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Chemically sulfated polysaccharides from natural sources: Assessment of extraction-sulfation efficiencies, structural features and antiviral activities
- Source :
- International journal of biological macromolecules. 136
- Publication Year :
- 2019
-
Abstract
- The provisioning of compound libraries with a high degree of diversity and attractive pharmacological properties is a limiting step in drug development. This study reports the production of highly bioactive sulfated polysaccharides, originally present in a nonsulfated, dormant state in natural sources, and demonstrates their antiviral activity (human cytomegalovirus EC 50 values of 2.34–7.77 μg/mL) at a low degree of cytotoxicity. Furthermore, data strongly suggested the inhibition of virus entry as the main mode of antiviral action. Remarkably, the utilized oleum-DMF reagent was able to generate a range of sulfated polysaccharides from various natural sources, possessing varying saccharide compositions, degrees of sulfation (0.4–1.7) and molecular masses (38–94,000 g/mol). Typically, in a matter of minutes, this reagent not only solubilized polysaccharides but also chemically converted their hydroxyl functionality into sulfates. The most active sulfated polysaccharide (EC 50 of 2.62 μg/mL) proved to be a 94,000 g/mol branched glucan with sulfates at C-6/C-3,6/C-2,3,6 positions. In conclusion, the important determinants of such compounds' antiviral activity are: (i) degree of sulfation, (ii) molecular mass and (iii) structural features. Thus, our approach offers a huge prospect for the improvement of natural source-derived libraries based on biologically active polysaccharides with diversified chemical profiles.
- Subjects :
- Glycosylation
Cytomegalovirus
02 engineering and technology
Herpesvirus 1, Human
Polysaccharide
Virus Replication
Biochemistry
Antiviral Agents
03 medical and health sciences
Structure-Activity Relationship
Sulfation
Structural Biology
Polysaccharides
Organic chemistry
Humans
Cytotoxicity
Molecular Biology
030304 developmental biology
Glucan
chemistry.chemical_classification
0303 health sciences
Biological Products
Molecular mass
Chemistry
Sulfates
Extraction (chemistry)
Biological activity
General Medicine
Plants
021001 nanoscience & nanotechnology
Molecular Weight
Reagent
0210 nano-technology
Subjects
Details
- ISSN :
- 18790003
- Volume :
- 136
- Database :
- OpenAIRE
- Journal :
- International journal of biological macromolecules
- Accession number :
- edsair.doi.dedup.....696ab3f19f0602f4d48116af352563fc