ArticleChembiochem : a European journal of chemical biology2017
A Thioacetal Photocage Designed for Dual Release: Application in the Quantitation of Therapeutic Release by Synchronous Reporter Decaging.
Article in Chembiochem : a European journal of chemical biology, 2017. 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.
- Control of Gemcitabine Activity With Blue and Red Light.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Conditional PROTAC: Recent Strategies for Modulating Targeted Protein Degradation.ChemMedChem · 2024Review
- Phototriggered structures: Latest advances in biomedical applications.Acta pharmaceutica Sinica. B · 2023Review
- Dual photo-controlled release system for fipronil and dinotefuran.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2023Article
- Development of Photoremovable Linkers as a Novel Strategy to Improve the Pharmacokinetics of Drug Conjugates and Their Potential Application in Antibody-Drug Conjugates for Cancer Therapy.Pharmaceuticals (Basel, Switzerland) · 2022Review
- Review
- Photo cleavable thioacetal block copolymers for controlled release.Polymer chemistry · 2021Article
- Spacer-Mediated Control of Coumarin Uncaging for Photocaged Thymidine.The Journal of organic chemistry · 2020Article
- One- and Two-Photon Uncaging: Carbazole Fused o-Hydroxycinnamate Platform for Dual Release of Alcohols (Same or Different) with Real-Time Monitoring.Organic letters · 2018Article
- Control of an Unusual Photo-Claisen Rearrangement in Coumarin Caged Tamoxifen through an Extended Spacer.ACS chemical biology · 2017Article
Corrections and comments
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Authors and funding
10 authors.
Funding
Abstract
Despite the immense potential of existing photocaging technology, its application is limited by the paucity of advanced caging tools. Here, we report on the design of a novel thioacetal ortho-nitrobenzaldehyde (TNB) dual arm photocage that enabled control of the simultaneous release of two payloads linked to a single TNB unit. By using this cage, which was prepared in a single step from commercial 6-nitroverataldehyde, three drug-fluorophore conjugates were synthesized: Taxol-TNB-fluorescein, Taxol-TNB-coumarin, and doxorubicin-TNB-coumarin, and long-wavelength UVA light-triggered release experiments demonstrated that dual payload release occurred with rapid decay kinetics for each conjugate. In cell-based assays performed in vitro, dual release could also be controlled by UV exposure, resulting in increased cellular fluorescence and cytotoxicity with potency equal to that of unmodified drug towards the KB carcinoma cell line. The extent of such dual release was quantifiable by reporter fluorescence measured in situ and was found to correlate with the extent of cytotoxicity. Thus, this novel dual arm cage strategy provides a valuable tool that enables both active control and real-time monitoring of drug activation at the delivery site.
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Registered trials
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