Journal
ACS APPLIED MATERIALS & INTERFACES
Volume 7, Issue 18, Pages 9516-9525Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsami.5b00755
Keywords
molecularly imprinted polymer; drug delivery; crown compounds; chirality; enantioselectivity
Funding
- Hungarian Scientific Research Fund [OTKA K81127, PD108462]
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Enantioselective discrimination of chiral amines is of great importance as their biological properties often differ. Therefore, here we report the development of synthetic receptors for their enantioselective recognition and pH-sensitive drug release. This paper reports the preparation of three pyridine and two benzene derivatives containing an allyloxy group [(S,S)-5, 6-9] as well as their evaluation as functional monomer anchors for chiral imprinting of amines. The enantiomeric enriching ability and controlled release of the imprinted polymers (IPs) were evaluated using racemic mixture of 1-(1-naphthyl)ethylamine hydrogen perchlorate (1). The effect of the enantiomeric purity of the template on the enantioseparation performance was investigated. Racemic template in combination with enantiomerically pure macrocyclic anchors and vice versa yields IPs with excellent enantiomeric recognition. In vitro drug delivery, enantiomeric enrichment and pH-sensitive release were investigated through kinetic models.
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