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3 pages, 189 KiB

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Editorial: Advance in Molecularly Imprinted Polymers

by Michał Cegłowski

Polymers 2023, 15(15), 3199; https://doi.org/10.3390/polym15153199 - 27 Jul 2023

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Abstract

Molecularly imprinted polymers (MIPs), due to their unique recognition properties, have found various applications, mainly in extraction and separation techniques; however, their implementation in other research areas, such as sensor construction and drug delivery, has also been substantial [...] Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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15 pages, 19467 KiB

Open AccessArticle

Ion-Imprinted Polymer Structurally Preorganized Using a Phenanthroline-Divinylbenzoate Complex with the Cu(II) Ion as Template and Some Adsorption Results

by Egla Yareth Bivián-Castro, Abraham Zepeda-Navarro, Jorge Luis Guzmán-Mar, Marcos Flores-Alamo and Brenda Mata-Ortega

Polymers 2023, 15(5), 1186; https://doi.org/10.3390/polym15051186 - 26 Feb 2023

Cited by 12 | Viewed by 2148

Abstract

The novel [Cuphen(VBA)₂H₂O] complex (phen: phenanthroline, VBA: vinylbenzoate) was prepared and used as a functional monomer to preorganize a new ion-imprinted polymer (IIP). By leaching the Cu(II) from the molecular imprinted polymer (MIP), [Cuphen(VBA)₂H₂O-co [...] Read more.

The novel [Cuphen(VBA)₂H₂O] complex (phen: phenanthroline, VBA: vinylbenzoate) was prepared and used as a functional monomer to preorganize a new ion-imprinted polymer (IIP). By leaching the Cu(II) from the molecular imprinted polymer (MIP), [Cuphen(VBA)₂H₂O-co-EGDMA]_n (EGDMA: ethylene glycol dimethacrylate), the IIP was obtained. A non-ion-imprinted polymer (NIIP) was also prepared. The crystal structure of the complex and some physicochemical, spectrophotometric techniques were also used for the MIP, IIP, and NIIP characterization. The results showed that the materials are nonsoluble in water and polar solvents, which are the main features of polymers. The surface area of the IIP is higher than the NIIP demonstrated by the blue methylene method. The SEM images show monoliths and particles smoothly packed together on spherical and prismatic-spherical surfaces in the morphology of MIP and IIP, respectively. Moreover, the MIP and IIP could be considered as mesoporous and microporous materials, shown by the size of the pores determined by the BET and BJH methods. Furthermore, the adsorption performance of the IIP was studied using copper(II) as a contaminant heavy metal. The maximum adsorption capacity of IIP was 287.45 mg/g at 1600 mg/L Cu²⁺ ions with 0.1 g of IIP at room temperature. The Freundlich model was found to best describe the equilibrium isotherm of the adsorption process. The competitive results indicate that the stability of the Cu-IIP complex is higher than the Ni-IIP complex with a selectivity coefficient of 1.61. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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21 pages, 4272 KiB

Open AccessArticle

Application of Molecular Imprinting for Creation of Highly Selective Sorbents for Extraction and Separation of Rare-Earth Elements

by Ruslan Kondaurov, Yevgeniy Melnikov and Laura Agibayeva

Polymers 2023, 15(4), 846; https://doi.org/10.3390/polym15040846 - 8 Feb 2023

Cited by 4 | Viewed by 1895

Abstract

The aim of the work is to study the effectiveness of a molecular imprinting technique application for the creation of highly selective macromolecular sorbents for selective sorption of light and heavy rare-earth metals (for example, samarium and gadolinium, respectively) with subsequent separation from [...] Read more.

