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Synthesis of molecularly printed methyl methacrylate-based polymers for the detection of di(2-ethylhexyl) phthalate and dibutyl phthalate

Fauziah St, Soekamto Nunuk Hariani, Prastawa Budi, Rasyid Herlina, Haedar Nur, Hustim Muraalia, Marlina Marlina, Sulaiman Magfirah, Sapar Ajuk

Polimery

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2023

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Vol. 68, nr 7-8

413--423

EN

Molecularly imprinted polymers (MIP) were obtained by precipitation polymerization for the detection of DEHP and DBP from polymer packaging in drinking water. MIP was obtained by cross-linking DEHP and DBP with methyl methacrylate (MMA) and trimethylolpropane trimethacrylate (TRIM). FTIR, SEM-EDS, UV-Vis and SAA were used to determine properties of polymers (MIP_DEHP, MIP_DBP). The obtained materials were characterized by a mesoporous structure with small, uniform, and porous grains. The surface area and total pore volume of MIP_DEHP were more than twice smaller than MIP_DBP, with a slightly larger pore diameter. Lower C content may indicate the formation of MIP_DEHP and MIP_DBP. The FTIR method confirmed the presence of functional groups –CH, –CO, –C=C and –C=O. The adsorption capacity of MIP_DEHP and MIP_DBP was 0.68 mg/g and 1.06 mg/g, respectively, and was consistent with the Freundlich isothermal adsorption model.

PL

Streszczenie: Metodą polimeryzacji strąceniowej otrzymano polimery z nadrukiem molekularnym (MIP) do wykrywania DEHP i DBP z opakowań polimerowych w wodzie pitnej. MIP otrzymano poprzez sieciowanie DEHP i DBP metakrylanem metylu (MMA) i trimetakrylanem trimetylolopropanu (TRIM). Do oceny właściwości polimerów (MIP_DEHP, MIP_DBP) zastosowano FTIR, SEM-EDS, UV-Vis i SAA. Otrzymane materiały charakteryzowały się mezoporowatą strukturą o małych, jednolitych i porowatych ziarnach. Pole powierzchni i całkowita objętość porów MIP_DEHP były ponad dwukrotnie mniejsze niż MIP_DBP, przy nieznacznie większej średnicy porów. Mniejsza zawartość C może świadczyć o tworzeniu się MIP_DEHP i MIP_DBP. Metodą FTIR potwierdzono obecność grup funkcyjnych -CH, –CO, –C=C i –C=O. Zdolność adsorpcyjna MIP_DEHP i MIP_DBP wynosiła odpowiednio 0,68 mg/g i 1,06 mg/g i była zgodna z izotermicznym modelem adsorpcji Freundlicha.

2

Zastosowanie cyklodekstryn w technologii wdrukowania molekularnego

Pokajewicz Katarzyna, Poliwoda Anna, Wieczorek Piotr P.

Wiadomości Chemiczne

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2022

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[Z] 76, 7-8

677--699

EN

In the last decade molecular imprinted polymers (MIP) have gained great interest in the area of selective recognition various type substances. Scientific work in this field is carried out very intensively - the methods of synthesis are modified and improved, new types of hydride materials are created, as well as new reagents for synthesis. In this case, cyclodextrins (CD) and their analogues show good molecular recognition ability for its unique physical and chemical properties and suitable cavity structure. As a result, these supramolecular ligands can perform various functions in the MIP technology, and the resulting polymeric materials are characterized by high selectivity and binding specificity (recognition) of analytes structurally matched to the MIP cavity. Of particular importance is the fact that cyclodextrins enable the imprinting not only of low-molecular-weight biologically active compounds, but also of high-molecular molecules (proteins, peptides). The numerous hydroxyl groups available in cyclodextrins are active sites that can form different types of linkages. They can be cross-linked with one another, or they can be derivatized to produce monomers that can form linear or branched networks. This article provides a detailed review of MIPs based on CD and their application in the field of separation science and analytical chemistry in recent years. The discussion is grouped according to the different role of CD in MIPs, that is, functional monomer, carrier modifier, etc.

3

Zastosowania materiałów opartych na polimerach z odciskiem molekularnym i ich wpływ na rozwój chemii supramolekularnej

Lusina Aleksandra, Cegłowski Michał

Wiadomości Chemiczne

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2022

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[Z] 76, 7-8

491--507

EN

Molecularly Imprinted Polymers (MIPs) are the group of polymers that possess an ability to selective recognize analytes or groups of analytes, which are similar by their structural construction. The recognizing ability, which is generated during the synthesis of material, is determined by various factors such as shape, size, and the presence of functional groups in the MIP cavity. This molecular recess is created as a result of removing the specific analyte from the inclusive complex (polymeranalyte). Thanks to the valuable properties of molecularly imprinted polymers, these materials are commonly used in various fields. The multitude of their applications results from their properties such as high physical stability to harsh chemical and physical conditions, straightforward preparation, remarkable robustness, excellent reusability, and relative low-cost synthesis. Due to the attractiveness of MIPs widely demonstrated in the literature, as well as the possibilities of their application in various fields, these materials also have gained the favor of Professor Grzegorz Schroeder’s research group, in which numerous scientific works devoted to the subject of their use have been published.

