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

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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.

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Acknowledgments

This research was funded by ANR-10-TECS-0004. Aleksandra Krstulja is grateful to ANR for a doctoral scholarship. Stefania Lettieri is grateful to the University of Kent for a doctoral scholarship. The authors also thank Dr. Panagiotis Manesiotis (Queen’s University, Belfast) for fruitful discussions.

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Author notes

  1. Raphael Delépée

    Present address: Centre François Baclesse, ABTE EA4651, UNICAEN, 3 Avenue du Général Harris, 14000, Caen, France

Authors and Affiliations

  1. ICOA UMR CNRS 7311, Université d’Orléans, 45067, Orléans Cedex 2, France

    Aleksandra Krstulja, Raphael Delépée, Patrick Favetta & Luigi A. Agrofoglio

  2. Medway School of Pharmacy, Universities of Greenwich & Kent, Chatham, Kent, ME4 4 TB, UK

    Stefania Lettieri & Andrew J. Hall

Authors
  1. Aleksandra Krstulja
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  2. Stefania Lettieri
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  3. Andrew J. Hall
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  4. Raphael Delépée
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  5. Patrick Favetta
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  6. Luigi A. Agrofoglio
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Corresponding authors

Correspondence to Andrew J. Hall or Luigi A. Agrofoglio.

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Krstulja, A., Lettieri, S., Hall, A.J. et al. Evaluation of molecularly imprinted polymers using 2′,3′,5′-tri-O-acyluridines as templates for pyrimidine nucleoside recognition. Anal Bioanal Chem 406, 6275–6284 (2014). https://doi.org/10.1007/s00216-014-8017-z

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  • DOI: https://doi.org/10.1007/s00216-014-8017-z

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