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DYES AND PIGMENTS · 2024 · IF 4.1

Near-infrared probes based on the phenanthridinium for dynamic monitoring of viscosity fluctuations during mitophagy

Hong-Xia Wang,Jing-Yu Zhao,Hui Wang,Huan Ma,Jian-Feng Ge,Ru Sun

Abnormal changes in the mitochondrial microenvironment can cause a variety of diseases. Consequently, based on the twisted intramolecular charge transfer (TICT) theory, three hemicyanine fluorescent probes 1a-c were designed and developed by linking the phenanthridine group with different electron donor groups for the dynamic detection of mitochondrial viscosity in this paper. They have the advantages of near-infrared emission, excellent pH stability and viscosity sensitivity. Optical experiments showed that the maximum absorption and emission wavelengths of the probes in different solvents located at 411 − 529 nm and 623 − 684 nm with large Stokes shifts of 133 – 230 nm. In addition, when the viscosity increased from 0.89 cP to 856 cP, their fluorescence intensities in glycerol enhanced by 115-fold, 83-fold and 303-fold compared with water, respectively. The fluorescence intensities of probes showed excellent fit to the Forster Hoffmann equation, and exhibited nearly OFF-ON response to viscosity. Moreover, the probe 1a with good photostability and low cytotoxicity could target mitochondria. It was verified that 1a also could detect variation in mitochondrial viscosity during autophagy by modelling starvation and drug-induced (rapamycin and nystatin) in HeLa cells. Therefore, this study provides a useful probe for the analysis of mitophagy process in HeLa cells by the viscosity variation of mitochondria.

研究领域: 细胞生物学 · 医学 · 生物化学
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CHEMICAL ENGINEERING JOURNAL · 2021 · IF 13.273

Construction of chitosan-based fluorescent probe for real-time monitoring of viscosity changes in living cells with low cytotoxicity and high photostability

Qingyu Xu,Mingguang Ren,Keyin Liu,Xiaohui Wang,Jian-Yong Wang,Shoujuan Wang,Fangong Kong

Viscosity is a crucial factor influencing diffusion-controlled processes in biological systems. An abnormal increase or decrease in the viscosity level is closely related to various human diseases, such as malignant tumors, coronary heart disease, and cerebral thrombosis. We report a “turn-on” chitosan-based viscosity fluorescent probe (CS-V) for cell-level viscosity measurement . Under viscous conditions, the fluorescence intensity of the probe at a wavelength of 530 nm increased by approximately 56 times and was sensitive to changes in the viscosity level. The probe CS-V was constructed using chitosan (CS) with low toxicity and high biological activity, combined with mitochondrial targeting groups and luminescent groups. As the first chitosan-based probe for viscosity detection, it not only exhibited excellent selectivity and rapid response but also had lower toxicity, better biocompatibility and excellent photostability than small-molecule probes, and can be used for long time fluorescence imaging.

CAS / MDL: 98-59-9
研究领域: 生物化学 · 分子生物学 · 医学诊断
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ACS Food Science & Technology · 2021 · IF 0

Noninvasive Viscosity Detection in Beverages with an Aggregation-Induced Emission-Based Molecular Rotor

Lingfeng Xu,Ying Zou,Mei Zeng,Siqi Duan,Kui Wu,Runlin Han,Limin Liu

Noninvasive and effective viscosity inspection during the deterioration process is expected to ease the burden of foodborne illnesses, since viscosity is closely related to spoilage extent. In this study, a novel molecular rotor, DPMBEQ, was developed to monitor the beverage microenvironmental viscosity alterations to achieve food safety inspection. This rotor comprised the typical triphenylamine donor and quinolinium acceptor and displayed aggregation-induced emission features, with a large Stokes shift of 184 nm in glycerol. DPMBEQ possesses a highly sensitive response toward viscosity change and features with good photostability and high selectivity in complex media. With the assistance of the fluorescent analytical technique, DPMBEQ achieved identifying the thickening effect of food gum. More importantly, DPMBEQ was explored to visualize viscosity variations during the beverage deterioration process. We expect that our trial can facilitate the continued perfection of food analytical methods toward food quality and safety inspection.

