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Rapid chemiexcitation of phenoxy-dioxetane luminophores yields ultrasensitive chemiluminescence assays

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Abstract

The utility of dioxetane-based chemiluminescent probes in biosensing and bioimaging is being increasingly recognized. While phenoxy-dioxetane luminophores with fast chemiexcitation kinetics are highly desired, current luminophores suffer from slow chemiexcitation. Herein we describe a rational, computationally-supported design of phenoxy-dioxetanes with fast chemiexcitation kinetics. These new luminophores were designed to contain a substituent that promotes rapid chemiexcitation, emitting light up to 100-fold faster than currently known dioxetanes. We demonstrate the superiority of the new phenoxy-dioxetanes by preparing three chemiluminescent probes for NAD(P)H, which differ from each other in the rate of the chemiexcitation. Comparison of these probes reveals a correlation between the chemiexcitation rate and the probe sensitivity. We anticipate that these new phenoxy-dioxetanes could serve as an ideal platform for designing chemiluminescence probes with enhanced sensitivity for numerous bioassays.

Graphical abstract: Rapid chemiexcitation of phenoxy-dioxetane luminophores yields ultrasensitive chemiluminescence assays

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Publication details

The article was received on 26 Sep 2018, accepted on 12 Nov 2018 and first published on 19 Nov 2018


Article type: Edge Article
DOI: 10.1039/C8SC04280B
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY license
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    Rapid chemiexcitation of phenoxy-dioxetane luminophores yields ultrasensitive chemiluminescence assays

    N. Hananya, J. P. Reid, O. Green, M. S. Sigman and D. Shabat, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC04280B

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