Partial and total C-6 oxidation of gelling carrageenans. Modulation of the antiviral activity with the anionic character.

Autor: Cosenza VA; Departamento de Química Orgánica - CIHIDECAR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina., Navarro DA; Departamento de Química Orgánica - CIHIDECAR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina., Pujol CA; Laboratorio de Virología, Departamento de Química Biológica - IQUIBICEN, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina., Damonte EB; Laboratorio de Virología, Departamento de Química Biológica - IQUIBICEN, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina., Stortz CA; Departamento de Química Orgánica - CIHIDECAR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina. Electronic address: stortz@qo.fcen.uba.ar.
Jazyk: angličtina
Zdroj: Carbohydrate polymers [Carbohydr Polym] 2015 Sep 05; Vol. 128, pp. 199-206. Date of Electronic Publication: 2015 Apr 23.
DOI: 10.1016/j.carbpol.2015.04.030
Abstrakt: The optimal conditions for the full C-6 oxidation of κ- and ι-carrageenans using (2,2,6,6-tetramethylpiperidinyl)oxy (TEMPO) in the presence of sodium hypochlorite and sodium bromide were assessed. The fully oxidized products were characterized by NMR spectroscopy. Partially oxidized products were also obtained and analyzed by chemical and spectroscopical methods. The antiviral activity of carrageenans against herpes simplex virus HSV-1 and HSV-2 determined by plaque reduction assay, was not largely affected by full oxidation of the polysaccharides, but an increase in activity was detected by partial oxidation. A specific overoxidation on C-2 of the 3,6-anhydrogalactose moiety of κ-carrageenan was identified, solved experimentally and rationalized through the application of molecular modeling.
(Copyright © 2015 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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