Bioorthogonal release of sulfonamides and mutually orthogonal liberation of two drugs

Zhuzhou Shao, Wei Liu, Huimin Tao, Fang Liu, Ruxin Zeng, Pier Alexandre Champagne, Yang Cao, K. N. Houk, Yong Liang

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)14089-14092
Number of pages4
JournalChemical Communications
Volume54
Issue number100
DOIs
StatePublished - 2018
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

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