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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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Publication details

The article was received on 25 Oct 2018, accepted on 16 Nov 2018 and first published on 16 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC08533A
Citation: Chem. Commun., 2018,54, 14089-14092
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    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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