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hemicyanine
DYES AND PIGMENTS · 2025 · IF 4.2

Sulfur-Substituted Hemicyanine Nanosensors Enable Noninvasive Evaluation of Diabetic Liver Dysfunction through Cysteine Detection

Ren-Wei-Yang Zhang,Tong Wang,Zhi-Gang Hu,Kai Wang

Diabetic liver dysfunction is characterized by oxidative stress and disrupted cysteine (Cys) metabolism, but noninvasive monitoring tools remain lacking. Here, we developed a sulfur-substituted hemicyanine-based nanosensor (S-Nanoprobe) that generates enhanced near-infrared photoacoustic signals upon selective Cys recognition. The sulfur substitution improved vibrational relaxation efficiency, yielding a stronger photoacoustic signal than oxygen-substituted analogs, with a 0.12 μM detection limit and exceptional selectivity (no interference from homocysteine or glutathione). In streptozotocin-induced diabetic mice, the probe enabled noninvasive tracking of hepatic Cys dynamics, revealing significant Cys accumulation in diabetic mice (higher than controls), while metformin-treated mice showed intermediate levels. Histopathological analysis confirmed correlations between Cys levels and liver injury severity. This technology provides a novel molecular imaging approach for early assessment of diabetic liver dysfunction and establishes a versatile platform for studying thiol metabolism. The probe’s high specificity, biocompatibility, and signal-to-noise ratio make it promising for translational applications in metabolic disease monitoring.

研究领域: 生物医学工程 · 纳米技术 · 分子成像 · 糖尿病研究 · 代谢疾病 · 生物化学
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EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY · 2019 · IF 4.833

A hemicyanine derivative for near-infrared imaging of β-amyloid plaques in Alzheimer's disease

Hua-Li Yang,Si-Qiang Fang,Yan-Wei Tang,Cheng Wang,Heng Luo,Lai-Liang Qu,Jin-Hua Zhao,Cun-Jian Shi,Fu-Cheng Yin,Xiao-Bing Wang,Ling-Yi Kong

The formation of amyloid- β (A β ) plaques in the brain is one of the main pathological features of Alzheimer's disease (AD). The imaging probes, capable of detecting A β deposition, are important tools for early diagnosis of AD. In this article, we designed, synthesized and evaluated a cyanine-based near-infrared fluorescence (NIRF) probe ZT-1 for the detection of A β deposits in the brain. The probe had excellent fluorescent properties with an emission maximum above 720 nm upon binding to A β aggregates with affinity of 445.0 nM ( K d ). Furthermore, ZT-1 exhibited good biostability, photostability, and binding selectivity toward A β 1-42 aggregates by in vitro fluorescence staining experiments. In vivo NIRF imaging result also revealed that our probe could efficiently differentiate transgenic and wild-type mice. All these studies indicated that ZT-1 is a promising fluorescent probe for A β plaques in the AD brains.

CAS / MDL: 9048-46-8
研究领域: 医学 · 神经科学 · 分子影像学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ACS Applied Materials & Interfaces · 2025 · IF 8.2

Symmetry-Engineered Multifunctional Hemicyanine Hole Transport Material for High Performance Blue Perovskite Light-Emitting Diodes

Wuyan Hou,Lichao Li,Chang Liu,Boying Ding,Jiahao Cui,Longni Chen,Yuan Qiu,Zhiqiang Jiao,Juan Zhang,Shougen Yin,Xiaoming Wu

As an essential component in blue perovskite light-emitting diodes (PeLEDs), functionally tailored hole transport materials (HTMs) play a decisive role in reducing the hole injection barrier, mitigating interfacial defects, and thus enhancing device performance. Herein, we report two solution-processable D-π-A hemicyanine dyes, which exhibit asymmetric/symmetric configurations and contain electron-withdrawing groups and Lewis base donors. As multifunctional HTMs, two dyes not only present high hole mobilities with improved energy level alignment in PeLEDs, but also enable the perovskite defects passivation and n phases manipulation. Interestingly, the symmetric dye achieves dual-channel hole injection and multisite anchoring for the quasi-2D perovskite (PEACsPbBr2.1Cl0.9). The passivated perovskite film forms an augmented distribution of large n phases and suppressed small n phases, thereby promoting radiative exciton recombination. Consequently, symmetric dye-treated PeLED exhibits an impressive blue electroluminescence (EL) with a maximum luminance reaching 5842 cd m–2, a peak external quantum efficiency (EQE) of 13.71% and an improved operational half lifetime (T50) of 6.7 min at 100 cd m–2, demonstrating its performance advantages over the reported PEACsPb(BrxCl1–x)3 PeLEDs. This work provides an innovative perspective for designing multifunctional HTMs by conformation engineering and gains insight into the interfacial contact for high performance perovskite optoelectronics.

