期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 25, 页码 7508-7512出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802143
关键词
activity-based sensing; chemiluminescence; formaldehyde; one-carbon metabolism; oxetane
资金
- NIH [NIEHS 28096, NIEHS 04705]
- NSF graduate fellowship
- NIH Ruth L. Kirschstein NRSA Fellowship [F32 GM122248]
- NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES [R01ES028096] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [F32GM122248] Funding Source: NIH RePORTER
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 invitro biochemical to cell to animal models.
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