Synthesis of substrate‐selective polymers by host‐guest polymerization

Arshady, Reza; Mosbach, Klaus

doi:10.1002/macp.1981.021820240

Cited by 614 publications

(213 citation statements)

References 9 publications

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“…In Table 2 are shown the imprinting factors (IF = k'Mip/k'NrW) obtained for the different MIP/NIP combinations when injecting the template (2). In general agreement with the association constant data derived from the NMR titration experiments, it can be seen that PM (3) and PN( 3 ) exhibit the same behaviour; (2) is equally weakly retained on both polymers and no imprinting effect is observed. For Pm(4) and PN ( 4 ), we observe a difference in the retention behaviour of(2) on the respective polymers and a mild imprinting effect is seen.…”

Section: Polymer Preparation and Chromatographic Evaluationsupporting

confidence: 71%

“…H NMR titrations were performed by adding increasing amounts of monomer (0.5-10rmM in CDCI 3 ) to solutions of either (1) or (2) (1mM in CDCI 3 ) and the spectra were recorded using a Bruker Advance DRX 400 spectrometer. The complex induced shift (CIS) of the imide proton of(l) or (2) was followed.…”

Section: Methodsmentioning

confidence: 99%

“…A survey of this literature shows that much MIP research has focused on the use of commercially available functional monomers, e.g. methacrylic acid, to create the binding sites in such noncovalent MIPs [3]. Among the exceptions is the use of 2,6-bis(acrylamido)pyridine (5) as a functional monomer for the imprinting of alloxan, where the selectivity of the MIP over the nonimprinted polymer (NIP) with respect to the recognition of thymine was also assessed [4].…”

Section: Introductionmentioning

confidence: 99%

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Molecularly Imprinted Polymers (MIPs) Against Uracils: Functional Monomer Design, Monomer-Template Interactions In Solution And MIP Performance In Chromatography

et al. 2002

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The interaction of N1-substituted uracils (cyclohexyl (1) and benzyl (2)) with three polymerisable recognition elements, the novel monomers 9-(3/4-vinylbenzyl)adenine (3) and 2,6-diamino-9-(3/4-vinylbenzyl)purine (4) and the previously synthesised monomer 2,6-bis(acrylamido)pyridine (5), has been studied via1H NMR in deuterio-chloroform solution. MIPs against (2) have been prepared using each of the monomers and tested in the chromatographic mode. The effect of the number and type of hydrogen bonds formed between the templates and the functional monomers is reflected in the values of the apparent association constants obtained from the solution study and by the performance of the subsequently prepared MIPs in the chromatographic mode.

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Section: Polymer Preparation and Chromatographic Evaluationsupporting

confidence: 71%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Molecularly Imprinted Polymers (MIPs) Against Uracils: Functional Monomer Design, Monomer-Template Interactions In Solution And MIP Performance In Chromatography

et al. 2002

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“…[1][2][3] Formation of a self-assembled pre-polymerization complex between a template molecule and functional monomers, followed by polymerization with a cross-linker in a porogenic solvent and the subsequent extraction of the template, produces a molecularly imprinted polymer (MIP) possessing specifically sized and shaped cavities capable of molecular recognition. 4,5 MIPs are generally highly crosslinked thermosets, and therefore porosity is a necessary feature of their morphology to allow permeability and transport of templates molecules to the bulk polymer phase.…”

mentioning

confidence: 99%

Influence of Polymer Morphology on the Capacity of Molecularly Imprinted Resins to Release or to Retain their Template

et al. 2009

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This paper deals with the specific ability of molecularly imprinted polymers (MIPs) to release and/or to retain their template. MIPs for caffeine with various MIP:porogen volume ratios were prepared by a non-covalent route. Formation of a prepolymerization complex between the template and the functional monomer was confirmed by nuclear magnetic resonance and computer simulation. The MIP monoliths were successively grinded, sieved, and dried under vacuum. The morphology of the imprinted particles was investigated by scanning electron microscopy, swelling experiments and nitrogen adsorption. Typical release patterns of as-synthesised MIP particles in solvents can be decomposed in three fractions: initial release ( 0 ), slow release over several hours (Á Release ), permanent retention/encapsulation within the MIP (Á Reservoir ). The effect of MIP:porogen volume ratio (related to the MIP porosity) on the releasing/retaining profiles of the materials has been investigated. Finally, the results were critically compared with the available literature and the applicability of MIP reservoirs is briefly discussed.KEY WORDS: Molecular Imprinting / Polymer Morphology / Controlled Release / Polymer Reservoir / Self-Assembly / Molecular imprinting is an emerging technology, which allows the molecular design of polymeric materials containing highly specific receptor sites with an affinity for target compounds.1-3 Formation of a self-assembled pre-polymerization complex between a template molecule and functional monomers, followed by polymerization with a cross-linker in a porogenic solvent and the subsequent extraction of the template, produces a molecularly imprinted polymer (MIP) possessing specifically sized and shaped cavities capable of molecular recognition. 4,5 MIPs are generally highly crosslinked thermosets, and therefore porosity is a necessary feature of their morphology to allow permeability and transport of templates molecules to the bulk polymer phase.To date, a number of promising applications have been proposed for MIPs. For instance, imprinted polymers are used in chromatography as the stationary phase for separation and isolation of racemates.6,7 A related area is solid-phase extraction, where imprinted polymers are employed as a selective sorbent to concentrate the molecule of interest.8 MIPs are also used in immunoassays-type analyses as synthetic antibody 9 and in catalysis as enzyme mimics. 10,11 In the emerging field of biosensors, MIPs demonstrate a potential as the recognition element, although their performance and selectivity in aqueous systems is still a limiting factor. 12,13The application of desorption properties of MIPs is a relatively new area.14,15 Chromatographic data have shown that the MIP-template dissociation kinetics can be controlled by varying the local environment (MIP composition, solvent. . .). Therefore, it seems feasible that MIPs could form highly specific rate limiting reservoirs releasing active compounds at well-defined rates. Early studies delivered promising results and showe...