CAS / MDL: 3446-89-7
研究领域: 材料科学 · 光电子学 · 纳米技术 · 应用物理学 · 化学工程
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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
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ANALYTICAL CHEMISTRY · 2025 · IF 6.7

pH-/Viscosity-Activatable NIR Fluorescent Probes via Acceptor Engineering of Hemicyanine Dyes for High-Contrast Bioimaging

Da Feng,Li Guo,Yihan Zhao,Fang Yuan,Lulu Ning,Yuan Guo,Jianjian Zhang

Real-time monitoring of the lysosomal microenvironment using small-molecule probes is critical for understanding the complex interactions between organelles and diseases associated with lysosomal dysfunction. Most traditional fluorescent-dye-based lysosome probes rely on the protonation of the nitrogen atom in the morpholine unit to visualize the lysosomal microenvironment by inhibiting the photoinduced electron transfer (PET) effect. However, these probes often face selectivity issues within the complex cellular microenvironment. For instance, classic hemicyanine dyes (HD) show nonspecific fluorescence responses in the liver due to inappropriate pKa value, leading to low imaging contrast and the risk of false positives. Herein, a series of novel pH/viscosity-activatable, lysosomal-targeted near-infrared (NIR) fluorescent probes were developed by incorporating naphthalimide dye with hemicyanine dyes. These probes exhibit no fluorescence at physiological pH and weak fluorescence under acidic conditions (key 1), with substantial fluorescence activation triggered by abnormal viscosity in pathological tissues (key 2). Notably, NpCy-4 demonstrated a superior signal-to-background ratio (SBR) for cellular imaging and proved effective for real-time in situ diagnosis of acute gastritis.

研究领域: 生物化学 · 医学影像学 · 分子生物学
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JOURNAL OF PHYSICAL CHEMISTRY B · 2017 · IF 3.177

Stimuli-Responsive Supramolecular Assemblies between Twisted Cucurbit[14]uril and Hemicyanine Dyes and Their Analysis Application

Jing Zhang,Qing Tang,Zhong-Zheng Gao,Ying Huang,Xin Xiao,Zhu Tao

Two supramolecular assemblies between twisted cucurbit[14]uril and hemicyanine dyes have been successfully constructed on the basis of host–guest recognition. These supramolecular assemblies could be reversibly switched under acidic and neutral conditions. Furthermore, they responded to selected chemical stimuli such as methyl violet, thereby exhibiting potential analysis application.

CAS / MDL: 8004-87-3
研究领域: 化学 · 材料科学
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Small · 2022 ·Vol. 18 ·期 28 ·2202263 · IF 15.153

A Hemicyanine-Assembled Upconversion Nanosystem for NIR-Excited Visualization of Carbon Monoxide Bio-Signaling In Vivo

Minan Ye,Jie Zhang,Detao Jiang,Qi Tan,Jingyun Li,Cheng Yao,Chenjie Zhu,Yi Zhou

Carbon monoxide (CO) is considered as the second gasotransmitter involved in a series of physiological and pathological processes. Although a number of organic fluorescent probes have been developed for imaging CO, these probes display excitation within the ultraviolet or visible range, which restrict their applications in the complex biosystems. In the present work, a strategy is developed to construct an upconversion nanoparticles-based nanosystem for upconversion luminescent (UCL) sensing CO. This nanosystem exhibits a fast response to CO with high sensitivity and selectivity in aqueous solution by a near-infrared-excited ratiometric UCL detection method. Meanwhile, laser scanning upconversion luminescence microscope experiments demonstrate that this nanosystem can visualize the endogenous CO bio-signaling in living cells, deep tissues, zebrafish, and living mice by ratiometric UCL imaging. In particular, this nanosystem has been successfully employed in visualization of the endogenous CO bio-signaling through up-regulation of heme oxygenase-1 (HO-1) in the progression of hypoxia, acute inflammation, or ischemic injury. This work demonstrates that the outstanding performance of the nanosystem not only can provide an effective tool for further understanding the role of CO in the physiological and pathological environment, but also may have great potential ability for tracking the expression of HO-1 in living systems.

研究领域: 生物医学工程 · 纳米技术 · 分子生物学 · 生物物理学 · 分析化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF PHYSICAL CHEMISTRY B · 2024 · IF 2.8

Design and Screening of Fluorescent Probes Based upon Hemicyanine Dyes for Monitoring Mitochondrial Viscosity in Living Cells

Xiufeng Zhang,Xiaoying Ma,Buyue Zhang,Dawei Yang,Ruiyang Bai,Yuexing Gao,Hongxia Sun,Yalin Tang,Lei Shi

Viscosity, at the subcellular level, plays a crucial role as a physicochemical factor affecting microenvironment homeostasis. Abnormal changes in mitochondrial viscosity often lead to various diseases in the organism. Based on the twisted intramolecular charge transfer mechanism, four hemicyanine dye fluorescent probes (HT-SA, HT-SA-S, HT-Bzh, and HT-NA) were designed and synthesized for viscosity response. The single bond between the nitrogen-containing heterocycle and the carbon–carbon double in the structure of the probe bond served as the viscosity response site. Finally, the probe HT-Bzh was screened as the optimal mitochondrial viscosity probe according to its responsiveness, targeting, and interference resistance. The fluorescence intensity of the probe HT-Bzh increased 22-fold when the viscosity was increased from 13.75 to 811.2 cP. In summary, all four viscosity probes we have developed can be used in different applications depending on the external environment, providing a valuable reference for the design of potential tools to address viscosity monitoring in biological systems.

