Electrochemically degradable polymers
AssigneeTrustees of Tufts College
InventorsMarc d'Alarcao, Pericles Calias
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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.
Claims13
An electrically-degradable polymer moiety comprising
- a quinone compound of the formula:
- wherein R1, R2, R3, R4, R5, and R6 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,
- such that the polymer moiety is capable of degrading upon exposure to a change in electric potential.
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 R1, R2, R3, R4, R5, and R6 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.
A drug-impregnated polymer comprising:
- an electrically-controlled polymer comprising at least one moiety of the formula:
- wherein R1, R2, R3, R4, R5, and R6 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
- one or more pharmaceutical agents impregnated within the electrically-controlled polymer.
A drug delivery system comprising:
- an electrically-degradable polymer comprising at least one moiety of the formula:
- wherein R1, R2, R3, R4, R5, and R6 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,
- one or more pharmaceutical agents impregnated within the electrically-degradable polymer;
- and
- a current producing device electrically coupled to the impregnated polymer, wherein the polymer is capable of undergoing electrochemical reduction resulting in the hydrolysis of the cross-linkers and controlled release of one or more pharmaceutical agents.
Dependencies are inferred from the claim text.