PMID- 28791744
OWN - NLM
STAT- MEDLINE
DCOM- 20190920
LR  - 20190920
IS  - 1099-1352 (Electronic)
IS  - 0952-3499 (Linking)
VI  - 31
IP  - 3
DP  - 2018 Mar
TI  - Assessment of the imprinting efficiency of an imide with a "stoichiometric" 
      pyridine-based functional monomer in precipitation polymerisation.
LID - 10.1002/jmr.2655 [doi]
AB  - The efficiency of the stoichiometric non-covalent imprinting of the imide 
      2,3,5-tri-O-acetyluridine (TAU) with 2,6-bis(acrylamido)pyridine (BAAPy) as 
      functional monomer due to their strong 
      donor-acceptor-donor/acceptor-donor-acceptor (DAD/ADA) hydrogen bond array 
      interaction has been evaluated by bulk imprinting. This study is the first to 
      investigate the imprinting and template rebinding efficiencies of the TAU/BAAPy 
      molecularly imprinted polymeric (MIP) system prepared by precipitation 
      polymerisation. We found that the stoichiometric 1:1 T:FM ratio has not been 
      maintained in precipitation polymerisation and an optimal TAU:BAAPy ratio of 
      1:2.5 was obtained in acetonitrile without agitation affording an affinity 
      constant (1.7 x 10(4) M(-1) ) and a binding capacity (3.69 mumol/g) higher than 
      its bulk counterpart. Molecular modelling, NMR studies, and selectivity assays 
      against analogues uridine and 2,3,5-tri-O-acetyl cytidine (TAC) indicate that, 
      aside from the DAD/ADA hydrogen bond interaction, BAAPy also interacts with the 
      acetyl groups of TAU. Template incorporation and rebinding in precipitation MIPs 
      are favoured by a moderate initiator concentration, ie, initiator:total monomer 
      (I:TM) ratio of 1:131, while low I:TM ratio (ie, 1:200) drastically reduced 
      template incorporation and binding capacity. Vigorous agitation by stirring 
      showed higher template incorporation but significantly lower template rebinding 
      compared to that prepared without agitation. While the imprinting efficiencies 
      for the best performing bulk and precipitation TAU MIPs generated in this study 
      were moderate, 41% and 60%, respectively, their rebinding capacities were only 
      between 3 and 4% of the incorporated template. We also present quantitative 
      nuclear magnetic resonance spectroscopy as an efficient method for MIP 
      characterisation.
CI  - Copyright (c) 2017 John Wiley & Sons, Ltd.
FAU - Lim, K Fremielle
AU  - Lim KF
AD  - Discipline of Chemistry, School of Environmental and Life Sciences, University of 
      Newcastle, Callaghan, New South Wales, 2308, Australia.
FAU - Hall, Andrew J
AU  - Hall AJ
AD  - Medway School of Pharmacy, Universities of Greenwich and Kent at Medway, Anson 
      Building, Central Avenue, Chatham Maritime, Chatham, Kent, ME4 4TB, UK.
FAU - Lettieri, Stefania
AU  - Lettieri S
AD  - Medway School of Pharmacy, Universities of Greenwich and Kent at Medway, Anson 
      Building, Central Avenue, Chatham Maritime, Chatham, Kent, ME4 4TB, UK.
AD  - Istituto Italiano di Tecnologia, Via Morego, 30, 16163, Genoa, Italy.
FAU - Holdsworth, Clovia I
AU  - Holdsworth CI
AUID- ORCID: 0000-0002-6039-0974
AD  - Discipline of Chemistry, School of Environmental and Life Sciences, University of 
      Newcastle, Callaghan, New South Wales, 2308, Australia.
LA  - eng
PT  - Journal Article
DEP - 20170809
PL  - England
TA  - J Mol Recognit
JT  - Journal of molecular recognition : JMR
JID - 9004580
RN  - 0 (Acetates)
RN  - 0 (Imides)
RN  - 0 (Macromolecular Substances)
RN  - 0 (Polymers)
RN  - 0 (Pyridines)
RN  - 2WP61F175M (uridine triacetate)
RN  - WHI7HQ7H85 (Uridine)
SB  - IM
MH  - Acetates/chemistry
MH  - Hydrogen Bonding
MH  - Imides/chemical synthesis/chemistry
MH  - Macromolecular Substances/chemical synthesis/*chemistry
MH  - *Molecular Imprinting
MH  - Polymerization
MH  - Polymers/chemical synthesis/*chemistry
MH  - Pyridines/chemical synthesis/chemistry
MH  - Uridine/analogs & derivatives/chemistry
OTO - NOTNLM
OT  - 2,6-bis(acrylamido)pyridine
OT  - donor-acceptor-donor hydrogen bond array
OT  - molecularly imprinted polymers
OT  - precipitation imprinting
OT  - precipitation polymerisation
OT  - quantitative NMR
EDAT- 2017/08/10 06:00
MHDA- 2019/09/21 06:00
CRDT- 2017/08/10 06:00
PHST- 2017/04/06 00:00 [received]
PHST- 2017/06/22 00:00 [revised]
PHST- 2017/07/05 00:00 [accepted]
PHST- 2017/08/10 06:00 [pubmed]
PHST- 2019/09/21 06:00 [medline]
PHST- 2017/08/10 06:00 [entrez]
AID - 10.1002/jmr.2655 [doi]
PST - ppublish
SO  - J Mol Recognit. 2018 Mar;31(3). doi: 10.1002/jmr.2655. Epub 2017 Aug 9.