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JOURNAL OF HAZARDOUS MATERIALS · 2017 · IF 6.065

A novel “turn-on” fluorescent probe based on triphenylimidazole-hemicyanine dyad for colorimetric detection of CN− in 100% aqueous solution

Shuzhi Liu,Min Yang,Yijiang Liu,Hongbiao Chen,Huaming Li

A new colorimetric fluorescent probe (MCy) for CN − is designed and synthesized based on triphenylimidazole-hemicyanine dyad. The probe shows high selectivity towards CN − in 100% aqueous solution even in the presence of other competitive anions such as F − , Cl − , AcO − , NO 2 − , H 2 PO 4 − , I − , SCN − , SO 4 2− , NO 3 − , HCO 3 − , Br − and S 2− . Upon nucleophilic addition of CN − to the indolium group, the probe displays large blue-shift in UV–vis spectrum and remarkable “turn-on” fluorescence owing to the disruption of intramolecular charge transfer. Meanwhile, the probe also undergoes a naked-eye discernible color change from orange to light pink in the sunlight as well as an obvious fluorescence color change from non-emissive to bright blue under a UV lamp. The detection limit of CN − in aqueous solution can be as low as 20.6   nM, which is much lower than the permissible level of CN − in drinking water according to the WHO. In addition, the probe has been successfully used to determine CN − in real water samples as well as to fabricate test paper kit for CN − detection.

研究领域: 分析化学 · 环境科学
✓ 已验证 DOI PubMed 高影响因子
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FREE RADICAL BIOLOGY AND MEDICINE · 2025 · IF 8.2

A hemicyanine-based dual-modal probe for fluorescence and mass spectrometry imaging of peroxynitrite in biosamples

Yuejie Zhang,Jingfeng Zhang,Weiwei Tang,Bin Li

Peroxynitrite (ONOO - ) is a highly reactive oxidant formed by the reaction of nitric oxide with superoxide. Excessive ONOO - can be produced by the body in response to multiple diseases, resulting in cell death through oxidation and nitration processes. However, technical challenges arise in detection due to its high reactivity and very short lifespan. In this work, we rationally designed and synthesized a novel tetrazine-hemicyanine-based probe (TZN-HCY). This probe demonstrates the ability to capture ONOO - with high selectivity and sensitivity, enabling the detection and imaging of ONOO - in biological samples with both fluorescence and MALDI MS. The 3,6-disubstituted tetrazine moiety could react with ONOO - , and the hemicyanine skeleton with a permanent positive charge could enhance MALDI MS detection. The responsive performances of the TZN-HCY probe were verified on cell models and livers of hepatic ischemia-reperfusion injury (HIRI) model mice. Due to the applicability to dual-mode imaging, the formation of ONOO - and its content change in the liver of living mice were visualized by fluorescence imaging, while the fine-scale spatial distribution of ONOO - in liver tissues was revealed by MALDI MS imaging. This dual-modal probe could serve as a powerful tool for elucidating the diverse and complex roles of biogenic ONOO - in ischemia-reperfusion injury.

CAS / MDL: 1122-58-3
研究领域: 生物化学 · 医学影像学 · 分子生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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MOLECULES · 2024 ·Vol. 29 ·期 3 ·618 · IF 4.2

A Coumarin–Hemicyanine Deep Red Dye with a Large Stokes Shift for the Fluorescence Detection and Naked-Eye Recognition of Cyanide

Dongmei Li,Senlin Peng,Xu Zhou,Lingyi Shen,Xianjiong Yang,Hong Xu,Carl Redshaw,Chunlin Zhang,Qilong Zhang

In this study, we synthesized a coumarin–hemicyanine-based deep red fluorescent dye that exhibits an intramolecular charge transfer (ICT). The probe had a large Stokes shift of 287 nm and a large molar absorption coefficient (ε = 7.5 × 105L·mol−1·cm−1) and is best described as a deep red luminescent fluorescent probe withλem= 667 nm. The color of probe W changed significantly when it encountered cyanide ions (CN−). The absorption peak (585 nm) decreased gradually, and the absorption peak (428 nm) increased gradually, so that cyanide (CN−) could be identified by the naked eye. Moreover, an obvious fluorescence change was evident before and after the reaction under irradiation using 365 nm UV light. The maximum emission peak (667 nm) decreased gradually, whilst the emission peak (495 nm) increased gradually, which allowed for the proportional fluorescence detection of cyanide (CN−). Using fluorescence spectrometry, the fluorescent probe W could linearly detect CN−over the concentration range of 1–9 μM (R2= 9913, RSD = 0.534) with a detection limit of 0.24 μM. Using UV-Vis spectrophotometry, the linear detection range for CN−was found to be 1–27 μM (R2= 0.99583, RSD = 0.675) with a detection limit of 0.13 μM. The sensing mechanism was confirmed by1H NMR spectroscopic titrations,13C NMR spectroscopy, X-ray crystallographic analysis and HRMS. The recognition and detection of CN−by probe W was characterized by a rapid response, high selectivity, and high sensitivity. Therefore, this probe provides a convenient, effective and economical method for synthesizing and detecting cyanide efficiently and sensitively.

