Molecular Imprinted Photonic Crystal for Sensing of Biomolecules

Mol. Impr. 2016; 4: 1–12

Review Open Access

Wei Chen, Zihui Meng*, Min Xue, Kenneth J Shea Molecular imprinted photonic crystal for sensing of biomolecules

DOI 10.1515/molim-2016-0001 environmental monitoring and food quality control. Thus, Received December 8, 2015; accepted January 29, 2016 different biochemical sensors have been developed to detect biologically active molecules and determine the Abstract: Molecularly imprinted polymers (MIPs) concentration of these molecules. Due to the structure are highly cross-linked polymers with high binding complexity and large size of the biomolecules, it is a big capacity and selectivity to the target molecules. MIPs challenge to develop a good biosensor. An ideal biosensor become increasingly important because of the potential should possess the advantages of high specificity, applications in drug delivery, purification and separation. sensitivity, quick response rate as well as low cost. Thus, In spite of the tremendous progress that has been made in developing new technology for biomolecules detection the molecular imprinting field, many challenges remain has attracted much attention. [2-5] to be addressed, especially in transforming the binding The common detection methods include high event into a detectable optical signal. The combination performance liquid chromatography (HPLC) [6-7], mass of photonic crystal and molecular imprinting technique spectrometry (MS) [8-9], fluorescence [10-11], surface- is becoming a popular research idea. Compared to the enhanced Raman scattering (SERS) [12-14], enzyme- conventional MIPs, the molecularly imprinted photonic linked immunosorbent assay [15-16] and immunoassays crystal sensors (MIPCB) have the advantage of directly [17-18]. Each of these methods suffers from one or more convert the molecule recognition process into optical disadvantages, such as require complicated screening and signal. This review comprehensively summarizes various concentration processes prior to sensing, high cost and MIPCB, including the principle of molecular imprinted time consuming. Among those methods, immunoassays photonic crystal sensors, recent development, some using labeled antibodies are the most popular methods challenges and effective strategies for MIPCB. for the detection of biomolecules with high sensitivity and selectivity [19]. However, labeling protocols are time- Keywords: Molecularly imprinted polymer, photonic consuming and expensive, and may lead to denature of the crystal, biomolecules, sensors antibodies. Therefore, label-free detectors for biomolecules have drawn increasing interest for researches in the field of proteomics, clinical diagnostics and environmental 1 Introduction monitoring. In label-free sensors, target molecules are detected in their natural forms without any label process. Biomolecules are present in living organisms, including These types of sensors have the advantages of eliminating large macromolecules such as proteins, polysaccharides, the time-consuming and expensive labeling steps, as lipids, and nucleic acids, as well as small molecules such well as allowing for kinetic measurement of molecular as glycolipids, sterols, glycerolipids and vitamins. [1] interactions. Recently, molecularly imprinted photonic Detection and quantification of biomolecules has attracted crystal biosensors as a new kind of bioassay techniques considerable attention in the fields of clinical diagnostics, have attracted substantial interest due to their great potential for label-free detection of biomolecular [20-22]. In this review, we provide an overview of different *Corresponding author Zihui Meng, School of Chemical Engineering molecularly imprinted photonic crystal biosensors & Environment, Beijing Institute of Technology, Beijing, 100081, P.R. China, E-mail: [email protected] (MIPCB) developed until now (Table 1). After introducing Wei Chen, Min Xue, School of Chemical Engineering & Environment, the concept of molecularly imprinting and photonic Beijing Institute of Technology, Beijing, 100081, P.R. China crystal sensors, we focus on the applications of molecular Kenneth J Shea, Department of Chemistry, University of California, imprinted photonic crystal biosensors. Finally, we Irvine, California, 92697, United States

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Table 1 Overview of different MIPCB

Template Monomer and cross-linker Structure Reference

Protein BSA MAA,EGDMA Inverse opal [20] Hb IDA, PTMS, APTMS Opal [23] IDA, PTMS, APTMS Hollow spheres array [24] Hb, HRP, BSA AAm, BIS Inverse opal [21] Chiral biomolecules L-Dopa MAA,EGDMA Inverse opal [25] L-Phenylalanine AAm, MAA,BIS Inverse opal [26] MAH-β-CD, AAc, BIS Inverse opal [27] (-)-Norephedrine G0-3TCOOH Opal [28] Other biomolecules Cholic acid MAA, EGDMA Inverse opal [29] Atropine MAA, EGDMA Inverse opal [30] Diethylstilbestrol MMA, AAm, Opal [31] Imidacloprid MAA, EGDMA Inverse opal [5] Theophylline, ephed- MAA, EGDMA Inverse opal [32] rine Tetracyclines AAm, AAc, BIS Inverse opal [22] Cholesterol MAA, EGDMA Inverse opal [33] Bisphenol A MMA,EGDMA Opal [34] MMA,EGDMA Inverse opal [35] 17β-estradiol MMA, AAm, BIS Opal [36] Vanillin MAA,EGDMA Inverse opal [37] Atrazine MAA,EGDMA Inverse opal [30]

