Site-specific post-imprinting modification of molecularly imprinted polymer nanocavities with a modifiable functional monomer for prostate cancer biomarker recognition

A molecularly imprinted polymer (MIP) that is selective to ketoprofen was synthesized and applied in the adsorption of the target compound from water. The MIP was synthesized using a bulk polymerization method at high temperatures (60–80°C), where ketoprofen, 2-vinylpyridine, ethylene glycol dimethacrylate, toluene and 1,1´-azobis(cyclohexanecarbonitrile) were used as template, functional monomer, cross-linker, porogen and initiator, respectively. Non-imprinted polymer (NIP) was synthesized similarly to the MIP but in the absence of ketoprofen. From molecular dynamics simulation, the nature of interactions that occurred between the template and the functional monomer were found to be based on hydrogen bonding. This was confirmed experimentally, where a high extraction efficiency of ≥ 90% was obtained at acidic conditions (pH 5) due to the protonation of ketoprofen. A contact time of 45 min was sufficient for the maximum adsorption of ketoprofen from 10 mL spiked water using 8 mg of the adsorbent. MIP showed greater selectivity than NIP by achieving a relative selectivity coefficient of 7.7 towards ketoprofen in the presence of structurally related pharmaceuticals. Furthermore, the order of sorption onto the MIPs from water was ketoprofen > fenoprofen > gemfibrozil. From a modelling perspective, the Langmuir adsorption isotherm and pseudo-second-order kinetic model gave the best fit, with maximum adsorption capacity of 8.24 mg·g−1 and sorption rate constant of 0.25 mg·g−1·min−1 for MIP. This was translated to chemisorption of ketoprofen onto the homogeneous MIP binding sites. This work demonstrated the great potential of MIP in selective recognition of ketoprofen from wastewater relative to closely related compounds.

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Stoichiometric molecular imprinting using polymerisable urea and squaramide receptors for the solid phase extraction of organo-arsenic compound roxarsone

Analytical Methods ◽

10.1039/d0ay01635g ◽

2020 ◽

Vol 12 (47) ◽

pp. 5729-5736

Author(s):

Simone Cavalera ◽

Fabio Di Nardo ◽

Giulia Spano ◽

Laura Anfossi ◽

Panagiotis Manesiotis ◽

...

Keyword(s):

Solid Phase Extraction ◽

Molecular Imprinting ◽

Surface Waters ◽

Molecularly Imprinted Polymer ◽

Solid Phase ◽

Phase Extraction ◽

Functional Monomer ◽

Arsenic Compound ◽

Imprinted Polymer ◽

Molecularly Imprinted

A selective molecularly imprinted polymer prepared with a squaramide-based functional monomer was used for the solid phase extraction of roxarsone from surface waters.

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Computational Modeling and Theoretical Calculations on the Interactions between Spermidine and Functional Monomer (Methacrylic Acid) in a Molecularly Imprinted Polymer

Journal of Chemistry ◽

10.1155/2015/216983 ◽

2015 ◽

Vol 2015 ◽

pp. 1-9 ◽

Cited By ~ 2

Author(s):

Yujie Huang ◽

Qiujin Zhu

Keyword(s):

Binding Energy ◽

Methacrylic Acid ◽

Molecularly Imprinted Polymer ◽

Single Point ◽

Basis Set ◽

Stable Complex ◽

Functional Monomer ◽

Imprinted Polymer ◽

Point Energy ◽

Molecularly Imprinted

This paper theoretically investigates interactions between a template and functional monomer required for synthesizing an efficient molecularly imprinted polymer (MIP). We employed density functional theory (DFT) to compute geometry, single-point energy, and binding energy (ΔE) of an MIP system, where spermidine (SPD) and methacrylic acid (MAA) were selected as template and functional monomer, respectively. The geometry was calculated by using B3LYP method with 6-31+(d) basis set. Furthermore, 6-311++(d, p) basis set was used to compute the single-point energy of the above geometry. The optimized geometries at different template to functional monomer molar ratios, mode of bonding between template and functional monomer, changes in charge on natural bond orbital (NBO), and binding energy were analyzed. The simulation results show that SPD and MAA form a stable complex via hydrogen bonding. At 1 : 5 SPD to MAA ratio, the binding energy is minimum, while the amount of transferred charge between the molecules is maximum; SPD and MAA form a stable complex at 1 : 5 molar ratio through six hydrogen bonds. Optimizing structure of template-functional monomer complex, through computational modeling prior synthesis, significantly contributes towards choosing a suitable pair of template-functional monomer that yields an efficient MIP with high specificity and selectivity.

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Molecularly imprinted polymer for selective extraction and simultaneous determination of four tropane alkaloids from Przewalskia tangutica Maxim. fruit extracts using LC-MS/MS

RSC Advances ◽

10.1039/c5ra18608k ◽

2015 ◽

Vol 5 (115) ◽

pp. 94997-95006 ◽

Cited By ~ 18

Author(s):

Shaomei Zeng ◽

Yongxin She ◽

Bining Jiao ◽

Guangyang Liu ◽

Jing Wang ◽

...

Keyword(s):

Simultaneous Determination ◽

Molecularly Imprinted Polymer ◽

Tropane Alkaloids ◽

Selective Extraction ◽

Functional Monomer ◽

Imprinted Polymer ◽

Molecularly Imprinted ◽

Fruit Extracts ◽

Przewalskia Tangutica

A class-specific molecularly imprinted polymer (MIP) for selectively extracting four tropane alkaloids has been prepared using anisodine, methacrylic, and trimethylolpropane trimethacrylate as template, functional monomer and crosslinker, respectively.

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Synthesis of a novel cross-linker doubles as a functional monomer for preparing a water compatible molecularly imprinted polymer

Analytical Methods ◽

10.1039/c4ay01651c ◽

2014 ◽

Vol 6 (23) ◽

pp. 9483-9489 ◽

Cited By ~ 3

Author(s):

Xiao Zhang ◽

Feng Shen ◽

Zhe Zhang ◽

Yue Xing ◽

Xueqin Ren

Keyword(s):

Molecularly Imprinted Polymer ◽

Naproxen Sodium ◽

Functional Monomer ◽

Imprinted Polymer ◽

Molecularly Imprinted ◽

Imprinted Polymers ◽

Bifunctional Monomer ◽

Cross Linker

A new bifunctional monomer acting as both a cross-linker and a functional monomer was synthesized and applied in the preparation of water-compatible naproxen sodium imprinted polymers.

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