A BODIPY fluorescence probe modulated by selenoxide spirocyclization reaction for peroxynitrite detection and imaging in living cells

Wang, Bingshuai; Yu, Fabiao; Sun, Xiaofei; Han, Keli

doi:10.1016/j.dyepig.2012.09.006

Cited by 75 publications

(32 citation statements)

References 45 publications

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“…Han et al reported another fluorescent probe based on selenoxide spirocyclization for the selective peroxynitrite detection (Fig. 21) [63]. Probe 28 has an absorption maximum at 559 nm and a strong fluorescence at 572 nm.…”

Section: Detection Of Peroxynitrite In Living Cellsmentioning

confidence: 99%

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Reaction-based BODIPY probes for selective bio-imaging

Kölemen

Akkaya

2018

Coordination Chemistry Reviews

299

112

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Complex intracellular environment of cells, which involves interaction of a large variety of bio-molecules, is a dynamic medium with full of important information that can be recovered as well as many unanswered questions. It is highly critical to image and track biologically relevant molecules in their native media without interfering with the regular cellular processes in order to gather as much data as possible to illuminate intricacies of the biological mechanisms. To that end, small-molecule fluorescent probes have been extensively developed during the last few decades with the help of current advances in imaging technologies. Although conventional probes utilizing non-covalent supramolecular interactions with the analyte of interest are successful, significant effort has been also put into the design of reaction-based probes (chemodosimeters). Chemodosimeters exploit selective reactions of analytes with fluorophores in attempt to improve the selectivity of the probes, address the limitations of former sensors and broaden the palette of useful probes. Various types of fluorophore scaffolds can be used in the design of chemodosimeters for visualization of different analytes. In this review, we highlight the 4,4-difluoro-4bora-3a,4a-diaza-s-indacene (BODIPY) based chemodosimeters which have been used to image bio-thiols, reactive oxygen/nitrogen species, and gaseous molecules in living cells.

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Section: Detection Of Peroxynitrite In Living Cellsmentioning

confidence: 99%

“…22) [64,65]. Compound 29 contains two diphenylphosphinobenzyl groups as selective reaction sites for HNO [63]. Upon HNO addition, one unit forms aza-ylide and a further intramolecular reaction gives a phenol, whereas the other diphenylphosphinobenzyl moiety yields phosphine oxide.…”

Section: Detection Of Nitroxyl In Living Cellsmentioning

confidence: 99%

Reaction-based BODIPY probes for selective bio-imaging

Kölemen

Akkaya

2018

Coordination Chemistry Reviews

299

112

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“…Another fluorescent probe, 35, containing a BODIPY moiety, was developed by the same group for peroxynitrite sensing (Scheme 6). 69 The probe is highly sensitive and selective as a consequence of peroxynitrite-promoted oxidation at the organoselenium center under physiological conditions. The ensuing spirocyclization reaction at selenium gives rise to free 3-ethylamino-styryl-BODIPY in concert with an observable color change from purple to blue.…”

Section: Fluorescent Probes Containing Selenium For Other Significantmentioning

confidence: 99%

Fluorescent Probes Containing Selenium as a Guest or Host

Chen

Kwon

et al. 2016

Chem

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Selenium is an important trace element in living systems. Proteins incorporating selenium have a wide range of biological effects, ranging from anti-oxidant and antiinflammatory effects to the production of active thyroid hormones. In the past decades, selenium has drawn enormous attention because of its important role in biology, which can be ascribed partly if not solely to its redox and hard and soft donor properties. With the use of chemical mimicry, a large number of seleniumrelated fluorescent probes have been developed for monitoring physiological and pathological processes. This review, which summarizes recent progress made in this area, comprises two major sections. In the first section, fluorescent probes for selenium-containing species, such as selenocysteine (Sec), hydrogen selenide, thioredoxin reductases (TrxRs), and selenite, are described. This is followed by a discussion of fluorescent probes that contain selenium and detect reactive oxygen, nitrogen, and sulfur species, as well as cations and anions.

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“…Although over the last 5 years an array of fluorogenic probes for the detection of ONOO − has been reported (e.g., Li et al 2015; Peng et al 2014; Wang et al 2013; Xu et al 2011; Zhou et al 2015), boronate-based probes seem to be best suited for that purpose. We have previously shown that boronate-based compounds react with peroxynitrite either added as a bolus or cogenerated from simultaneous generation of • NO and O 2 •− nearly six orders of magnitude (10 6 -fold) greater than H 2 O 2 (Sikora et al 2009; Zielonka et al 2010).…”

Section: Probes For Peroxynitrite Detectionmentioning

confidence: 99%

A Critical Review of Methodologies to Detect Reactive Oxygen and Nitrogen Species Stimulated by NADPH Oxidase Enzymes: Implications in Pesticide Toxicity

2016

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In this review, potential fluorescent probe applications for detecting reactive oxygen and nitrogen species (ROS/RNS) generated from NADPH oxidases (e.g., Nox2) and nitric oxide synthase enzymes are discussed in the context of pesticide toxicology. Identification of the specific marker products derived from the interaction between ROS/RNS and the fluorescent probes (e.g., hydroethidine and coumarin boronate) is critical. Due to the complex nature of reactions between the probes and ROS/RNS, we suggest avoiding the use of fluorescence microscopy for detecting oxidizing/nitrating species. We also critically examined the viability of using radiolabeling or positron emission tomography (PET) for ROS/RNS detection. Although these techniques differ in sensitivity and detection modalities, the chemical mechanism governing the reaction between these probes and ROS/RNS should remain the same. To unequivocally detect superoxide with these probes (i.e., radiolabeled and PET-labeled hydroethidine analogs), the products should be isolated and characterized by LC-MS/MS or HPLC using an appropriate standard.

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A BODIPY fluorescence probe modulated by selenoxide spirocyclization reaction for peroxynitrite detection and imaging in living cells

Cited by 75 publications

References 45 publications

Reaction-based BODIPY probes for selective bio-imaging

Reaction-based BODIPY probes for selective bio-imaging

Fluorescent Probes Containing Selenium as a Guest or Host

A Critical Review of Methodologies to Detect Reactive Oxygen and Nitrogen Species Stimulated by NADPH Oxidase Enzymes: Implications in Pesticide Toxicity

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