considered the challenges presently encountered and MIPs were created by the polymerization of a mixture of some feasible resolutions. cross-linkers and functional monomers in the presence of a template dissolved in proper solvent, followed by the removal of template from polymer, specific recognition 2 Molecular imprinting polymers and binding sites exhibit high selectivity to the target MIPs molecule was formed in the highly cross-linked polymer network, the detailed process was demonstrated in Molecularly imprinted polymers (MIPs) have been called Figure 1. Compared to the antibody in nature, molecularly ‘‘antibody mimics’’ or “plastic antibodies” because these imprinting polymers have higher physical strength, systems attempt to mimic the specific recognition between flexibility, robustness and resistance to elevated pressure antibodies and antigen in the immune system [38-40]. which make them attractive in usage for bioreceptor

Unauthenticated Download Date | 4/28/16 10:14 AM Molecular imprinted photonic crystal for sensing of biomolecules 3 and cost-effective detect materials. In general terms, the stable emulsion of a cross-linking monomer. The binding approaches to molecular imprinting can be distinguished experiments showed that bacterial recognition on the BIP by the interaction between the template molecules and beads is dependent on the nature of the pre-polymers and the functional monomers. They are covalent molecular the target bacteria. The functional materials for microbial imprinting, non-covalent molecular imprinting and recognition showed great potential for constructing metal-coordinating molecular imprinting [41-42]. cell-cell communication networks, biosensors, and new Since the idea of molecular imprinting was first put platforms for testing antibiotic drugs. forward by Pauling in 1940s [43], over the past decades, Despite the advantages of MIPs with high selectivity it is well known that molecular imprinting is a very and strong affinity, there remains some drawback of promising and rapidly evolving technology, with many the difficulty in transforming the binding event into a possible applications such as preparative analytical detectable optical signal which is a hurdle for the wider separations [44-45], enzyme-like catalysis [46-47], solid- applications. phase extractions [48-49], chemical sensors [50-51] and drug delivery [52-53], etc. Molecular imprinting has proven to be particularly successful for small molecules. Recent 3 Photonic crystals years, much attention has been paid to the imprinting Photonic crystals (PhCs) are composed of a periodic of biomolecules such as proteins [54-55], DNA [56], and arrangement of regularly shaped materials with different even whole cells [57] and viruses [58-59] for its potential dielectric constants, owing to the periodicity in dielectric, applications in biomaterials separation, purification, these materials exhibit a photonic band gap (PBG), biosensor, and mimicking enzyme and antibody [60]. certain wavelength of light located in the band gap can’t Rossetti et al. synthesized molecularly imprinted polymers (MIPs) targeting the proteotypic peptide of ProGRP by surface-initiated reversible addition-fragmentation chain transfer polymerization. [40] As shown in Figure 2, the polymerization was performed on the surface of RAFT- modified wide-pore silica beads using hydrophobic cross- linker divinylbenzene (DVB) and functional monomers N-(2-aminoethyl) methacrylamide hydrochloride (EAMA). The MIPs have high affinity and selectivity for a proteotypic peptide in aqueous buffered media. Also the MIPs were used as sorbents for the cleanup and enrichment of a ProGRP signature peptide from typically treated serum samples. This fundamental property makes the MIPs promising in biological sample cleanup and cost-effective biomarker analysis. In another study, a bacteria-imprinted polymer (BIP) was prepared by Ye et al. using Pickering emulsion polymerization [61]. The imprinting process was described in Figure 3, a complex of negatively charged Figure 3 Interfacial bacteria imprinting by Pickering emulsion poly- bacteria and positively charged vinyl-containing pre- merization. Reprinted with permission from Reference 62. Copyright polymer was used as the particle stabilizer to construct a 2014, Wiley.