The aim of the work is to study the effectiveness of a molecular imprinting technique application for the creation of highly selective macromolecular sorbents for selective sorption of light and heavy rare-earth metals (for example, samarium and gadolinium, respectively) with subsequent separation from each other. These sorbents seem to be promising due to the fact that only the target rare-earth metal will be sorbed owing to the fact that complementary cavities are formed during the synthesis of molecularly imprinted polymers. In other words, the advantage of the proposed macromolecules is the absence of accompanying sorption of metals with close chemical properties. Two types of molecularly imprinted polymers (MIP) were synthetized based on methacrylic acid (MAA) and 4-vinylpyridine (4VP) functional monomers. The sorption properties (extraction degree, exchange capacity) of the MIPs were studied. The impact of template removal cycle count (from 20 to 35) on the sorption effectivity was studied. Laboratory experiments on selective sorption and separation of samarium and gadolinium from a model solution were carried out. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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15 pages, 3168 KiB

Open AccessArticle

Molecularly Imprinted Ligand-Free Nanogels for Recognizing Bee Venom-Originated Phospholipase A2 Enzyme

by Anamaria Zaharia, Ana-Mihaela Gavrila, Iuliana Caras, Bogdan Trica, Anita-Laura Chiriac, Catalina Ioana Gifu, Iulia Elena Neblea, Elena-Bianca Stoica, Sorin Viorel Dolana and Tanta-Verona Iordache

Polymers 2022, 14(19), 4200; https://doi.org/10.3390/polym14194200 - 7 Oct 2022

Cited by 3 | Viewed by 1802

Abstract

In this study, ligand-free nanogels (LFNGs) as potential antivenom mimics were developed with the aim of preventing hypersensitivity and other side effects following massive bee attacks. For this purpose, poly (ethylene glycol) diacrylate was chosen as a main synthetic biocompatible matrix to prepare [...] Read more.

In this study, ligand-free nanogels (LFNGs) as potential antivenom mimics were developed with the aim of preventing hypersensitivity and other side effects following massive bee attacks. For this purpose, poly (ethylene glycol) diacrylate was chosen as a main synthetic biocompatible matrix to prepare the experimental LFNGs. The overall concept uses inverse mini-emulsion polymerization as the main route to deliver nanogel caps with complementary cavities for phospholipase A2 (PLA2) from bee venom, created artificially with the use of molecular imprinting (MI) technologies. The morphology and the hydrodynamic features of the nanogels were confirmed by transmission electron microscopy (TEM) and dynamic light scattering (DLS) analysis. The following rebinding experiments evidenced the specificity of molecularly imprinted LFNG for PLA2, with rebinding capacities up to 8-fold higher compared to the reference non-imprinted nanogel, while the in vitro binding assays of PLA2 from commercial bee venom indicated that such synthetic nanogels are able to recognize and retain the targeted PLA2 enzyme. The results were finally collaborated with in vitro cell-viability experiments and resulted in a strong belief that such LFNG may actually be used for future therapies against bee envenomation. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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24 pages, 3163 KiB

Open AccessArticle

Molecularly Imprinted Solid Phase Extraction Strategy for Quinic Acid

by Sarah H. Megahed, Mohammad Abdel-Halim, Amr Hefnawy, Heba Handoussa, Boris Mizaikoff and Nesrine A. El Gohary

Polymers 2022, 14(16), 3339; https://doi.org/10.3390/polym14163339 - 16 Aug 2022

Cited by 5 | Viewed by 2305

Abstract

Quinic acid (QA) and its ester conjugates have been subjected to in-depth scientific investigations for their antioxidant properties. In this study, molecularly imprinted polymers (MIPs) were used for selective extraction of quinic acid (QA) from coffee bean extract. Computational modelling was performed to [...] Read more.

Quinic acid (QA) and its ester conjugates have been subjected to in-depth scientific investigations for their antioxidant properties. In this study, molecularly imprinted polymers (MIPs) were used for selective extraction of quinic acid (QA) from coffee bean extract. Computational modelling was performed to optimize the process of MIP preparation. Three different functional monomers (allylamine, methacrylic acid (MAA) and 4-vinylpyridine (4-VP)) were tested for imprinting. The ratio of each monomer to template chosen was based on the optimum ratio obtained from computational studies. Equilibrium rebinding studies were conducted and MIP C, which was prepared using 4-VP as functional monomer with template to monomer ratio of 1:5, showed better binding performance than the other prepared MIPs. Accordingly, MIP C was chosen to be applied for selective separation of QA using solid-phase extraction. The selectivity of MIP C towards QA was tested versus its analogues found in coffee (caffeic acid and chlorogenic acid). Molecularly imprinted solid-phase extraction (MISPE) using MIP C as sorbent was then applied for selective extraction of QA from aqueous coffee extract. The applied MISPE was able to retrieve 81.918 ± 3.027% of QA with a significant reduction in the amount of other components in the extract. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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12 pages, 3588 KiB

