title: Role of chirality and macroring in imprinted polymers with enantiodiscriminative power.
abstract: 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.
authors.affiliation: ‡Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4., Budapest H-1111, Hungary.
authors.forename: Jozsef
authors.initials: J
authors.lastname: Kupai
authors.affiliation: ‡Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4., Budapest H-1111, Hungary.
authors.forename: Eszter
authors.initials: E
authors.lastname: Rojik
authors.affiliation: ‡Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Szent Gellért tér 4., Budapest H-1111, Hungary.
authors.forename: Peter
authors.initials: P
authors.lastname: Huszthy
authors.affiliation: †School of Chemical Engineering and Analytical Science, The University of Manchester, The Mill, Sackville Street, Manchester M13 9PL, United Kingdom.
authors.forename: Gyorgy
authors.initials: G
authors.lastname: Szekely
mesh_terms: D000327:Adsorption; D065546:Drug Liberation; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008855:Microscopy, Electron, Scanning; D054802:Molecular Imprinting; D011108:Polymers / Q000737:chemistry*; D016062:Porosity; D013237:Stereoisomerism; D013696:Temperature
chemical_list: D011108:Polymers
keywords: chirality; crown compounds; drug delivery; enantioselectivity; molecularly imprinted polymer