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Recent Advances in Macromolecularly Imprinted Polymers by Controlled Radical Polymerization Techniques

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Recent Advances in Macromolecularly Imprinted Polymers by Controlled Radical Polymerization Techniques Mol. Impr. 2015; 3: 35–46 Review Article Open Access Huiqi Zhang* Recent Advances in Macromolecularly Imprinted Polymers by Controlled Radical Polymerization Techniques DOI 10.1515/molim-2015-0005 success in the practical applications of such biological Received August 11, 2015; accepted Ocotber 27, 2015 receptors, their inherent drawbacks, including poor physical Abstract: Molecularly imprinted polymers (MIPs) are and chemical stability, batch-to-batch variation and high synthetic receptors with tailor-made recognition sites for cost, significantly limit their more broad uses. To address the target molecules. Their high molecular recognition this issue, many efforts have been devoted to developing ability, good stability, easy preparation, and low cost strategies for the preparation of synthetic receptors with make them highly promising substitutes for biological an affinity and specificity approaching those achieved in receptors. Recent years have witnessed rapidly increasing nature. One strategy that has attracted rapidly increasing interest in the imprinting of biomacromolecules and interest nowadays is the molecular imprinting technique, especially proteins because of the great potential of which has been demonstrated to be highly versatile for these MIPs in such applications as proteome analysis, preparing synthetic receptors (or namely molecularly clinical diagnostics, and biomedicine. So far, some imprinted polymers (MIPs)) with tailor-made recognition useful strategies have been developed for the imprinting sites for the target molecules [5-15]. The resulting MIPs of proteins and controlled radical polymerization have proven promising substitutes for biological receptors techniques have proven highly versatile for such purpose. because of their high specific molecular recognition ability, This mini-review describes recent developments in the good stability, ease of preparation, and low cost, and they controlled preparation of proteins-imprinted polymers have shown great potential in such areas as separation via such advanced polymerization techniques. and purification, antibody mimics (immunoassay or biomedicine), chemical sensors, biomimetic catalysis, drug Keywords: Molecularly imprinted polymers, Synthetic development, and drug delivery. receptors, Proteins, Controlled radical polymerization The molecular imprinting technique can be simply techniques. defined as a template-induced polymerization approach for the generation of synthetic receptors. It typically involves the copolymerization of a functional monomer and a crosslinking monomer in the presence of a target 1 Introduction analyte called a “template” in a porogenic solvent, and the subsequent removal of the template from the resulting In nature, biological receptors with high specific molecular crosslinked polymer networks leads to MIPs with binding recognition ability (e.g. antibody and enzyme) play an sites complementary to the shape, size and functionality important role in virtually all life processes [1]. They have of the template (Fig. 1). So far, three types of molecular drawn great attention in both research and industry because imprinting approaches (covalent, noncovalent, and semi- of their high impact in selective separations, catalytic covalent) have been developed on the basis of the different processes, and sensitive chemical assays [2-4]. Despite much interactions used between the template and functional monomer (or functional group in the binding sites) during *Corresponding author Huiqi Zhang, Key Laboratory of Functional the imprinting and rebinding steps [8,9]. Among them, Polymer Materials (Ministry of Education), State Key Laboratory the noncovalent molecular imprinting approach is mostly of Medicinal Chemical Biology, Collaborative Innovation Center used nowadays because it can be easily accomplished of Chemical Science and Engineering (Tianjin), and College of without the need of complicated organic syntheses and is Chemistry, Nankai University, Tianjin 300071, P. R. China. E-mail: [email protected]. applicable to a wide range of template molecules. © 2015 Huiqi Zhang, published by De Gruyter Open. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License. 