Rapid chemiexcitation of phenoxy-dioxetane luminophores yields ultrasensitive chemiluminescence assays

Chemical Science
Nir HananyaDoron Shabat

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.

References

Jul 1, 1989·Journal of Bioluminescence and Chemiluminescence·I BronsteinJ C Voyta
Apr 25, 2002·Journal of the American Chemical Society·Stéphane SabelleCharles Mioskowski
May 26, 2004·Trends in Biotechnology·Aldo RodaMassimo Guardigli
Oct 18, 2007·Organic Letters·Jean-Alexandre RichardPierre-Yves Renard
Mar 5, 2014·Chembiochem : a European Journal of Chemical Biology·Wenhui ZhouPoncho Meisenheimer
Feb 25, 2015·Chemical Science·J CaoA R Lippert
May 14, 2013·Journal of Chemical Theory and Computation·Ling Yue, Ya-Jun Liu
Sep 23, 2016·Journal of the American Chemical Society·Celine B SantiagoMatthew S Sigman
Aug 31, 2017·Journal of the American Chemical Society·Ori GreenDoron Shabat
Feb 10, 2018·Chemical Communications : Chem Comm·Samer GnaimDoron Shabat
Mar 2, 2018·Chemical Reviews·Morgane VacherRoland Lindh
Jun 12, 2018·Chembiochem : a European Journal of Chemical Biology·Okoh Adeyi Okoh, Philipp Klahn

❮ Previous
Next ❯

Citations

Jul 4, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jon Miranda-ApodacaJuan B Arellano
Sep 16, 2020·Analytical Methods : Advancing Methods and Applications·Houman Kholafazad Kordasht, Mohammad Hasanzadeh
Sep 16, 2020·Chemical Society Reviews·Mingwang YangXiaojun Peng
Nov 4, 2020·Biomedical Materials·Yan XuBingbo Zhang
Jul 31, 2019·Journal of the American Chemical Society·Alec H ChristianF Dean Toste
Oct 15, 2021·Chemical Communications : Chem Comm·Omri ShelefJonathan L Sessler

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.