Influence of intramolecular hydrogen bond of templates on molecular recognition of molecularly imprinted polymers

Zhang, Tieli; Liu, Feng; Chen, Wen; Wang, Jun; Li, Kèan

doi:10.1016/s0003-2670(01)01390-3

Cited by 95 publications

(43 citation statements)

References 21 publications

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“…387 Amongst the basic monomers, 4-vinylpyridine is the most commonly employed, [388][389][390] but other basic monomers such as N,N-diethylaminoethyl methacrylate, 391,392 aminostyrene 393,394 and vinylimidazole 388,395 have also been used. Among the neutral monomers, acrylamide, [396][397][398][399][400][401] vinyl pyrrolidone [402][403][404][405][406][407][408][409] and 2-hydroxyethyl methacrylate (HEMA) [410][411][412] have all been used. Incorporation of HEMA in methacrylate-based MIPs makes the polymers less hydrophobic which helps in the diffusion of hydrophilic templates.…”

Section: 329mentioning

confidence: 99%

“…The effect of template size on the selectivity of MIPs has been studied, 903 as has the effect of intramolecular H-bonding in the template on its imprint. 401 Allender et al have attempted to explain the observed crossreactivities in binding to MIPs for amino acid derivatives in terms of the ligand structures, 904 and Spivak and Campbell have performed a similar study on amine-imprinted MIPs. 905 The effect of template structure and acidity has been compared in the imprinting of nitrophenol and hydroxybenzoic acid isomers.…”

Section: Recognition and Bindingmentioning

confidence: 99%

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Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Andersson²,

et al. 2006

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Over 1450 references to original papers, reviews and monographs have herein been collected to document the development of molecular imprinting science and technology from the serendipitous discovery of Polyakov in 1931 to recent attempts to implement and understand the principles underlying the technique and its use in a range of application areas. In the presentation of the assembled references, a section presenting reviews and monographs covering the area is followed by papers dealing with fundamental aspects of molecular imprinting and the development of novel polymer formats. Thereafter, literature describing attempts to apply these polymeric materials to a range of application areas is presented.

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Section: 329mentioning

confidence: 99%

Section: Recognition and Bindingmentioning

confidence: 99%

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Andersson²,

et al. 2006

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“…The FA molecule has a larger size than that of VA; so the specific binding capacity of MIP for FA is lower than for VA. The lower recovery of SA indicates the weak interaction with the binding sites in MIPs, which is probably induced by the intramolecular hydrogen bonding between the carboxylic and the adjacent hydroxyl group in the SA molecular [31].…”

Section: Evaluation Of Mip-spe Capacity and Selectivitymentioning

confidence: 99%

Molecularly imprinted polymer microspheres for solid‐phase extraction of protocatechuic acid in Rhizoma homalomenae

Chen

Wang

Shi

2011

J of Separation Science

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Molecularly imprinted polymers (MIPs) had been prepared by precipitation polymerization method using acrylamide as the functional monomer, ethylene glycol dimethacrylate as the cross-linker, acetonitrile as the porogen solvent and protocatechuic acid (PA), one of phenolic acids, as the template molecule. The MIPs were characterized by scanning electron microscopy and Fourier transform infrared, and their performance relative to non-imprinted polymers was assessed by equilibrium binding experiments. Six structurally similar phenolic acids, including p-hydroxybenzoic acid, gallic acid, salicylic acid, syringic acid, vanillic acid, ferulic acid were selected to assess the selectivity and recognition capability of the MIPs. The MIPs were applied to extract PA from the traditional Chinese medicines as a solid-phase extraction sorbent. The resultant cartridge showed that the MIPs have a good extraction performance and were able to selectively extract almost 82% of PA from the extract of Rhizoma homalomenae. Thus, the proposed molecularly imprinted-solid phase extraction-high performance liquid chromatography method can be successfully used to extract and analyse PA in traditional Chinese medicines.

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“…Then the crosslinker EDMA (30 mmol) and the initiator AIBN (30.0 mg) were added. The ratios of reagents for the preparation of polymer were taken from [20]. The polymerization was carried out in a water bath at 608C for 24 h. Prepared polymer was passed through a 40-lm sieve, fine particles were removed by flotation in acetone and final product was dried under vacuum at 608C for 1 h. The template was removed from the MIP by Soxhlet extraction with 70 mL of a mixture of methanol/ acetic acid (9 : 1, v/v) for 8 h. Nonimprinted, control polymer (NIP) was prepared and treated in the same manner as MIP but in the absence of template molecule during polymerization.…”

Section: Polymer Preparationmentioning

confidence: 99%

“…However, binding of the molecule of GeA in the specific binding sites of MIP is possible (specific binding capacity of 4.58 lg/g of MIP), probably due to some other interactions between GeA and MIP. The low value of specific binding capacity indicates the weak interaction between GeA and binding sites in MIP, which can be explained by intramolecular hydrogen bonding between the carboxylic group and the adjacent hydroxy group in the GeA molecule [20]. In the case of VA the only difference between the structure of VA and PA is the presence of a methoxy group (in position 3) instead of a hydroxy group.…”

Section: Selectivity Of Mipmentioning

confidence: 99%

Selective extraction of derivates ofp-hydroxy-benzoic acid from plant material by using a molecularly imprinted polymer

Karasová

Lehotay²,

Sádecká

et al. 2005

J. Sep. Science

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Selective SPE of derivates of p-hydroxybenzoic acid (pHBA) from plant extract of Melissa officinalis is presented using a molecularly imprinted polymer (MIP) made with protocatechuic acid (PA) as template molecule. MIP was prepared with acrylamide as functional monomer, ethylene glycol dimethacrylate as crosslinking monomer and ACN as porogen. MIP was evaluated towards six phenolic acids: PA, gallic acid, pHBA, vanillic acid (VA), gentisic acid (GeA) and syringic acid (SyrA), and then steps of molecularly imprinted SPE (MISPE) procedure were optimized. The best specific binding capacity of MIP was obtained for PA in ACN (34.7 microg/g of MIP). Other tested acids were also bound on MIP if they were dissolved in this solvent. ACN was chosen as solvent for sample application. M. officinalis was extracted into methanol/water (4:1, v/v), the extract was then evaporated to dryness and dissolved in ACN before application on MIP. Water and ACN were used as washing solvents and elution of benzoic acids was performed by means of a mixture methanol/acetic acid (9:1, v/v). pHBA, GA, PA and VA were extracted with recoveries of 56.3-82.1% using this MISPE method. GeA was not determined in plant extract.

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Influence of intramolecular hydrogen bond of templates on molecular recognition of molecularly imprinted polymers

Cited by 95 publications

References 21 publications

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003

Molecularly imprinted polymer microspheres for solid‐phase extraction of protocatechuic acid in Rhizoma homalomenae

Selective extraction of derivates ofp-hydroxy-benzoic acid from plant material by using a molecularly imprinted polymer

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