A Concise Synthetic Approach to Highly Reactive Click‐to‐Release <i>Trans</i>‐Cyclooctene Linkers**-Reference-Cited by-同舟云学术

A Concise Synthetic Approach to Highly Reactive Click‐to‐Release Trans‐Cyclooctene Linkers**

Published:2023-07-14 Issue:45 Volume:29 Page:
ISSN:0947-6539
Container-title:Chemistry – A European Journal
language:en
Short-container-title:Chemistry A European J

Author:

Liu Bing¹,ten Hoeve Wolter²,Versteegen Ron M.³,Rossin Raffaella¹,Kleijn Laurens H. J.¹,Robillard Marc S.¹^ORCID

Affiliation:

1. Tagworks Pharmaceuticals Toernooiveld 1 6525 ED Nijmegen The Netherlands

2. Symeres Kadijk 3 9747 AT Groningen The Netherlands

3. SyMO-Chem Den Dolech 2 5612 AZ Eindhoven The Netherlands

Abstract

AbstractAn increase in the click‐to‐release reaction rate between cleavable trans‐cyclooctenes (TCO) and tetrazines would be beneficial for drug delivery applications. In this work, we have developed a short and stereoselective synthesis route towards highly reactive sTCOs that serve as cleavable linkers, affording quantitative tetrazine‐triggered payload release. In addition, the fivefold more reactive sTCO exhibited the same in vivo stability as current TCO linkers when used as antibody linkers in circulation in mice.

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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