研究领域: 化学 · 分析化学 · 环境科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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SENSORS AND ACTUATORS B-CHEMICAL · 2017 · IF 5.401

A novel turn-on fluorescent probe for cyanide detection in aqueous media based on a BODIPY-hemicyanine conjugate

Yanhua Yu,Tingting Shu,Bingjie Yu,Yun Deng,Cheng Fu,Yangguan Gao,Changzhi Dong,Yibin Ruan

A novel BODIPY-hemicyanine based fluorescent probe 1 for cyanide (CN − ) detection was designed and synthesized. Among the tested anions, the probe showed high selectivity towards CN − . Only addition of CN − to probe 1 in aqueous solution (V H2O /V EtOH   =   1/1) could result in a remarkable blue shift of the absorption band from 385   nm to 265   nm and induce 20-fold fluorescence enhancement at 515   nm. The sensing mechanism was based on nucleophilic addition between CN − and indolium group, which was confirmed by 1 H NMR and mass spectrum analysis. Plot of fluorescence intensity as a function of CN − concentrations exhibited a good linear relationship in the range of 0–10   μM, with a detection limit to be 1.53   ppb. Moreover, the proposed sensing approach could work in a wide pH range from 5.0–9.0 and reach an equilibrium instantaneously. Finally, probe 1 was successfully applied in detection of CN − in natural water samples and on test paper strips with satisfactory results.

研究领域: 分析化学 · 环境科学 · 生物医学
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ANALYST · 2022 ·Vol. 148 ·期 4 ·876-887 · IF 5.227

Rational design of a turn-on near-infrared fluorescence probe for the highly sensitive and selective monitoring of carboxylesterase 2 in living systems

Zhixin Chen,Jiaying Yu,Kai Sun,Jia Song,Lucheng Chen,Yong Jiang,Zhifei Wang

In vivo selective fluorescence imaging of carboxylesterase 2 (CES2) remains a great challenge because existing fluorescence probes can potentially suffer from interference by other hydrolases. In addition, some fluorescent probes that have been separately reported for measuring CES2 activity in vitro are affected by autofluorescence and absorption of the biological matrix due to their limited emission wavelength or short Stokes shift. Herein, based on the substrate preference and catalytic performance of CES2, a novel and NIR fluorescent probe was developed, in which a hemi-cyanine dye ester derivative was used as the basic fluorescent group. In the presence of CES2, the probe was hydrolyzed to expose the fluorophore CZX-OH (λabs ∼ 675 nm, λem ∼ 850 nm), which led to a notable red-shift in the fluorescence (∼175 nm) spectrum. Confocal imaging of cells and live mice demonstrated that the fluorescent signal of this probe was related to the real activities of CES2 in cancer cells. All these results will powerfully promote the screening of CES2 regulators and the analysis of CES2-related physiological and pathological processes.

研究领域: 生物化学 · 分子生物学 · 药理学 · 生物医学工程
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2024 · IF 4.3

In vivo imaging of alkaline phosphatase in lipid metabolic diseases with a photoacoustic probe

Chun-Pu Mao,Xu-Yang Chen,Jie Han,Ting Jiang,Xiao-Xin Yan,Dong-Lin Hao,Jian-Hua Jin,Biao Yu,Jie-Li Zhou,Kai Wang,Li-Ting Zhang

Lipid metabolic diseases have become an important challenge to global public health. Along with lifestyle changes, the incidence of obesity, diabetes and other metabolic syndromes is on the rise, and the number of patients with fatty liver disease is also increasing. Therefore, it is particularly important to develop effective lipid imaging strategies to monitor and manage fatty liver disease. Herein, based on the essential role of alkaline phosphatase (ALP) in both AS and OB, in vivo imaging of ALP was achieved in two lipid metabolic diseases models with a photoacoustic (PA) probe phosphorylated hemicyanine ( P-Hcy ). After being triggered by ALP, P-Hcy responded in different modalities including absorbance, fluorescence and, most significantly, PA-reporting. Notably, the PA signal showed the reliable linear correlation to the ALP level within the range of 0–800 U/L. The probe P-Hcy exhibited the advantages including high sensitivity, high selectivity, and steadiness in required biological conditions. The intracellular imaging results ensured that P-Hcy could visualize the ALP level in the foam cells induced from mouse mononuclear macrophages. In the healthy and lipid metabolic diseases models, P-Hcy was able to distinguish well between a lipid metabolic disease model and a healthy mouse model by photoacoustic imaging. By combining the ALP detection with P-Hcy in PA/fluorescence modality and traditional techniques such as blood biochemical testing and immunohistochemically staining, more potential strategy to accurately diagnose lipid metabolic diseases in the pre-clinical trials might be developed in future.

