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Molecules 2017, 22(8), 1253; doi:10.3390/molecules22081253

Synthesis, Characterization and In Vitro Evaluation of a Novel Glycol Chitosan-EDTA Conjugate to Inhibit Aminopeptidase-Mediated Degradation of Thymopoietin Oligopeptides

1
National Engineering Laboratory for AIDS Vaccine, School of Life Sciences, Jilin University, Changchun 130012, China
2
Key Laboratory for Molecular Enzymology and Engineering the Ministry of Education, School of Life Sciences, Jilin University, Changchun 130012, China
3
Institute of Pharmaceutical Science, King’s college London, Franklin-Wilkins Building, 150 Stamford Street, London SE1 9NH, UK
4
Department of Pharmaceutics, School of Pharmacy, Jilin Medical University, Jilin 132013, China
*
Author to whom correspondence should be addressed.
Received: 21 June 2017 / Revised: 14 July 2017 / Accepted: 24 July 2017 / Published: 26 July 2017
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Abstract

In this study, a novel conjugate consisting of glycol chitosan (GCS) and ethylene diamine tetraacetic acid (EDTA) was synthesized and characterized in terms of conjugation and heavy metal ion chelating capacity. Moreover, its potential application as a metalloenzyme inhibitor was evaluated with three thymopoietin oligopeptides in the presence of leucine aminopeptidase. The results from FTIR and NMR spectra revealed that the covalent attachment of EDTA to GCS was achieved by the formation of amide bonds between the carboxylic acid group of EDTA and amino groups of GCS. The conjugated EDTA lost part of its chelating capacity to cobalt ions compared with free EDTA as evidenced by the results of cobalt ion chelation-mediated fluorescence recovery of calcein. However, further investigation confirmed that GCS-EDTA at low concentrations significantly inhibited leucine aminopeptidase-mediated degradation of all thymopoietin oligopeptides. View Full-Text
Keywords: chitosan; peptide degradation; chelation; conjugation chitosan; peptide degradation; chelation; conjugation
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Feng, J.; Chen, Y.; Li, F.; Cui, L.; Shi, N.; Kong, W.; Zhang, Y. Synthesis, Characterization and In Vitro Evaluation of a Novel Glycol Chitosan-EDTA Conjugate to Inhibit Aminopeptidase-Mediated Degradation of Thymopoietin Oligopeptides. Molecules 2017, 22, 1253.

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