatures to establish good imprinting conditions. Under the optimized imprinting conditions, the chromatographic behavior of the thermosensitive MIP monolith exhibited strong retention ability for the lysozyme template (target antigen) in relation to the nonimprinting monolith (NIP monolith). The imprinting factor (IF) for lysozyme reached 3.48 at 20 °C. Moreover, this new type of artificial antibody displayed favorable binding characteristics for lysozyme over competitive proteins and was further evaluated to selectively separate lysozyme in a real sample by using an on‐line method. The run‐to‐run and column‐to‐column repeatability measurements of the thermosensitive MIP monoliths were also satisfactory.

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Section: Introductionmentioning

confidence: 99%

A Thermosensitive Monolithic Column as an Artificial Antibody for the On‐line Selective Separation of the Protein

Qin

Man

et al. 2010

Chemistry A European J

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“…We then review the experiments that have been done on adsorption of target molecules by random gels, detailing the dependence of their adsorption affinity on adsorber monomer concentration [21], salt concentration [75], and cross-linker concentration [76]. We then compare the properties of random and imprinted gels and show the early successes of the imprinting method [77][78][79][80][81][82][83][84].…”

Section: Introductionmentioning

confidence: 99%

Multiple point adsorption in a heteropolymer gel and the Tanaka approach to imprinting: experiment and theory

Ito

Chuang

Alvarez‐Lorenzo

et al. 2003

Progress in Polymer Science

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Heteropolymer gels can be engineered to release specific molecules into or absorb molecules from a surrounding solution. This remarkable ability is the basis for developing gel applications in extensive areas such as drug delivery, waste cleanup, and catalysis. Furthermore, gels are a model system for proteins, many of whose properties they can be created to mimic. A key aspect of gels is their volume phase transition, which provides a macroscopic mechanism for effecting microscopic changes. The phase transition allows one to control the gel's affinity for target molecules through tiny changes in the solution temperature, salt concentration, pH, or the like. We summarize recent experiments that systematically characterize the gel affinity as a function of adsorbing monomer concentration, solution salt concentration, and cross-linker concentration, on both sides of the phase transition. We provide a physical theory that explains the results and discuss enhancements via imprinting.

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“…To date, however, few cross-linkers controllable by external stimuli have been reported. 5 In this study, aiming at performing reversible molecular imprinting upon external stimuli, we examine [4 þ 4] photodimerization of anthryl groups as cross-linking step (Figure 1). It is known that anthracene and its derivatives form a dimer upon exposure to longwave UV and the dimer is restored to an original monomer by irradiation of shortwave UV.…”

mentioning

confidence: 99%

Photodimerization of Anthryl Moieties in a Poly(methacrylic acid) Derivative as Reversible Cross-linking Step in Molecular Imprinting

Matsui¹,

Ochi²,

Tamaki³

2005

Chemistry Letters

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A methodology for reversible molecular imprinting is presented. A molecularly imprinted polymer (MIP) is prepared by photo-cross-linking poly(methacrylic acid) (PMAA) with anthryl moieties as photo-cross-linking sites in the presence of an antimalarial drug cinchonidine as a template molecule, resulting in enhanced binding capacity to cinchonidine, compared with non-imprinted polymers. MIP is then ''initialized'' by exposure to shortwave UV that cleaves the anthracene-dimer-based crosslinks, resulting in the reduced binding capacity comparable to the non-imprinted polymers.Molecular imprinting is a methodology to produce a polymer with functional groups arranged for recognition of specific target molecules.1 Polymers obtained by molecular imprinting (molecularly imprinted polymers, MIPs) have often been compared to enzymes and antibodies, and utilized in various applications ranging from analysis 2 to catalysis. 3 In typical MIP syntheses, functional monomers, complexed with a template molecule, are polymerized (cross-linked) to preserve the arrangement of the monomers complementary to the template molecule. Even after removal of the template molecule from the resultant network polymer, it is believed that the complementarity can be still preserved in terms of both shape and functionality, allowing the polymer to specifically bind the template molecule. Cross-linking manners are greatly important for constructing binding sites, and have been the central theme for establishing the imprinting techniques. 4 Although radical polymerization has been the most commonly used in the MIP synthesis, the reaction is not quite appropriate for controlling and monitoring cross-linking degree. Furthermore, once the radical polymerization proceeds, the structure and property of resultant MIPs can not be changed due to inert cross-links. To date, however, few cross-linkers controllable by external stimuli have been reported. 5In this study, aiming at performing reversible molecular imprinting upon external stimuli, we examine [4 þ 4] photodimerization of anthryl groups as cross-linking step (Figure 1). It is known that anthracene and its derivatives form a dimer upon exposure to longwave UV and the dimer is restored to an original monomer by irradiation of shortwave UV.6 Various polymeric materials have been reported utilizing this reaction, 7,8 and our design of molecular imprinting is based on these studies demonstrating interesting reversible properties. Another point in our design is a use of a linear polymer with cross-linkable moieties (a pre-polymer); it is appropriate to use pre-polymers as MIP precursors rather than monomers for constructing network structure by dimerization-based cross-linking. We previously reported that poly(methacrylic acid) (PMAA) with styryl moieties can be used for preparing cinchonidine-selective MIPs, 9 in which carboxyl moieties of PMAA are supposedly immobilized as complementary to cinchonidine by cross-linking. 10 In this study, we designed a PMAA-based pre-polymer bearing anthryl moieties t...

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Effect of Reversible Cross-linker, N,N‘-Bis(acryloyl)cystamine, on Calcium Ion Adsorption by Imprinted Gels

Cited by 69 publications

References 19 publications

A Thermosensitive Monolithic Column as an Artificial Antibody for the On‐line Selective Separation of the Protein

A Thermosensitive Monolithic Column as an Artificial Antibody for the On‐line Selective Separation of the Protein

Multiple point adsorption in a heteropolymer gel and the Tanaka approach to imprinting: experiment and theory

Photodimerization of Anthryl Moieties in a Poly(methacrylic acid) Derivative as Reversible Cross-linking Step in Molecular Imprinting

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