36 H. Zhang Figure 1. Schematic representation for the generation of molecularly imprinted polymers: (a) complex formation; (b) copolymerization; (c) removal of template and (d) template rebinding. Adapted with permission of Elsevier B. V. from [14]. So far, a great number of MIPs have been designed rather hard to control with regard to chain propagation and for many different template molecules including both termination, which makes it difficult to prepare surface- small analytes (molecular weight (MW) < 1500 Da, such as imprinted polymer layers with well-defined and desired amino acids, drugs, pesticides, etc.), biomacromolecules thickness. In addition, they normally lead to crosslinked (MW > 1500 Da, such as proteins and polypeptides), and polymer networks with heterogeneous structures [23], even living organisms (e.g. bacteria). Despite significant which might be responsible for some of the inherent progress made in the molecular imprinting of small drawbacks of the MIPs such as the broad binding site templates and the successful commercial application of heterogeneity and the relatively low affinity and selectivity. MIPs in solid-phase extraction area in the past four decades, Therefore, it can be envisioned that the controlled the imprinting of biomacromolecules remains a big preparation of well-defined MIPs with homogeneous challenge, mainly because of their large sizes, complexed network structures will be of significant importance both for structures, and conformational variability [16-21]. better understanding the structure-property relationship of These inherent characteristics of biomacromolecules the MIPs and for obtaining MIPs with improved binding lead to many significant problems for the resulting properties. In this respect, CRPs are perfectly suited for macromolecularly imprinted polymers (mMIPs) such as the this purpose. The negligible chain termination in CRPs laborious removal of large templates and their slow access and their thermodynamically controlled processes allow to the binding sites as well as the difficult choice of suitable a more constant rate for the polymer chain growth, functional monomers and polymerization conditions (for leading to homogeneous polymer networks with a narrow example several functional monomers are usually used distribution of the network chain length. Many different together for the imprinting of proteins instead of using polymer networks with homogeneous structures have been only one as in conventional molecular imprinting, and prepared via CRPs [23-26]. careful choice of pH and salt concentration is necessary for CRPs have drawn great attention over the past decades preserving the native conformation of the template protein for providing simple and robust routes to the synthesis of and for controlling the charge state of the protein). well-defined polymers [27-31]. They have now become one The past three decades have witnessed considerable of the most rapidly developing areas in the field of polymer efforts being devoted to addressing the above-mentioned science. In comparison with living anionic polymerization, problems. Some promising strategies (including the surface CRPs can now offer similar control over the synthetic imprinting and epitope imprinting approaches [9,16-21]) process, although with somehow lower precision. On the have been developed for the synthesis of mMIPs to solve the other hand, CRPs can offer great advantages in terms of problems caused by the large sizes of biomacromolecules their much milder and less restricted reaction conditions (i.e. difficult removal of such large templates and their and their applicability to a larger range of monomers. In slow access to the binding sites). In addition, recent analogue with living cationic polymerization, the control years have also seen rapidly increasing interest in the over CRPs depends on creating a dynamic equilibrium application of controlled/“living” radical polymerization between the active and dormant species (Scheme 1a-d), techniques (CRPs) in the imprinting of biomacromolecules which eventually leads to negligible radical termination and especially proteins [22]. It is well known that MIPs and thus controlled polymerizations. Nowadays, the are normally prepared by a conventional free radical most investigated CRPs include iniferter-induced radical polymerization mechanism, mainly due to its tolerance of polymerization [27], atom transfer radical polymerization a wide range of functional groups in the monomers and (ATRP) [28,29], reversible addition-fragmentation chain templates as well as its mild reaction conditions. However, transfer (RAFT) polymerization [30], and nitroxide- conventional radical polymerization processes are usually mediated living radical polymerization (NMP) [31]. So Recent Advances in Macromolecularly Imprinted Polymers by Controlled Radical Polymerization Techniques 37 a) b) Addition * Fragmentation c) Pn* + S C S R Pn S C S R Pn S C S + R* Addition Z Fragmentation Z Z Propagating CTA Intermediate Dormant Fragment radical radical species radical d) Scheme 1. The mechanism of controlled radical polymerization techniques including (a) iniferter-induced radical polymerization, (b) ATRP, Scheme(c) RAFT polymerization,1. The mechanism and (d) NMP. of controlled radical polymerization
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