ArticleACS chemical biology2017
Control of an Unusual Photo-Claisen Rearrangement in Coumarin Caged Tamoxifen through an Extended Spacer.
Article in ACS chemical biology, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 52 citations in OpenAlex.
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- Development of label-free light-controlled gene expression technologies using mid-IR and terahertz light.Frontiers in bioengineering and biotechnology · 2024Review
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- Multi-Photon-Sensitive Chromophore for the Photorelease of Biologically Active Phenols.ACS chemical neuroscience · 2023Article
- The Development and Application of Opto-Chemical Tools in the Zebrafish.Molecules (Basel, Switzerland) · 2022Review
- A serotonergic axon-cilium synapse drives nuclear signaling to alter chromatin accessibility.Cell · 2022Article
- Optochemical Control of Bacterial Gene Expression: Novel Photocaged Compounds for Different Promoter Systems.Chembiochem : a European journal of chemical biology · 2022Article
- Optical control of adenosine APharmacological research · 2021Article
- Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.Chemical reviews · 2020Article
- Controlling gene expression with light: a multidisciplinary endeavour.Biochemical Society transactions · 2020Review
- Spacer-Mediated Control of Coumarin Uncaging for Photocaged Thymidine.The Journal of organic chemistry · 2020Article
- A Coumarin Triflate Reagent Enables One-Step Synthesis of Photo-Caged Lipid Metabolites for Studying Cell Signaling.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019Article
- Cyanine Photocages Enable Spatial Control of Inducible Cre-Mediated Recombination.Chembiochem : a European journal of chemical biology · 2018Article
- Illuminating cytochrome P450 binding: Ru(ii)-caged inhibitors of CYP17A1.Chemical communications (Cambridge, England) · 2017Article
Corrections and comments
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Authors and funding
9 authors at 2 institutions in 1 country.
Funding
Abstract
The use of coumarin caged molecules has been well documented in numerous photocaging applications including for the spatiotemporal control of Cre-estrogen receptor (Cre-ERT2) recombinase activity. In this article, we report that 4-hydroxytamoxifen (4OHT) caged with coumarin via a conventional ether linkage led to an unexpected photo-Claisen rearrangement which significantly competed with the release of free 4OHT. The basis for this unwanted reaction appears to be related to the coumarin structure and its radical-based mechanism of uncaging, as it did not occur in ortho-nitrobenzyl (ONB) caged 4OHT that was otherwise linked in the same manner. In an effort to perform design optimization, we introduced a self-immolative linker longer than the ether linkage and identified an optimal linker which allowed rapid 4OHT release by both single-photon and two-photon absorption mechanisms. The ability of this construct to actively control Cre-ERT2 mediated gene modifications was investigated in mouse embryonic fibroblasts (MEFs) in which the expression of a green fluorescent protein (GFP) reporter dependent gene recombination was controlled by 4OHT release and measured by confocal fluorescence microscopy and flow cytometry. In summary, we report the implications of this photo-Claisen rearrangement in coumarin caged compounds and demonstrate a rational linker strategy for addressing this unwanted side reaction.
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Registered trials
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