Enzyme Models Based on Molecularly Imprinted Polymers with Strong Esterase Activity

Wulff, Günter; Groß, Thomas; Schönfeld, Rainer

doi:10.1002/anie.199719621

Cited by 279 publications

(143 citation statements)

References 18 publications

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“…116 In other words, the templating guest serves as the transition state analogue around which the host is assembled. Although several research groups have been pursuing this approach by making use of molecularly imprinted polymers, 117 it is difficult to obtain well-defined binding sites whose structures can be altered in a controlled manner. For this reason, research has been directed to solution chemistry in which the bond formation processes in the receptor synthesis are covalent, yet reversible.…”

Section: Noncovalent Systemsmentioning

confidence: 99%

Self‐Assembled Nanoreactors

et al. 2005

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Section: Noncovalent Systemsmentioning

confidence: 99%

Self‐Assembled Nanoreactors

et al. 2005

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“…Muitas das dificuldades inerentes a este método podem ser ultrapassadas pelo uso de sistemas que associam estequiometricamente monómeros e moléculas-molde. [26][27][28][29] Este processo tem proporcionado a obtenção de uma grande variedade de receptores, que apresentam elevada capacidade e grande eficácia de reconhecimento molecular em meio aquoso.…”

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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“…A new approach to the synthesis of phosphonate ester-imprinted polymer catalysts was recently demonstrated by Wulff,28 who reasoned that since a complementary shape to a transition state analogue is not in itself sufficient to produce strong esterolytic activity, new functionality must be introduced into the polymer in order to improve the efficiency of catalysis. The indication that arginine residues play an important role in the catalytic mechanism of some antibodies raised against phosphonate ester haptens led Wulff and co-workers to investigate monomers bearing amidine functionality, which is the carbon analogue of the guanidine side group of arginine.…”

Section: Catalysismentioning

confidence: 99%

“…The polymers of Wulff 28 showing strong esterase activity were prepared with the transition state analogue (38) and the new polymerizable amidine (39) which can be used in stoichiometric amounts in the imprinting step. The resultant polymers catalyse the alkaline hydrolysis of 40 with Michaelis-Menton kinetics.…”

Section: Figure 15mentioning

confidence: 99%

Imprinted Polymers: Versatile New Tools in Synthesis

Whitcombe

Alexander²,

Vulfson³

2000

Synlett

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Abstract:The use of molecularly imprinted polymers in synthetic organic chemistry is reviewed. These materials are prepared in the presence of a template for which they carry a functional and stereochemical "memory" and can be likened to artificial antibodies or enzymes. Their unique properties have been exploited by the use of imprinted polymers as stereo-and regio-selective solid supports in condensation reactions and hydride reduction, as protecting groups in the acylation of polyols and as catalysts to enhance the rates of reactions as diverse a Diels-Alder reaction, an Aldol condensation, β-elimination, the benzisoxazole isomerization, transesterification and ester hydrolyses.Key words: molecular imprinting, imprinted polymer, selectivity, chemical modification, synthesis IntroductionThe technique of molecular imprinting, in which a crosslinked polymer is assembled around a template, utilizing its interaction with functional monomers to create a recognition site, complementary in both shape and functionality to the original occupant, has become well established and many research groups are currently active in this field. [1][2][3][4][5][6][7][8][9][10][11] A schematic diagram of the imprinting process is shown in Figure 1.There have now been a number of examples illustrating the spectacular performance of imprinted polymers in a range of applications from chiral chromatographic separations 12-14 to the binding of ligands with a specificity rivaling that of antibodies. [15][16] However, it is becoming clear that the versatility of the imprinting methodology can be exploited to generate polymers for uses beyond those involving simply the recognition or separation of small organic molecules. In particular, researchers have begun to explore the use of imprinted polymers in synthesis, with a view to creating novel and robust reactive supports, as "protecting groups" and catalysts. In this short review we focus on the above applications, and outline some recent work which has taken the field of imprinted polymers into the realms of organic, inorganic, and biomimetic chemistry. "Microreactors" for chiral synthesisThe use of the imprinted recognition sites as potential chiral cavities for enantioselective synthesis was first described by the research groups of Shea 17 and Neckers, 18 and synthetic transformations including enantioselective protonation-deprotonation 19 and selective hydrolysis 20 have also been carried out in imprinted sites. However, perhaps the most elegant early work in this area was due to Wulff and co-workers, who targeted their initial studies to C-C bond formation in a biomimetic synthesis of aamino acids from glycine. 21 The model system set out by Wulff involved alkylation of a polymer-bound glycine, present as an ester enolate. The synthetic scheme on which this is based is shown in Figure 2, in which the glycine-Schiff base (1) is deprotonated to the enolate (2) amenable to alkylation via appropriate routes (alkyl halide, aldol condensation, Michael addition) to give the substituted amino...

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Enzyme Models Based on Molecularly Imprinted Polymers with Strong Esterase Activity

Cited by 279 publications

References 18 publications

Self‐Assembled Nanoreactors

Self‐Assembled Nanoreactors

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

Imprinted Polymers: Versatile New Tools in Synthesis

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