Open AccessArticle

N-(2-Arylethyl)-2-methylprop-2-enamides as Versatile Reagents for Synthesis of Molecularly Imprinted Polymers

by Monika Sobiech, Dorota Maciejewska and Piotr Luliński

Polymers 2022, 14(13), 2738; https://doi.org/10.3390/polym14132738 - 4 Jul 2022

Cited by 2 | Viewed by 1654

Abstract

The paper describes the formation of six aromatic N-(2-arylethyl)-2-methylprop-2-enamides with various substituents in benzene ring, viz., 4-F, 4-Cl, 2,4-Cl₂, 4-Br, 4-OMe, and 3,4-(OMe)₂ from 2-arylethylamines and methacryloyl chloride in ethylene dichloride with high yields (46–94%). The structure of the [...] Read more.

The paper describes the formation of six aromatic N-(2-arylethyl)-2-methylprop-2-enamides with various substituents in benzene ring, viz., 4-F, 4-Cl, 2,4-Cl₂, 4-Br, 4-OMe, and 3,4-(OMe)₂ from 2-arylethylamines and methacryloyl chloride in ethylene dichloride with high yields (46–94%). The structure of the compounds was confirmed by ¹H NMR, ¹³C NMR, IR, and HR-MS. Those compounds were obtained to serve as functionalized templates for the fabrication of molecularly imprinted polymers followed by the hydrolysis of an amide linkage. In an exemplary experiment, the imprinted polymer was produced from N-(2-(4-bromophenyl)ethyl)-2-methylprop-2-enamide and divinylbenzene, acting as cross-linker. The hydrolysis of 2-(4-bromophenyl)ethyl residue proceeded and the characterization of material including SEM, EDS, ¹³C CP MAS NMR, and BET on various steps of preparation was carried out. The adsorption studies proved that there was a high affinity towards the target biomolecules tyramine and L-norepinephrine, with imprinting factors equal to 2.47 and 2.50, respectively, when compared to non-imprinted polymer synthesized from methacrylic acid and divinylbenzene only. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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8 pages, 1476 KiB

Open AccessArticle

Iodo Silanes as Superior Substrates for the Solid Phase Synthesis of Molecularly Imprinted Polymer Nanoparticles

by Stanislav S. Piletsky, Alvaro Garcia Cruz, Elena Piletska, Sergey A. Piletsky, Eric O. Aboagye and Alan C. Spivey

Polymers 2022, 14(8), 1595; https://doi.org/10.3390/polym14081595 - 14 Apr 2022

Cited by 10 | Viewed by 2932

Abstract

Current state-of-the-art techniques for the solid phase synthesis of molecularly imprinted polymer (MIP) nanoparticles typically rely on amino silanes for the immobilisation of template molecules prior to polymerisation. An investigation into commonly used amino silanes identified a number of problematic side reactions which [...] Read more.

Current state-of-the-art techniques for the solid phase synthesis of molecularly imprinted polymer (MIP) nanoparticles typically rely on amino silanes for the immobilisation of template molecules prior to polymerisation. An investigation into commonly used amino silanes identified a number of problematic side reactions which negatively affect the purity and affinity of these polymers. Iodo silanes are presented as a superior alternative in a case study describing the synthesis of MIPs against epitopes of a common cancer biomarker, epidermal growth factor receptor (EGFR). The proposed iodo silane outperformed the amino silane by all metrics tested, showing high purity and specificity, and nanomolar affinity for the target peptide. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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14 pages, 5508 KiB