4

Zastosowanie techniki MIP-SPME do terapeutycznego monitorowania leków w próbkach biologicznych

Janiszewska Daria, Szultka-Młyńska Małgorzata, Buszewski Bogusław

Analityka : nauka i praktyka

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2022

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nr 2

10--19

PL

Terapeutyczne monitorowanie leków oraz ich aktywnie farmakologicznych metabolitów umożliwia ocenę ich farmakokinetyki i metabolizmu, jak również ustalenia odpowiedniego dawkowania pod kątem terapii pacjenta. Technika MIP-SPME stwarza nowe możliwości w zakresie selektywnej ekstrakcji leków i ich potencjalnych metabolitów.

5

Propozycje innowacyjnych sorbentów w przygotowaniu próbek biologicznych

Pajewska-Szmyt Martyna, Gadzała-Kopciuch Renata, Buszewski Bogusław

Wiadomości Chemiczne

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2021

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[Z] 75, 7-8

1075--1088

EN

The sample preparation stage is a critical step in the whole analytical procedure as it often determines the efficiency of the process. What is particularly noticeable in the area of biological samples. Blood, milk, urine, saliva or tissue are only few examples of complicated biological matrix, that require a optimization of sample pre-treatment method for particular analytes. For these purpose, the aim of following chapter was to characterized main problems with sample preparation method as well as highlighted some innovative ways how to improve sample preparation stage. Attention was particularly focused on the use of dispersive solid phase extraction (dSPE), which has achieved high growth in interest in recent years, mainly due to the simplicity and rapidity of performance. This method is not only used with commercially available sorbents, but also provides a basis for trying to apply new analytical tools for separation of analytes from matrix. Following the trends of nanotechnology and within the rules of green analytical chemistry, scientists are facing the challenges of determining and identifying compounds from various chemical groups. Frequently targeting analytes at trace concentration levels as well biological samples. In addition, attention is also focused on reagents reduction and shorter analysis time but also in terms of minimization of sample volume, which should to be collected. Herein the chapter presented describes exemplary new proposals in sorbents such as molecularly imprinted polymers (MIPs), supported ionic liquids (ILs), dendrimers and metal-organic framework (MOFs). In addition, it also looked at the potential use of magnetic nanoparticles as carriers. New sorbents in sample preparation together with modem instrumental techniques therefore allow the development of a procedure that will be characterized by high selectivity and specificity.

6

Application of Molecular Imprinted Polymers for Selective Solid Phase Extraction of Bisphenol A

Poliwoda A., Mościpan M., Wieczorek P. P.

Ecological Chemistry and Engineering. S

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2016

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Vol. 23, nr 4

651--664

EN

Selective molecularly imprinted polymers (MIPs) with bisphenol A as template were synthesized using the non-covalent imprinting approach. MIPs were prepared using thermally initiated polymerization with 1,1’-azobis(cyclohexanecarbonitryle) (ACHN) as initiator and ethylene glycol dimethacrylate (EDMA) as a cross-linking agent. The tested functional monomers included methacrylic acid, acrylamide, and 4-vinylpyridine. The selectivity of the BPA-MIP for the solid phase extraction of bisphenol A was tested in samples containing other related alkylphenols. The polymers prepared in acetonitrile using methacrylic acid or acrylamide as monomer showed the highest selectivity towards target analyte (the selectivity ratio 8:1, respectively for MIP and NIP). The proposed procedure has been proven to be an effective for selective extraction of bisphenol A in aqueous samples (recoveries over 85%) enabling detection and quantification limits of 25 and 70 μg/dm3, respectively based on 10 cm3 of sample volume, with relative standard deviations (RSD) lower than 6%. The obtained molecularly imprinted material showed interesting properties for selective extraction and preconcentration of studied analyte from large volumes of aqueous samples without any problems of cartridge clogging.

7

Polimery z odciskiem molekularnym jako biomimetyki metaloenzymów

Czulak J., Trochimczuk A., Marcinkowska A.