Unauthenticated Download Date | 4/28/16 10:14 AM 4 W. Chen, et al. transmission through the material and reflected. [62] If polystyrene colloidal array was embedded in a hydrogel the PBG is located in the visible light region, the structural which consists of 4-amino-3-fluorophenylboronic acid color of the PhCs can be directly observed by the naked eye and 4-carboxy-3- fluorophenylboronic acid as recognition without the need of complicated and expensive apparatuses elements to achieve sensing at physiologic pH values. The to read the signals [63]. Such bright structural colors make structure color of the photonic glucose-sensing material PhCs the potential application in the area of optical fibers, changed from red to blue over the physiologically relevant photovoltaic devices, displays, sensors and so on. tear-fluid glucose concentrations. Hu developed a kind of According to variations in the refractive index and photonic ionic liquids polymer for naked-eye detection of period in space, three kinds of structures of PhCs may anions by combination of the unique properties of both be discerned, including one-dimensional (1D), two- ionic liquids (IL) and photonic crystals. [73] It is shown that dimensional (2D) and three-dimensional (3D) [63-64] the prepared photonic IL film exhibits different reflection (Figure 4). As 3D PhCs periodicity potentially manipulates wavelength shifts upon soaking in various aqueous anion the flow of light in all directions, it has attracted more solutions. The induced color changes of the photonic and more attention in the fields of biomolecule detection, ionic liquid film upon soaking in different anions aqueous real-time monitoring of enzyme activity, cell morphology solutions was shown in Figure 5. More interestingly, these research, and so on. Specifically, if these highly ordered reflection wavelength shifts can be directly observed by structures are made from hydrogel polymers, they can the naked eye which makes it promising for rapid and swell or shrink in response to different stimuli, leading sensitive naked-eye detection of anions. to a change in reflection wavelength accompanied by a visually structure color change. Asher and co-workers pioneered the concept of 3D photonic sensors based on ordered crystalline colloidal array embedded within functional hydrogel matrices, and used to detect various stimuli including pH [65], glucose [66], creatinine [67], ionic strength [68], temperature [69] and so on. Other groups such as Li [70], Wolfbeis [64], and Yin [71] also devoted to studying 3D photonic sensors that display a tunable optical response sensitive to various analyte. For Figure 4 Representation of 1D, 2D and 3D photonic crystals. The instance, Asher developed a photonic crystal glucose- different colors represent materials with different dielectric cons- sensing material which can be used for monitoring tants. Reprinted with permission from Reference 65. Copyright 2014, of glucose in tear fluid with high selectivity [72]. A Wiley.

Figure 5 SEM images of the fabricated photonic ionic liquid film with opened pore structure (A) and closed pore structure (B). C) Stop band shifts of the photonic ionic liquid film upon soaking in diversified anions aqueous solutions. D) The induced color changes of the photonic ionic liquid film upon soaking in diversified anions aqueous solutions. Reprinted with permission from Reference 74. Copyright 2008, Wiley.

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Among those photonic sensors, most of them showed According to the above theory, the reflection reasonably wide range of color change which makes wavelength of PhCs depends largely on refractive index them very promising in label-free detection of different contrast between two periodic media (neff) and the analyte. However, specific functional groups should be lattice constant (D). During the molecular recognition copolymerized or modified in the hydrogel as recognition process, the target molecule binds to the nanocavities agents to improve the sensing properties. The applications of the imprinted photonic crystal. The neff will change of such sensors in wide range of filed were limited since not as the refractive index of the target molecule is different all the target molecule has specific recognition functional from the photonic crystal host matrix, and thus Bragg groups. Meanwhile, the hydrogel usually display poor diffraction peak shifts. Meanwhile, the framework of the selectivity behavior. So the combination of MIPs and photonic crystal can swell or shrink upon binding the photonic crystal would create optical readout MIPs which target molecular, which lead to the changes of the lattice would be “ideal” for developing molecular sensors with a constant. The principle of MIPCB was illustrated in Figure series of desired features. 6. In brief, the specific binding of target molecules on the imprinted nanocavities of the PhCs leads to changes in the average refractive index and the swelling or shrink of 4 Principle of molecularly imprinted the PhCs, both of which are reported through a shift of the photonic crystal sensors Bragg diffraction peak.