Open AccessArticle

EGDMA- and TRIM-Based Microparticles Imprinted with 5-Fluorouracil for Prolonged Drug Delivery

by Michał Cegłowski, Joanna Kurczewska, Aleksandra Lusina, Tomasz Nazim and Piotr Ruszkowski

Polymers 2022, 14(5), 1027; https://doi.org/10.3390/polym14051027 - 4 Mar 2022

Cited by 11 | Viewed by 2344

Abstract

Imprinted materials possess designed cavities capable of forming selective interactions with molecules used in the imprinting process. In this work, we report the synthesis of 5-fluorouracil (5-FU)-imprinted microparticles and their application in prolonged drug delivery. The materials were synthesized using either ethylene glycol [...] Read more.

Imprinted materials possess designed cavities capable of forming selective interactions with molecules used in the imprinting process. In this work, we report the synthesis of 5-fluorouracil (5-FU)-imprinted microparticles and their application in prolonged drug delivery. The materials were synthesized using either ethylene glycol dimethacrylate (EGDMA) or trimethylolpropane trimethacrylate (TRIM) cross-linkers. For both types of polymers, methacrylic acid was used as a functional monomer, whereas 2-hydroxyethyl methacrylate was applied to increase the final materials’ hydrophilicity. Adsorption isotherms and adsorption kinetics were investigated to characterize the interactions that occur between the materials and 5-FU. The microparticles synthesized using the TRIM cross-linker showed higher adsorption properties towards 5-FU than those with EGDMA. The release kinetics was highly dependent upon the cross-linker and pH of the release medium. The highest cumulative release was obtained for TRIM-based microparticles at pH 7.4. The IC₅₀ values proved that 5-FU-loaded TRIM-based microparticles possess cytotoxic activity against HeLa cell lines similar to pure 5-FU, whereas their toxicity towards normal HDF cell lines was ca. three times lower than for 5-FU. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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21 pages, 6528 KiB

Open AccessArticle

Application of the Remote Interaction Effect and Molecular Imprinting in Sorption of Target Ions of Rare Earth Metals

by Talkybek Jumadilov, Ruslan Kondaurov and Aldan Imangazy

Polymers 2022, 14(2), 321; https://doi.org/10.3390/polym14020321 - 13 Jan 2022

Cited by 4 | Viewed by 1867

Abstract

The goal of the present work is a comparative study of the effectiveness of the application of intergel systems and molecularly imprinted polymers for the selective sorption and separation of neodymium and scandium ions. The following physico-chemical methods of analysis were used in [...] Read more.

The goal of the present work is a comparative study of the effectiveness of the application of intergel systems and molecularly imprinted polymers for the selective sorption and separation of neodymium and scandium ions. The following physico-chemical methods of analysis were used in this study: colorimetry and atomic-emission spectroscopy. The functional polymers of polyacrylic acid (hPAA) and poly-4-vinylpyridine (hP4VP) in the intergel system undergo significant changes in the initial sorption properties. The remote interaction of the polymers in the intergel system hPAA–hP4VP provides mutual activation of these macromolecules, with subsequent transfer into a highly ionized state. The maximum sorption of neodymium and scandium ions is observed at molar ratios of 83%hPAA:17%hP4VP and 50%hPAA:50%hP4VP. Molecularly imprinted polymers MIP(Nd) and MIP(Sc) show good results in the sorption of Nd and Sc ions. Based on both these types of these macromolecular structures, principally new sorption methods have been developed. The method based on the application of the intergel system is cheaper and easier in application, but there is some accompanying sorption (about 10%) of another metal from the model solution during selective sorption and separation. Another method, based on the application of molecularly imprinted polymers, is more expensive and the sorption properties are higher, with the simultaneous sorption of the accompanying metal from the model solution. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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11 pages, 2025 KiB

