Nucleophile-Triggered Degradable Materials and Methods of Making and Using the Same

Abstract

Degradable materials including the reaction product of an oxanorbornadiene crosslinker or derivative thereof and a multivalent nucleophile-terminated compound, wherein the reaction product is a degradable elastic solid capable of entraining cargo. Degradable materials include a polymeric and hyperbranched crosslinked material made with oxanorbornadiene linkage that can be activated for cleavage at a predetermined rate by addition of a nucleophile. Methods of making and using degradable materials are included.

What is claimed is: 
     
         1 . A degradable material comprising:
 the reaction product of:
 an oxanorbornadiene compound or derivative thereof; and 
 a multivalent nucleophile-containing compound; 
   wherein the reaction product is a degradable elastic solid capable of entraining cargo.   
     
     
         2 . The degradable material of  claim 1 , wherein the oxanorbornadiene compound or derivative thereof is divalent or multivalent; and
 wherein the multivalent nucleophile-containing compound comprises a multivalent nucleophile-containing monomer.   
     
     
         3 . The degradable material of  claim 1 , wherein the multivalent nucleophile-containing compound comprises a thiol-containing multivalent polyethylene glycol. 
     
     
         4 . The degradable material of  claim 1 , wherein the multivalent nucleophile-containing compound has a valency of 4, 5, 6, or 8. 
     
     
         5 . The degradable material of  claim 1 , wherein the multivalent nucleophile-containing compound comprises groups labeled with a probe or cargo. 
     
     
         6 . The degradable material of  claim 1  further comprising a macromer comprising groups labeled with a probe or cargo. 
     
     
         7 . The degradable material of  claim 1  further comprising an additive selected from the group consisting of a buffer, a catalytic base, and a combination thereof. 
     
     
         8 . The degradable material of  claim 1 , wherein the multivalent nucleophile-containing compound is present in a concentration of from 2.5 wt % to 80 wt % of a solution including the multivalent nucleophile-containing compound; and
 wherein the solution becomes a gel.   
     
     
         9 . The degradable material of  claim 1 , wherein the reaction product is post-functionalized with a second oxanorbornadiene crosslinker or derivative thereof. 
     
     
         10 . The degradable material of  claim 1 , wherein the degradable material is selected from the group consisting of a hyperbranched crosslinked and polymeric material, an elastic hydrogel, an organogel, and a combination thereof. 
     
     
         11 . The degradable material of  claim 1 , wherein the oxanorbornadiene compound or derivative thereof includes at least one C═C double bond with one or two electron-withdrawing substituents at that double bond. 
     
     
         12 . A method for producing a degradable material comprising:
 combining a solution of a multivalent nucleophile-containing compound and an oxanorbornadiene compound or derivative thereof to yield elastic solids capable of entraining cargo; and   triggering programmed fragmentation of adducts.   
     
     
         13 . The method of  claim 12 , wherein the reaction between the multivalent nucleophile-containing compound and the oxanorbornadiene compound or derivative thereof trigger the programmed fragmentation of adducts. 
     
     
         14 . The method of  claim 13 , wherein the programmed fragmentation of adducts causes the material to degrade. 
     
     
         15 . The method of  claim 14 , wherein combining takes place at a temperature from 20° C. to 40° C. 
     
     
         16 . The method of  claim 14 , wherein the combining takes place at a pH from 6 to 8. 
     
     
         17 . The method of  claim 14 , wherein the programmed fragmentation of adducts takes place at a half-life of adduct fragmentation of from 30 seconds to four months. 
     
     
         18 . The method of  claim 14 , wherein the programmed fragmentation of adducts takes place at a half-life of adduct fragmentation of from 10 hours to one month. 
     
     
         19 . The method of  claim 14 , wherein the multivalent nucleophile-containing compound has a valency of 4, 5, 6, or 8. 
     
     
         20 . The method of  claim 14 , wherein the oxanorbornadiene compound or derivative thereof includes at least one C═C double bond with one or two electron-withdrawing substituents at that double bond.