Comparison of the interaction of the anti-viral chemotherapeutic agents amantadine and tromantadine with model phospholipid membranes |
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Authors: | James J. Cheetham Richard M. Epand |
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Affiliation: | (1) Department of Biochemistry, McMaster University, Health Sciences Centre, 1200 Main Street West, L8N 3Z5 Hamilton, Ontario, Canada |
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Abstract: | Amantadine and tromantadine are agents used against influenza and herpes infections, respectively. Tromantadine raises the bilayer to hexagonal phase transition temperature of synthetic phosphatidylethanolamines and is less disruptive to phospholipid packing. Tromantadine acts similar to cyclosporin A, previously demonstrated to inhibit viral-induced cell-cell fusion. We suggest the balance between the hydrophobic and hydrophilic group sizes would allow tromantadine to prevent membrane fusion more than amantadine and thus inhibit infection by viruses such as Herpes, which fuse with the plasma membrane. Study of agents which stabilize the bilayer phase of membranes may lead to efficacious inhibitors of viral infections requiring cell fusion events.Abbreviations DEPE dielaidoyl phosphatidylethanolamine - POPE 1-palmitoyl-2-oleoyl phosphatidylethanolamine - DMPC dimyristoyl phosphatidylcholine - DSC differential scanning calorimetry - PIPES piperazine-N,N-bis(2-ethanesulphonic acid) - NMR nuclear magnetic resonance - tromantadine N-1-adamantyl-N-[2-(dimethylamino)ethoxy]a(ethoxy]acetamide-hydrochloride - amantadine (1-adamantamine)-hydrochloride - HSV Herpes Simplex Virus |
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Keywords: | amantadine tromantadine virus chemotherapy phospholipid phase transition bilayerhexagonal change |
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