186320-10-5Relevant academic research and scientific papers
Traceless Release of Alcohols Using Thiol-Sensitive Oxanorbornadiene Linkers
Aioub, Allison G.,Higginson, Cody J.,Finn
, p. 3233 - 3236 (2018/06/11)
A class of ester-amide oxanorbornadiene (EA-OND) molecules was developed to release alcohol cargos by succinimide formation upon addition of a thiol reagent. The resulting ring-closed adducts undergo further fragmentation by retro-Diels-Alder reaction to release a furan moiety in a manner similar to oxanorbornadiene diesters. The rates of each of these fragmentation pathways in the same medium were found to be sensitive to the steric nature of the amide substituent. Alcohol release was much faster in protic solvents than in aprotic ones, suggesting that this system may be useful for rapid response to thiols in biological environments. Accordingly, the attachment and thiol-dependent release of cholesterol was characterized as an example of the manipulation of a drug-like cargo.
NUCLEOPHILE-TRIGGERED DEGRADBLE MATERIALS AND METHODS OF MAKING AND USING THE SAME
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Paragraph 00117, (2016/06/28)
Disclosed herein are degradable materials comprising the reaction product of an oxanorbomadiene 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 oxanorbomadiene 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.