Open AccessArticle

Upconversion Nanoparticles Encapsulated with Molecularly Imprinted Amphiphilic Copolymer as a Fluorescent Probe for Specific Biorecognition

by Hsiu-Wen Chien, Chien-Hsin Yang, Yan-Tai Shih and Tzong-Liu Wang

Polymers 2021, 13(20), 3522; https://doi.org/10.3390/polym13203522 - 13 Oct 2021

Cited by 4 | Viewed by 2140

Abstract

A fluorescent probe for specific biorecognition was prepared by a facile method in which amphiphilic random copolymers were encapsulated with hydrophobic upconversion nanoparticles (UCNPs). This method quickly converted the hydrophobic UCNPs to hydrophilic UNCPs. Moreover, the self-folding ability of the amphiphilic copolymers allowed [...] Read more.

A fluorescent probe for specific biorecognition was prepared by a facile method in which amphiphilic random copolymers were encapsulated with hydrophobic upconversion nanoparticles (UCNPs). This method quickly converted the hydrophobic UCNPs to hydrophilic UNCPs. Moreover, the self-folding ability of the amphiphilic copolymers allowed the formation of molecular imprinting polymers with template-shaped cavities. LiYF₄:Yb³⁺/Tm³⁺@LiYF₄:Yb³⁺ UCNP with up-conversion emission in the visible light region was prepared; this step was followed by the synthesis of an amphiphilic random copolymer, poly(methacrylate acid-co-octadecene) (poly(MAA-co-OD)). Combining the UCNPs and poly(MAA-co-OD) with the templates afforded a micelle-like structure. After removing the templates, UCNPs encapsulated with the molecularly imprinted polymer (MIP) (UCNPs@MIP) were obtained. The adsorption capacities of UCNPs@MIP bound with albumin and hemoglobin, respectively, were compared. The results showed that albumin was more easily bound to UCNPs@MIP than to hemoglobin because of the effect of protein conformation. The feasibility of using UCNPs@MIP as a fluorescent probe was also studied. The results showed that the fluorescence was quenched when hemoglobin was adsorbed on UCNPs@MIP; however, this was not observed for albumin. This fluorescence quenching is attributed to Förster resonance energy transfer (FRET) and overlap of the absorption spectrum of hemoglobin with the fluorescence spectrum of UCNPs@MIP. To our knowledge, the encapsulation approach for fabricating the UCNPs@MIP nanocomposite, which was further used as a fluorescent probe, might be the first report on specific biorecognition. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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14 pages, 3239 KiB

Open AccessArticle

Synergetic Effect of Dual Functional Monomers in Molecularly Imprinted Polymer Preparation for Selective Solid Phase Extraction of Ciprofloxacin

by Ut Dong Thach, Hong Hanh Nguyen Thi, Tuan Dung Pham, Hong Dao Mai and Tran-Thi Nhu-Trang

Polymers 2021, 13(16), 2788; https://doi.org/10.3390/polym13162788 - 19 Aug 2021

Cited by 15 | Viewed by 3423

Abstract

Background: Ciprofloxacin (CIP), an important broad-spectrum fluoroquinolone antibiotic, was often used as a template molecule for the preparation of imprinted materials. In this study, methacrylic acid and 2-vinylpyridine were employed for the first time as dual functional monomers for synthesizing ciprofloxacin imprinted polymers. [...] Read more.

Background: Ciprofloxacin (CIP), an important broad-spectrum fluoroquinolone antibiotic, was often used as a template molecule for the preparation of imprinted materials. In this study, methacrylic acid and 2-vinylpyridine were employed for the first time as dual functional monomers for synthesizing ciprofloxacin imprinted polymers. Methods: The chemical and physicochemical properties of synthesized polymers were characterized using Fourier transform-infrared spectroscopy, thermogravimetric analysis-differential scanning calorimetry, scanning electron microscopy, and nitrogen adsorption-desorption isotherm. The adsorption properties of ciprofloxacin onto synthesized polymers were determined by batch experiments. The extraction performances were studied using the solid phase extraction and HPLC-UV method. Results: The molecularly imprinted polymer synthesized with dual functional monomers showed a higher adsorption capacity and selectivity toward the template molecule. The adsorbed amounts of ciprofloxacin onto the imprinted and non-imprinted polymer were 2.40 and 1.45 mg g⁻¹, respectively. Furthermore, the imprinted polymers were employed as a selective adsorbent for the solid phase extraction of ciprofloxacin in aqueous solutions with the recovery of 105% and relative standard deviation of 7.9%. This work provides an alternative approach for designing a new adsorbent with high adsorption capacity and good extraction performance for highly polar template molecules. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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Review

