Synthesis and Photochemical Properties of Fluorescent Metabolites Generated from Fluorinated Benzoylmenadiones in Living Cells Article Swipe
Nathan Trometer
,
B. Cichocki
,
Quentin Chevalier
,
Jéremy Pecourneau
,
Jean‐Marc Strub
,
Andréa Hemmerlin
,
Alexandre Specht
,
Elisabeth Davioud‐Charvet
,
Mourad Elhabiri
·
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1021/acs.joc.3c00620
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1021/acs.joc.3c00620
This work describes the reactivity and properties of fluorinated derivatives (F-PD and F-PDO) of plasmodione (PD) and its metabolite, the plasmodione oxide (PDO). Introduction of a fluorine atom on the 2-methyl group markedly alters the redox properties of the 1,4-naphthoquinone electrophore, making the compound highly oxidizing and particularly photoreactive. A fruitful set of analytical methods (electrochemistry, absorption and emission spectrophotometry, and HRMS-ESI) have been used to highlight the products resulting from UV photoirradiation in the absence or presence of selected nucleophiles. With F-PDO and in the absence of nucleophile, photoreduction generates a highly reactive ortho-quinone methide (o-QM) capable of leading to the formation of a homodimer. In the presence of thiol nucleophiles such as β-mercaptoethanol, which was used as a model, o-QMs are continuously regenerated in sequential photoredox reactions generating mono- or disulfanylation products as well as various unreported sulfanyl products. Besides, these photoreduced adducts derived from F-PDO are characterized by a bright yellowish emission due to an excited-state intramolecular proton transfer (ESIPT) process between the dihydronapthoquinone and benzoyl units. In order to evidence the possibility of an intramolecular coupling of the o-QM intermediate, a synthetic route to the corresponding anthrones is described. Tautomerization of the targeted anthrones occurs and affords highly fluorescent stable hydroxyl-anthraquinones. Although probable to explain the intense visible fluorescence emission also observed in tobacco BY-2 cells used as a cellular model, these coupling products have never been observed during the photochemical reactions performed in this study. Our data suggest that the observed ESIPT-induced fluorescence most likely corresponds to the generation of alkylated products through reduction species, as demonstrated with the β-mercaptoethanol model. In conclusion, F-PDO thus acts as a novel (pro)-fluorescent probe for monitoring redox processes and protein alkylation in living cells.
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/acs.joc.3c00620
- OA Status
- green
- Cited By
- 7
- References
- 75
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4379113841
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4379113841Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1021/acs.joc.3c00620Digital Object Identifier
- Title
-
Synthesis and Photochemical Properties of Fluorescent Metabolites Generated from Fluorinated Benzoylmenadiones in Living CellsWork title
- Type
-
articleOpenAlex work type
- Language
-
enPrimary language
- Publication year
-
2023Year of publication
- Publication date
-
2023-06-02Full publication date if available
- Authors
-
Nathan Trometer, B. Cichocki, Quentin Chevalier, Jéremy Pecourneau, Jean‐Marc Strub, Andréa Hemmerlin, Alexandre Specht, Elisabeth Davioud‐Charvet, Mourad ElhabiriList of authors in order
- Landing page
-
https://doi.org/10.1021/acs.joc.3c00620Publisher landing page
- Open access
-
YesWhether a free full text is available
- OA status
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greenOpen access status per OpenAlex
- OA URL
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https://hal.science/hal-04157610/documentDirect OA link when available
- Concepts
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Chemistry, Nucleophile, Photochemistry, Intramolecular force, Fluorescence, Tautomer, Fluorophore, Adduct, Quinone, Reactivity (psychology), Quinone methide, Moiety, Electrophile, Redox, Stereochemistry, Organic chemistry, Alternative medicine, Medicine, Pathology, Quantum mechanics, Physics, CatalysisTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
7Total citation count in OpenAlex
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2025: 2, 2024: 4, 2023: 1Per-year citation counts (last 5 years)
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75Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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| referenced_works | https://openalex.org/W2112229424, https://openalex.org/W2078705645, https://openalex.org/W2128711500, https://openalex.org/W2021139704, https://openalex.org/W2952954468, https://openalex.org/W1508250552, https://openalex.org/W2135136746, https://openalex.org/W2118117491, https://openalex.org/W1536811093, https://openalex.org/W2080075217, https://openalex.org/W2997818589, https://openalex.org/W1966590073, https://openalex.org/W2075723481, https://openalex.org/W2086029617, https://openalex.org/W1973826676, https://openalex.org/W2130484163, https://openalex.org/W2000159731, https://openalex.org/W1943516400, https://openalex.org/W1998259224, https://openalex.org/W2072262035, https://openalex.org/W2039197709, https://openalex.org/W3156143231, https://openalex.org/W2171384023, https://openalex.org/W3193433704, https://openalex.org/W1986616668, https://openalex.org/W2009650616, https://openalex.org/W2461154291, https://openalex.org/W2990149054, https://openalex.org/W2949377280, https://openalex.org/W2039039364, https://openalex.org/W2951070883, https://openalex.org/W2789722992, https://openalex.org/W2171302328, https://openalex.org/W2296025156, https://openalex.org/W2330107646, https://openalex.org/W2950493794, https://openalex.org/W2010528591, https://openalex.org/W2052821871, https://openalex.org/W1964699916, https://openalex.org/W2091808919, https://openalex.org/W2047077060, https://openalex.org/W2032982803, https://openalex.org/W2952831635, https://openalex.org/W1539589462, https://openalex.org/W2015694441, https://openalex.org/W3087997764, https://openalex.org/W1972437470, https://openalex.org/W1581023273, https://openalex.org/W2044787351, https://openalex.org/W2082316278, https://openalex.org/W3180446930, https://openalex.org/W1941916315, https://openalex.org/W1984656092, https://openalex.org/W2086367200, https://openalex.org/W2166953979, https://openalex.org/W2030877267, https://openalex.org/W2029335737, https://openalex.org/W2004329247, https://openalex.org/W2148210119, https://openalex.org/W2144278433, https://openalex.org/W4211239589, https://openalex.org/W4304957537, https://openalex.org/W1974222847, https://openalex.org/W2061620357, https://openalex.org/W2898257166, https://openalex.org/W3133679342, https://openalex.org/W2296141397, https://openalex.org/W2941354611, https://openalex.org/W1986155860, https://openalex.org/W1989992411, https://openalex.org/W3029705091, https://openalex.org/W2980788547, https://openalex.org/W1988706188, https://openalex.org/W2007028503, https://openalex.org/W3216927687 |
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