Solid-Phase Extraction of Active Compounds from Natural Products by Molecularly Imprinted Polymers: Synthesis and Extraction Parameters

Sijam, Kamaruzaman; Nasir, Najihah Mohammad; Faudzi, Siti Munirah Mohd; Yahaya, Noorfatimah; Hanapi, Nor Suhaila Mohamad; Ibrahim, Wan Nazihah Wan

doi:10.3390/polym13213780

Cited by 16 publications

(8 citation statements)

References 112 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is described that, in MIP preparation, when phase separation occurs, the surface area of the resulting polymer is reduced. 64 This effect was evident in MIP-1 compared to the corresponding NIP-1, where no pre-polymerization template/monomer complex was formed.…”

Section: Resultsmentioning

confidence: 98%

“…The lower surface area for MIP-1 , assessed using BET, may be due to the fact that IA is not completely soluble in DCM, the porogen used in MIP synthesis, chosen to favor the establishment of non-covalent interactions between the template and the monomer. It is described that, in MIP preparation, when phase separation occurs, the surface area of the resulting polymer is reduced . This effect was evident in MIP-1 compared to the corresponding NIP-1, where no pre-polymerization template/monomer complex was formed.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Greener Strategy for Lupanine Purification from Lupin Bean Wastewaters Using a Molecularly Imprinted Polymer

Esteves

Ferreira

Mota

et al. 2022

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

Lupanine is an alkaloid used in the pharma industry as a building block or precursor in the synthesis of sparteine and also explored for drug synthesis in the pharma industry as a chiral selector. This alkaloid is found in lupin bean processing wastewaters originated from the debittering process to make these beans edible. In this work, a computational chemistry approach was taken to design molecularly imprinted polymers (MIPs) selecting itaconic acid, a biobased building block, as a functional monomer that can provide higher affinities for lupanine. MIP-1 was prepared using lupanine as the template, itaconic acid as a functional monomer, and ethylene glycol dimethacrylate as a cross-linker by bulk polymerization. Lupanine was concentrated from lupin bean wastewater by nanofiltration, extracted with ethyl acetate, and purified using the synthesized MIP. MIP-1 was able to selectively recognize lupanine and improve the purity of lupanine from 78 to 88%, with 82% recovery of the alkaloid. These results show the potential application of this strategy to render the industrial process more sustainable.

show abstract

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Greener Strategy for Lupanine Purification from Lupin Bean Wastewaters Using a Molecularly Imprinted Polymer

Esteves

Ferreira

Mota

et al. 2022

ACS Appl. Mater. Interfaces

View full text Add to dashboard Cite

show abstract

“…Analyte may leak out during the desorption process. 40,41 For this reason, template leakage or template bleeding during the use of MIPs in the MISPE process cannot be ignored. 42,43 Leakage of template molecules has been considered to damage the accuracy of sample quantification and identification, especially in trace-level analysis and causing poor separation in chromatography.…”

Section: Dummy Templatesmentioning

confidence: 99%

Dummy template molecularly imprinted polymers as potential sorbents in the separation and purification of active compounds in natural products

Ariani,

Zuhrotun,

Manesiotis

et al. 2023

Polymers for Advanced Techs

View full text Add to dashboard Cite

Molecular imprinting technology is a promising technique for separating, purifying, and enriching target compounds with high selectivity and sensitivity. The molecularly imprinted polymer (MIP) technique has developed rapidly in the separation and purification of chemical compounds and secondary metabolites of natural products. However, there are real challenges to the isolation of target compounds in natural products such as the unavailability of target compounds and high cost, so it is necessary to develop another approach to MIP synthesis. The dummy template is a solution to the unavailability of target compounds as it will produce a binding site that is specific enough for the target compound through covalent or non‐covalent bonds and the presence of the same functional groups between the target compound and the dummy will result in an interaction between the target compound and the binding site made using the dummy template. In addition, this dummy MIP (DMIP) is the best solution for overcoming the template leakage in traditional MIPs so that the DMIP technique is very good for removing and purifying compounds that are allergenic or toxic in natural product samples (high traceability). This review article will discuss the development of DMIPs in the separation and purification of compounds in natural products and the factors that affect their performance. Our discussion highlights the importance of selecting the right dummy template for optimal DMIP performance. This selection should be based on factors such as functional group similarity, being in the same bioactive compound group, and structural skeleton similarity. In addition, the selection and composition of other DMIP components can also affect the analytical performance of the DMIP.

show abstract

“…The present work is focused on the development of a novel purification approach for [ 11 C]RAC that will exploit specifically tailored shape-recognition polymers with the aim to substitute the standard single-pass HPLC purification with an in-flow trap and release sequence. In particular, MIT applied to solid phase extraction (MISPE) [ 14 , 18 , 19 , 20 ] was studied in order to develop a setting able to selectively extract [ 11 C]RAC in a mixture containing a high amount of its precursor, DM-RAC, a condition that occurs after [ 11 C]RAC radiolabeling step. To prepare two MIPs able to bind unlabeled RAC and DM-RAC, a thermal polymerization was used.…”

Section: Introductionmentioning

confidence: 99%

Raclopride-Molecularly Imprinted Polymers: A Promising Technology for Selective [11C]Raclopride Purification

et al. 2023

View full text Add to dashboard Cite

In this work, we developed a novel approach to purify [11C]Raclopride ([11C]RAC), an important positron emission tomography radiotracer, based on tailored shape-recognition polymers, with the aim to substitute single-pass HPLC purification with an in-flow trap & release process. Molecular imprinting technology (MIT) applied to solid phase extraction (MISPE) was investigated to develop a setting able to selectively extract [11C]RAC in a mixture containing a high amount of its precursor, (S)-O-Des-Methyl-Raclopride (DM-RAC). Two imprinted polymers selective for unlabeled RAC and DM-RAC were synthesized through a radical polymerization at 65 °C using methacrylic acid and trimethylolpropane trimethacrylate in the presence of template molecule (RAC or DM-RAC). The prepared polymer was characterized by scanning electron microscopy and Fourier transform infrared spectroscopy and tested in MISPE experiments. The polymers were used in testing conditions, revealing a high retention capacity of RAC-MISPE to retain RAC either in the presence of similar concentrations of RAC and DM-RAC precursor (96.9%, RSD 6.6%) and in the presence of a large excess of precursor (90%, RSD 4.6%) in the loading solution. Starting from these promising results, preliminary studies for selective purification of [11C]Raclopride using this RAC-MISPE were performed and, while generally confirming the selectivity capacity of the polymer, revealed challenging applicability to the current synthetic process, mainly due to high backpressures and long elution times.

show abstract

Solid-Phase Extraction of Active Compounds from Natural Products by Molecularly Imprinted Polymers: Synthesis and Extraction Parameters

Cited by 16 publications

References 112 publications

Greener Strategy for Lupanine Purification from Lupin Bean Wastewaters Using a Molecularly Imprinted Polymer

Greener Strategy for Lupanine Purification from Lupin Bean Wastewaters Using a Molecularly Imprinted Polymer

Dummy template molecularly imprinted polymers as potential sorbents in the separation and purification of active compounds in natural products

Raclopride-Molecularly Imprinted Polymers: A Promising Technology for Selective [11C]Raclopride Purification

Contact Info

Product

Resources

About