The Application of Template Selectophores for the Preparation of Molecularly Imprinted Polymers

Abstract

Abstract:Molecularly imprinted polymers are versatile materials with wide application scope for the detection, capture and separation of specific compounds present in complex feed stocks. A major challenge associated with their preparation has been the need to sacrifice one mole equivalent of the template molecule to generate the complementary polymer cavities that selectively bind the target molecule. Moreover, template molecules can often be difficult to synthesise, expensive or lack stability. In this study, we describe a new approach, directed at the use of synthetic selectophores, chosen as readily prepared and low cost structural analogues with recognition groups in similar three-dimensional arrangements as found in the target molecule. To validate the approach, a comparative study of selectophores related to the polyphenolic compound (E)-resveratrol has been undertaken using traditional and green chemical synthetic approaches. These molecular mimic compounds were employed as polymer templates and also as binding analytes to interrogate the recognition sites associated with the molecularly imprinted polymers. Importantly, the study confirms that the use of selectophores has the potential to confer practical advantages, including access to more efficient methods for selection and preparation of suitable template molecules with a broader range of molecular diversity, as well as delivering imprinted polymers capable of recognizing the target compound and structurally related products.

Synthesis, in vitro activity, and molecular docking of caffeic acid and resveratrol derivatives against Alzheimer's disease-related enzymes

“…Compound 1 was synthesized in a one step process, as previously reported, without any modification [50]. A condensation reaction between 4-aminophenol and 3,5-dihydroxybenzoic acid in dry DMF under N2 atmosphere was catalyzed by the presence of N-ethyl-N'-(3dimethylaminopropyl)carbodiimide hydrochloride (EDC) at room temperature to yield the pure product in good yields.…”

Advances in the development of molecularly imprinted polymers for the separation and analysis of proteins with liquid chromatography

“…Upon removal of the trapped template molecules from the highly cross‐linked polymeric matrix through the disruption of polymer–template interactions by washing and/or extraction (or hydrolysis in case of covalent imprinting), porous polymeric materials with nanocavities of predetermined shape and complimentary binding or catalytic site features toward the template are generated, which constitute their "molecular memory." These materials afford template, template fragment, or template analogue recognition through a combination of shape complementarity and multiple, stereochemically defined noncovalent interactions, such as hydrogen bonds and hydrophobic and electrostatic interactions . Alternatively, discrimination between molecules of different shapes and chemical functionalities can be achieved through utilization of reversible covalent bonds or a hybrid approach, where a monomer–template composite compound with a labile covalent bond is used, which is cleaved after synthesis, thereby activating noncovalent interaction sites, termed semicovalent approach .…”

Phytosterol Recognition via Rationally Designed Molecularly Imprinted Polymers

“…MIPs are porous materials, designed to contain complimentary 'receptor-like' binding sites capable of recognising a specific molecular template [10]. Such MIPs can exhibit a 'molecular memory' for the template or structurally related molecular analogues [11][12][13].…”