Deamidation of pseudopeptidic molecular hydrogelators and its application to controlled release
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Otros documentos de la autoría: Angulo-Pachón, César A.; Navarro Barreda, Diego; Rueda, Celia M.; Galindo, Francisco; Miravet, Juan
Metadatos
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comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
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INVESTIGACIONMetadatos
Título
Deamidation of pseudopeptidic molecular hydrogelators and its application to controlled releaseAutoría
Fecha de publicación
2017-07Editor
ElsevierCita bibliográfica
ANGULO-PACHÓN, César A., et al. Deamidation of pseudopeptidic molecular hydrogelators and its application to controlled release. Journal of Colloid and Interface Science, 2017, vol. 505, p. 1111-1117.Tipo de documento
info:eu-repo/semantics/articleVersión de la editorial
http://www.sciencedirect.com/science/article/pii/S0021979717307737Versión
info:eu-repo/semantics/submittedVersionPalabras clave / Materias
Resumen
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 ... [+]
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 1H 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. [-]
Proyecto de investigación
Ministerio de Economía y Competitividad of Spain (grant CTQ2015-71004-R) and Universitat Jaume I (grant P1.1B2015-76).Derechos de acceso
© 2017 Elsevier Inc. All rights reserved.
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info:eu-repo/semantics/openAccess
http://rightsstatements.org/vocab/InC/1.0/
info:eu-repo/semantics/openAccess
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