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Recent Advances and Challenges in Luminescent Imaging: Bright Outlook for Chemiluminescence of Dioxetanes in Water

[Image: see text] Chemiluminescence is gradually being recognized as a powerful tool for sensing and imaging. Most known light-emitting compounds undergo chemiexcitation through spontaneous decomposition of cyclic peroxide moieties. A ground-breaking milestone in the chemistry of such compounds was...

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Autores principales: Hananya, Nir, Shabat, Doron
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6598152/
https://www.ncbi.nlm.nih.gov/pubmed/31263754
http://dx.doi.org/10.1021/acscentsci.9b00372
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author Hananya, Nir
Shabat, Doron
author_facet Hananya, Nir
Shabat, Doron
author_sort Hananya, Nir
collection PubMed
description [Image: see text] Chemiluminescence is gradually being recognized as a powerful tool for sensing and imaging. Most known light-emitting compounds undergo chemiexcitation through spontaneous decomposition of cyclic peroxide moieties. A ground-breaking milestone in the chemistry of such compounds was achieved 30 years ago with the discovery of triggerable dioxetanes by Schaap’s group. Our group has recently developed a distinct methodology to significantly improve the light emission efficiency of such phenoxy-dioxetane luminophores under physiological conditions. Introduction of an electron-withdrawing substituent at the ortho position of the phenoxy-dioxetane resulted in an approximately 3000-fold increase of the chemiluminescence quantum yield in aqueous media. Furthermore, we discovered that the emission wavelength and the kinetics of the chemiexcitation could be determined by the electronic nature of the substituent incorporated on the dioxetane luminophore. This recent development has provided scientists with new powerful chemiluminophores that can act as single-component probes for in vivo and in vitro detection and imaging of various analytes and enzymes. This outlook describes the recent progress toward applications of synthetic chemiluminescence luminophores suitable for sensing and imaging in aqueous environments.
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spelling pubmed-65981522019-07-01 Recent Advances and Challenges in Luminescent Imaging: Bright Outlook for Chemiluminescence of Dioxetanes in Water Hananya, Nir Shabat, Doron ACS Cent Sci [Image: see text] Chemiluminescence is gradually being recognized as a powerful tool for sensing and imaging. Most known light-emitting compounds undergo chemiexcitation through spontaneous decomposition of cyclic peroxide moieties. A ground-breaking milestone in the chemistry of such compounds was achieved 30 years ago with the discovery of triggerable dioxetanes by Schaap’s group. Our group has recently developed a distinct methodology to significantly improve the light emission efficiency of such phenoxy-dioxetane luminophores under physiological conditions. Introduction of an electron-withdrawing substituent at the ortho position of the phenoxy-dioxetane resulted in an approximately 3000-fold increase of the chemiluminescence quantum yield in aqueous media. Furthermore, we discovered that the emission wavelength and the kinetics of the chemiexcitation could be determined by the electronic nature of the substituent incorporated on the dioxetane luminophore. This recent development has provided scientists with new powerful chemiluminophores that can act as single-component probes for in vivo and in vitro detection and imaging of various analytes and enzymes. This outlook describes the recent progress toward applications of synthetic chemiluminescence luminophores suitable for sensing and imaging in aqueous environments. American Chemical Society 2019-05-29 2019-06-26 /pmc/articles/PMC6598152/ /pubmed/31263754 http://dx.doi.org/10.1021/acscentsci.9b00372 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Hananya, Nir
Shabat, Doron
Recent Advances and Challenges in Luminescent Imaging: Bright Outlook for Chemiluminescence of Dioxetanes in Water
title Recent Advances and Challenges in Luminescent Imaging: Bright Outlook for Chemiluminescence of Dioxetanes in Water
title_full Recent Advances and Challenges in Luminescent Imaging: Bright Outlook for Chemiluminescence of Dioxetanes in Water
title_fullStr Recent Advances and Challenges in Luminescent Imaging: Bright Outlook for Chemiluminescence of Dioxetanes in Water
title_full_unstemmed Recent Advances and Challenges in Luminescent Imaging: Bright Outlook for Chemiluminescence of Dioxetanes in Water
title_short Recent Advances and Challenges in Luminescent Imaging: Bright Outlook for Chemiluminescence of Dioxetanes in Water
title_sort recent advances and challenges in luminescent imaging: bright outlook for chemiluminescence of dioxetanes in water
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6598152/
https://www.ncbi.nlm.nih.gov/pubmed/31263754
http://dx.doi.org/10.1021/acscentsci.9b00372
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