Role of chirality and macroring in imprinted polymers with enantiodiscriminative power

Jozsef Kupai, Eszter Rojik, P. Huszthy, Gyorgy Szekely

Research output: Contribution to journalArticle

40 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)9516-9525
Number of pages10
JournalACS Applied Materials and Interfaces
Volume7
Issue number18
DOIs
Publication statusPublished - May 13 2015

Fingerprint

Chirality
Anchors
Amines
Polymers
Benzene Derivatives
Artificial Receptors
Drug delivery
Pyridine
Hydrogen
Benzene
Monomers
Derivatives
Kinetics
Pharmaceutical Preparations
pyridine
perchlorate
1-(1-naphthyl)ethylamine

Keywords

  • chirality
  • crown compounds
  • drug delivery
  • enantioselectivity
  • molecularly imprinted polymer

ASJC Scopus subject areas

  • Materials Science(all)

Cite this

Role of chirality and macroring in imprinted polymers with enantiodiscriminative power. / Kupai, Jozsef; Rojik, Eszter; Huszthy, P.; Szekely, Gyorgy.

In: ACS Applied Materials and Interfaces, Vol. 7, No. 18, 13.05.2015, p. 9516-9525.

Research output: Contribution to journalArticle

Kupai, Jozsef ; Rojik, Eszter ; Huszthy, P. ; Szekely, Gyorgy. / Role of chirality and macroring in imprinted polymers with enantiodiscriminative power. In: ACS Applied Materials and Interfaces. 2015 ; Vol. 7, No. 18. pp. 9516-9525.
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