研究领域: 食品科学 · 分析化学
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Analytical Methods · 2022 ·Vol. 14 ·期 22 ·2204-2211 · IF 3.532

Activatable molecular rotor based on bithiophene quinolinium toward viscosity detection in liquids

Lingfeng Xu,Jingyi Zhao,Fangzhi Xiong,Yanrong Huang,Yan Sui

The development of non-invasive and effective viscosity inspection methods during the liquid deterioration process is urgently needed since viscosity is one of the most important physical parameters of liquids. Methods featuring rapid detection, high sensitivity, cheap equipment, and fast result output are greatly desired. In this study, a viscosity-sensitive molecular rotor (BTPEQ) with a large Stokes shift (187 nm), and long emission wavelength (648 nm) has been developed. The rotor is comprised of a bithiophene donor and quinolinium acceptor, and displays a typical twisted intramolecular-charge transfer (TICT) feature, with good photostability, selectivity, and universality in various commercial liquids. With the aid of BTPEQ, the thickening effects of liquid thickeners can be determined. More importantly, BTPEQ was explored to visualize the viscosity variations in liquids at different metamorphic stages, and it was found that the viscosity level in microenvironments is highly dependent on the liquid food metamorphic period. It is worth noting that this approach can facilitate the continued perfection of fluorescent analytical methods for food quality and safety inspection.

研究领域: 化学 · 食品科学 · 分析化学
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Sensors & Diagnostics · 2022 ·Vol. 2 ·期 1 ·168-175 · IF 0

Salicylaldehyde-based molecular sensor with one facile step toward visual detection of viscosity

Lingfeng Xu,Yuefeng Wang,Chuan Jiang,Yanrong Huang,Genhe He,Limin Liu

Liquid safety has become one of the urgent affairs in global public health studies, and a noninvasive and effective viscosity inspection method is expected to ease the burden of continuously increasing health problems. In this study, one kind of activatable molecular sensor (DTPMP) based on a salicylaldehyde derivate has been synthesized via the Schiff base condensation reaction. This sensor is comprised of a donor–acceptor conjugated structure. We proposed the viscosity of the liquid microenvironment as a marker, and a rotatable conjugate structure was utilized as the recognition site. The molecular sensor was synthesized in a one-step facile way, and DTPMP displayed a longer emission wavelength and larger Stokes shift (142.5 nm in water, 116.8 nm in glycerol), which endows the sensor with the capacity of avoiding auto-fluorescence and achieving high signal-to-noise ratio imaging. The rotation of aromatic rings in DTPMP is restricted in a high-viscosity microenvironment, with the gradually increasing fluorescence emission signal at 532 nm. Moreover, the DTPMP sensor exhibits high adaptability, selectivity, sensitivity, and good photostability in various commercial liquids. Significantly, this sensor has successfully been applied not only in the determination of the thickening effects of food gum but also in the detection of viscosity enhancement during the liquid food spoilage process, which may be helpful in screening the metamorphic stage. We expected that this unique strategy will reinvigorate the continued perfection of the fluorescence technique toward liquid safety investigation.

研究领域: 分析化学 · 生物医学工程 · 公共健康
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Journal of Food Measurement and Characterization · 2023 ·Vol. 17 ·期 4 ·3918-3926 · IF 3.4

Polydatin-based natural product as an activatable molecular sensor toward viscosity detection in liquid

Xu Lingfeng,Zou Ying,Wu Kui,Han Runlin,Huang Yanrong,Yi Xiuguang

Effective and non-invasive inspection method toward viscosity is expected to ease the burden of continued increased health problems worldwide. Herein, we proposed that viscosity is one of the most important markers in the liquid microenvironment. Then, a natural product was further developed from resveratrol derivate, polydatin, as an activatable molecular sensor for monitoring liquid micro-environmental viscosity alterations for metamorphic extent determination. This natural molecular sensor was constructed by the single double bond alternating conjugate structure, which can rotate freely in the low viscosity media, and in the highly viscous media, bright fluorescent signals are specifically activated (around 383 nm, 53-fold), endowing the natural sensor with the capacity to avoid autofluorescence from the additives and achieving high signal-to-noise ratio imaging. With the lower detection limit 1.125 cP, the sensor polydatin exhibits higher viscosity sensitive coefficient (0.60), and 75.5 nm of Stokes shift was found in the distilled water. Afterward, polydatin achieved non-invasively identifying the thickening effects of food thickeners. In addition, the capability of polydatin to evaluate the deterioration extent of liquids with viscosity as a robust marker was explored. It was found that the viscosity level in microenvironments is highly dependent on the liquid food metamorphic period. The fluorescent intensity increment and viscosity value changes were fitted into a linear equation. We expected that this approach would reinvigorate the fluorescent analytical methods toward liquid safety inspection.

