Nucleophile-triggered degradable materials and methods of making and using the same
Disclosed herein are degradable materials comprising 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. Also disclosed herein are degradable materials comprising 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. Also disclosed herein are methods of making and using the same.
1. A degradable material comprising:
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.
2. The degradable material of claim 1 ,
wherein the oxanorbornadiene crosslinker or derivative thereof is multivalent, and
wherein the multivalent nucleophile-terminated compound comprises a multivalent nucleophile-terminated monomer.
3. The degradable material of claim 1 , wherein the multivalent nucleophile-terminated compound comprises a thiol-terminated multivalent polyethylene glycol.
4. The degradable material of claim 1 , wherein the multivalent nucleophile-terminated compound has a valency of 4, 5, 6, or 8.
5. The degradable material of claim 1 , wherein the multivalent nucleophile-terminated compound comprises endgroups labeled with a probe or cargo.
6. The degradable material of claim 1 , further comprising a macromer comprising endgroups labeled with a probe or cargo.
7. The degradable material of claim 1 , further comprising an additive, wherein the additive comprises a buffer, catalytic base, or combination thereof.
8. The degradable material of claim 1 , wherein the multivalent nucleophile-terminated compound is present in a concentration of 2.5 wt % to 80 wt % of a solution including the multivalent nucleophile-terminated compound, 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 a hyperbranched crosslinked and polymeric material, an elastic hydrogel, an organogel, or a combination thereof.
11. A method for producing a degradable material, the method comprising:
combining a solution of a multivalent nucleophile-terminated compound and an oxanorbornadiene crosslinker to yield elastic solids capable of entraining cargo,
wherein the reaction between the multivalent nucleophile-terminated compound and oxanorbornadiene trigger programmed fragmentation of adducts, and
wherein the programmed fragmentation of adducts causes the material to degrade.
12. The method of claim 11 , wherein the combining takes place at a temperature from 20° C. to 40° C.
13. The method of claim 11 , wherein the combining takes place at a pH from 6 to 8.
14. The method of claim 11 , wherein the programmed fragmentation of adducts takes place at a half-life of adduct fragmentation of 30 seconds to 4 months.
15. The method of claim 14 , wherein the half-life of adduct fragmentation is from 12 hours to 1 month.
16. The method of claim 11 , wherein the multivalent nucleophile-terminated compound has a valency of 4, 5, 6, or 8.