研究领域: 医学影像 · 代谢疾病 · 生物化学 · 药学
✓ 已验证 DOI PubMed 高影响因子
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Advanced Healthcare Materials · 2023 · IF 10

Near-Infrared Ii Hemicyanine Dye with Large Stokes Shift Designed by Tict Regulation for Boosting Imaging-Guided Photothermal Therapy

Liang Zhao,Han Zhu,You-Yang Duo,Dai-Wen Pang,Zhi-Gang Wang,Shu-Lin Liu

The serious threat that cancer poses to human health highlights the significance of early detection and effective treatment. The integration of fluorescence diagnosis and photothermal therapy in NIR-II has gained attention due to its high sensitivity, fast response, and non-invasiveness. Fluorescence, produced by the radiative relaxation process of electrons in a molecule, and photothermal, generated by the non-radiative relaxation process of electrons in a molecule, are competing photophysical processes. Hence, it is a challenge for the molecule to balance between the properties of fluorescence and photothermal. In this study, we designed a NIR-II hemicyanine with TICT character to obtain molecules with both better fluorescence and photothermal properties, utilizing positively charged pyridine salt and triphenylamine as electron acceptor and donor, respectively, and oxole as the conjugated π-bridge. HCY-995 , one of the synthesized compounds, had a quantum yield of 0.09%, photothermal conversion efficiency of 54.90%, and a significant Stoke shift of 232 nm, which made it appropriate for the integration of photothermal therapy and high-resolution imaging. This study provides new insights into the development of NIR-II molecules with fluorescent and photothermal integrated properties. This article is protected by copyright. All rights reserved

研究领域: 生物医学工程 · 分子影像 · 癌症治疗
✓ 已验证 DOI PubMed 高影响因子
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Analytical Methods · 2023 ·Vol. 15 ·期 23 ·2868-2875 · IF 3.1

Colorimetric detection of ozone in aqueous solution and imaging in living cells using a novel hemicyanine dye

Xia Gao,Guo Yu,Xuehan Liu,Yinlan Xu,Pengbo Zhang,Weidong Wu

Ozone (O3) is ubiquitous in the environment and exposure to high levels of O3 has been associated with various respiratory diseases, such as asthma, emphysema, and bronchitis. Therefore, it is necessary to develop a simple and efficient detection method for monitoring O3 in the environment and living cells. In this study, an intramolecular charge-transfer (ICT) compound was designed and synthesized based on a phenol-type hemicyanine dye and 4-bromo-1-butene, which could specifically detect O3 in aqueous solution. Due to the ICT process, the absorption spectrum, fluorescence spectrum, and color of the probe hemicyanine-butyl-3-enyl (HCB) changed significantly and thus the rapid and sensitive detection of O3 was realized. The interaction between O3 and the probe HCB could be completed within 40 min, and the detection limit of O3 was as low as 2.15 × 10−7 mol L−1. Finally, the proposed method was successfully applied to the visual detection of O3 in a simulated O3 environment and living cells.

研究领域: 环境科学 · 分析化学 · 生物医学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Acta Biomaterialia · 2021 · IF 8.947

Sequential enzyme-activated macrotheranostic probe for selective tumor mitochondria targeting

Di Ma,Qingyu Zong,Yuchen Du,Fangzhou Yu,Xuan Xiao,Rong Sun,Yuan Guo,Xinhua Wei,Youyong Yuan

Subcellular organelle targeted imaging and therapy are of enormous interest in cancer theranostics. However, the lack of tumor-selective organelle targeting has compromised their efficacy and safety. In this work, we found that the near-infrared (NIR) fluorophore hemicyanine (CyNH 2 ) can selectively target mitochondria with strong cytotoxicity through decreasing the mitochondrial membrane potential and increasing the intracellular reactive oxygen species (ROS) levels. A macrotheranostic probe (denoted as PLCy) based on conjugating CyNH 2 with an acetylated lysine group was developed with masked fluorescence and cytotoxicity, which could both be unmasked through sequential activation by cancer cells overexpressing histone deacetylases (HDACs) and cathepsin L (CTSL) enzymes for selective cancer cell mitochondria-targeted imaging and therapy. In vitro and in vivo studies confirmed that the specific fluorescence turn-on and toxicity were restored in cancer cells and efficiently inhibited tumor growth. This macrotheranostic probe with sequential enzyme activation and mitochondrial targeting is expected to have promising applications in imaging-guided cancer therapy with high specificity and efficiency. Statement of significance To improve the targeting efficiency and enhance the anti-cancer activities of macrotheranostic probe. We designed macrotheranostic probe PLCy that can be activated via sequential enzymes for selective tumor mitochondria targeting. More importantly, the activated CyNH 2 can decrease the mitochondrial membrane potential and elevate the reactive oxygen species level in cancer cells without light irradiation, which can further induce apoptosis of tumor cells for chemotherapy. Therefore, the use of sequential enzyme activation and mitochondria targeting strategies in the context of enzymatic activation may provide a general strategy for organelle-targeted imaging and therapy with high specificity and efficiency.

研究领域: 癌症治疗诊断 · 分子成像 · 药物递送 · 生物化学 · 生物医学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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