研究领域: 生物化学 · 分析化学 · 食品科学
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DYES AND PIGMENTS · 2024 · IF 4.1

Molecular rotor bearing naphthol hydrazone Schiff base for sensing viscosity changes in solutions and biosystems

Yongdi Liang,Tingting Pan,Qiang Li,Brian Musikavanhu,HaoChen Wang,Quanhong Ma,Zhaoli Xue,Lei Feng,Long Zhao

Viscosity is an important parameter in cells since it is closely related to a few severe human diseases. The development of fluorescent probes that can detect changes in intracellular viscosity has become an effective tool for monitoring the intracellular microenvironment. In this work, an efficient Schiff base molecular rotor, NaForm , is designed and synthesized by covalently linking a naphthol hydrazine derivative with the methyl 4-formylbenzoate group for the optical detection of viscosity changes. By increasing the viscosity of solvents, a significant enhancement of fluorescence for the probe at the yellow-green channel is observed. The probe also exhibits the advantages of high sensitivity and large Stokes shift of 128 nm. Both theoretical calculations and spectroscopic measurements suggest that the inhibition of chemical bond rotation between the hydrazine and the benzene ring leads to such a profound turn-on response. The successful applications of the probe in HeLa cells and zebrafish sufficiently demonstrate the privilege of NaForm as a practical viscosity-dependant chemosensor in aqueous samples and organisms. This chemosensor holds great promise for studying intracellular viscosity effects in various biological contexts.

研究领域: 生物化学 · 分析化学 · 细胞生物学
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Scientific Reports · 2024 ·Vol. 14 ·期 1 ·1-11 · IF 3.8

Golgi-targeting viscosity probe for the diagnosis of Alzheimer’s disease

Wu Wenjing,Zhao Lingyu,Zhang Yuanyuan,Wei Jinchao,Han Juanjuan,Zhang Yangyang,Zhao Zhenwen

Early diagnosis and intervention of Alzheimer’s disease (AD) are particularly important to delay the pathological progression. Although fluorescent probes have been widely employed for investigating and diagnosing AD, their biological applications are significantly restricted due to the low penetration ability of the blood–brain barrier (BBB) in vivo. In this study, we reported the first Golgi-targeted two-photon (TP) fluorescent probe, DCM-DH, for detecting viscosity in the Golgi apparatus. The probe was rationally designed to exhibit superior analytical performance including high sensitivity, specific Golgi-targeting, efficient BBB penetration ability, and deep tissue penetration (247 μm) in the brains of AD model mice. Using the probe, we demonstrated that the fluorescence intensity in the human liver cancer cell (HepG2 cells) was higher than that of human normal liver cell (LO2 cells), and the brain viscosity of AD model mice increased significantly. We anticipate that this competent tool could be easily extended to other AD biomarkers for fundamental research on this detrimental disease.

研究领域: 生物医学 · 神经科学 · 分子影像学
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Materials Advances · 2022 ·Vol. 3 ·期 8 ·3545-3553 · IF 0

A near-infrared intelligent molecular rotor with aggregation induced-emission for viscosity detection of liquids

Lingfeng Xu,Yanrong Huang,Xinkang Peng,Kui Wu,Chunfang Huang,Limin Liu

Liquid safety has become a widespread issue, due to the potential adverse effects on public health. To the best of our knowledge, viscosity might be a representative physical parameter during the food deterioration process. Monitoring viscosity variation during the food spoilage process is of great importance, thus a convenient inspection technique with rapid detection, high sensitivity, a simple detection process, and fast results output needs to be found. Herein, a near-infrared intelligent molecular rotor (DPADQ) is proposed to describe the micro-viscosity via a fluorescence analytical method with a typical turn-on fluorescence signal. This molecular rotor has a flexible donor–π–acceptor conjugated structure and forms a typical twisted intramolecular charge transfer system. DPADQ features a large Stokes shift (203 nm in the highly viscous glycerol system), longer wavelength emission (725 nm) and typical aggregation-induced emission character. Due to its excellent optical properties, especially the viscosity-sensitive coefficient of 0.55, a thickening effect with various food gums was determined. And the capability of DPADQ to evaluate the spoilage extent of beverages with viscosity variations as a robust indicator was explored as well. The results indicated that a linear relationship can be found between the viscosity variations and fluorescence fluctuations. This strategy can motivate us to design multi-functional molecular tools for food safety inspection with the use of the fluorescence analytical technique.

