Recognition of ephedrine enantiomers by molecularly imprinted polymers designed using a computational approach

Piletsky, Sergey A.; Karim, Khalku; Piletska, Elena; Day, Caroline; Freebairn, Keith; Legge, Coulton H.; Turner, Anthony P. F.

doi:10.1039/b102426b

Cited by 272 publications

(176 citation statements)

References 9 publications

(9 reference statements)

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“…Reports on successful method development with MIPs usually appear to reflect a trial and error approach. Computer modelling at the molecular dynamics or quantum chemical level has proved useful in the design of particular MIPs [11][12][13][14][15][16][17] but this does not directly concern the problem discussed here.…”

Section: Introductionmentioning

confidence: 99%

Isotherm charts for material selection and method development with molecularly imprinted polymers and other sorbents

Dorkó

Tamás

Horvai

2017

Talanta

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A simple and efficient method is presented for assessing molecularly imprinted polymers (MIP) and other sorbents from the point of view of practical applications. The adsorption isotherms of the compounds, which need to be separated or detected in an application, are constructed from a small number of measured points on a log-log chart and then are compared graphically. Despite its simplicity and robustness this method reveals the information needed for optimal selection between MIPs and alternative sorbents. The design of separation or detection methods with MIPs is also supported by the proposed graphical isotherm comparison. Many experimental isotherms are presented supporting the proposed method.

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Section: Introductionmentioning

confidence: 99%

Isotherm charts for material selection and method development with molecularly imprinted polymers and other sorbents

Dorkó

Tamás

Horvai

2017

Talanta

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“…14,15,16,17,18,19 In the earlier studies the statistical and the molecular mechanics/classical molecular dynamics studies are predominant and quantum chemical methods have only been applied in recent years due to rapid development in computational power. Most of the computational studies in the imprinting literature focus on rapid functional monomer screening.…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical investigation of the complexation of methacrylic acid and diisopropyl urea

Pogány

Razali

Székely

2017

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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The present paper explores the complexation ability of methacrylic acid which is one of the most abundant functional monomer for the preparation of molecularly imprinted polymers. Host-guest interactions and the mechanism of complex formation between methacrylic acid and potentially genotoxic 1,3-diisopropylurea were investigated in the pre-polymerization solution featuring both experimental (NMR, IR) and in silico density functional theory (DFT) tools. The continuous variation method revealed the presence of higher-order complexes and the appearance of self-association which were both taken into account during the determination of the association constants. The quantum chemical calculations -performed at B3LYP 6-311++G(d,p) level with basis set superposition error (BSSE) corrections -are in agreement with the experimental observations, reaffirming the association constants and justifying the validity of computational investigation of such systems. Furthermore, natural bond orbital analysis was carried out to appraise the binding properties of the complexes.

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“…28 Separation of the corresponding isomers was achieved; however, the recognition mechanism was not mentioned. Piletsky et al 29 used a computational approach to design MIPs specific for ephedrine, but the resolution ability of (-)-ephedrine and (+)-ephedrine was not satisfactory. Allender et al 30 studied ephedrine MIPs as biological receptor mimics, and produced retention data for ephedrine and some of its analogues.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Evaluation of Uniform-size (-)-Ephedrine-imprinted Polymeric Microspheres by Multi-step Swelling and Suspension Polymerization

Zhang

et al. 2006

ANAL. SCI.

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Ephedrine-imprinted polymeric microspheres have been prepared in an aqueous system by multi-step swelling and suspension polymerization, using methacrylic acid (MAA) as a functional monomer, and ethylene glycol dimethacrylate (EGDMA) as a cross-linker. Scanning electron microscopy (SEM) was used as a means to identify the structure features of the obtained polymers. Further, we examined the recognition mechanism of the polymers and the influences of some chromatographic conditions, such as the mobile-phase composition, flow-rate, column temperature and sample amount on the retentivity and selectivity for (-)-ephedrine and (+)-ephedrine. The results reveal that stable macroporous polymer beads with good size monodispersity were obtained, the average size of which was 3 -5 μm. Baseline chiral separation of the template isomers was achieved on a short column (50 mm × 4.6 mm i.d.) when the prepared polymer beads were used as a stationary phase, while the non-imprinted polymers (NIPs) did not show such ability. The optimized chromatographic condition was as follows: acetonitrile-acetic acid (99.8/0.2, v/v) as the mobile phase; sample amount, 40 -80 μg; flow rate, 1.0 ml min -1 ; and column temperature, room temperature, respectively. It is assumed that two classes of binding sites exist in the porous polymers, one being hydrophilic binding sites, the other being hydrophobic binding sites.

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Recognition of ephedrine enantiomers by molecularly imprinted polymers designed using a computational approach

Cited by 272 publications

References 9 publications

Isotherm charts for material selection and method development with molecularly imprinted polymers and other sorbents

Isotherm charts for material selection and method development with molecularly imprinted polymers and other sorbents

Experimental and theoretical investigation of the complexation of methacrylic acid and diisopropyl urea

Preparation and Evaluation of Uniform-size (-)-Ephedrine-imprinted Polymeric Microspheres by Multi-step Swelling and Suspension Polymerization

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