Rapid chemiexcitation of phenoxy-dioxetane luminophores yields ultrasensitive chemiluminescence assays

Nir Hananya, Jolene P. Reid, Ori Green, Matthew S. Sigman, Doron Shabat

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)1380-1385
Number of pages6
JournalChemical Science
Volume10
Issue number5
DOIs
StatePublished - 2019

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