研究领域: 食品安全 · 光学检测 · 分子设计
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ANALYST · 2022 ·Vol. 147 ·期 18 ·4132-4140 · IF 5.227

Triphenylamine indanedione as an AIE-based molecular sensor with one-step facile synthesis toward viscosity detection of liquids

Lingfeng Xu,Fangzhi Xiong,Minqing Kang,Yanrong Huang,Kui Wu

Viscosity is one of the most important physical parameters in a liquid, noninvasive, and effective viscosity inspection method toward liquid safety that needs to be developed urgently. In this study, two kinds of novel molecular sensors, namely, DPBID and DPTMID, were strategically constructed by the triphenylamine indanedione derivates; the rotatable conjugate structure was utilized as the recognition site and fluorescence quencher. This couple of molecular sensors was synthesized in a one-step facile manner. DPTMID displayed longer emission wavelength and larger Stokes shift (195 nm in water, 138 nm in glycerol) with a narrower energy band. Moreover, DPTMID exhibited high selectivity, sensitivity, and significant fluorescence signal enhancement toward a higher viscous microenvironment. The molecular sensor displayed good photostability, selectivity, and universality in various commercial liquids and featured with typical aggregation-induced emission (AIE). With the aid of DPTMID, the thickening effects of liquid thickeners can be captured. More importantly, DPTMID was explored to visualize the viscosity fluctuations during the metamorphic stages of liquids, and it was found that the microenvironment viscosity level is closely related to the spoilage degree of liquids. The method with rapid detection, high sensitivity, cheap equipment, and fast results output toward food quality and safety inspection can be achieved through this study.

研究领域: 化学 · 材料科学 · 食品安全
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2025 · IF 4.6

Mitochondria-immobilized fluorescent probes for viscosity and cellular imaging

Lingchen Wang,Wenqiang Song,Fengxia Li,Shaomin Shuang,Shengmei Song,Yunfeng Yang,Yue Huang,Kun Wang

A mitochondria-immobilized fluorescent probe Mito-CDM was designed and synthesized for viscosity sensing via the twisted intramolecular charge transfer (TICT) mechanism. The N , N -diethylaminophenyl group is the viscosity-sensitive unit in the prepared Mito-CDM molecular structure, while the pyridinium cation is the mitochondria-targeting group that is responsible for monitoring mitochondrial viscosity. As the viscosity increased from 0.55 cp (0% glycerol) to 950 cp (100% glycerol), the fluorescence intensity of Mito-CDM at 586 nm enhanced gradually and there is a good linear relationship between fluorescence intensity and viscosity ( n  = 11, R 2  = 0.9957). In high-viscosity media, Mito-CDM exhibits a 166-fold fluorescence enhancement at 586 nm. It is crucial to note that the benzyl chloride group has the ability to react with highly reactive thiols on mitochondrial proteins, which enables Mito-CDM to be immobilized on mitochondria for extended periods. Additionally, Mito-CDM was successfully used to monitor mitochondrial viscosity changes during nystatin and lipopolysaccharide-induced inflammation in HeLa cells.

研究领域: 生物化学 · 细胞生物学 · 分析化学 · 生物物理 · 分子成像
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MOLECULES · 2024 ·Vol. 29 ·期 9 ·1993 · IF 4.2

A Red-Emission Fluorescent Probe with Large Stokes Shift for Detection of Viscosity in Living Cells and Tumor-Bearing Mice

Beilei Wang,Dezhi Yang,Xiaohong Zhong,Yuhui Liu,Yong Huang

Abnormal viscosity is closely related to the occurrence of many diseases, such as cancer. Therefore, real-time detection of changes in viscosity in living cells is of great importance. Fluorescent molecular rotors play a critical role in detecting changes in cellular viscosity. Developing red emission viscosity probes with large Stokes shifts and high sensitivity and specificity remains an urgent and important topic. Herein, a novel viscosity-sensitive fluorescent probe (TCF-VIS1) with a large stokes shift and red emission was prepared based on the 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF) skeleton. Due to intramolecular rotation, the probe itself does not fluorescence at low viscosity. With the increase in viscosity, the rotation of TCF-VIS1 is limited, and its fluorescence is obviously enhanced. The probe has the advantages of simple preparation, large Stokes shift, good sensitivity and selectivity, and low cytotoxicity, which make it successfully used for viscosity detection in living cells. Moreover, TCF-VIS1 showed its potential for cancer diagnosis at the cell level and in tumor-bearing mice by detecting viscosity. Therefore, the probe is expected to enrich strategies for the detection of viscosity in biological systems and offer a potential tool for cancer diagnosis.

研究领域: 生物化学 · 分子生物学 · 癌症研究 · 荧光光谱学 · 生物医学工程
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