A two-photon excitable and ratiometric fluorogenic nitric oxide photoreleaser and its biological applications

Xie, Xilei; Fan, Jilin; Liang, Muwen; Li, Yong; Jiao, Xiaoyun; Wang, Xu; Tang, Bo

doi:10.1039/c7cc06820d

Cited by 64 publications

(47 citation statements)

References 37 publications

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“…Its coumarinyl-substituted analog 301 also releases NO upon UV irradiation or 2P excitation at λ irr = 800 nm, with a chemical yield of 79%. 1228 …”

Section: Photorelease Of Gasotransmittersmentioning

confidence: 99%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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Photoactivatable (alternatively, photoremovable, photoreleasable, or photocleavable) protecting groups (PPGs), also known as caged or photocaged compounds, are used to enable non-invasive spatiotemporal photochemical control over the release of species of interest. Recent years have seen the development of PPGs activatable by biologically and chemically benign visible and near-infrared (NIR) light. These long-wavelength-absorbing moieties expand the applicability of this powerful method and its accessibility to non-specialist users. This review comprehensively covers organic and transition metal-containing photoactivatable compounds (complexes) that absorb in the visible- and NIR-range to release various leaving groups and gasotransmitters (carbon monoxide, nitric oxide, and hydrogen sulfide). The text also covers visible- and NIR-light-induced photosensitized release using molecular sensitizers, quantum dots, and upconversion and second-harmonic nanoparticles, as well as release via photodynamic (photooxygenation by singlet oxygen) and photothermal effects. Release from photoactivatable polymers, micelles, vesicles, and photoswitches, along with the related emerging field of photopharmacology, is discussed at the end of the review.

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“…Its coumarinyl-substituted analog 301 also releases NO upon UV irradiation or 2P excitation at λ irr = 800 nm, with a chemical yield of 79%. 1228 …”

Section: Photorelease Of Gasotransmittersmentioning

confidence: 99%

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

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“…In 2017, Tang and colleagues reported a two-photon FRET-based system for monitoring in situ release of NO. 19 Probe 16 was constructed by conjugation of coumarin and naphthalimide cores with NO ( Fig. 10).…”

Section: Fret-based Sensors For Small Neutral Moleculesmentioning

confidence: 99%

Förster resonance energy transfer (FRET)-based small-molecule sensors and imaging agents

et al. 2020

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“…L was gained through a typical amidation reaction [51][52][53][54]. To a solution of benzocoumarin-3carboxylic acid [55][56][57] (0.239 g, 1 mmol) in 20 mL CH 2 Cl 2 , pyridin-2-ylmethanamine (0.108 g, 1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (0.383 g, 1 mmol) and a catalytic amount of 4-(dimethylamino)pyridine (DMAP) (12 mg) were added sequentially and the mixture was stirred for 8 h. The solution was washed with water (2 × 8 mL) and dried over anhydrous sodium sulfate, and the solvent was removed under a pressure-reducing condition.…”

Section: Synthesis Of Fluorescent Ligand Lmentioning

confidence: 99%

“…Among them, a Cu 2+ -ensemble based fluorescence chemosensor features simple synthetic route, improved water solubility, a fluorescence "OFF-ON" response pattern as well as desired reversibility [44][45][46]. By the way, our group has been involved in longstanding exploration of the synthesis and application of this class of fluorescence chemosensors [47][48][49][50][51][52][53][54][55][56][57][58][59]. Herein, we designed and synthesized a novel benzocoumarin-Cu 2+ ensemble based fluorescence chemosensor for the selective detection of biothiols under simulated physiological conditions and in human urine.…”

mentioning

confidence: 99%

A Copper (II) Ensemble-Based Fluorescence Chemosensor and Its Application in the ‘Naked–Eye’ Detection of Biothiols in Human Urine

Wang

Feng

et al. 2020

Sensors

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Quick and effective detection of biothiols in biological fluids has gained increasing attention due to its vital biological functions. In this paper, a novel reversible fluorescence chemosensor (L-Cu 2+ ) based on a benzocoumarin-Cu 2+ ensemble has been developed for the detection of biothiols (Cys, Hcy and GSH) in human urine. The chemosensing ensemble (L-Cu 2+ ) contains a 2:1 stoichiometry structure between fluorescent ligand L and paramagnetic Cu 2+ . L was found to exclusively bond with Cu 2+ ions accompanied with a dramatic fluorescence quenching maximum at 443 nm and an increase of an absorbance band centered at 378 nm. Then, the in situ generated fluorescence sluggish ensemble, L-Cu 2+ , was successfully used as a chemosensor for the detection of biothiols with a fluorescence "OFF-ON" response modality. Upon the addition of biothiols, the decomplexation of L-Cu 2+ led to the liberation of the fluorescent ligand, L, resulting in the recovery of fluorescence and absorbance spectra. Studies revealed that L-Cu 2+ possesses simple synthesis, excellent stability, high sensitivity, reliability at a broad pH range and desired renewability (at least 5 times). The practical application of L-Cu 2+ was then demonstrated by the detection of biothiols in human urine sample. developing safe, highly specific and sensitive detection methods for biothiols in living systems is strongly desired in biochemistry and biomedicine research fields [14].Among various conventional methods such as electrochemical approaches [15,16], high-performance liquid chromatography (HPLC) [17,18], gas chromatography [19,20] and mass spectrometry (MS) [21], fluorescence analysis using a responsive molecular probe or chemosensor has been recognized as one of the most promising approaches due to its excellent sensitivity, selectivity, and capability of detecting analytes in live biological specimens [22][23][24][25][26]. To date, a large number of fluorescence chemosensors aiming to distinguish biothiols from other amino acids and bioactive species have been developed based on several sensing mechanisms: (1) Michael addition [27-29]; (2) cyclization with aldehyde [30,31]; (3) the cleavage of sulfonamide, sulfonate esters, selenium-nitrogen bonds and disulfide bonds [32][33][34][35][36][37][38]; (4) intramolecular elimination [39,40]. However, most organic reaction-based fluorescence chemodosimeters suffer several problems such as time-consuming synthesis and the synthesis procedure commonly requires strict reaction condition, which somehow limit the practical application in biosystems [41]. Moreover, to the best of our knowledge, few of them could achieve analyzing biothiols in body fluids, such as human urine [42,43].Recently, indicator displacement-based fluorescence chemosensor, as a new strategy, has emerged for the detection of certain biomolecules in living systems. Among them, a Cu 2+ -ensemble based fluorescence chemosensor features simple synthetic route, improved water solubility, a fluorescence "OFF-ON" response pattern as well as desi...

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A two-photon excitable and ratiometric fluorogenic nitric oxide photoreleaser and its biological applications

Cited by 64 publications

References 37 publications

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Förster resonance energy transfer (FRET)-based small-molecule sensors and imaging agents

A Copper (II) Ensemble-Based Fluorescence Chemosensor and Its Application in the ‘Naked–Eye’ Detection of Biothiols in Human Urine

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