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Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs.


ABSTRACT: Sulfonamide derivatives have been used in pharmaceutics for decades. Here we report a new approach to release sulfonamides efficiently using a bioorthogonal reaction of sulfonyl sydnonimines and dibenzoazacyclooctyne (DIBAC). The second-order rate constant of the cycloaddition reaction can be up to 0.62 M-1 s-1, and the reactants are highly stable under physiological conditions. Most significantly, we also discovered the mutual orthogonality between the sydnonimine-DIBAC and benzonorbornadiene-tetrazine cycloaddition pairs, which can be used for selective and simultaneous liberation of sulfonamide and primary amine drugs.

SUBMITTER: Shao Z 

PROVIDER: S-EPMC6314811 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs.

Shao Zhuzhou Z   Liu Wei W   Tao Huimin H   Liu Fang F   Zeng Ruxin R   Champagne Pier Alexandre PA   Cao Yang Y   Houk K N KN   Liang Yong Y  

Chemical communications (Cambridge, England) 20181201 100


Sulfonamide derivatives have been used in pharmaceutics for decades. Here we report a new approach to release sulfonamides efficiently using a bioorthogonal reaction of sulfonyl sydnonimines and dibenzoazacyclooctyne (DIBAC). The second-order rate constant of the cycloaddition reaction can be up to 0.62 M-1 s-1, and the reactants are highly stable under physiological conditions. Most significantly, we also discovered the mutual orthogonality between the sydnonimine-DIBAC and benzonorbornadiene-t  ...[more]

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