Bright and sensitive ratiometric fluorescent probe enabling endogenous FA imaging and mechanistic exploration of indirect oxidative damage due to FA in various living systems

Dou, Kun; Chen, Guang; Yu, Fabiao; Liu, Yuxia; Chen, Lingxin; Cao, Ziping; Chen, Tao; Li, Yulin; You, Jinmao

doi:10.1039/c7sc03719h

Cited by 85 publications

(37 citation statements)

References 63 publications

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“…Reminiscent variations in the optical characteristics due to an emission switch to the ILCT mode have been recently described for a phenanthro-imidazole probe for formaldehyde. 81 Treatment of L3 and L4 with the acid leads to a large decrease in fluorescence intensity without a considerable change in emission energy ( Figure S14 ). This effect might be attributed to the increased electron-withdrawing ability of the diimine motif that facilitates photoinduced electron transfer from the anthracene-based donor.…”

Section: Resultsmentioning

confidence: 99%

Chromophore-Functionalized Phenanthro-diimine Ligands and Their Re(I) Complexes

et al. 2018

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A series of diimine ligands has been designed on the basis of 2-pyridyl-1H-phenanthro[9,10-d]imidazole (L1, L2). Coupling the basic motif of L1 with anthracene-containing fragments affords the bichromophore compounds L3–L5, of which L4 and L5 adopt a donor–acceptor architecture. The latter allows intramolecular charge transfer with intense absorption bands in the visible spectrum (lowest λabs 464 nm (ε = 1.2 × 104 M–1 cm–1) and 490 nm (ε = 5.2 × 104 M–1 cm–1) in CH2Cl2 for L4 and L5, respectively). L1–L5 show strong fluorescence in a fluid medium (Φem = 22–92%, λem 370–602 nm in CH2Cl2); discernible emission solvatochromism is observed for L4 and L5. In addition, the presence of pyridyl (L1–L5) and dimethylaminophenyl (L5) groups enables reversible alteration of their optical properties by means of protonation. Ligands L1–L5 were used to synthesize the corresponding [Re(CO)3X(diimine)] (X = Cl, 1–5; X = CN, 1-CN) complexes. 1 and 2 exhibit unusual dual emission of singlet and triplet parentage, which originate from independently populated 1ππ* and 3MLCT excited states. In contrast to the majority of the reported Re(I) carbonyl luminophores, complexes 3–5 display moderately intense ligand-based fluorescence from an anthracene-containing secondary chromophore and complete quenching of emission from the 3MLCT state presumably due to the triplet–triplet energy transfer (3MLCT → 3ILCT).

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Section: Resultsmentioning

confidence: 99%

Chromophore-Functionalized Phenanthro-diimine Ligands and Their Re(I) Complexes

et al. 2018

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“…The original BD-CHO exhibits almost no fluorescence due to the poor electron withdrawing ability of the homoallylamine moiety. After addition of FA, the amine reacts selectively with FA to form an imine intermediate, which simultaneously undergoes 2-Aza-Cope rearrangement and final hydrolysis to produce an aldehyde group with power electron withdrawing ability (Figure 1 ) (Brewer et al, 2017 ; Dou et al, 2017 ). As a result, the intramolecular charge transfer (ICT) process from π-conjugated electron donor (dimethylamine group) to the aldehyde group is opened, showing a “turn-on” fluorescence response.…”

Section: Resultsmentioning

confidence: 99%

Imaging of Formaldehyde in Live Cells and Daphnia magna via Aza-Cope Reaction Utilizing Fluorescence Probe With Large Stokes Shifts

Yang

Fan

et al. 2018

Front. Chem.

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Formaldehyde (FA), a highly reactive carbonyl species, plays significant role in physiological and pathological functions. However, elevated FA will lead to cognitive impairments, memory loss and various neurodegenerative diseases due to its potent DNA and protein cross-linking mechanisms. In this work, a fluorescence probe, BD-CHO, based on benz-2-oxa-1, 3- diazole (BD) skeleton, was designed and synthesized for detection of FA via Aza-Cope reaction with high selectivity and large Stokes shifts (about 118 nm). BD-CHO was successfully applied to monitor the changes FA level in living cells, and kidney tissues of mice. Importantly it was the first time that BD-CHO was used for visualizing exogenous FA changes in Daphnia magna through fluorescence microscopy, demonstrating its potential application for studies of biological processes associated with FA.

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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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Bright and sensitive ratiometric fluorescent probe enabling endogenous FA imaging and mechanistic exploration of indirect oxidative damage due to FA in various living systems

Abstract: Herein, we present the design and multi-application of a bright and sensitive ratiometric fluorescent probe, PIPBA, for the imaging of formaldehyde (FA) in living systems.

Cited by 85 publications

References 63 publications

Chromophore-Functionalized Phenanthro-diimine Ligands and Their Re(I) Complexes

Chromophore-Functionalized Phenanthro-diimine Ligands and Their Re(I) Complexes

Imaging of Formaldehyde in Live Cells and Daphnia magna via Aza-Cope Reaction Utilizing Fluorescence Probe With Large Stokes Shifts

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

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