Enhanced selectivity of a molecularly imprinted polymer toward the target molecule via esterification of non‐specific binding sites with diazomethane

Alenazi, Noof A.; Lai, Edward P. C.; Manthorpe, Jeffrey M.

doi:10.1002/jmr.2402

Cited by 7 publications

(10 citation statements)

References 33 publications

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“…CE-UV analysis was performed on a laboratory-built system [40]. The background electrolyte (BGE) was composed of 10 mM Na 2 HPO 4 in deionized distilled water (DDW) to attain pH 7.5 ± 0.2.…”

Section: Methodsmentioning

confidence: 99%

“…This study examined both the site-selective chemical modification (SSCM) technique, which employs partial esterification of the residual carboxylic acid groups using diazomethane [39,40,41], and optimization of the template to functional monomer to cross-linker molar ratio [42,43]. The aim was to eliminate non-specific binding sites in the MIP.…”

Section: Introductionmentioning

confidence: 99%

“…The binding selectivity of diazomethane-treated molecularly imprinted polymers (TMIPs) and non-treated MIPs, as well as diazomethane-treated non-imprinted polymers (TNIPs) and non-treated NIPs, toward BPA was evaluated, by capillary electrophoresis (CE) with ultraviolet (UV) detection, against three widely prescribed pharmaceutical compounds (baclofen, diclofenac and metformin) which are abundantly distributed in environment waters [44]. In our previous article [40] we tested cross reactivity with the same compounds and also used competitive CE-UV binding tests. The present article contains more data on the systematic optimization of the TMIP to demonstrate an improvement of selective binding results.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Selectivity Enhancement in Molecularly Imprinted Polymers for Binding of Bisphenol A

Alenazi

Manthorpe

Lai

2016

Sensors

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Bisphenol A (BPA) is an estrogen-mimicking chemical that can be selectively detected in water using a chemical sensor based on molecularly imprinted polymers (MIPs). However, the utility of BPA-MIPs in sensor applications is limited by the presence of non-specific binding sites. This study explored a dual approach to eliminating these sites: optimizing the molar ratio of the template (bisphenol A) to functional monomer (methacrylic acid) to cross-linker (ethylene glycol dimethacrylate), and esterifying the carboxylic acid residues outside of specific binding sites by treatment with diazomethane. The binding selectivity of treated MIPs and non-treated MIPs for BPA and several potential interferents was compared by capillary electrophoresis with ultraviolet detection. Baclofen, diclofenac and metformin were demonstrated to be good model interferents to test all MIPs for selective binding of BPA. Treated MIPs demonstrated a significant decrease in binding of the interferents while offering high selectivity toward BPA. These results demonstrate that conventional optimization of the molar ratio, together with advanced esterification of non-specific binding sites, effectively minimizes the residual binding of interferents with MIPs to facilitate BPA sensing.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Selectivity Enhancement in Molecularly Imprinted Polymers for Binding of Bisphenol A

Alenazi

Manthorpe

Lai

2016

Sensors

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“…13,14 However, most MIPs suffer from poor binding affinity or specificity. 15,16 At the same time, it is difficult to produce a fluorescence signal for binding.…”

Section: Introductionmentioning

confidence: 99%

Molecularly Imprinted Polymers with DNA Aptamer Fragments as Macromonomers

Zhang

Liu

2016

ACS Appl. Mater. Interfaces

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Molecularly imprinted polymers (MIPs) are produced in the presence of a template molecule. After removing the template, the cavity can selectively rebind the template. MIPs are attractive functional materials with a low cost and high stability, but traditional MIPs often suffer from low binding affinity. This study employs DNA aptamer fragments as macromonomers to improve MIPs. The DNA aptamer for adenosine was first split into two halves, fluorescently labeled, and co-polymerized into MIPs. With a fluorescence quenching assay, the importance of imprinting was confirmed. Further studies were carried out using isothermal titration calorimetry (ITC).Compared to the mixture of the free aptamer fragments, their MIPs doubled the binding affinity.Each free aptamer fragment alone cannot bind adenosine, while MIPs containing each fragment are effective binders. We further shortened one of the aptamer fragments, and the DNA length was pushed to as short as six nucleotides, yielding MIPs with a dissociation constant of 27 µM adenosine. This study provides a new method for preparing functional MIP materials by combining high affinity biopolymer fragments with low cost synthetic monomers, allowing higher binding affinity and providing a method for signaling binding based on DNA chemistry.

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“…The target might associate with the polymer using intermolecular forces such as hydrogen bonding, 10 hydrophobic and electrostatic interactions. 11,12 Even after removing the template molecule, the recognition cavities still remain in shape for rebinding.…”

Section: Introductionmentioning

confidence: 99%

Improving molecularly imprinted nanogels by pH modulation

Zhang

Liu

2015

RSC Adv.

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Molecularly imprinted polymers (MIPs) are polymerized in the presence of a template molecule. After removing the template, the polymer scaffold can selectively rebind the template. Imprinting factor (IF) refers to the rebinding ratio of imprinted and non-imprinted polymers. Generally, the IF of most reported MIPs are still quite low (e.g. below 3.0). This is partially attributable to strong non-specific interactions.In this study, imprinted nanogels are prepared using two common dyes as templates, sulforhodamine B (SRhB) and fluorescein. By varying the buffer pH, non-specific electronic interactions between the template and the gels are reduced, leading to improved IF for the SRhB-MIPs from 1.5 (at pH 7.2) to 7.4 (at pH 9.0). At the same time, the binding capacity of the MIP remained similar. On the other hand, while pH tuning also improved the IF of the fluorescein-imprinted nanogels, the binding capacity dropped significantly. Using isothermal titration calorimetry (ITC), the SRhB-imprinted nanogels display a much higher affinity (Ka = 2.9 ×10 4 M -1 ) than the non-imprinted (Ka = 0.031 ×10 4 M -1 ) when rebinding is conducted in high pH (pH 9.0). This difference is mainly driven by enthalpy. This study suggests that pH tuning can be used to further improve MIPs.3

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Enhanced selectivity of a molecularly imprinted polymer toward the target molecule via esterification of non‐specific binding sites with diazomethane

Cited by 7 publications

References 33 publications

Selectivity Enhancement in Molecularly Imprinted Polymers for Binding of Bisphenol A

Selectivity Enhancement in Molecularly Imprinted Polymers for Binding of Bisphenol A

Molecularly Imprinted Polymers with DNA Aptamer Fragments as Macromonomers

Improving molecularly imprinted nanogels by pH modulation

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