The iridescent colorful of the PCs materials can be ascribed to interference and reflection, which can be described by 5 Molecular imprinted photonic Bragg’s and Snell’s laws. crystal sensors for biomolecules detection

5.1 Sensing of protein

Where λ is the wavelength of the reflected light, neff Proteins are of great importance in medical and biological is the average refractive index of the photonic materials, fields. A multitude of potential methods have been D is the distance of diffracting plane spacing, and θ is developed for specific and sensitive detection of protein the Bragg angle of incidence of the light falling on the [26, 74-75]. Recently, several molecular imprinted photonic nanostructures. [64] crystal sensors were used for protein detection. The first

Figure 6 Principle of molecularly imprinted photonic crystal sensors

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MIPCB for protein detection was proposed by Li et al. sensitivity and specificity to BSA. More importantly, the [20] In his report, photonic crystals were combined with molecular recognition process could be clearly detected surface molecular imprinting to construct a biosensor by the naked eye through a distinct color change in the using BSA as template molecule. The fabrication process sensor film. Meng et al. prepared a 3D colloidal array of the MIPCB was illustrated in Figure 7. The template assembled by surface imprinted silica (SIS) for Hb protein was coated onto the surface of 3D silica colloidal detection. [23] Protein imprinting was performed on the array by spin-casting, an aqueous solution of saccharose 3-Glycidoxypropyltrimethoxysilane (GLYMO) modified was used to prevent the protein from denature. Then the silica surface. The monodisperse SIS was assembled into pre-gel containing methacrylic acid (MAA) as functional close-packed 3D MIPCB by evaporation-induced self- monomer, ethylene glycol dimethylacrylate (EGDMA) assembly. Due to the diameter changes of the SIS colloid as cross-linker and azobisisobutyronitrile (AIBN) as upon the absorption of target protein, the structure color initiator was infiltrated in the space of the silica array. of the MIPCB changes in response to different protein After radical polymerization, the silica nanoparticles concentrations. Later, to improve the mass transfer rate of and the imprinted protein were removed. The obtained the MIPCB, the silica core of the SIS was removed by HF after hydrogel films with inverse-opal structure have high surface imprinting. As shown in Figure 8, the molecularly

Figure 7 a) Schematic illustrating the fabrication of a protein-imprinted hydrogel film exhibiting a hierarchical structure. SEM images of b) the silica-colloidal crystal template and c) the resulting photonic MIP film with ordered and interconnected macroporous structure. Reprin- ted with permission from Reference 20. Copyright 2007, Wiley.

Figure 8 Fabrication schematic diagram of MIPCB [24]

Unauthenticated Download Date | 4/28/16 10:14 AM Molecular imprinted photonic crystal for sensing of biomolecules 7 imprinted hollow spheres (MIHS) were assembled into a 5.2 Sensing of chiral biomolecules close-packed 3D colloidal array by the same method. The reflection wavelength of the MIPCB has a larger red shift Chirality was first discovered by Pasteur and played an in response to Hb accompanied by greater structure color important role in nature since the building blocks of life change. [24] This technology has promising potential in comprise chiral units such as amino acids and sugars. the naked-eye detection of biomacromolecules. [76] Various analytical methods for chiral biomolecules Imprinted suspension array was another kind of recognition have been reported, such as circular MIPCB which was developed by Gu. In this approach, the dichroism(CD) [77], optical rotatory dispersion (ORD) silica colloidal crystal beads (SCCBs) was prepared using [78] and Raman optical activity (ROA) [79]. Although a co-flow microfluid device by droplet template method. big progress has been made in the field of instrumental [21] The protein template was immobilized onto the analytical methods, low-cost and label-free sensors pore surface of the SCCBs by covalent bonding method, for chiral recognition have also attracted considerable followed by infusion of polyacrylamide in the voids of attentions. the SCCBs, after polymerization, the silica nanoparticles Li et al. developed an imprinted photonic polymer and the protein templates was removed yielded a MIPCB with highly ordered 3D structure which displays highly with inverse opal structure. Three kinds of MIPCB selective and specific chiral molecular recognition imprinted with bovine Hb, HRP, and BSA was prepared to properties. [25] The precursors containing MAA as demonstrate the multiplexing capabilities of the imprinted functional monomer, l-3, 4-dihydroxyphenyalanine suspension array. The MIPCB have high sensitivity and (l-dopa) as template, EGDMA as cross-linker and specificity to the template protein. And the molecular AIBN as initiator were infiltration into silica colloidal recognition event can be reported by the red shift of the array. After photopolymerized in an ice bath, the silica reflection wavelength. This new type of suspension array nanoparticles were removed with 1% hydrofluoric acid, is very promising in biosensors and medical diagnostics and l-dopa was eluted with 0.1M acetic acid. As shown for multiplex label-free detection of proteins. in Figure 9, the reflection wavelength of the MIPCB has

Figure 9 UV/Vis spectra of blank MIPCB exposed to l-dopa (A) and d-dopa (B) in phosphate buffer at different concentrations. C) Three blank MIPCB exposed to phosphate buffer, d-dopa, and l-dopa in phosphate buffer. Reprinted with permission from Reference 25. Copyright 2006, Wiley.

