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ANALYST · 2016 ·Vol. 141 ·期 15 ·4676-4684 · IF 4.033

Monitoring drug–lipid membrane interactions via a molecular rotor probe

Qinqin Xu,Tao Zhao,Zhihua Sun

Molecular rotors are fluorescent molecules with a viscosity-sensitive fluorescence quantum yield that are often used to measure viscosity changes in biological membranes. Herein, we report the use of a lipophilic molecular rotor probe to monitor the interactions between the local anesthetic tetracaine (TTC) and small unilamellar vesicles (SUVs) in a label-free manner. The probe was developed by modifying the fluorescent molecular rotor CCVJ with an amphiphilic anchor group that enables adequate integration of the rotor group into the hydrophobic core of lipid bilayers. The temperature-dependent profile of the quantum yield of the probe clearly exhibited the subtransition, pretransition and main phase transition of the lipid bilayers as drastic changes in the activation energies. The temperature-TTC phase diagrams were determined based on an Arrhenius fitting. The results show that TTC has a significant chain ordering effect on liquid-crystalline phase lipids compared to solid-gel phase lipids, especially subgel phase lipids. A TTC-induced interdigitated gel (LβI) phase appeared at the pretransition temperature. The LβI phase spread both its ends in a TTC-dependent fashion, and the low-temperature end merged to the subtransition at a TTC concentration of 25 mM. Adding cholesterol (CHOL) to the SUVs stabilizes the LβI phase and reduces the insertion of TTC into the bilayers. The paper demonstrates that our method is highly sensitive to the microenvironment of the lipid membrane, providing a facile and efficient new tool to study drug–membrane interactions. Also, molecular rotors may potentially be exploited as screen probes for drug development and analysis.

研究领域: 生物物理学 · 药理学
✓ 已验证 DOI PubMed 高影响因子
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ANALYTICA CHIMICA ACTA · 2021 · IF 6.558

A novel near-infrared viscosity probe based on synergistic effect of AIE property and molecular rotors for mitophagy imaging during liver injury

Chao Peng,Xinyu Ma,Dan Lin,Xiaowen Feng,Huan Yu,Yinhui Li

Mitophagy , a specialized form of autophagy, holds the key to cellular metabolism and physiology. Viscosity is a significant marker for visualization of the mitophagy process in real-time. Hence, development of well-performing viscosity probe is beneficial to study mitophagy-related dynamic physiological and pathological processes. Here, a new strategy was proposed by combination of AIE property and molecular rotors to design novel viscosity probe. The probe named TPA-Py was obtained by Knoevenagel condensation reaction of AIE unit and pyridine salt, which giving the probe excellent near-infrared emission, good water-solubility and mitochondrial targeting ability. Most importantly, TPA-Py owns two rotatable parts of triphenylamine and double bond , enabling the probe to equip with AIE property and sensitive recognition units for viscosity. With the environmental viscosity increasing, the rotation of the molecular rotor and the AIE unit is restricted effectively, the probe displayed strong fluorescence. Then, TPA-Py was successfully employed for monitoring the mitophagy process in A549 cells by imaging viscosity alterations. As mitophagy constitutes an important consideration in the pathogenesis of drug-induced liver injury, TPA-Py was also applied to explore the variation of viscosity in production and remediation pathways of APAP-induced liver injury. These results demonstrated that TPA-Py was a highly sensitive viscosity probe which holds great potential of biological applications.

研究领域: 生物化学 · 医学影像 · 细胞生物学
✓ 已验证 DOI 高影响因子
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Analytical Methods · 2021 ·Vol. 13 ·期 28 ·3181-3186 · IF 2.896

Real-time imaging of viscosity in the mitochondrial matrix by a red-emissive molecular rotor

Lin Yuan,Dong Wang,Shan Shan,Juan Chen,Wei Huang,Guangmei Han,Xiaohe Tian,Ruilong Zhang,Zhongping Zhang,Zhengjie Liu

