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Issue 100, 2018
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Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs

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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.

Graphical abstract: Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs

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Supplementary files

Article information


Submitted
25 Oct 2018
Accepted
16 Nov 2018
First published
16 Nov 2018

Chem. Commun., 2018,54, 14089-14092
Article type
Communication

Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs

Z. Shao, W. Liu, H. Tao, F. Liu, R. Zeng, P. A. Champagne, Y. Cao, K. N. Houk and Y. Liang, Chem. Commun., 2018, 54, 14089
DOI: 10.1039/C8CC08533A

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