Chemiluminescent Probes for Activity-Based Sensing of Formaldehyde Released from Folate Degradation in Living Mice

Kevin J. Bruemmer, Ori Green, Timothy A. Su, Doron Shabat*, Christopher J. Chang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Formaldehyde (FA) is a common environmental toxin that is also produced naturally in the body through a wide range of metabolic and epigenetic processes, motivating the development of new technologies to monitor this reactive carbonyl species (RCS) in living systems. Herein, we report a pair of first-generation chemiluminescent probes for selective formaldehyde detection. Caging phenoxy-dioxetane scaffolds bearing different electron-withdrawing groups with a general 2-aza-Cope reactive formaldehyde trigger provides chemiluminescent formaldehyde probes 540 and 700 (CFAP540 and CFAP700) for visible and near-IR detection of FA in living cells and mice, respectively. In particular, CFAP700 is capable of visualizing FA release derived from endogenous folate metabolism, providing a starting point for the use of CFAPs and related chemical tools to probe FA physiology and pathology, as well as for the development of a broader palette of chemiluminescent activity-based sensing (ABS) probes that can be employed from in vitro biochemical to cell to animal models.

Original languageEnglish
Pages (from-to)7508-7512
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number25
DOIs
StatePublished - 18 Jun 2018

Funding

FundersFunder number
National Science Foundation
National Institutes of HealthNIEHS 28096, NIEHS 04705
National Institute of General Medical SciencesF32GM122248
National Institute of Environmental Health SciencesR01ES028096
Israel National Road Safety AuthorityF32 GM122248

    Keywords

    • activity-based sensing
    • chemiluminescence
    • formaldehyde
    • one-carbon metabolism
    • oxetane

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