Mitochondrial matrix contains numerous metabolism-related proteins/enzymes and nucleic acids, which play key roles in the process of energy generation and signal transduction. The fluctuations in mitochondrial biomacromolecular levels lead to the changes in the mitochondrial matrix viscosity; therefore, real-time measuring the mitochondrial matrix viscosity is of great significance for the in-depth understanding of the mitochondrial physiology and pathobiology. However, investigations are limited due to the lack of a mitochondrial matrix-specific molecular rotor. Herein, we report a design of a molecular rotor that is specifically enriched in the mitochondrial matrix. The red fluorescence of the rotor switches on when the viscosity increases, enabling the real-time monitoring of the viscosity change therein. Interestingly, the rotor showed non-fluorescence behaviour in the liposome (mimicking membrane structure), avoiding fluorescence interference from the mitochondrial bilayer membrane. Super-resolution imaging reveals that the viscosity is uneven in an individual mitochondrion.

研究领域: 细胞生物学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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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
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Analytical Methods · 2022 ·Vol. 15 ·期 3 ·361-367 · IF 3.532

Highly selective and discriminative detection of small alcohols based on a dual-emission macrocyclic samarium complex

Chengjian Zhang,Sichen Li,Ruijie Zheng,Shengdi Tai,Kang Yang,Kun Zhang

Lower alcohols (C1–C7) have a close relationship with our lives and some of them are harmful to our body's health. For example, liquor mixed with a tiny amount of methanol is harmful to our health. Much of this study is about identifying one or two low-level alcohols. How to detect low-level alcohol and high-throughput and distinguish between analogues of alcohol remains a tremendous challenge. In this study, a new large ring Schiff base Sm(III) complex (Sm-2r) is synthesized with a double emission matrix using the template method. Its dynamic imine bond (CN) and organic ligands (H2L2r) with molecular rotor properties can respond to changes in viscosity and polarity in external environments. The PCA method is used to turn the data matrix into a fingerprint spectrum to distinguish different alcohols (C1–C7). Sm-2r enables the quantization of cyclopropyl and glycerol. Linear ranges of cyclopropanol and glycerol are 0–9.0% and 0–3.0% (v/v), respectively. In addition, Sm-2r has an excellent ability to distinguish the mixtures of n-PrOH and i-PrOH, C5H9OH and C6H11OH, n-PeOH and n-HeOH, 1,3-PDO and 1,2-PDO, MeOH and EtOH, 1,2-EG and 1,2-PDO at different volume ratios. We have provided a way to distinguish alcohol species based on their molecular polarity and viscosity.

研究领域: 分析化学 · 生物医学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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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
✓ 已验证 产品关联 DOI 高影响因子
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NEW JOURNAL OF CHEMISTRY · 2024 ·Vol. 48 ·期 24 ·10973-10978 · IF 2.7

A targetable fluorescent probe for detecting mitochondrial viscosity in live cells by using fluorescence lifetime imaging

Zheng Gong,Xue Wang,Haowen Ma,Bing Wei,Xiaojuan Wang,Yingzhong Zhu,Zhangjun Hu,Kajsa Uvdal,Zhengjie Liu,Zhongping Zhang

Intracellular viscosity plays an important role in regulating cellular morphology and physiology and is closely related to a host of diseases. Especially, the changes in mitochondrial viscosity will cause some common diseases such as hyperlipidemia, Alzheimer's disease and cancer. In this work, we report the design of a red-emissive molecular rotor for the detection of mitochondrial viscosity in live cells. The probe showed fascinating performance, such as specific targeting to mitochondria, high sensitivity to viscosity, and rapid fluorescence response, especially the dual response mode of fluorescence intensity and fluorescence lifetime. By using this probe, we realized monitoring of the mitochondrial viscosity variations in live cells under different physiological processes. Our study offers an opportunity to discover potential tools for mitochondria-related physiology and pathology investigation.

研究领域: 生物化学 · 医学诊断 · 细胞生物学
✓ 已验证 产品关联 DOI 高影响因子
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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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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
✓ 已验证 产品关联 DOI PubMed 高影响因子
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