A 2-aza-Cope reactivity-based platform for ratiometric fluorescence imaging of formaldehyde in living cells

Brewer, Thomas F.; Burgos-Barragan, Guillermo; Wit, Niek J. de; Patel, Ketan; Chang, Christopher J.

doi:10.1039/c7sc00748e

Cited by 97 publications

(65 citation statements)

References 49 publications

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“…One such probe, FAP-573, was capable of visualizing increased endogenous FA levels in ADH5 knockout cells compared to the wildtype counterpart. We have also utilized this motif to develop a first-generation ratiometric FA probe with visible excitation and emission profiles [57 • ]. Overall, this aforementioned collection of fluorescent probes demonstrates the broad applicability of the 2-aza-Cope reaction for detection of biological FA, and further extensions of this strategy will allow for tuning of excitation/emission wavelengths and subcellular localization, as well as expansion to other imaging modalities.…”

Section: Fa Probes Utilizing the 2-aza-cope Reactionmentioning

confidence: 99%

Fluorescent probes for imaging formaldehyde in biological systems

Bruemmer

Brewer

Chang

2017

Current Opinion in Chemical Biology

102

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Formaldehyde (FA) is a common environmental toxin but is also endogenously produced through a diverse array of essential biological processes, including mitochondrial one-carbon metabolism, metabolite oxidation, and nuclear epigenetic modifications. Its high electrophilicity enables reactivity with a wide variety of biological nucleophiles, which can be beneficial or detrimental to cellular function depending on the context. New methods that enable detection of FA in living systems can help disentangle the signal/stress dichotomy of this simplest reactive carbonyl species (RCS), and fluorescent probes for FA with high selectivity and sensitivity have emerged as promising chemical tools in this regard.

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Section: Fa Probes Utilizing the 2-aza-cope Reactionmentioning

confidence: 99%

Fluorescent probes for imaging formaldehyde in biological systems

Bruemmer

Brewer

Chang

2017

Current Opinion in Chemical Biology

102

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“…The small and transient nature of FA has motivated growing interest in developing new activity‐based sensing (ABS) methods for selective FA detection, including aza‐Cope, aminal, and formimine reaction‐based approaches. Indeed, recent progress in developing fluorescent probes for FA detection in cells has elucidated more sophisticated biological roles for FA as both an exogenous toxin and an endogenous signaling molecule.…”

Section: Methodsmentioning

confidence: 99%

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

Bruemmer

Green

et al. 2018

Angewandte Chemie

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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.

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“…A series of ratiometric formaldehyde probe indicators have been developed for the excitation-ratiometric fluorescence imaging of formaldehyde production in living systems. 32 On reaction with formaldehyde, the coumarin derived homoallylamines (e.g. 34) are converted to an aldehyde congener through an aza-Cope rearrangement, resulting in an approximate 50 nm shift in excitation wavelength.…”

Section: -Phenylfuran-2-yl-β-alanine Ethyl Esters Have Been Efficienmentioning

confidence: 99%

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Hill

Sutherland

2017

Nat. Prod. Rep.

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A 2-aza-Cope reactivity-based platform for ratiometric fluorescence imaging of formaldehyde in living cells

Abstract: We present the first ratiometric fluorescent probes for formaldehyde, a major reactive species in biology, operating in the visible region.

Cited by 97 publications

References 49 publications

Fluorescent probes for imaging formaldehyde in biological systems

Fluorescent probes for imaging formaldehyde in biological systems

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

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