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A highly lipophilic sulfated tetrasaccharide glycoside related to muparfostat (PI-88) exhibits virucidal activity against herpes simplex virus.

Journal article
Authors Maria Ekblad
Beata Adamiak
Tomas Bergström
Ken D Johnstone
Tomislav Karoli
Ligong Liu
Vito Ferro
Edward Trybala
Published in Antiviral research
Volume 86
Issue 2
Pages 196-203
ISSN 1872-9096
Publication year 2010
Published at Institute of Biomedicine, Department of Infectious Medicine
Pages 196-203
Language en
Links dx.doi.org/10.1016/j.antiviral.2010...
Keywords Animals, Antiviral Agents, chemistry, pharmacology, Bodily Secretions, Cell Line, Cercopithecus aethiops, Herpesvirus 1, Human, drug effects, physiology, Herpesvirus 2, Human, drug effects, physiology, Humans, Microbial Viability, drug effects, Microscopy, Electron, Transmission, Molecular Structure, Oligosaccharides, chemistry, pharmacology, Plaque Assay
Subject categories Microbiology in the medical area, Pharmaceutical microbiology, Infectious Medicine

Abstract

Although sulfated polysaccharides potently inhibit the infectivity of herpes simplex virus (HSV) and human immunodeficiency virus in cultured cells, these compounds fail to show protective effects in humans, most likely due to their poor virucidal activity. Herein we report on sulfated oligosaccharide glycosides related to muparfostat (formerly known as PI-88) and their assessment for anti-HSV activity. Chemical modifications based on the introduction of specific hydrophobic groups at the reducing end of a sulfated oligosaccharide chain enhanced the compound's capability to inhibit the infection of cells by HSV-1 and HSV-2 and abrogated the cell-to-cell transmission of HSV-2. Furthermore, modification with a highly lipophilic cholestanyl group provided a compound with virucidal activity against HSV. This glycoside targeted the viral particle and, to a lesser degree, the cell, and exhibited an antiviral mode of action typical for sulfated polysaccharides and virucides, i.e., interference with the virus attachment to cells and irreversible inactivation of virus infectivity, respectively. The virucidal activity was decreased in the presence of human cervical secretions suggesting that higher doses of this glycoside might be needed for in vivo application. Altogether, the sulfated oligosaccharide-cholestanyl glycoside exhibits potent anti-HSV activity and is, therefore, a good candidate for development as a virucide.

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