A novel xanthylene-based effective mitochondria-targeting ratiometric cysteine probe and its bioimaging in living cells

Yang, Xiu-Zhi; Wei, Xue-Rui; Sun, Rong; Xu, Yu-Jie; Ge, Jian‐Feng

doi:10.1016/j.talanta.2019.120580

Cited by 20 publications

(7 citation statements)

References 34 publications

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“…The mechanism by which the acrylates work as the responsive groups to Cys is as follows: Michael addition of Cys to the acrylates to yield the thioether intermediates, which are intramolecularly cyclized to give lactams and to release free fluorophores. ,,− To further rationalize the sensing mechanism of SDP-A toward Cys, we carried out the related product analysis by HRMS (ESI) and 1 H NMR. Upon addition of significant excess of Cys, the molecular ion peak ([M] + ) of the probe SDP-A , found as 425.1317 ( m / z ) (Figure S7A), almost disappeared along with appearance of two new signal peaks, corresponding to the free fluorophore SDP at 371.1212 ( m / z ) and the thioether intermediate at 546.1513 ( m / z ) (Figure S7B).…”

Section: Resultsmentioning

confidence: 99%

Cooperation of ESIPT and ICT Processes in the Designed 2-(2′-Hydroxyphenyl)benzothiazole Derivative: A Near-Infrared Two-Photon Fluorescent Probe with a Large Stokes Shift for the Detection of Cysteine and Its Application in Biological Environments

et al. 2020

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A rationally designed near-infrared two-photon fluorescent probe (SDP-A) for selectively detecting cysteine (Cys) has been developed based on a newly designed conjugation-enhanced 2-(2′hydroxyphenyl)benzothiazole derivative as the fluorophore, an acrylate moiety as the Cys reaction site, and an N-methylpyridinium scaffold as both the unit of organelle targeting and improving water solubility. The probe SDP-A alone essentially emitted no fluorescence, whereas it achieved a superb near-infrared fluorescence emission (713 nm) enhancement within 15 min with a significant Stokes shift (302 nm) in the presence of Cys. The photoluminescence mechanism of the probe SDP-A toward Cys was modulated by excited-state intramolecular proton transfer (ESIPT) and intramolecular charge transfer (ICT) processes. It exhibited high selectivity and sensitivity (LOD = 102 nM) for monitoring Cys over other analytes such as Hcy/GSH/H 2 S owing to a specific conjugate addition−cyclization reaction between Cys and the acrylate moiety. More importantly, the released fluorophore SDP exhibits elevated quantum yields (1.52−18.17%) in different solvents and strong two-photon excited fluorescence with a sizeable two-photon action cross-section (Φ) of 213.5 GM at 820 nm in acetonitrile−PBS medium, which is highly desirable for two-photon fluorescence imaging of the living samples. Therefore, SDP-A was successfully applied to the imaging of Cys in live cells, zebrafish, mouse brain, and abdominal cavity down to a depth of more than 200 μm using a one/two-photon fluorescence microscope.

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Section: Resultsmentioning

confidence: 99%

Cooperation of ESIPT and ICT Processes in the Designed 2-(2′-Hydroxyphenyl)benzothiazole Derivative: A Near-Infrared Two-Photon Fluorescent Probe with a Large Stokes Shift for the Detection of Cysteine and Its Application in Biological Environments

et al. 2020

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“…In fact, replacement of the azo substitution for another diethylamino in 132 increased the quantum yield to 0.39 in PBS. [181] Despite the charged core oxygen atom in this molecule, mitochondrial accumulation was also ensured via pyridinium cation substitution on the amine on position 9. These peripheral motifs resulted in a significant red shift when compared to 131 (λ abs/ em max = 365/500 and 590/605 nm for 131 and 132 in PBS buffer, respectively) and small Stokes shift (Δλ = 420.23 cm À 1 ).…”

Section: Xanthenesmentioning

confidence: 98%

Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

Crawford

Dimitriadi

Bassin

et al. 2022

Chemistry A European J

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The last decade has seen an increasingly large number of studies reporting on the development of novel small organic conjugated systems for mitochondrial imaging exploiting optical signal transduction pathways. Mitochondria are known to play a critical role in a number of key biological processes, including cellular metabolism. Importantly, irregularities on their working function are nowadays understood to be intimately linked to a range of clinical conditions, highlighting the importance of targeting mitochondria for therapeutic benefits. In this work we carry out an in‐depth evaluation on the progress to date in the field to pave the way for the realization of superior alternatives to those currently existing. The manuscript is structured by commonly used chemical scaffolds and comprehensively covers key aspects factored in design strategies such as synthetic approaches as well as photophysical and biological characterization, to foster collaborative work among organic and physical chemists as well as cell biologists.

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“…19 2.1 Designing mitochondria-targeting ratiometric uorescent probes Since the mitochondrial membrane typically has a potential of −180 mV, this property is employed to direct lipophilic positively charged probes into the mitochondria. 20 The common mitochondrial-targeting units include the quaternized pyridine moiety, 21 triphenylphosphonium (TPP), 22,23 indole, 24 cyanine, 25,26 pyridinium, 27,28 and rhodamine 29 (Fig. 2a).…”

Section: Design Principlesmentioning

confidence: 99%

“…8 , Table 1 ). 21 The probe 4 containing an acryloyl moiety (responsive site for cysteine) and a benzyl group (for easy distribution in the mitochondria) showed strong red fluorescence at λ em = 605 nm ( λ ex = 490 nm). In the presence of cysteine, probe 4 underwent ratiometric fluorescence change with the formation of new emission maxima at 540 nm and the simultaneous decrease in emission intensity at 605 nm.…”

Section: Mitochondria-targeting Ratiometric Fluorescent Probesmentioning

confidence: 99%

Organelle-targeting ratiometric fluorescent probes: design principles, detection mechanisms, bio-applications, and challenges

et al. 2023

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A novel xanthylene-based effective mitochondria-targeting ratiometric cysteine probe and its bioimaging in living cells

Cited by 20 publications

References 34 publications

Cooperation of ESIPT and ICT Processes in the Designed 2-(2′-Hydroxyphenyl)benzothiazole Derivative: A Near-Infrared Two-Photon Fluorescent Probe with a Large Stokes Shift for the Detection of Cysteine and Its Application in Biological Environments

Cooperation of ESIPT and ICT Processes in the Designed 2-(2′-Hydroxyphenyl)benzothiazole Derivative: A Near-Infrared Two-Photon Fluorescent Probe with a Large Stokes Shift for the Detection of Cysteine and Its Application in Biological Environments

Mitochondrial Targeting and Imaging with Small Organic Conjugated Fluorophores: A Review

Organelle-targeting ratiometric fluorescent probes: design principles, detection mechanisms, bio-applications, and challenges

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