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21 pages, 3853 KiB

Open AccessReview

Molecularly Imprinted Polymers as State-of-the-Art Drug Carriers in Hydrogel Transdermal Drug Delivery Applications

by Aleksandra Lusina and Michał Cegłowski

Polymers 2022, 14(3), 640; https://doi.org/10.3390/polym14030640 - 8 Feb 2022

Cited by 35 | Viewed by 5326

Abstract

Molecularly Imprinted Polymers (MIPs) are polymeric networks capable of recognizing determined analytes. Among other methods, non-covalent imprinting has become the most popular synthesis strategy for Molecular Imprinting Technology (MIT). While MIPs are widely used in various scientific fields, one of their most challenging [...] Read more.

Molecularly Imprinted Polymers (MIPs) are polymeric networks capable of recognizing determined analytes. Among other methods, non-covalent imprinting has become the most popular synthesis strategy for Molecular Imprinting Technology (MIT). While MIPs are widely used in various scientific fields, one of their most challenging applications lies within pharmaceutical chemistry, namely in therapeutics or various medical therapies. Many studies focus on using hydrogel MIPs in transdermal drug delivery, as the most valuable feature of hydrogels in their application in drug delivery systems that allow controlled diffusion and amplification of the microscopic events. Hydrogels have many advantages over other imprinting materials, such as milder synthesis conditions at lower temperatures or the increase in the availability of biological templates like DNA, protein, and nucleic acid. Moreover, one of the most desirable controlled drug delivery applications is the development of stimuli-responsive hydrogels that can modulate the release in response to changes in pH, temperature, ionic strength, or others. The most important feature of these systems is that they can be designed to operate within a particular human body area due to the possibility of adapting to well-known environmental conditions. Therefore, molecularly imprinted hydrogels play an important role in the development of modern drug delivery systems. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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18 pages, 2970 KiB

Open AccessReview

A Review on Molecularly Imprinted Polymers Preparation by Computational Simulation-Aided Methods

by Zhimin Liu, Zhigang Xu, Dan Wang, Yuming Yang, Yunli Duan, Liping Ma, Tao Lin and Hongcheng Liu

Polymers 2021, 13(16), 2657; https://doi.org/10.3390/polym13162657 - 10 Aug 2021

Cited by 51 | Viewed by 6376

Abstract

Molecularly imprinted polymers (MIPs) are obtained by initiating the polymerization of functional monomers surrounding a template molecule in the presence of crosslinkers and porogens. The best adsorption performance can be achieved by optimizing the polymerization conditions, but this process is time consuming and [...] Read more.

Molecularly imprinted polymers (MIPs) are obtained by initiating the polymerization of functional monomers surrounding a template molecule in the presence of crosslinkers and porogens. The best adsorption performance can be achieved by optimizing the polymerization conditions, but this process is time consuming and labor-intensive. Theoretical calculation based on calculation simulations and intermolecular forces is an effective method to solve this problem because it is convenient, versatile, environmentally friendly, and inexpensive. In this article, computational simulation modeling methods are introduced, and the theoretical optimization methods of various molecular simulation calculation software for preparing molecularly imprinted polymers are proposed. The progress in research on and application of molecularly imprinted polymers prepared by computational simulations and computational software in the past two decades are reviewed. Computer molecular simulation methods, including molecular mechanics, molecular dynamics and quantum mechanics, are universally applicable for the MIP-based materials. Furthermore, the new role of computational simulation in the future development of molecular imprinting technology is explored. Full article

(This article belongs to the Special Issue Advance in Molecularly Imprinted Polymers)

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