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Hexagonal-shaped chondroitin sulfate self-assemblies have exalted anti-HSV-2 activity.

Abstract
The initial step in mucosal infection by the herpes simplex virus type 2 (HSV-2) requires its binding to certain glycosaminoglycans naturally present on host cell membranes. We took advantage of this interaction to design biomimetic supramolecular hexagonal-shaped nanoassemblies composed of chondroitin sulfate having exalted anti-HSV-2 activity in comparison with native chondroitin sulfate. Nanoassemblies were formed by mixing hydrophobically-modified chondroitin sulfate with α-cyclodextrin in water. Optimization of alkyl chain length grafted on chondroitin sulfate and the ratio between hydrophobically-modified chondroitin sulfate and α-cyclodextrin showed that more cohesive and well-structured nanoassemblies were obtained using higher α-cyclodextrin concentration and longer alkyl chain lengths. A structure-activity relationship was found between anti-HSV-2 activity and the amphiphilic nature of hydrophobically-modified chondroitin sulfate. Also, antiviral activity of hexagonal nanoassemblies against HSV-2 was further improved in comparison with hydrophobically-modified chondroitin sulfate. This work suggests a new biomimetic formulation approach that can be extended to other heparan-sulfate-dependent viruses.
AuthorsAurélia Galus, Jean-Maurice Mallet, David Lembo, Valeria Cagno, Madeleine Djabourov, Hugues Lortat-Jacob, Kawthar Bouchemal
JournalCarbohydrate polymers (Carbohydr Polym) Vol. 136 Pg. 113-20 (Jan 20 2016) ISSN: 1879-1344 [Electronic] England
PMID26572336 (Publication Type: Journal Article)
CopyrightCopyright © 2015 Elsevier Ltd. All rights reserved.
Chemical References
  • Amines
  • Antiviral Agents
  • alpha-Cyclodextrins
  • Water
  • Chondroitin Sulfates
  • stearylamine
Topics
  • Amines (chemistry)
  • Antiviral Agents (chemistry, pharmacology)
  • Carbohydrate Conformation
  • Chemistry, Pharmaceutical
  • Chondroitin Sulfates (chemistry, pharmacology)
  • Herpesvirus 2, Human (drug effects)
  • Hydrophobic and Hydrophilic Interactions
  • Models, Molecular
  • Structure-Activity Relationship
  • Water (chemistry)
  • alpha-Cyclodextrins (chemistry)

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