ArticleChembiochem : a European journal of chemical biology2022
Tetrazine-Triggered Bioorthogonal Cleavage of trans-Cyclooctene-Caged Phenols Using a Minimal Self-Immolative Linker Strategy.
Article in Chembiochem : a European journal of chemical biology, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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The trial behind it
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Who cites it
9 citing papers in PubMed, 10 citations in OpenAlex.
- Organelle-Resolved Tetrazine-trans-Cyclooctene Click Chemistry for Cargo Delivery and Release.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Programmable nanomedicine via bioorthogonal molecular engineering.Nano convergence · 2026Review
- Biomaterial-Assisted Strategies in Corneal Endothelial Cell Therapy: Toward a Platform-Based Approach.Pharmaceutics · 2026Review
- Iontronic click-to-release enables electrically controlled delivery of drugs and biomolecules beyond charge and size limitations.Nature communications · 2026Article
- Investigation of Proteome-Tetrazine Reactivity for a Highly Selective Tetrazine Ligation in Live Cells.ACS central science · 2025Article
- Click-Triggered Bioorthogonal Bond-Cleavage Reactions.Topics in current chemistry (Cham) · 2025Review
- Scission-Enhanced Molecular Imaging (SEMI).Bioconjugate chemistry · 2024Article
- Oxidative Desymmetrization Enables the Concise Synthesis of a trans-Cyclooctene Linker for Bioorthogonal Bond Cleavage.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Tetrazine-Triggered Bioorthogonal Cleavage of trans-Cyclooctene-Caged Phenols Using a Minimal Self-Immolative Linker Strategy.Chembiochem : a European journal of chemical biology · 2022Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
Bond-cleavage reactions triggered by bioorthogonal tetrazine ligation have emerged as strategies to chemically control the function of (bio)molecules and achieve activation of prodrugs in living systems. While most of these approaches make use of caged amines, current methods for the release of phenols are limited by unfavorable reaction kinetics or insufficient stability of the Tz-responsive reactants. To address this issue, we have implemented a self-immolative linker that enables the connection of cleavable trans-cyclooctenes (TCO) and phenols via carbamate linkages. Based on detailed investigation of the reaction mechanism with several Tz, revealing up to 96 % elimination after 2 hours, we have developed a TCO-caged prodrug with 750-fold reduced cytotoxicity compared to the parent drug and achieved in situ activation upon Tz/TCO click-to-release.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.