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

193 Citations (Scopus)

1 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

Access to Document

10.1002/anie.201305969

Cite this

@article{6670debe073e4eea92d207773d97967c,

title = "Click to release: instantaneous doxorubicin elimination upon tetrazine ligation",

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.",

keywords = "cycloaddition, elimination, pyridazines, tetrazines, trans-cyclooctene",

author = "Versteegen, {Ron M.} and Raffaella Rossin and {ten Hoeve}, Wolter and Janssen, {Henk M.} and Robillard, {Marc S.}",

year = "2013",

month = dec,

day = "23",

doi = "10.1002/anie.201305969",

language = "English",

volume = "52",

pages = "14112--14116",

journal = "Angewandte Chemie - International Edition",

issn = "0570-0833",

publisher = "Wiley",

number = "52",

}

Click to release : instantaneous doxorubicin elimination upon tetrazine ligation. / Versteegen, Ron M.; Rossin, Raffaella; ten Hoeve, Wolter; Janssen, Henk M.; Robillard, Marc S. (Corresponding author).

In: Angewandte Chemie - International Edition, Vol. 52, No. 52, 23.12.2013, p. 14112-14116.

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

TY - JOUR

T1 - Click to release

T2 - instantaneous doxorubicin elimination upon tetrazine ligation

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

N2 - 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.

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

UR - http://www.scopus.com/inward/record.url?scp=84890704870&partnerID=8YFLogxK

U2 - 10.1002/anie.201305969

DO - 10.1002/anie.201305969

M3 - Article

C2 - 24281986

AN - SCOPUS:84890704870

VL - 52

SP - 14112

EP - 14116

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 0570-0833

IS - 52

ER -

Click to release: instantaneous doxorubicin elimination upon tetrazine ligation

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this