Click to release: instantaneous doxorubicin elimination upon tetrazine ligation

Ron M. Versteegen; Raffaella Rossin; Wolter ten Hoeve; Henk M. Janssen; Marc S. Robillard

doi:10.1002/anie.201305969

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)

Macromolecular and Organic Chemistry

Research output: Contribution to journal › Article › Academic › peer-review

344 Citations (Scopus)

4 Downloads (Pure)

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 language	English
Pages (from-to)	14112-14116
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	52
DOIs	https://doi.org/10.1002/anie.201305969
Publication status	Published - 23 Dec 2013

Keywords

cycloaddition
elimination
pyridazines
tetrazines
trans-cyclooctene

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AU - Versteegen, Ron M.

AU - Rossin, Raffaella

AU - ten Hoeve, Wolter

AU - Janssen, Henk M.

AU - Robillard, Marc S.

PY - 2013/12/23

Y1 - 2013/12/23

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AB - 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.

KW - cycloaddition

KW - elimination

KW - pyridazines

KW - tetrazines

KW - trans-cyclooctene

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 52

ER -

Click to release: instantaneous doxorubicin elimination upon tetrazine ligation

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Keywords

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