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

Vanina A Cosenza; Diego A Navarro; Carlos A Pujol; Elsa B Damonte; Carlos A Stortz

doi:10.1016/j.carbpol.2015.04.030

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

Carbohydr Polym. 2015 Sep 5:128:199-206. doi: 10.1016/j.carbpol.2015.04.030. Epub 2015 Apr 23.

Authors

Vanina A Cosenza¹, Diego A Navarro¹, Carlos A Pujol², Elsa B Damonte², Carlos A Stortz³

Affiliations

¹ Departamento de Química Orgánica - CIHIDECAR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina.
² Laboratorio de Virología, Departamento de Química Biológica - IQUIBICEN, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina.
³ 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.

PMID: 26005156
DOI: 10.1016/j.carbpol.2015.04.030

Abstract

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.

Keywords: Antiviral activity; Carrageenans; Oxidation; TEMPO; Uronic acids.

Publication types

Research Support, Non-U.S. Gov't