Chromatographic characteristics of cholesterol-imprinted polymers prepared by covalent and non-covalent imprinting methods

Hwang, Ching-Chiang; Lee, Wen‐Chien

doi:10.1016/s0021-9673(02)00559-9

Cited by 118 publications

(55 citation statements)

References 31 publications

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“…Thermal disruption of this hydrogen bond during polymerisation would account for the low specific binding levels of the derived polymer. Analogous experiences have been reported for cholesterol as the template with self-assembling imprinting procedures [17,20]. Therefore, an alternative strategy was adopted based on the use of a semi-covalent MIP approach with the functional monomer and template combined via a formal covalent linkage.…”

Section: Resultsmentioning

confidence: 96%

“…Upon polymerisation with N,N -dimethylacrylamide (N,N -DMAAM) as the co-monomer, the molecular template, stigmasteryl-3-O-methacrylate, generated a MIP which can be hydrolyzed to afford a complimentary cavity housing carboxylic acid and N,N -dimethylamido group functionalities as hydrogen bonding recognition units [17,28]. On the basis of molecular modelling investigations, it was anticipated that this MIP would be able to recognize not only stigmasterol but also the more valuable campesterol and brassicasterol.…”

Section: Selection Of the Molecular Templatementioning

confidence: 99%

“…Such MIPs can exhibit a 'molecular memory' for the template or structurally related molecular analogues [11][12][13]. To date, most studies involving sterol-related molecularly imprinted polymers, usually involving non-covalent self-assembly approaches, have focused on cholesterol [14][15][16][17][18][19][20][21][22][23] or estradiol [24][25][26][27]. The focus of this investigation was to explore an alternative method for the generation of a covalently imprinted MIP based on the use of the cleavable stigmasterol methacrylate as template, in silico determination of optimal co-monomer-template ratios, batch binding studies with several sterol analogues, and molecular modeling of the binding interactions.…”

Section: Introductionmentioning

confidence: 99%

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Phytosterol Recognition via Rationally Designed Molecularly Imprinted Polymers

Schwarz

Leung

Danylec

et al. 2018

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Abstract:Molecularly imprinted polymers (MIPs) prepared via a semi-covalent imprinting strategy using stigmasteryl methacrylate as a polymerisable template have been evaluated by static binding methods for their ability to selectively capture other valuable phytosterol targets, including campesterol and brassicasterol. Design criteria based on molecular modelling procedures and interaction energy calculations were employed to aid the selection of the co-monomer type, as well as the choice of co-monomer:template ratios for the formation of the pre-polymerisation complex. These novel hybrid semi-covalently imprinted polymers employed N,N -dimethylacryl-amide (N,N -DMAAM) as the functional co-monomer and displayed specific binding capacities in the range 5.2-5.9 mg sterol/g MIP resin. Their binding attributes and selectivities towards phytosterol compounds were significantly different to the corresponding MIPs prepared via non-covalent procedures or when compared to non-imprinted polymers. Cross-reactivity studies using stigmasterol, ergosterol, cholesterol, campesterol, and brassicasterol as single analytes revealed the importance of the A-ring C-3-β-hydroxyl group and the orientational preferences of the D-ring alkyl chain structures in their interaction in the templated cavity with the N,N -dimethylamide functional groups of the MIP. Finally, to obtain useful quantities of both campersterol and brassicasterol for these investigations, improved synthetic routes have been developed to permit the conversion of the more abundant, lower cost stigmasterol via a reactive aldehyde intermediate to these other sterols.

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Section: Resultsmentioning

confidence: 96%

Section: Selection Of the Molecular Templatementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Phytosterol Recognition via Rationally Designed Molecularly Imprinted Polymers

Schwarz

Leung

Danylec

et al. 2018

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“…The binding sites obtained by molecular imprinting show different characteristics, depending on the type of imprinted approach. The average affinity of binding site prepared using bonding by non-covalent forces is generally weaker than those prepared using covalent methods because electrostatic, hydrogen bonding, π-π and hydrophobic interactions, between the template and the functional monomers, are used exclusively in forming the molecular assemblies (Hwang & Lee, 2002). However, when covalent bonds are established between the template and the functional monomer prior to polymerization, this gives rise to better defined and more homogeneous binding sites than the non-covalent approach, since the template-functional monomer interactions are far more stable and defined during the imprinting process.…”

Section: Molecularly Imprinted Polymers (Mips): Highly Selective Matementioning

confidence: 99%

Carbon Nanotubes – Imprinted Polymers: Hybrid Materials for Analytical Applications

Cirillo¹,

Hampel²,

Puoci³

et al. 2012

Materials Science and Technology

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“…O primeiro trabalho com emprego de MIP em quí-mica analítica é datado de 1972, onde Wulff e Sarhan 20 descreveram a síntese do polímero com sítios seletivos para separação enantiomérica de racematos de açúcares. Desde então, os referidos materiais vêm sendo amplamente empregados em preparo de amostras atuando em processos de extração em fase sólida (SPE-"solid phase extraction") 21 e microextração em fase sólida (SPME-"solid phase microextraction") 22 , em técnicas de separação, tais como, cromatografia líquida de alta eficiência (HPLC-"high performance liquid chromatography") 23 , eletroforese capilar (CE-"capillary electrophoresis") 24 , eletrocromatografia capilar (CEC-"capillary electrochromatography") 25 e cromatografia em camada delgada (TLC-"thin layer chromatography") 26 visando, principalmente, a separação de espécies enantioméricas. Também, há um amplo campo de pesquisa dos MIP em associação com técnicas eletroanalíticas 27 enfocando o desenvolvimento de sensores seletivos, bem como em espectrofluorimetria 28 .…”

Section: Introductionunclassified