ArticleJournal of the American Chemical Society2022
Strategy for Engineering High Photolysis Efficiency of Photocleavable Protecting Groups through Cation Stabilization.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed, 79 citations in OpenAlex.
- Spin Manipulation Effect in Photodeprotection Reaction Using Triplet Ground-State Cation.Journal of the American Chemical Society · 2026Article
- Image-guided activation of drugs with electromagnetic radiation.Nature chemical biology · 2026Review
- BODIPY Photocage-Based Injectable Hydrogel for Light-Controlled Nanoparticle Release.Small (Weinheim an der Bergstrasse, Germany) · 2026Article
- Optimized Xanthenium Photocages with Fused Ring Systems for Photoactivated Chemotherapy and G Protein-Coupled Receptor Photopharmacology.Journal of the American Chemical Society · 2026Article
- Wash-Free Multi-Target Super-Resolution Microscopy With Photocaged DNA Labels.Angewandte Chemie (International ed. in English) · 2026Article
- Coumarin-Based Prodrugs: Therapeutic Promise or Still Confined to Preclinical Exploration?Pharmaceutics · 2026Review
- Development of silicon-fluorescein-based photolabile protecting groups with enhanced uncaging quantum yield.RSC advances · 2026Article
- Engineering the Photophysics of Cyanines by Chain C1' Substituents.The Journal of organic chemistry · 2025Article
- Photocleavable Systems for Cell Biology: Conceptual Design across Molecular Modalities.Chembiochem : a European journal of chemical biology · 2025Review
- Mechanism Inversion in Visible Light-Induced Photoclick Reactions.Journal of the American Chemical Society · 2025Article
- Engineering Photolabile Cyclopentane-Fused Coumarins: From One-Pot Synthesis to Mechanistic Study for Visible Light-Triggered Photolysis.Chemistry, an Asian journal · 2025Article
- Breaking Bonds with Short-Wave Infrared Light: BODIPY Photocages for Two-Photon Activation in the 900-1500 nm NIR-II Window.Journal of the American Chemical Society · 2025Article
- Green-Light-Activatable Penicillin for Light-Dependent Spatial Control of Bacterial Growth, Biofilm Formation, andACS central science · 2025Article
- Remote Silyl Groups Enhance Hydrolytic Stability and Photocleavage Efficiency in Carbamates for Protein Release.Angewandte Chemie (International ed. in English) · 2025Article
- New Visible-Light-Sensitive Dicyanocoumarin- and COUPY-Based Caging Groups with Improved Photolytic Efficiency.Molecules (Basel, Switzerland) · 2025Article
- Exploring the Phototherapeutic Applications of Mitochondria-Targeted COUPY Photocages of Antitumor Drugs.Journal of medicinal chemistry · 2025Article
- A hydrophobic photouncaging reaction to profile the lipid droplet interactome in tissues.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Design, Synthesis, and Biological Evaluation of BODIPY-Caged Resiquimod as a Dual-Acting Phototherapeutic.Journal of medicinal chemistry · 2025Article
- Surfing the limits of cyanine photocages one step at a time.Chemical science · 2025Article
- Synthesis of Caged HMG-CoA Reductase Substrates for the Elucidation of Cellular Pathways.The Journal of organic chemistry · 2024Article
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Photolabile protecting groups (PPGs) enable the precise activation of molecular function with light in many research areas, such as photopharmacology, where remote spatiotemporal control over the release of a molecule is needed. The design and application of PPGs in recent years have particularly focused on the development of molecules with high molar absorptivity at long irradiation wavelengths. However, a crucial parameter, which is pivotal to the efficiency of uncaging and which has until now proven highly challenging to improve, is the photolysis quantum yield (QY). Here, we describe a novel and general approach to greatly increase the photolysis QY of heterolytic PPGs through stabilization of an intermediate chromophore cation. When applied to coumarin PPGs, our strategy resulted in systems possessing an up to a 35-fold increase in QY and a convenient fluorescent readout during their uncaging, all while requiring the same number of synthetic steps for their preparation as the usual coumarin systems. We demonstrate that the same QY engineering strategy applies to different photolysis payloads and even different classes of PPGs. Furthermore, analysis of the DFT-calculated energy barriers in the first singlet excited state reveals valuable insights into the important factors that determine photolysis efficiency. The strategy reported herein will enable the development of efficient PPGs tailored for many applications.
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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.