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Evaluation of molecularly imprinted polymers using 2?,3?,5?-tri-O-acyluridines as templates for pyrimidine nucleoside recognition

Krstulja, Aleksandra, Lettieri, Stefania, Hall, Andrew J., Delepee, Raphael, Favetta, Patrick, Agrofoglio, Luigi A. (2014) Evaluation of molecularly imprinted polymers using 2?,3?,5?-tri-O-acyluridines as templates for pyrimidine nucleoside recognition. Analytical and Bioanalytical Chemistry, 406 (25). pp. 6275-6284. ISSN 1618-2642. E-ISSN 1618-2650. (doi:10.1007/s00216-014-8017-z) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided. (Contact us about this Publication)
Official URL
http://dx.doi.org/10.1007/s00216-014-8017-z

Abstract

In this paper, we describe the synthesis and evaluation of molecularly imprinted polymers (MIPs), prepared using 2?,3?,5?-tri-O-acyluridines as 'dummy' templates, for the selective recognition of uridine nucleosides. The MIPs were synthesised using a non-covalent approach with 2,6-bis-acrylamidopyridine (BAAPy) acting as the binding monomer and ethylene glycol dimethacrylate (EGDMA) as the cross-linking agent. The MIPs were evaluated in terms of capacity, selectivity and specificity by analytical and frontal liquid chromatography measurements. The results obtained in organic mobile phases suggest that the nucleosides are specifically bound to the polymer by the complementary hydrogen bonding motifs of the binding monomer and the nucleoside bases. The MIPs exhibited relatively high imprinting factors for 2?,3?,5?-tri-O-acyluridines, while they did not show any binding capacity for other nucleosides lacking the imide moiety on their base. Moreover, the presence of ester-COO groups in the EGDMA cross-linker may lead to the formation of additional hydrogen bonds with the 2?,3? and/or 5?-OH of sugar part, allowing enhancement of the recognition of the uridine nucleosides. In aqueous media, results show that the binding is driven by hydrophobic interactions.

Item Type: Article
DOI/Identification number: 10.1007/s00216-014-8017-z
Uncontrolled keywords: 2?,3?,5?-Tri-O-acyluridines; Hydrogen bonds; Imprinting; Molecular recognition; Nucleosides
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Sciences > Medway School of Pharmacy
Depositing User: Andrew Hall
Date Deposited: 17 Oct 2014 11:07 UTC
Last Modified: 29 May 2019 13:13 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/43448 (The current URI for this page, for reference purposes)
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