Anti-viral azide-containing compounds

Abstract

Methods of using azide-modified biomolecules, such as fatty acids, carbohydrates and lipids, to treat a plant or an animal infected with a virus or to inhibit infectivity of a virus, such as the human immunodeficiency virus, are provided. Also provided are methods of labeling a human immunodeficiency virus with an azide-modified biomolecule, such as a fatty acid, a carbohydrate, or an isoprenoid lipid. The azide-modified biomolecules may be combined with a pharmaceutically acceptable excipient to produce a pharmaceutical composition, optionally containing another anti-viral agent and/or a delivery agent, such as a liposome.

1 . A method of producing a human immunodeficiency virus labeled with an azide-modified fatty acid, an azide-modified carbohydrate, or an azide-modified isoprenoid lipid, the method comprising contacting a cell infected with the human immunodeficiency virus with the azide-modified fatty acid, the azide-modified carbohydrate, or the azide-modified isoprenoid lipid so that the azide-modified fatty acid, the azide-modified carbohydrate, or the azide-modified isoprenoid lipid enters the cell and is incorporated into a protein of the virus, thereby producing the labeled virus. 
     
     
         2 . The method of  claim 1 , wherein the azide-modified fatty acid is a saturated fatty acid. 
     
     
         3 . The method of  claim 1 , wherein the azide-modified fatty acid is 15-azidopentadecanoic acid. 
     
     
         4 . The method of  claim 1 , wherein the azide-modified fatty acid is 12-azidododecanoic acid. 
     
     
         5 . The method of  claim 1 , wherein the azide-modified carbohydrate is an N-linked carbohydrate or an O-linked carbohydrate. 
     
     
         6 . The method of  claim 1 , wherein the azide-modified carbohydrate is tetraacetylated N-azidoacetylgalactosamine, tetraacetylated N-azidoacetyl-D-mannosamine, or tetraacetylated N-azidoacetylglucosamine. 
     
     
         7 . The method of  claim 1 , wherein the azide-modified isoprenoid lipid comprises a farnesyl group or a geranylgeranyl group. 
     
     
         8 . The method of  claim 7 , wherein the azide-modified isoprenoid lipid is an azido farnesyl diphosphate, an azido farnesyl alcohol, an azido geranylgeranyl diphosphate, or an azido geranylgeranyl alcohol. 
     
     
         9 . The method of any one of  claims 1 - 8 , wherein the cell is a human cell.