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“…22,23 O segundo maior avanço verificado na tecnologia de moldagem molecular de polímeros orgânicos ocorreu em 1981, quando Arshady e Mosbach prepararam um MIP orgânico com base num processo diferente. 24 Esta abordagem foi designada moldagem não-covalente, por oposição à covalente usada por Wulff. O mecanismo não-covalente, implicando uma metodologia simples, veio incrementar marcadamente os estudos nesta área que ocorreram durante a década de 90.…”

Section: Reconhecimento Molecular: Considerações Históricasunclassified

Polímeros com capacidade de reconhecimento molecular no controlo da libertação de fármacos. Parte 1: síntese e caracterização

Sousa¹,

Barbosa²

2009

Quím. Nova

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Recebido em 30/8/08; aceito em 20/1/09; publicado na web em 10/8/09MOLECULARLY IMPRINTED POLYMERS FOR CONTROLLING DRUG RELEASE. PART 1: SYNTHESIS AND CHARACTERIZATION. Molecularly imprinted polymers (MIPs) consist of synthetic macromolecular matrix, obtained through molecular imprinting-based methods that show ability to selectively recognize important biological molecules and its application in the drug delivery field is under development. In the present review the main aspects related to the synthesis and characterization of MIPs are studied. The fundamental variables participating in the synthesis process, such as template molecule, functional monomers, cross-linking agents, solvents and imprinting approaches are discussed. Moreover, the main available methods for MIPs chemical and morphological characterization are presented and the importance of the obtained information is discussed.Keywords: molecularly imprinted polymers (MIPs); imprinting approaches; MIPs characterization. INTRODUÇÃOO reconhecimento molecular é definido como a capacidade de uma molécula se ligar a outra que apresenta uma forma complementar com a primeira.1 Os polímeros com capacidade de reconhecimento molecular (designados na literatura anglo-saxónica molecularly imprinted polymers -MIPs) encontram-se actualmente bem definidos. Consistem em matrizes macromoleculares sintéticas, obtidas com base em métodos de moldagem molecular, que apresentam a capacidade de reconhecer selectivamente moléculas importantes do ponto de vista biológico, como fármacos, proteínas e biomoléculas.2-6 Com efeito, as tecnologias baseadas na moldagem molecular permitem disponibilizar sistemas poliméricos eficientes, com capacidade para reconhecer moléculas bioactivas específicas, em que a interacção depende das propriedades e da concentração da molécula-molde presente no meio circundante.O reconhecimento molecular constitui já uma ferramenta bem desenvolvida na área analítica, principalmente no que se refere à separação e quantificação de diferentes substâncias, como fármacos e moléculas bioactivas, presentes em matrizes mais ou menos complexas.7-10 Presentemente, encontram-se comercializados alguns produtos baseados nesta tecnologia.11,12 Embora estes materiais ainda não tenham alcançado uma aplicação clínica no domínio do controlo da libertação de fármacos, vários autores referem que esta tecnologia apresenta grande potencial no desenvolvimento de formas farmacêuticas mais adequadas.13-16 Outra razão que tem vindo a promover o interesse pelos MIPs reside no facto de estes poderem mimetizar receptores biológicos em estudos de desenvolvimento de novas substâncias com actividade farmacológica e também poderem detectar substâncias específicas em fluidos biológicos (como, por exemplo, nos testes de detecção de drogas de abuso).12,17 De acordo com Mosbach e Ramström, 18 esta especificidade é comparável à dos anticorpos monoclonais utilizados em técnicas imunológicas. O presente trabalho constitui uma revisão de conjunto relativa à síntese e caracterização de MIPs. No ...

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Synthesis of substrate‐selective polymers by host‐guest polymerization

Cited by 614 publications

References 9 publications

Molecularly Imprinted Polymers (MIPs) Against Uracils: Functional Monomer Design, Monomer-Template Interactions In Solution And MIP Performance In Chromatography

Molecularly Imprinted Polymers (MIPs) Against Uracils: Functional Monomer Design, Monomer-Template Interactions In Solution And MIP Performance In Chromatography

Influence of Polymer Morphology on the Capacity of Molecularly Imprinted Resins to Release or to Retain their Template

Polímeros com capacidade de reconhecimento molecular no controlo da libertação de fármacos. Parte 1: síntese e caracterização

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