Wiadomości Chemiczne

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2014

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[Z] 68, 9-10

783--809

EN

This paper presents methods of the synthesis and applications of biomimetic catalytic systems produced from molecularly imprinted polymers (MIP). MIPs contain cavities, which are complementary to the imprinted template, thus possess high selectivity and affinity for the molecules resembling template. MIPs have various applications such as: sorption, chromatography, solid phase extraction, drugs transport and catalysis. However, this article is a review of catalytic systems containing in their active sides one of the selected metal ions: copper(II), cobalt(II), zinc(II), iron(III) or nickel(II). Presented catalytic systems are used in hydrolysis, oxidations, hydrogenations and aldol condensation reactions. This review deals with papers published till 2013.

8

Preparation of molecularly imprinted polymer for chiral recognition of racemic 1,1′-binaphthalene-2,2′-diamine by HPLC

Dong H., Wang Y., Ou Y., She J., Shen X., Li J., Zhang Ch., Liu L.

Acta Chromatographica

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2014

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Vol. 26, no. 4

683--693

EN

Molecularly imprinted polymers (MIPs) were synthesized by imprinting a new template—S(-)-1,1′-binaphthalene-2,2′-diamine (S-DABN) and applied as chiral stationary phases for chiral separation of DABN racemates by high-performance liquid chromatography (HPLC). The influence of some key factors on the chiral recognition ability of MIPs, such as the type of functional monomers and porogen and the molar ratio of template to monomer, was systematically investigated. The chromatographic conditions, such as mobile phase composition, sample loading, and flow rate, were also measured. The chiral separation for DABN racemates under the optimum chromatographic conditions by using MIP chiral stationary phase (CSP) of P3, prepared with the S-DABN/MAA ratio = 1/4 and used acetonitrile (2 mL) and chloroform (4 mL) as porogen, showed the highest separation factor (2.14). Frontal analysis was used to evaluate affinity to the target molecule of MIPs. The binding sites (Bt) of MIPs and dissociation constant (Kd) were estimated as 4.56 μmol g−1 and 1.40 mmol L−1, respectively. In comparison with the previous studies, this approach had the advantages, such as the higher separation factor, easy preparation, and cost-effectiveness, it not only has the value for research but also has a potential in industrial application.

9

Polimery ze śladem molekularnym w naukach farmaceutycznych. Cz. II. Zastosowanie w analizie farmaceutycznej

Luliński P.

Polimery

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2011

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T. 56, nr 1

3-10

PL

Artykuł stanowi drugą część pracy przeglądowej dotyczącej zastosowania polimerów ze śladem molekularnym w naukach farmaceutycznych. Omówiono przydatność tej klasy polimerów w analizie farmaceutycznej, gdzie polimery ze śladem molekularnym są wykorzystywane do rozdziału i izolacji substancji leczniczych, jako selektywna faza stacjonarna w chromatografii oraz w procesie ekstrakcji do fazy stałej, jak również jako składniki czujników do oznaczania substancji leczniczych w produktach żywnościowych i różnych postaciach farmaceutycznych.

EN

This paper constitutes a second part of the review on the applications of molecularly imprinted polymers (MIPs) in pharmaceutical sciences. The applicability of these special polymers in pharmaceutical analysis for the selective separation and isolation of drugs in solid stationary phase chromatography, in solid phase extraction, as sensors or sensor components in the characterization of pharmaceutical compounds in food products as well as in various pharmaceutical forms has been discussed.

10

Polimery ze śladem molekularnym w naukach farmaceutycznych. Cz. I. podstawy procesu tworzenia śladu molekularnego. Zastosowanie w syntezie leków i technologii postaci leku

Luliński P.

Polimery

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2010

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T. 55, nr 11-12

799-805

PL

Artykuł stanowi przegląd literaturowy dotyczący polimerów ze śladem molekularnym. Dzięki zdolności do selektywnej i wielokrotnej adsorpcji określonych molekuł omawiana klasa polimerów znalazła szerokie zastosowanie w medycynie i farmacji. Omówiono podstawy procesu tworzenia śladu molekularnego, możliwości wykorzystania polimerów ze śladem molekularnym w syntezie leków oraz w technologii postaci leku. Druga część artykułu będzie poświęcona zastosowaniu polimerów ze śladem molekularnym w analizie farmaceutycznej.

EN

This paper is a review of the literature of studies on molecularly imprinted polymers. The studied polymers have found a wide range of applications in medicine and pharmacy due to their ability for selective and multiple adsorption of specific molecules. The fundamentals of the molecular imprinting process (Fig. 1.), and the possibilities of the application of molecularly imprinted polymers in drug synthesis and delivery systems have been presented. The application of molecularly imprinted polymers in pharmaceutical analysis is also discussed in the second part of the paper.