Quinolizinium-based tunable pH fluorescent probes for imaging in live cells

Sit, Hoi-Yi; Deng, Jie‐Ren; Chan, Willy; Ko, Ben C.B.; Wong, Man Leung

doi:10.1016/j.dyepig.2022.110541

Cited by 10 publications

(3 citation statements)

References 85 publications

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“…Fluorescent tunable materials have been extensively of concern due to their potential applications in bioimaging, immunoassay, fluorescent probes, and display devices. Typically, groups with electron donating or withdrawing properties are introduced into p‐conjugated aromatic rings by organic synthesis methods to obtain different fluorescent colors 1–4 . Another method is to prepare inorganic phosphor by high‐temperature calcination and combine them with an organic binder to obtain luminescent material.…”

Section: Introductionmentioning

confidence: 99%

“…Typically, groups with electron donating or withdrawing properties are introduced into p-conjugated aromatic rings by organic synthesis methods to obtain different fluorescent colors. [1][2][3][4] Another method is to prepare inorganic phosphor by high-temperature calcination and combine them with an organic binder to obtain luminescent material. The disadvantage is that the phosphor dispersion and the luminous efficiency could be improved.…”

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confidence: 99%

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A waterborne polyurethane‐based fluorescent tunable carbon quantum dot

Cheng,

Hu,

Chen

et al. 2024

Journal of Polymer Science

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Fluorescent tunable materials have potential applications in lighting, display, anti‐counterfeiting, biological probes, and so on. Herein, carbon quantum dots (CQDs) with blue fluorescence (BCDs), and yellow fluorescence (YCDs) were synthesized by solvothermal method using bio‐based citric acid and lignin as carbon sources, respectively. BCDs and YCDs were anchored on polyurethane chains to prepare waterborne polyurethane‐based blue fluorescent carbon quantum dots (BCDs1.0‐WPU) and waterborne polyurethane‐based yellow fluorescent carbon quantum dots (YCDs1.0‐WPU), respectively. Compared with the corresponding BCDs and YCDs, the fluorescence intensity of both BCDs1.0‐WPU and YCDs1.0‐WPU is markedly enhanced, and the emission peaks obviously show a hypochromatic shift. A waterborne polyurethane‐based fluorescent tunable carbon quantum dots (BCDsxYPDs1‐x‐WPU) is prepared by mixing the ratio of BCDs1.0‐WPU and YCDs1.0‐WPU with the RGB method. It is noteworthy that BCDsxYCDs1‐x‐WPU not only achieves a fluent change of fluorescence from blue to yellow but also emits strong white fluorescence (CIE coordinates: X = 0.28, Y = 0.32). The absolute value of the Zeta potential of BCDsxYCDs1‐x‐WPU is greater than 40, indicating good storage stability. Furthermore, the thermal decomposition temperature is above 225 °C, implying good thermal stability. Furthermore, BCDsxYCDs1‐x‐WPU uses water as a continuous phase and has potential applications in environmentally friendly luminescence, anti‐counterfeiting and biological probes.

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Section: Introductionmentioning

confidence: 99%

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confidence: 99%

A waterborne polyurethane‐based fluorescent tunable carbon quantum dot

Cheng,

Hu,

Chen

et al. 2024

Journal of Polymer Science

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“…Compared to common neutral fluorescent scaffolds, cationic heterocycles, such as quinolinium and quinolizinium, have attracted attention because they provide opportunities for solving the solubility problem. Nevertheless, studies on the use of quinolinium and quinolizinium as agents for imaging intracellular organelles, such as mitochondria, [28][29][30] endoplasmic reticula, and lysosomes, [31,32] are limited.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Intracellular Localization of 5,6‐Disubsutituted Pyrido[1′,2′;2,3]imidazo[5,1‐a]isoquinolinium Iodides

Kawakubo,

Inoh,

Inaguma

et al. 2023

ChemistrySelect

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Novel pyrido[1’,2’;2,3]imidazo[5,1‐a]isoquinolinium iodides independently substituted at their 5‐ and 6‐position were prepared from 5‐iodopyrido[1’,2’;2,3]imidazo[5,1‐a]isoquinolinium iodides using Suzuki‐Miyaura cross‐coupling reaction. The desired coupling products had cationic extended π‐conjugated skeletons and fluoresced strongly in the 420–460 nm region in methanol. In cell staining assay, the 5‐styryl‐substituted compounds, which showed lower fluorescence quantum yields in methanol, emitted high fluorescence in the intracellular environment and were specifically distributed to the endoplasmic reticulum.

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Isoindolium‐Based Allenes: Reactivity Studies and Applications in Fluorescence Temperature Sensing and Cysteine Bioconjugation

Wa-Yi

Cui

et al. 2023

Angewandte Chemie

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The reaction of a series of electron‐deficient isoindolium‐based allenes with sulfhydryl compounds has been studied, leading to the formation of isoindolium‐based vinyl sulfides. The vinyl sulfides generated could be readily converted into the corresponding indanones and amines upon heating at 30–70 °C with good yields up to 61 %. The thermal cleavage reaction of vinyl sulfides was further studied for developing temperature‐sensitive systems. Notably, a novel FRET‐based fluorescent temperature sensor was designed and synthesized for temperature sensing at 50 °C, giving a 6.5‐fold blue fluorescence enhancement. Moreover, chemoselective bioconjugation of cysteine‐containing peptides with the isoindolium‐based allenes for the construction of multifunctional peptide bioconjugates was investigated. Thermal cleavage of isoindoliums on the modified peptides at 35–70 °C gave indanone bioconjugates with up to >99 % conversion. These results indicated the biocompatibility of this novel temperature‐sensitive reaction.

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Quinolizinium-based tunable pH fluorescent probes for imaging in live cells

Cited by 10 publications

References 85 publications

A waterborne polyurethane‐based fluorescent tunable carbon quantum dot

A waterborne polyurethane‐based fluorescent tunable carbon quantum dot

Synthesis and Intracellular Localization of 5,6‐Disubsutituted Pyrido[1′,2′;2,3]imidazo[5,1‐a]isoquinolinium Iodides

Isoindolium‐Based Allenes: Reactivity Studies and Applications in Fluorescence Temperature Sensing and Cysteine Bioconjugation

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