Synthetic oligomannosides, preparation and uses thereof

Abstract

A pharmaceutical composition including a therapeutically effective amount of at least one oligomannoside produced by chemical synthesis which is homologous to a wall oligomannoside of an infectious organism or pathogen, or a derivative thereof, and a pharmaceutically acceptable vehicle.

1 . A pharmaceutical composition comprising: 
 a therapeutically effective amount of at least one oligomannoside produced by chemical synthesis which is devoid of cellular components and homologous to a wall oligomannoside of an infectious organism or pathogen, and a pharmaceutically acceptable vehicle.    
   
   
       2 . The pharmaceutical composition according to  claim 1 , wherein the synthetic oligomannoside is homologous to a wall oligomannoside of a yeast, a fungus, a virus or a bacterium whose cellular envelope contains oligomannosides.  
   
   
       3 . The pharmaceutical composition according to one of claims  1  or  2 , wherein the synthetic oligomannoside is homologous to an oligomannoside of the cellular envelope of  Candida albicans  or  Saccharomyces cerevisiae.    
   
   
       4 . The pharmaceutical composition according to  claim 1 , wherein at least one functional group of the synthetic oligomannoside is substituted by a marker group or a connector group.  
   
   
       5 . The pharmaceutical composition according to  claim 1 , wherein the synthetic oligomannoside corresponds to the following general formula:  
       (Manα(1-3)) p (Manα(1-2)) q (Manβ(1-2)) r (α or β)Man-OR  
     in which: 
 R represents a hydrogen atom, a C 1  to C 20  alkyl, or a connector group, optionally labeled, or by a substance capable of making the synthetic oligomannosides immunogenic,  
 p, q and r are whole numbers between 0 and 19, and the sum p+q+r is between 1 and 19,  
 the three parts of (Manα(1-3))p(Manα(1-2))q(Manβ(1-2))r can be inverted or repeated.  
 
   
   
       6 . The pharmaceutical composition according to  claim 1 , wherein the synthetic oligomannoside corresponds to formula (I):  
     
       
         
         
             
             
         
       
     
     wherein R represents a hydrogen atom, a C 1  to C 20  alkyl, or an optionally labeled connector group, or by a substance capable of making the synthetic oligomannosides immunogenic, or a derivative thereof in which one or more of the hydroxyl groups are substituted.  
   
   
       7 . The pharmaceutical composition according to  claim 1 , wherein the synthetic oligomannoside corresponds to formula (II):  
     
       
         
         
             
             
         
       
     
     wherein R represents a hydrogen atom, a C 1  to C 20  alkyl, an optionally labeled connector group, or by a substance capable of making the synthetic oligomannosides immunogenic, or a derivative thereof in which one or more of the hydroxyl groups are substituted.  
   
   
       8 . The pharmaceutical composition according to  claim 1 , wherein the synthetic oligomannoside corresponds to formula (III):  
     
       
         
         
             
             
         
       
     
     wherein R represents a hydrogen atom, a C 1  to C 20  alkyl, an optionally labeled connector group, or by a substance capable of making the synthetic oligomannosides immunogenic, or a derivative thereof in which one or more of the hydroxyl groups are substituted.  
   
   
       9 . The pharmaceutical composition according to  claim 4 , wherein the connector is a chemical group enabling coupling of a synthetic oligomannoside on a support.  
   
   
       10 . The pharmaceutical composition according to  claim 9 , wherein the connector comprises a carboxylic acid functional group which can be activated for coupling onto a surface which is itself activated.  
   
   
       11 . The pharmaceutical composition according to  claim 1 , wherein the synthetic oligomannoside is conjugated with a substance capable of making the sugars immunogenic.  
   
   
       12 . The pharmaceutical composition according to  claim 1 , which inhibits colonization by infectious agents or pathogens whose membranes contain oligomannosides.  
   
   
       13 . The pharmaceutical composition according to  claim 9 , wherein the chemical group enables covalent coupling.  
   
   
       14 - 25 . (canceled)  
   
   
       26 . A kit comprising at least a composition comprising at least one oligomannoside according to  claim 1 , affixed on a solid support, means for detecting formation of antigen-antibody complexes and, optionally, control reagents.  
   
   
       27 . A method for prevention and treatment of candidiasis comprising: administering synthetic oligosaccharides produced by chemical synthesis, the synthetic oligomannoside being devoid of cellular components and homologous to a wall oligomannoside of an infectious organism or pathogen, and a pharmaceutically acceptable vehicle.  
   
   
       28 . The method according to  claim 27 , wherein the synthetic oligomannoside is homologous to a wall oligomannoside of a yeast, a fungus, a virus or a bacterium whose cellular envelope contains oligomannosides.  
   
   
       29 . The method according to one of claims  27  or  28 , wherein the synthetic oligomannoside is homologous to an oligomannoside of the cellular envelope of  Candida albicans  or  Saccharomyces cerevisiae.    
   
   
       30 . The method according to  claim 27 , wherein the synthetic oligomannoside corresponds to the following general formula:  
       (Manα(1-3)) p (Manα(1-2)) q (Manβ(1-2)) r (α or β)Man-OR  
     in which: 
 R represents a hydrogen atom, a C 1  to C 20  alkyl, a connector comprising a carboxylic acid functional group or a C 1  to C 20  alkyl, or tetanus anatoxin,  
 p, q and r are whole numbers between 0 and 19 and the sum p+q+r is between 1 and 19, wherein at least one of the whole numbers p, q and r is 1 or greater, and wherein the three parts of (Manα(1-3))p(Manα(1-2))q(Manβ(1-2))r can be inverted or repeated.  
 
   
   
       31 . The method according to  claim 27 , wherein the synthetic oligomannoside corresponds to formula (I):  
     
       
         
         
             
             
         
       
     
     wherein R represents a hydrogen atom, a C 1  to C 20  alkyl, an optionally labeled connector group comprising a carboxylic acid functional group or a C 1  to C 20  alkyl, or tetanus anatoxin.  
   
   
       32 . The method according to  claim 27 , wherein the synthetic oligomannoside corresponds to formula (II):  
     
       
         
         
             
             
         
       
     
     wherein R represents a hydrogen atom, a C 1  to C 20  alkyl, or an optionally labeled connector group comprising a carboxylic acid functional group or a C 1  to C 20  alkyl, or tetanus anatoxin.  
   
   
       33 . The method according to  claim 27 , wherein the synthetic oligomannoside corresponds to formula (III):  
     
       
         
         
             
             
         
       
     
     wherein R represents a hydrogen atom, a C 1  to C 20  alkyl, an optionally labeled connector group comprising a carboxylic acid functional group or a C 1  to C 20  alkyl, or tetanus anatoxin.  
   
   
       34 . The method according to  claim 27 , wherein the connector is a chemical group enabling coupling of a synthetic oligomannoside on a support.