Unauthenticated Download Date | 4/28/16 10:14 AM 8 W. Chen, et al. a maximum red shift of 28 nm in response to 0.01 mm QCM crystal which was pre-coated with single layer of l-dopa accompanied by obvious color change, while no PS particles. The fabricated MIPCB had a much higher red shift was observed for MIPCB immersed in aqueous sensing response upon template rebinding than the solutions of d-dopa. Another MIPCB for amino acids conventional non-templated and flat MIP film as observed chiral recognition was developed by Yu et al. using in QCM in-situ measurements. polystyrene colloids array as sacrificial template. [26] The polymer was composed of AAm, MAA using l-phenylalanine (l-Phe) as template, APS and BIS as 5.3 Sensing of other biomolecules initiator and cross-linker, respectively. The reflection wavelength of the MIPCB has a distinct red-shift when Some biomolecules have adverse effects on endocrine l-Pga molecule was bound to the MIPCB with a very short function of wildlife and human, therefore, the detection response time of 5 min. When the concentration of l-Pga and measurement of biorelevant compounds is crucial was 0.01 mM, the red-shift was 20 nm. More importantly, to control environmental pollution and to ensure human the MIPCB has good recoverability and reproducibility health. Several MIPCB have been developed for sensing without changes in reflection wavelength over four the biomolecules, such as atropine, cholic acid [29], cycles. Later, they proposed a new type of MIPCB for diethylstilbestrol [31], antibiotics [22], imidacloprid [5], chiral amino acid recognition using maleic anhydride theophylline [32], and so on. modified β-cyclodextrin (β-CD) and acrylic acid as Li et al. developed a molecularly imprinted photonic functional monomers. [27] Throughout the optimization hydrogel(IPH) for detection of cholic acid using silica of polymerization, the MIPCB had rapid response rate, colloidal array as sacrificial template [29]. The unique 3D high sensitivity to the L-Phenylalanine. A red-shift up to ordered porous hydrogels was photopolymerized using 56 nm in reflection wavelength was observed when the MA as monomer and EGDMA as cross-linker. The optical MIPCB was immersed in L-Phe of 10-5M in pH 6 buffer diffraction of IPH is very sensitive to the rebinding of cholic solution. The recoveries of L-Phe in the diluted samples acid molecules, with the increase of the concentration ranged from 95 to 109%. of cholic acid, the peak shifts gradually to shorter Recently, Rigoberto combined the technique of wavelength. More importantly, as IPH has high surface- molecular imprinting and colloidal sphere layering via to-volume ratio, it can provide more complete removal of Langmuir–Blodgett (LB)-like technique for sensing of imprinted molecules to achieve a high density of efficient norephedrine. [28] As illustrated in Figure 10, the MIPCB recognition sites. Using the similar method, the MIPCS was electropolymerized using G0-3TCOOH as single with inverse opal structure for sensing of theophylline functional and cross-linking monomer on the gold (Au) and atrazine were also reported by the same group [32].

Figure 10 Fabrication of MIPCB onto QCM: 1) PS layering from SDS-PS solution, 2) CV electrodeposition of the MIP solution, 3) template and PS removal, and 4) template analyte sensing. Reprinted with permission from Reference 28. Copyright 2012, Wiley.

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Wang also reported a MIPCB with high selectivity for AAm as monomer, after removal of the template molecules, tetracyclines analysis in food using polystyrene (PS) the monodispersed DES-imprinted colloidal spheres were colloidal crystal as sacrificial templates [22]. In this report, assembled into high order colloidal array. The diffraction AAm and AAc were both used as monomers, BIS was peak intensity of the imprinted crystalline colloidal array used as crosslinker. It was shown in Figure 11, the MIPCB (ICCA) reduced gradually and also showed a slight red displays a 10 nm diffraction red-shift in the presence of shift in response to an increase in the concentration of the 0.04 mM TC after being immersed into the solution for 5 target molecules. While the diffraction peak intensity of minutes. non-imprinted crystalline colloidal array (NCCA) changed Another kind of MIPCB with opal structure was slightly upon the increase in the concentration of the proposed by Sai et al. for sensing of diethylstilbestrol [31]. target molecules. In addition, the ICCA exhibited rapid As shown in Figure 12, DES-imprinted spheres were first response to DES and possessed an ideal recoverability prepared by suspension polymerization using MMA and within four cycles.

Figure 11 Typical SEM image (a) and photograph (b) of the resulting MIPP film. (C).Diffraction response of MIPP1 to TC solution of varying concentrations. Reprinted with permission from Reference 22. Copyright 2012, Royal Society of Chemistry.

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