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.

Chiral Separation in Preparative Scale: A Brief Overview of Membranes as Tools for Enantiomeric Separation

“…The matrine surface-imprinting was carried out using ethylene glycol diglycidyl ether (EGDE) as crosslinker. As expected, the obtained imprinted membrane GMIM showed specific recognition selectivity and excellent binding affinity for matrine (21) [150].…”

Experimental and theoretical investigation of the complexation of methacrylic acid and diisopropyl urea

“…Imprinting is usually based on reversible non-covalent interactions, and one of the most common functional monomers is methacrylic acid. 2,3,4,5 This article deals with the pre-polymerisation complex of methacrylic acid (MAAH) and potentially genotoxic 1,3-diisopropylurea (IPU) template which were previously used for molecular imprinting as functional monomer and template, respectively ( Figure 1). 6 In order to better understand the complexation mechanism, multiple methods were applied to investigate the system (NMR, IR and DFT).…”

Piridin egységet tartalmazó királis koronaéterek néhány alkalmazása

“…[16][17][18][19] Kutatómunkánk során célunk volt egyrészt protonált primer aminok enantiomereinek elválasztására alkalmas koronaéter alapú MIP-ek szintézise, másrészt annak igazolása, hogy a hatékony mûködéshez szükség van a piridin-, illetve a makrogyûrû jelenlétére is. 20 Ehhez elõször a MIP-ek funkcionális monomereiként szolgáló terminális kettõskötést tartalmazó koronaétereket [(S,S)-4, 5 és 6] kellett szintetizálnunk. A makrogyûrû szerepének igazolásához a fenti koronaéterek "fej részét" (7, 8) is elõállítottuk (2. ábra).…”

“…A makrogyûrû szerepének igazolásához a fenti koronaéterek "fej részét" (7, 8) is elõállítottuk (2. ábra). 20 …”