ArticleThe Journal of organic chemistry2023
Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells.
Article in The Journal of organic chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 20 citations in OpenAlex.
- Toward Chromoselective Transformations in Biological Systems: Perspectives and Challenges.Angewandte Chemie (International ed. in English) · 2026Review
- Fluorescent TAPY-bodipy dyads as tools for imaging fungal mitochondria by confocal microscopy and flow cytometry.Analytical and bioanalytical chemistry · 2026Article
- Crystal structure of 2-oxo-2Acta crystallographica. Section E, Crystallographic communications · 2026Article
- Visible-light-triggered BMP-2 release from enzymatically crosslinked marine collagen-alginate hydrogel blends enhances osteogenesis in dental pulp stem cells.Frontiers in physiology · 2026Article
- Photocleavable Systems for Cell Biology: Conceptual Design across Molecular Modalities.Chembiochem : a European journal of chemical biology · 2025Review
- On the Photosensitizing Properties of Aloe-Emodin in Photodynamic Therapy: Insights from the Molecular Modeling.The journal of physical chemistry. B · 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
- Construction of a coumarin-based fluorescent probe for accurately visualizing hydrogen sulfide in live cells and zebrafish.RSC advances · 2024Article
- Exploring Structural-Photophysical Property Relationships in Mitochondria-Targeted Deep-Red/NIR-Emitting Coumarins.International journal of molecular sciences · 2023Article
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Releasing bioactive molecules in specific subcellular locations from the corresponding caged precursors offers great potential in photopharmacology, especially when using biologically compatible visible light. By taking advantage of the intrinsic preference of COUPY coumarins for mitochondria and their long wavelength absorption in the visible region, we have synthesized and fully characterized a series of COUPY-caged model compounds to investigate how the structure of the coumarin caging group affects the rate and efficiency of the photolysis process. Uncaging studies using yellow (560 nm) and red light (620 nm) in phosphate-buffered saline medium have demonstrated that the incorporation of a methyl group in a position adjacent to the photocleavable bond is particularly important to fine-tune the photochemical properties of the caging group. Additionally, the use of a COUPY-caged version of the protonophore 2,4-dinitrophenol allowed us to confirm by confocal microscopy that photoactivation can occur within mitochondria of living HeLa cells upon irradiation with low doses of yellow light. The new photolabile protecting groups presented here complement the photochemical toolbox in therapeutic applications since they will facilitate the delivery of photocages of biologically active compounds into mitochondria.
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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.