Chiral, pH-sensitive polyacrylamide hydrogels: Preparation and enantio-differentiating release ability. (26th June 2015)

• Record Type: Journal Article
• Authors: Cheng, Ru; Liu, Jie; Xie, Peng; Wu, Youping; Deng, Jianping
• Is Part Of: Polymer. Volume 68(2015)
• Page Start: 246
• Page End: 252
• Publication Date: 2015-06-26
• Subjects: Chiral hydrogels -- Enantio-differentiating release -- pH-sensitivity -- Radical polymerization; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; 547.7
• DOI: 10.1016/j.polymer.2015.05.034
• Languages: English
• ISSNs: 0032-3861

Abstract

Abstract: Both pH-sensitive hydrogels and chiral hydrogels have evoked large interest in recent years. In the study, we designed and prepared a novel type of hydrogels simultaneously showing pH-sensitivity and chirality. Such hydrogels were prepared by free radical co-polymerization using N -acryloyl-l -alanine as chiral hydrophilic monomer and octadecyl acrylate as hydrophobic monomer, with K2 S2 O8 as initiator and N, N ′-methylenebisacrylamide as chemical cross-linking agent. The obtained hydrogels exhibited remarkable pH-sensitive swelling ability in water. The optical activity of the hydrogels was characterized using circular dichroism spectroscopy. More interestingly, the hydrogels showed enantio-differentiating release ability towards proline enantiomers, in whichd -proline was preferentially released. The hydrogels also demonstrated remarkable enantio-differentiating release ability toward chiral drug ibuprofen. Graphical abstract: Highlights: Chiral, pH-sensitive hydrogels contained both chemical and physical cross-linking. The hydrogels showed enantio-differentiating release performance toward prolines. The hydrogels showed enantioselective release toward racemic ibuprofen drug.