研究领域: 化学 · 生物学 · 材料科学 · 生物医学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ACS Applied Materials & Interfaces · 2025 · IF 8.2

Mitochondria-Targeting and ROS-Cleavable Hemicyanine–Tranexamic Acid Conjugates as Radioprotective Agents Mitigated Radiation-Induced Skin Injury

Yan Zhou,Xie Huang,Han Liu,Zaizhi Du,Mingquan Gao,Zhengyu Zhang,Shihao Fu,Rong Li,Qiang Xiang,Shenglin Luo

Radiation-induced skin injury (RISI) is one of the most common illnesses in external beam radiotherapy. Although some commercial drugs for external use have been developed to prevent and alleviate RISI, a majority of them usually adopt a single chemical repair pathway by scavenging intracellular toxic reactive oxygen species (ROS) with limited treatment outcomes. Particularly, the therapeutic effect toward high-dosage acute radiation injury remains unsatisfactory in the clinic. Mitochondria play vital roles not only as cellular energy factories but also as the main organelles to produce intracellular ROS and maintain the balance of oxidation stress and inflammation. Thus, targeting the protection of mitochondria from radiation-induced damage may effectively improve RISI treatment. Herein, in this work, we designed and reported a series of mitochondria-targeting radioprotective hemicyanine (HCY) small molecules to treat acute RISI synergistically by antioxidation, anti-inflammation, and plasminogen inhibition for wound healing. Using ROS-cleavable enamine bonds, different mitochondria-targeting structures of HCY were chemically conjugated with tranexamic acid (TA), a plasminogen inhibitor previously reported for attenuating RISI by the regulation of mitochondrial function. Thus, the specific delivery and release of TA in mitochondria were achieved to enhance RISI treatment and minimize the side effect. Our findings in this work not only demonstrate a promising potential of HCY-TA conjugates for RISI treatment but also propose an innovative mitochondria-targeting delivery system to hopefully mitigate radiation-induced other diseases.

✓ 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
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ANALYTICAL CHEMISTRY · 2022 · IF 8.008

Bichromatic Imaging with Hemicyanine Fluorophores Enables Simultaneous Visualization of Non-alcoholic Fatty Liver Disease and Metastatic Intestinal Cancer

Weijia Xu,Senyao Liu,Zhaoming Chen,Fapu Wu,Wenwen Cao,Yang Tian,Hu Xiong

Simultaneous detection of different diseases via a single fluorophore is challenging. We herein report a bichromatic fluorophore named Cy-914 for the simultaneous diagnosis of non-alcoholic fatty liver disease (NAFLD) and metastatic intestinal cancer by leveraging its NIR-I/NIR-II dual-color imaging capability. Cy-914 with a pKa of 6.98 exhibits high sensitivity to pH and viscosity, showing turn-on NIR-I fluorescence at 795 nm in an acidic tumor microenvironment, meanwhile displaying intense NIR-II fluorescence at 914/1030 nm under neutral to slightly basic viscous conditions. Notably, Cy-914 could sensitively and noninvasively monitor viscosity variations in the progression of NAFLD. More importantly, it was able to simultaneously visualize NAFLD (ex/em = 808/1000–1700 nm) and intestinal metastases (ex/em = 570/810–875 nm) in two independent channels without spectral cross interference after topical spraying, further improving fluorescence-guided surgery of tiny metastases less than 3 mm. This strategy may provide an understanding for developing multi-color fluorophores for multi-disease diagnosis.

研究领域: 医学影像学 · 分子生物学 · 病理学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2025 · IF 4.6

An activatable Hemicyanine-based fluorescent probe for specific detection and imaging of aminopeptidase N in diabetic wound healing

Da-Ke Wen,Lu Fan,Jie-Li Zhou,Kai Wang

Aminopeptidase N (APN) plays crucial roles in wound healing and disease progression, yet tools for precise in vivo monitoring remain limited. We developed APN-activatable fluorescent probe, AFP, a hemicyanine-based probe that exhibits remarkable specificity and sensitivity toward APN through an enzymatic cleavage-mediated fluorescence turn-on mechanism. AFP demonstrates a bathochromic shift upon APN activation (λabs = 705 nm), with an increasing fluorescence response. The probe maintains excellent stability against reactive species and shows negligible cytotoxicity (<5% viability loss at 25 μM). In diabetic wound models, AFP reliably distinguished impaired healing through differential APN activity patterns, correlating with histopathological and biochemical markers of disease severity. Systemic biosafety evaluations confirmed no organ toxicity, supporting AFP's potential for clinical translation in wound management and beyond.

✓ 已验证 DOI PubMed 高影响因子
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