A chemiluminescent probe for cellular peroxynitrite using a self-immolative oxidative decarbonylation reaction

Cao, Jian; An, Weiwei; Reeves, Audrey G.; Lippert, Alexander R.

doi:10.1039/c7sc05087a

Cited by 110 publications

(88 citation statements)

References 58 publications

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“…[7][8][9] These methods apply different enrichment cultures and plating on selective agar media for the detection of bacteria. [19][20][21] Recently,o ur group has explored new approaches for amplifying chemiluminescence light intensity [22][23][24] under physiological conditions. In case of L. monocytogenes,asafe negative result is available after 96 h( 4days).…”

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confidence: 99%

Ultrasensitive Detection of Salmonella and Listeria monocytogenes by Small‐Molecule Chemiluminescence Probes

et al. 2019

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Detection of Salmonella and L. monocytogenes in food samples by current diagnostic methods requires relatively long time to results (2-6 days). Furthermore,t he ability to perform environmental monitoring at the factory site for these pathogens is limited due to the need for laboratory facilities. Herein, we report new chemiluminescence probes for the ultrasensitive direct detection of viable pathogenic bacteria. The probes are composed of ab right phenoxy-dioxetane luminophore masked by triggering group,whichisactivated by aspecific bacterial enzyme,and could detect their corresponding bacteria with an LOD value of about 600-fold lower than that of fluorescent probes.M oreover,w ew ere able to detect am inimum of 10 Salmonella cells within 6hincubation. The assayallows for bacterial enrichment and detection in one test tube without further sample preparation. We anticipate that this design strategy will be used to prepare analogous chemiluminescence probes for other enzymes relevant to specific bacteria detection and point-of-care diagnostics.

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confidence: 99%

Ultrasensitive Detection of Salmonella and Listeria monocytogenes by Small‐Molecule Chemiluminescence Probes

et al. 2019

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“…[56] Some of these probes comprise embedded dioxetanes that are cleavable—and thus emit light—in response to a variety of triggers. [57*,58] Unlike canonical caged luciferins, these reporters do not require a luciferase to produce light. Such probes further diversify the portfolio of tools for biological imaging.…”

Section: Monitoring New Facets Of Biologymentioning

confidence: 99%

Advances in bioluminescence imaging: new probes from old recipes

Yao

Zhang

Prescher

2018

Current Opinion in Chemical Biology

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Bioluminescent probes are powerful tools for visualizing biology in live tissues and whole animals. Recent years have seen a surge in the number of new luciferases, luciferins, and related tools available for bioluminescence imaging. Many were crafted using classic methods of optical probe design and engineering. Here we highlight recent advances in bioluminescent tool discovery and development, along with applications of the probes in cells, tissues, and organisms. Collectively, these tools are improving in vivo imaging capabilities and bolstering new research directions.

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“…Ac omparison was made to acell-permeable version of apreviously reported fluorescent probe for HNO,h erein named XF2 ( Figure 1D,f ull characterization can be found in the Supporting Information). [36] While the fluorescent probe XF2 yielded a2 0-fold turn-on response after 25 min, HNOCL-1 provided an 833-fold turnon response at the same time point ( Figure 1C). HNOCL-1 is soluble at 20 mm ( Figure S3) and stable in aqueous buffer ( Figure S4).…”

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confidence: 93%

“…[30] Chemiluminescence offers dramatic increases in signal-tonoise ratios and sensitivity over fluorescence techniques. [35][36][37][38][39][40][41][42][43] Recent advances in molecular design have yielded structures with high emission under aqueous conditions without the need for polymeric "Enhancer" solutions. [34] This strategy has been used to image numerous analytes in vitro,i nl iving cells,a nd in whole animals.…”

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confidence: 99%

“…[31,32] In particular, sterically stabilized 1,2-dioxetanes,s uch as Schaapsd ioxetane [33] enable reaction-based triggering of chemiluminescence emission using ac hemically initiated electron exchange luminescence (CIEEL) mechanism. [44][45][46] In line with our labo-ratorysg oal to develop probes for reactive sulfur,o xygen, and nitrogen (RSON) species, [36,38,39,[47][48][49][50] we designed areaction-based chemiluminescent probe for HNO, HNOCL-1,by linking atriaryl phosphine group to asterically stabilized 1,2dioxetane (Scheme 1). [35][36][37][38][39][40][41][42][43] Recent advances in molecular design have yielded structures with high emission under aqueous conditions without the need for polymeric "Enhancer" solutions.…”

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confidence: 99%

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A Chemiluminescent Probe for HNO Quantification and Real‐Time Monitoring in Living Cells

Ryan

Reeves

et al. 2018

Angewandte Chemie

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Azanone (HNO) is ar eactive nitrogen species with pronounced biological activity and high therapeutic potential for cardiovascular dysfunction. Ac ritical barrier to understanding the biology of HNO and furthering clinical development is the quantification and real-time monitoring of its delivery in living systems.H erein, we describe the design and synthesis of the first chemiluminescent probe for HNO, HNOCL-1,w hich can detect HNO generated from concentrations of Angeliss alt as lowa s1 38 nm with high selectivity based on the reaction with ap hosphine group to form as elfcleavable azaylide intermediate.W eh ave capitalized on this high sensitivity to develop ag eneralizable kinetics-based approach,whichprovides real-time quantitative measurements of HNO concentration at the picomolar level. HNOCL-1 can monitor dynamics of HNO delivery in living cells and tissues, demonstrating the versatility of this method for tracking HNO in living systems.Azanone (HNO,n itroxyl), is chemically related to nitric oxide (NO) by the addition of one electron and one proton. HNO rapidly dimerizes and eliminates to form nitrous oxide (k = 8 10 6 m À1 s À1 at 23 8 8C) [1] and reacts with molecular oxygen with estimated rate constants that range from 10 3 to 10 4 m À1 s À1 (k = 3 10 3 m À1 s À1 at 37 8 8C; [2] k = 1 10 4 m À1 s À1 at 23 8 8C; [3] k = 1.8 10 4 m À1 s À1 at 25 8 8C [4,5] ). Tw omajor biological targets responsible for HNO bioactivity are thiols,which react directly with HNO to form sulfinamides (k = 2 10 6 m À1 s À1 at 37 8 8C) [2] and the iron in heme-containing proteins. [6] While both HNO and NO can activate soluble guanylyl cyclase,only HNO acts apositive cardiac inotrope by direct reaction with cysteine residues on cardiac ryanodine receptors and the sarcoplasmic reticulum Ca 2+

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A chemiluminescent probe for cellular peroxynitrite using a self-immolative oxidative decarbonylation reaction

Abstract: Peroxynitrite is a damaging agent of oxidative stress that has been difficult to monitor in living cells. Here, an isatin-based chemiluminescent probe for peroxynitrite is reported.

Cited by 110 publications

References 58 publications

Ultrasensitive Detection of Salmonella and Listeria monocytogenes by Small‐Molecule Chemiluminescence Probes

Ultrasensitive Detection of Salmonella and Listeria monocytogenes by Small‐Molecule Chemiluminescence Probes

Advances in bioluminescence imaging: new probes from old recipes

A Chemiluminescent Probe for HNO Quantification and Real‐Time Monitoring in Living Cells

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