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Supramolecular hydrogels of β-cyclodextrin linked to calcium homopoly-l-guluronate for release of coumarins with trypanocidal activity.

Authors
  • Moncada-Basualto, M1
  • Matsuhiro, B2
  • Mansilla, A3
  • Lapier, M4
  • Maya, J D4
  • Olea-Azar, C5
  • 1 Departamento de Ciencias del Ambiente, Facultad de Química y Biología, Universidad de Santiago de Chile, Av. L. B. O'Higgins 3363, Santiago, Chile; Departamento de Química Inorgánica y Analítica, Facultad de Ciencias Química y Farmacéuticas, Universidad de Chile, Av. Sergio Livingstone 1007, Santiago, Chile. Electronic address: [email protected] , (Chile)
  • 2 Departamento de Ciencias del Ambiente, Facultad de Química y Biología, Universidad de Santiago de Chile, Av. L. B. O'Higgins 3363, Santiago, Chile. , (Chile)
  • 3 Laboratorio de Macroalgas Antárticas y Subantárticas, Universidad de Magallanes, Av. Bulnes 1465, Punta Arenas, Chile; Instituto de Ecología y Biodiversidad, Chile. , (Chile)
  • 4 Departamento de Farmacología Molecular y Clínica, Facultad de Medicina, Universidad de Chile, Av. Independencia 1107, Santiago, Chile. , (Chile)
  • 5 Departamento de Química Inorgánica y Analítica, Facultad de Ciencias Química y Farmacéuticas, Universidad de Chile, Av. Sergio Livingstone 1007, Santiago, Chile. , (Chile)
Type
Published Article
Journal
Carbohydrate polymers
Publication Date
Jan 15, 2019
Volume
204
Pages
170–181
Identifiers
DOI: 10.1016/j.carbpol.2018.10.010
PMID: 30366529
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

Association constants and thermodynamicsparameters on inclusion of four 3-amido coumarins that present trypanocidal activity, into 6-amino-β-cyclodextrin (1:1 stoichimetry) were determined. In addition, pure homopolymeric-α-l-guluronate fraction prepared by partial hydrolysis of sodium alginate from Sub-Antarctic Kelp Durvillaea antarctica was conjugated with 6-amino-β-cyclodextrin (64% yield). To glycoconjugates, 3-amido coumarins were incorporated (73% of encapsulation) and supramolecular hydrogels were prepared by gelation with Ca2+ ions. The trypanocidal activity of the inclusion complexes increased by 10%. Likewise, an increase in diffusion in artificial membrane was observed (13%). It was found that the inclusion complexes increased the variation of the mitochondrial potential of T. cruzi (17%). The lowest release of substituted amidocoumarins (ACS) from supramolecular hydrogels occurred at pH 1.2 whereas the maximum release (34%) was observed at pH 8.0. Encapsulation of lipophilic bioactive compounds in supramolecular hydrogels allows the generation of release systems sensitive to pH with potential application in biomedicine. Copyright © 2018 Elsevier Ltd. All rights reserved.

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