ArticleChemistryOpen2017
Sequential Uncaging with Green Light can be Achieved by Fine-Tuning the Structure of a Dicyanocoumarin Chromophore.
Article in ChemistryOpen, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- Toward Chromoselective Transformations in Biological Systems: Perspectives and Challenges.Angewandte Chemie (International ed. in English) · 2026Review
- Photocleavable Systems for Cell Biology: Conceptual Design across Molecular Modalities.Chembiochem : a European journal of chemical biology · 2025Review
- 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
- Highly efficient CaOrganic & biomolecular chemistry · 2024Article
- Recent Advances in Nanomedicine for Ocular Fundus Neovascularization Disease Management.Advanced healthcare materials · 2024Review
- Record release of tetramethylguanidine using a green light activated photocage for rapid synthesis of soft materials.Chemical science · 2023Article
- Light-responsive biomaterials for ocular drug delivery.Drug delivery and translational research · 2023Review
- Exploring Structure-Activity Relationships in Photodynamic Therapy Anticancer Agents Based on Ir(III)-COUPY Conjugates.Journal of medicinal chemistry · 2023Article
- Mitochondria-Targeted COUPY Photocages: Synthesis and Visible-Light Photoactivation in Living Cells.The Journal of organic chemistry · 2023Article
- COUPY Coumarins as Novel Mitochondria-Targeted Photodynamic Therapy Anticancer Agents.Journal of medicinal chemistry · 2021Article
- Thiocoumarin Caged Nucleotides: Synthetic Access and Their Photophysical Properties.Molecules (Basel, Switzerland) · 2020Article
- Green-Light-Sensitive BODIPY Photoprotecting Groups for Amines.The Journal of organic chemistry · 2018Article
- Sequential Uncaging with Green Light can be Achieved by Fine-Tuning the Structure of a Dicyanocoumarin Chromophore.ChemistryOpen · 2017Article
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Authors and funding
9 authors.
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No grant is acknowledged in the PubMed record.
Abstract
We report the synthesis and photochemical properties of a series of dicyanocoumarinylmethyl (DEAdcCM)- and dicyanocoumarinylethyl (DEAdcCE)-based photocages of carboxylic acids and amines with absorption maximum around 500 nm. Photolysis studies with green light have demonstrated that the structure of the coumarin chromophore as well as the nature of the leaving group and the type of bond to be photocleaved (ester or carbamate) have a strong influence on the rate and efficiency of the uncaging process. These experimental observations were also supported by DFT calculations. Such differences in deprotection kinetics have been exploited to sequentially photolyze two dicyanocoumarin-caged model compounds (e.g., benzoic acid and ethylamine), and open the way to increasing the number of functional levels that can be addressed with light in a single system, particularly when combining dicyanocoumarin caging groups with other photocleavable protecting groups, which remain intact under green light irradiation.
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