Amphiphilic cyclodextrin-based glycodendrimers

Abstract

The present application provides an amphiphilic cyclodextrin-based compound of the formula I: R-G-D-A (I) wherein R is one or more hydrophilic groups; G is one or more linkers; D is a cyclodextrin, and A is one or more aliphatic groups. In cer-tain embodiments, the hydrophilic group is a sugar such as lactose, the linker comprises —(CHR′CH20)n- where R′ is H or is an alkyl group substituted with —(CHR′CH20)n- where n is 1 to 20, typically n=4; the cyclodextrin is a B-cyclodextrin comprising 7 subunits, and the aliphatic groups are C6 alkyl groups. The compound can be used to enhance water solu-bility, bioavailability, cellular uptakes of active ingredients used in medicines, cosmetics and foods and other products, for detection, removal and immobilization of pathogenic organisms, toxins, and autoantibodies, and bio-markers on solid matrix, or for molecular biological techniques, such as ELISA, for example.

1 . A method of treating bacterial infections by administering an amphiphilic cyclodextrin-based compound of the formula II: 
       
         
           
           
               
               
           
         
         wherein 
         R is a hydrophilic group; 
         G is a linker, wherein G comprises a polyethylene glycol —(CHR′CH 2 O) n — where R′ is H or CH 3  and n is 1 to 20, or G is an alkyl group substituted with (CHR′CH 2 O) n — where R′ is H or CH 3  and n is 1 to 20; 
         each A is an aliphatic group; and 
         p is 6 to 8. 
       
     
     
         2 . The method of  claim 1 , wherein G further comprises a functional group 
     
     
         3 . The method of  claim 2 , wherein the functional group is 1,2,3-triazole. 
     
     
         4 . The method of  claim 1 , wherein G comprises an amide group. 
     
     
         5 . The method of  claim 1 , wherein n is 4. 
     
     
         6 . The method of  claim 1 , wherein p is 7. 
     
     
         7 . The method of  claim 1 , wherein the aliphatic group is a C 3  to C 18  alkyl group. 
     
     
         8 . The method of  claim 7  wherein the aliphatic group is a C 6  alkyl group.