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Dual‐Color Photoconvertible Fluorescent Probes Based on Directed Photooxidation Induced Conversion for Bioimaging

We herein present a new concept to produce dual‐color photoconvertible probes based on a mechanism called Directed Photooxidation Induced Conversion (DPIC). As a support of this mechanism, styryl‐coumarins (SCs) bearing Aromatic Singlet Oxygen Reactive Moieties (ASORMs) like furan and pyrrole have b...

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Autores principales: Saladin, Lazare, Breton, Victor, Dal Pra, Ophélie, Klymchenko, Andrey S., Danglot, Lydia, Didier, Pascal, Collot, Mayeul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107923/
https://www.ncbi.nlm.nih.gov/pubmed/36420823
http://dx.doi.org/10.1002/anie.202215085
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author Saladin, Lazare
Breton, Victor
Dal Pra, Ophélie
Klymchenko, Andrey S.
Danglot, Lydia
Didier, Pascal
Collot, Mayeul
author_facet Saladin, Lazare
Breton, Victor
Dal Pra, Ophélie
Klymchenko, Andrey S.
Danglot, Lydia
Didier, Pascal
Collot, Mayeul
author_sort Saladin, Lazare
collection PubMed
description We herein present a new concept to produce dual‐color photoconvertible probes based on a mechanism called Directed Photooxidation Induced Conversion (DPIC). As a support of this mechanism, styryl‐coumarins (SCs) bearing Aromatic Singlet Oxygen Reactive Moieties (ASORMs) like furan and pyrrole have been synthesized. SCs are bright fluorophores, which undergo a hypsochromic conversion upon visible light irradiation due to directed photooxidation of the ASORM that leads to the disruption of conjugation. SC‐P, a yellow emitting probe bearing a pyrrole moiety, converts to a stable blue emitting coumarin with a 68 nm shift allowing the photoconversion and tracking of lipid droplet in live cells. This new approach might pave the way to a new generation of photoconvertible dyes for advanced bioimaging applications.
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spelling pubmed-101079232023-04-18 Dual‐Color Photoconvertible Fluorescent Probes Based on Directed Photooxidation Induced Conversion for Bioimaging Saladin, Lazare Breton, Victor Dal Pra, Ophélie Klymchenko, Andrey S. Danglot, Lydia Didier, Pascal Collot, Mayeul Angew Chem Int Ed Engl Communications We herein present a new concept to produce dual‐color photoconvertible probes based on a mechanism called Directed Photooxidation Induced Conversion (DPIC). As a support of this mechanism, styryl‐coumarins (SCs) bearing Aromatic Singlet Oxygen Reactive Moieties (ASORMs) like furan and pyrrole have been synthesized. SCs are bright fluorophores, which undergo a hypsochromic conversion upon visible light irradiation due to directed photooxidation of the ASORM that leads to the disruption of conjugation. SC‐P, a yellow emitting probe bearing a pyrrole moiety, converts to a stable blue emitting coumarin with a 68 nm shift allowing the photoconversion and tracking of lipid droplet in live cells. This new approach might pave the way to a new generation of photoconvertible dyes for advanced bioimaging applications. John Wiley and Sons Inc. 2022-12-14 2023-01-23 /pmc/articles/PMC10107923/ /pubmed/36420823 http://dx.doi.org/10.1002/anie.202215085 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Saladin, Lazare
Breton, Victor
Dal Pra, Ophélie
Klymchenko, Andrey S.
Danglot, Lydia
Didier, Pascal
Collot, Mayeul
Dual‐Color Photoconvertible Fluorescent Probes Based on Directed Photooxidation Induced Conversion for Bioimaging
title Dual‐Color Photoconvertible Fluorescent Probes Based on Directed Photooxidation Induced Conversion for Bioimaging
title_full Dual‐Color Photoconvertible Fluorescent Probes Based on Directed Photooxidation Induced Conversion for Bioimaging
title_fullStr Dual‐Color Photoconvertible Fluorescent Probes Based on Directed Photooxidation Induced Conversion for Bioimaging
title_full_unstemmed Dual‐Color Photoconvertible Fluorescent Probes Based on Directed Photooxidation Induced Conversion for Bioimaging
title_short Dual‐Color Photoconvertible Fluorescent Probes Based on Directed Photooxidation Induced Conversion for Bioimaging
title_sort dual‐color photoconvertible fluorescent probes based on directed photooxidation induced conversion for bioimaging
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107923/
https://www.ncbi.nlm.nih.gov/pubmed/36420823
http://dx.doi.org/10.1002/anie.202215085
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