Deamidation of pseudopeptidic molecular hydrogelators and its application to controlled release

JOURNAL OF COLLOID AND INTERFACE SCIENCE

卷:505

Article

Angulo-Pachon, Cesar A.¹  Navarro-Barreda, Diego¹  Rueda, Celia M.¹  Galindo, Francisco¹  Miravet, Juan F.¹ 

[1] Univ Jaume 1, Dept Quim Inorgan & Organ, Castellon de La Plana 12071, Spain

关键词: Molecular gels;    Self-assembly;    Controlled release;    Deamidation;   

DOI  :  10.1016/j.jcis.2017.07.003

来源: Elsevier

【 摘 要 】

Hypothesis: The incorporation of a succinic acid-derived moiety in amino acid derivatives would favor an intramolecular catalysis of a deamidation reaction. Such reaction would permit controlled disassembly of molecular hydrogelators and the use of the hydrogels for controlled release of actives. Experimental: Low molecular weight hydrogelators containing a succinic acid-derived moiety were prepared by conventional organic synthesis procedures. Hydrogels were examined by electron microscopy and H-1 NMR studies were carried out to evaluate the solubility in water of the hydrogelators and the deamidation reaction. Liberation of Rose Bengal entrapped in the hydrogels was monitored by UV-Vis spectroscopy. Findings: Molecular hydrogels formed by pseudopeptidic derivatives of L-valine suffer a thermal deamidation reaction, leading to partial disassembly. The succinic acid-derived moiety present in the gelators is responsible of intramolecular catalysis of a deamidation reaction. Such neighboring group effect is reminiscent of biochemical processes such as protein deamidation and self-excision of inteins. It has been found that the thermodynamic equilibrium of the deamidation reaction is regulated by the efficiency of hydrogelation. As a proof of concept, the thermally promoted deamidation is applied to controlled release of Rose Bengal. (C) 2017 Elsevier Inc. All rights reserved.

【 授权许可】

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