Abstract
The infection of mammalian cells by enveloped viruses is triggered by the interaction of viral envelope glycoproteins with the glycosaminoglycan, heparan sulfate. By mimicking this carbohydrate, some anionic polysaccharides can block this interaction and inhibit viral entry and infection. As heparan sulfate carries both carboxyl and sulfate groups, this work focused on the derivatization of a (1→3)(1→6)-β-D-glucan, botryosphaeran, with these negatively-charged groups in an attempt to improve its antiviral activity. Carboxyl and sulfonate groups were introduced by carboxymethylation and sulfonylation reactions, respectively. Three derivatives with the same degree of carboxymethylation (0.9) and different degrees of sulfonation (0.1; 0.2; 0.4) were obtained. All derivatives were chemically characterized and evaluated for their antiviral activity against herpes (HSV-1, strains KOS and AR) and dengue (DENV-2) viruses. Carboxymethylated botryosphaeran did not inhibit the viruses, while all sulfonated-carboxymethylated derivatives were able to inhibit HSV-1. DENV-2 was inhibited only by one of these derivatives with an intermediate degree of sulfonation (0.2), demonstrating that the dengue virus is more resistant to anionic β-D-glucans than the Herpes simplex virus. By comparison with a previous study on the antiviral activity of sulfonated botryosphaerans, we conclude that the presence of carboxymethyl groups might have a detrimental effect on antiviral activity.
Highlights
IntroductionAnionic polysaccharides have attracted much attention over the past decades for their inhibitory activity against viruses [1,2]
Despite the lower antiviral activity of our sulfonated-carboxymethylated derivatives in comparison with sulfonated polysaccharides reported in the literature [31,32,33,34], our results demonstrated that the presence of sulfonate groups on a carboxymethylated β-glucan mostly enhanced its antiherpetic activity
The effective concentration that reduced the viral infection by 50% (IC50 ), compared to the cell and virus controls, was determined using linear regression analysis
Summary
Anionic polysaccharides have attracted much attention over the past decades for their inhibitory activity against viruses [1,2]. The sulfated polysaccharides, mainly from seaweeds, stand out as showing potent activity against several enveloped viruses, such as Herpes simplex (HSV-1 and HSV-2) [3,4], influenza [5], HIV-1 and. 2 [1,5,6], and Dengue (DENV 1-4) [7,8]. The latest studies revealed that heparin, a sulfated polysaccharide, inhibits cellular invasion by SARS-CoV-2, causative of Coronavirus disease (COVID-19) [9]. The elucidation of the infection mechanism of enveloped viruses paved
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