A fluorescent pH probe for acidic organelles in living cells

Chen, Jyun-Wei; Chen, Chih‐Ming; Chang, Cheng-Chung

doi:10.1039/c7ob02037f

Cited by 32 publications

(14 citation statements)

References 59 publications

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“…At present, one of the major problems encountered in optimizing optical sensors is achieving the right balance between the presence of the fluorogenic unit (soluble in organic solvents) and the water solubility. Water-soluble pH sensors may provide a diagnostic tool [22,23] by measuring intracellular pH gradient and evaluating the differences in pH between normal and altered cells.…”

Section: Introductionmentioning

confidence: 99%

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

et al. 2020

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A new 5-(4-((2-(benzothiazole-2-carbonyl)hydrazono)methyl)-3-hydroxyphenoxy)-N,N,N-trimethylpentan-1-aminium bromide (BTABr) fluorescent and colorimetric pH probe was easily synthesized by the condensation reaction of benzothiazole-2-carbohydrazide with 5-(4-formyl-3-hydroxyphenoxy)-N,N,N-trimethylpentan-1-aminium bromide. The benzothiazole moiety provided the emissive part of the molecule and the charged trimethyl amino group guaranteed outstanding solubility in water, for an organic molecule. pH titration experiments indicated that the probe is useful for monitoring acidic and alkaline solutions, turning reversibly in color/fluorescence just at a neutral pH value. Naked-eye colorimetric response was observed both in solution and in the solid state. In addition, the probe showed high stability and selectivity and large Stokes shifts. Because of these features, BTABr can potentially work as an on-off real-time pH sensor for intracellular pH imaging. The crystal structure of BTABr examined by single-crystal analysis showed a planar geometry of the molecule and confirmed the presence of a molecular stacking between molecules joined in a complex tridimensional hydrogen bonding pattern.

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Section: Introductionmentioning

confidence: 99%

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

et al. 2020

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“…Usually, these types of dyes are emissive in organic solvents as well as in the solid state, even though they exhibit a π-stacking pattern. Therefore, CSP should not be regarded as an AIEgen but rather as a "nonresonant exciton system" facilitating the AIEE and causing the CSP-containing nanoparticles to become emitter FONs [36][37][38]. Nevertheless, this result provides evidence that CSP possesses the emissive-aggregate potential to form FONs, which is the reason for the brighter fluorescence of powdered CSP.…”

Section: Pet and Aieementioning

confidence: 91%

Fabrication of Double Emission Enhancement Fluorescent Nanoparticles with Combined PET and AIEE Effects

Chang

2020

Molecules

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The major challenge in the fabrication of fluorescent silica nanoparticles (FSNs) based on dye-doped silica nanoparticles (DDSNs) is aggregation-caused fluorescence quenching. Here, we constructed an FSN based on a double emission enhancement (DEE) platform. A thio-reactive fluorescence turn-on molecule, N-butyl-4-(4-maleimidostyryl)-1,8-naphthalimide (CS), was bound to a silane coupling agent, (3-mercaptopropyl)-trimethoxysilane (MPTMS), and the product N-butyl-4-(3-(trimethoxysilyl-propylthio)styryl)-1,8-naphthalimide (CSP) was further used to fabricate a core–shell nanoparticle through the Stöber method. We concluded that the turn-on emission by CSP originated from the photoinduced electron transfer (PET) between the maleimide moiety and the CSP core scaffold, and the second emission enhancement was attributed to the aggregation-induced emission enhancement (AIEE) in CSP when encapsulated inside a core–shell nanoparticle. Thus, FSNs could be obtained through DEE based on a combination of PET and AIEE effects. Systematic investigations verified that the resulting FSNs showed the traditional solvent-independent and photostable optical properties. The results implied that the novel FSNs are suitable as biomarkers in living cells and function as fluorescent visualizing agents for intracellular imaging and drug carriers.

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“…Using this technique, it was proved that, in acidic solutions, OH • radicals are formed by the Fenton reaction, whereas in neutral solutions, where pH > 6, the product is Fe IV =O aq [ 20 ]. This proves that the Fenton reaction under physiological conditions does not form OH • radicals: However, this statement is not correct for the acidic organelles, e.g., lysosomes [ 21 ] and some peroxisomes [ 22 ]. This conclusion is correct for reactions of Fe(H 2 O) 6 2+ , but not for all Fenton-like reactions of Fe II L m , as seen below.…”

Section: The Fenton Reaction Is (Fe(h 2 O) ...mentioning

confidence: 99%

What Are the Oxidizing Intermediates in the Fenton and Fenton-like Reactions? A Perspective

Meyerstein

2022

Antioxidants

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The Fenton and Fenton-like reactions are of major importance due to their role as a source of oxidative stress in all living systems and due to their use in advanced oxidation technologies. For many years, there has been a debate whether the reaction of FeII(H2O)62+ with H2O2 yields OH• radicals or FeIV=Oaq. It is now known that this reaction proceeds via the formation of the intermediate complex (H2O)5FeII(O2H)+/(H2O)5FeII(O2H2)2+ that decomposes to form either OH• radicals or FeIV=Oaq, depending on the pH of the medium. The intermediate complex might also directly oxidize a substrate present in the medium. In the presence of FeIIIaq, the complex FeIII(OOH)aq is formed. This complex reacts via FeII(H2O)62+ + FeIII(OOH)aq → FeIV=Oaq + FeIIIaq. In the presence of ligands, the process often observed is Ln(H2O)5−nFeII(O2H) → L•+ + Ln−1FeIIIaq. Thus, in the presence of small concentrations of HCO3− i.e., in biological systems and in advanced oxidation processes—the oxidizing radical formed is CO3•−. It is evident that, in the presence of other transition metal complexes and/or other ligands, other radicals might be formed. In complexes of the type Ln(H2O)5−nMIII/II(O2H−), the peroxide might oxidize the ligand L without oxidizing the central cation M. OH• radicals are evidently not often formed in Fenton or Fenton-like reactions.

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A fluorescent pH probe for acidic organelles in living cells

Cited by 32 publications

References 59 publications

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

A Highly Water-Soluble Fluorescent and Colorimetric pH Probe

Fabrication of Double Emission Enhancement Fluorescent Nanoparticles with Combined PET and AIEE Effects

What Are the Oxidizing Intermediates in the Fenton and Fenton-like Reactions? A Perspective

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