Electrochemically degradable polymers

Abstract

The present invention discloses polymeric materials that incorporate a modified quinone moiety, either to cross-link the polymer or as a monomeric unit of the polymer These polymeric materials can be efficiently degraded through electrochemical reduction of the quinone leading to rapid hydrolysis of the pendant chemical groups and degradation of the polymer. Quinone-containing compositions and methods of producing electrochemically degradable polymers are disclosed. The methods and compositions of the present invention can be used in a wide variety of applications, including, but not limited to, drug delivery, tissue regeneration, biomedical implants, and electronic systems.

1 - 3 . (canceled) 
     
     
         4 . A method of controlled release of pharmaceutical agents within a subject comprising:
 implanting an electrically-controlled polymer comprising at least one moiety of the formula:   
       
         
           
           
               
               
           
         
         wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  are selected from the group comprising hydrogen, alkyl, aryl, alcohol, ether, thiol, thioether, amine, cyano, halo, nitro, ketone, aldehyde, ester, amide, thioester, carbonate, carbamate, and urea, 
         X and Y can be the same or different and are selected from the group comprising vinyl sulfone, epoxide, alkyl halide, alkene, amine, alcohol, acid halide, acid anhydride, sulfate, phosphate, isocyanate, isothiocyanate, and thiol alkyl groups, wherein at least one of X and Y is capable of degradation upon reduction of the quinone; and 
         electrically inducing chemical degradation of the polymer thereby releasing pharmaceutical agents. 
       
     
     
         5 . The method of  claim 4 , wherein the polymer further comprises at least one monomer selected from the group comprising styrene, acrylates, methacrylates, 1,3-butadiene, isoprene, 2-vinylpyridine, ethylene oxide, acrylonitrile, methyl vinyl ketone, alpha-cyanoacrylate vinylidene cyanide, propylene, butene, isobutylene, phosphorus acid, phosphonous acid, phosphinous acid, phosphoric acid, phosphonic acid, phosphinic acid, methylene bis (phosphonic acid), poly(vinylphosponic acid), aziridine, spermine, cadaverine, and putrecine. 
     
     
         6 . The method of  claim 4 , wherein the step of electrically inducing chemical degradation further includes applying voltage of at least 0.05 V. 
     
     
         7 . The method of  claim 4 , wherein the step of electrically inducing chemical degradation further includes utilizing a current producing device that is controlled by the subject. 
     
     
         8 . The method of  claim 4 , wherein the step of electrically inducing chemical degradation further includes a step of sensing at least one internal parameter within the subject. 
     
     
         9 . The method of  claim 4 , wherein the step of electrically inducing chemical degradation further includes a step of sensing at least one external parameter. 
     
     
         10 - 13 . (canceled)