PMID- 25080025 OWN - NLM STAT- MEDLINE DCOM- 20150521 LR - 20160512 IS - 1618-2650 (Electronic) IS - 1618-2642 (Linking) VI - 406 IP - 25 DP - 2014 Oct TI - Evaluation of molecularly imprinted polymers using 2',3',5'-tri-O-acyluridines as templates for pyrimidine nucleoside recognition. PG - 6275-84 LID - 10.1007/s00216-014-8017-z [doi] AB - 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. FAU - Krstulja, Aleksandra AU - Krstulja A AD - ICOA UMR CNRS 7311, Universite d'Orleans, 45067, Orleans Cedex 2, France. FAU - Lettieri, Stefania AU - Lettieri S FAU - Hall, Andrew J AU - Hall AJ FAU - Delepee, Raphael AU - Delepee R FAU - Favetta, Patrick AU - Favetta P FAU - Agrofoglio, Luigi A AU - Agrofoglio LA LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't DEP - 20140731 PL - Germany TA - Anal Bioanal Chem JT - Analytical and bioanalytical chemistry JID - 101134327 RN - 0 (Polymers) RN - WHI7HQ7H85 (Uridine) SB - IM MH - Hydrogen Bonding MH - Molecular Imprinting MH - Polymers/chemical synthesis/*chemistry MH - Stereoisomerism MH - Uridine/*chemistry EDAT- 2014/08/01 06:00 MHDA- 2015/05/23 06:00 CRDT- 2014/08/01 06:00 PHST- 2014/04/22 00:00 [received] PHST- 2014/07/01 00:00 [accepted] PHST- 2014/06/02 00:00 [revised] PHST- 2014/08/01 06:00 [entrez] PHST- 2014/08/01 06:00 [pubmed] PHST- 2015/05/23 06:00 [medline] AID - 10.1007/s00216-014-8017-z [doi] PST - ppublish SO - Anal Bioanal Chem. 2014 Oct;406(25):6275-84. doi: 10.1007/s00216-014-8017-z. Epub 2014 Jul 31.