Click to release: instantaneous doxorubicin elimination upon tetrazine ligation

Ron M. Versteegen, Raffaella Rossin, Wolter ten Hoeve, Henk M. Janssen, Marc S. Robillard (Corresponding author)

Research output: Contribution to journalArticleAcademicpeer-review

193 Citations (Scopus)
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Abstract

Eliminated without a trace: The fastest click reaction, the highly selective inverse-electron-demand Diels-Alder reaction, has been modified to enable selective bioorthogonal release. Thus, the click reaction of a tetrazine with a drug-bound trans-cyclooctene caused the instantaneous release of the drug and CO2 (see scheme). One possible application is the chemically triggered release, and thereby activation, of a drug from a tumor-bound antibody-drug conjugate.

Original languageEnglish
Pages (from-to)14112-14116
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number52
DOIs
Publication statusPublished - 23 Dec 2013

Keywords

  • cycloaddition
  • elimination
  • pyridazines
  • tetrazines
  • trans-cyclooctene

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