Fluorescent Molecularly Imprinted Polymers

Gawlitza, Kornelia; Wan, Wei; Wagner, S.; Rurack, Knut

doi:10.1002/9781119336181.ch3

Cited by 9 publications

(6 citation statements)

References 109 publications

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“…First, we opted for MIPs that contain a fluorescent probe monomer as the designated binding partner. Such fluorescent MIPs are not only very attractive sensor materials, but the functional monomer reports on its status (bound or not bound, microenvironmental polarity as well as acidity/basicity) at any time during the prepolymerization, polymerization, and rebinding steps simply through the band maxima in absorption and/or fluorescence and its fluorescence yield. , Second, we investigated a format that recently proved to possess superior sensing performance in the enantioselective recognition of amino acids, that is, a few-nanometer thin MIP layer grafted from silica core particles. The grafting is achieved by RAFT (reversible addition–fragmentation chain transfer) polymerization of a fluorescent monomer ( N -nitrobenzoxadiazole- N ′-ethyl methacrylate-functionalized urea 1 ), a skeletal comonomer (benzyl methacrylate, BMA), and a cross-linker (ethylene glycol dimethacrylate, EDMA) from the surface of aminopropyltriethoxysilane (APTES)- and RAFT agent-functionalized silica microparticles .…”

Section: Resultsmentioning

confidence: 99%

Role of Counterions in Molecularly Imprinted Polymers for Anionic Species

et al. 2018

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Small-molecule oxoanions are often imprinted noncovalently as carboxylates into molecularly imprinted polymers (MIPs), requiring the use of an organic counterion. Popular species are either pentamethylpiperidine (PMP) as a protonatable cation or tetraalkylammonium (TXA) ions as permanent cations. The present work explores the influence of the TXA as a function of their alkyl chain length, from methyl to octyl, using UV/vis absorption, fluorescence titrations, and HPLC as well as MD simulations. Protected phenylalanines (Z-l/d-Phe) served as templates/analytes. While the influence of the counterion on the complex stability constants and anion-induced spectral changes shows a monotonous trend with increasing alkyl chain length at the prepolymerization stage, the cross-imprinting/rebinding studies showed a unique pattern that suggested the presence of adaptive cavities in the MIP matrix, related to the concept of induced fit of enzyme-substrate interaction. Larger cavities formed in the presence of larger counterions can take up pairs of Z-x-Phe and smaller TXA, eventually escaping spectroscopic detection. Correlation of the experimental data with the MD simulations revealed that counterion mobility, the relative distances between the three partners, and the hydrogen bond lifetimes are more decisive for the response features observed than actual distances between interacting atoms in a complex or the orientation of binding moieties. TBA has been found to yield the highest imprinting factor, also showing a unique dual behavior regarding the interaction with template and fluorescent monomer. Finally, interesting differences between both enantiomers have been observed in both theory and experiment, suggesting true control of enantioselectivity. The contribution concludes with suggestions for translating the findings into actual MIP development.

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Section: Resultsmentioning

confidence: 99%

Role of Counterions in Molecularly Imprinted Polymers for Anionic Species

et al. 2018

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“…When ultimately aiming at straightforward onsite analysis, which commonly does not allow for complicated separation steps, an element endowing the system with selectivity is thus additionally required. A promising approach in this regard is the strategy of molecular imprinting, which becomes particularly attractive when polymerizable fluorescent probe derivatives are covalently integrated into a polymer network, thus combining target selectivity through a tailored network with the indication ability of a potent probe molecule [39,40]. Recently, several molecularly imprinted polymers (MIPs) have been developed for the detection of GPS, where these MIPs have been applied for the extraction, preconcentration and sample clean-up of GPS and its analogs from aqueous samples [41,42].…”

Section: Introductionmentioning

confidence: 99%

Red-Emitting Polymerizable Guanidinium Dyes as Fluorescent Probes in Molecularly Imprinted Polymers for Glyphosate Detection

et al. 2022

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The development of methodologies to sense glyphosate has gained momentum due to its toxicological and ecotoxicological effects. In this work, a red-emitting and polymerizable guanidinium benzoxadiazole probe was developed for the fluorescence detection of glyphosate. The interaction of the fluorescent probe and the tetrabutylammonium salt of glyphosate was studied via UV/vis absorption and fluorescence spectroscopy in chloroform and acetonitrile. The selective recognition of glyphosate was achieved by preparing molecularly imprinted polymers, able to discriminate against other common herbicides such as 2,4-dichlorophenoxyacetic acid (2,4-D) and 3,6-dichloro-2-methoxybenzoic acid (dicamba), as thin layers on submicron silica particles. The limits of detection of 4.8 µM and 0.6 µM were obtained for the sensing of glyphosate in chloroform and acetonitrile, respectively. The reported system shows promise for future application in the sensing of glyphosate through further optimization of the dye and the implementation of a biphasic assay with water/organic solvent mixtures for sensing in aqueous environmental samples.

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“…Cytosensing based on the cell shape recognition does not always provide an acceptable specificity due to the high degree of cell plasticity to easily undergo morphology changes under small influences. Moreover, the micrometer size of the cells and their three-dimensional features make it difficult to fabricate a very selective and rigid monomer [100]. Therefore, one critical element would be choosing the right monomers for the fabrication of highly selective and specific platforms.…”

Section: Bacteria Detectionmentioning

confidence: 99%

The Use of Aptamers and Molecularly Imprinted Polymers in Biosensors for Environmental Monitoring: A Tale of Two Receptors

et al. 2020

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Effective molecular recognition remains a major challenge in the development of robust receptors for biosensing applications. Over the last three decades, aptamers and molecularly imprinted polymers (MIPs) have emerged as the receptors of choice for use in biosensors as viable alternatives to natural antibodies, due to their superior stability, comparable binding performance, and lower costs. Although both of these technologies have been developed in parallel, they both suffer from their own unique problems. In this review, we will compare and contrast both types of receptor, with a focus on the area of environmental monitoring. Firstly, we will discuss the strategies and challenges involved in their development. We will also discuss the challenges that are involved in interfacing them with the biosensors. We will then compare and contrast their performance with a focus on their use in the detection of environmental contaminants, namely, antibiotics, pesticides, heavy metals, and pathogens detection. Finally, we will discuss the future direction of these two technologies.

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Fluorescent Molecularly Imprinted Polymers

Cited by 9 publications

References 109 publications

Role of Counterions in Molecularly Imprinted Polymers for Anionic Species

Role of Counterions in Molecularly Imprinted Polymers for Anionic Species

Red-Emitting Polymerizable Guanidinium Dyes as Fluorescent Probes in Molecularly Imprinted Polymers for Glyphosate Detection

The Use of Aptamers and Molecularly Imprinted Polymers in Biosensors for Environmental Monitoring: A Tale of Two Receptors

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