Systematic Modifications of a Simple Tolan: Another Category of Viscosity Sensor

Hong, Jung-Ho; Ko, Min-Sung; Rao, P. Sankara; Cho, Dong-Gyu

doi:10.1021/acs.orglett.9b04050

Cited by 5 publications

(4 citation statements)

References 30 publications

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“…Based on the advantage that the fluorescence lifetime as an inherent property of a fluorophore depends only on the environment, a standard curve in solution can be used for quantitative testing at the cellular level, which is also the usual research method in the previous literature. 63,64 Furthermore, we verified that the probe lifetime is independent of temperature and viscosity (Tables S4−S6). Taken together, our data highlight that both probes Mem-C 1 C 18 and Mem-C 18 C 18 are capable of sensitively sensing environmental changes and have a large T response range, which provides opportunities for their application in FLIM.…”

Section: ■ Introductionsupporting

confidence: 57%

Polarity-Sensitive and Membrane-Specific Probe Quantitatively Monitoring Ferroptosis through Fluorescence Lifetime Imaging

Hou

et al. 2022

Anal. Chem.

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As a new form of regulated cell death, ferroptosis is closely related to various diseases. To interpret this biological behavior and monitor related pathological processes, it is necessary to develop appropriate detection strategies and tools. Considering that ferroptosis is featured with remarkable lipid peroxidation of various cell membranes, it is logical to detect membranes’ structural and environmental changes for the direct assessment of ferroptosis. For this sake, we designed novel polarity-sensitive fluorescent probes Mem-C 1 C 18 and Mem-C 18 C 18 , which have superior plasma membrane anchorage, high brightness, and sensitive responses to environmental polarity by changing their fluorescence lifetimes. Mem-C 1 C 18 with much less tendency to aggregate than Mem-C 18 C 18 outperformed the latter in high resolution fluorescence labeling of artificial vesicle membranes and plasma membranes of live cells. Thus, Mem-C 1 C 18 was selected to monitor plasma membranes damaged along ferroptosis process for the first time, in combination with the technique of fluorescence lifetime imaging (FLIM). After treating HeLa cells with Erastin, a typical ferroptosis inducer, the mean fluorescence lifetime of Mem-C 1 C 18 displayed a considerable increase from 3.00 to 4.93 ns, with a 64% increase (corresponding to the polarity parameter Δf increased from 0.213 to 0.232). Therefore, our idea to utilize a probe to quantitate the changes in polarity of plasma membranes proves to be an effective method in the evaluation of the ferroptosis process.

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Section: ■ Introductionsupporting

confidence: 57%

Polarity-Sensitive and Membrane-Specific Probe Quantitatively Monitoring Ferroptosis through Fluorescence Lifetime Imaging

Hou

et al. 2022

Anal. Chem.

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“…We believe structural novelty and diversity provide different photophysical properties and uncovers new knowledge. For example, phthalide derivatives were developed as the first viscosity sensors obtained from various tolans 10 . Although the two phenyl groups of tolans freely rotate around an acetylene axis, tolan derivatives themselves are far less suitable than phthalide derivatives.…”

Section: Figurementioning

confidence: 99%

“…For example, phthalide derivatives were developed as the first viscosity sensors obtained from various tolans. 10 Although the two phenyl groups of tolans freely rotate around an acetylene axis, tolan derivatives themselves are far less suitable than phthalide derivatives. Specifically, the fluorescence intensity of tolan derivatives decreases as the viscosity of the medium increases.…”

mentioning

confidence: 99%

Systematic derivatives of 1‐(dicyanomethylene)indan and their photophysical properties as potential viscosity sensors

Roh,

Ko,

Desale

et al. 2024

Bulletin Korean Chem Soc

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This study focuses on derivatizing 1‐(dicyanomethylene)indan as a viscosity sensor. The indan was extended with various functionalized naphthaldehydes under a push–pull design strategy. Among synthesized derivatives, salt‐capped derivatives exhibited an excellent linearity between fluorescent intensity and viscosity (R2 = 0.99), and further investigation underscores the reversible nature of fluorescence intensity changes at two temperatures as an important trait of viscosity sensors.

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“…Recently, our group recognized the fluorescent dye properties of some tolan derivatives without the help of conjugation with other types of dyes. These tolans can function as switches [3,4], sensors [5][6][7], and β-turn mimics [8] depending on various installed motifs. They also exhibit a range of fluorescence quantum yields.…”

Section: Introductionmentioning

confidence: 99%

Tuned Cd2+ Selectivity: Showcase of Electronic and Regio-Effect of π-Extended Di-2-Picolylamine-Substituted Quinoline-Based Tolans

Rao

Cho

2021

Molecules

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π-Extended di-2-picolylamine (DPA)-substituted 8-hydroxyquinoline (8-HQ) tolans (2) were synthesized for testing electronic and regio-effects. The electron-poor CN-tolan (2b) showed clear selectivity for Cd2+ (>>Zn2+) over other metal ions via turn-on fluorescence, while the electron-rich MeO-tolan (2a) displayed no clear metal selectivity. Furthermore, considering that there was no significant energy difference between the Cd2+ complexes of 1 and 2b, the intended regio-effect (7- vs. 5-substituted effect) did not induce steric hindrance. Thus, the regio-effect is mainly electronic. Considering the above, 2a and 2b constitute a complete showcase in which electronic and regio-effects modulate the metal selectivity. The fluorescence titration of 2b (10 mM) with Cd2+ showed that the limit of detection (LOD) of the Cd2+-selective 2b was 158 nM in PBS (phosphate-buffered saline) (10 mM, pH 7.2) containing 50% MeOH.

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Systematic Modifications of a Simple Tolan: Another Category of Viscosity Sensor

Cited by 5 publications

References 30 publications

Polarity-Sensitive and Membrane-Specific Probe Quantitatively Monitoring Ferroptosis through Fluorescence Lifetime Imaging

Polarity-Sensitive and Membrane-Specific Probe Quantitatively Monitoring Ferroptosis through Fluorescence Lifetime Imaging

Systematic derivatives of 1‐(dicyanomethylene)indan and their photophysical properties as potential viscosity sensors

Tuned Cd2+ Selectivity: Showcase of Electronic and Regio-Effect of π-Extended Di-2-Picolylamine-Substituted Quinoline-Based Tolans

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