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dicyanoisophorone
NEW JOURNAL OF CHEMISTRY · 2019 ·Vol. 43 ·期 18 ·6848-6855 · IF 3.069

A novel near-infrared fluorescent hydrogen sulfide probe for live cell and tissue imaging

Xiaoting Huang,Haiyang Liu,Jiewen Zhang,Boren Xiao,Fengxu Wu,Yueying Zhang,Ying Tan,Yuyang Jiang

A dicyanoisophorone-based near-infrared fluorescent probe (NIR-NP) was successfully designed for hydrogen sulfide (H2S) detection. 7-Nitro-1,2,3-benzoxadiazole (NBD) amine, an electron-withdrawing group, was applied to quench the fluorescence of dicyanoisophorone-based fluorescent dyes and could be removed by H2S-specific thiolysis of an NBD amine bond, leading to a significant fluorescence turn-on response. The probe could quantitatively detect H2S with a lower detection limit (0.03 μM) in vitro and in living cells. The probe with a large Stokes shift (186 nm) showed a high selectivity to H2S in the presence of other biothiols, including glutathione, homocysteine, and cysteine. Moreover, the probe was successfully applied to image endogenous H2S in different tumor cells and in liver tissues. The excellent properties of the probe and its applications in cell and tissue imaging indicated its potential for further exploration and application of H2S in the pathophysiology of cancers and even in the diagnosis of H2S-related diseases.

研究领域: 分子影像学 · 肿瘤学 · 化学生物学 · 分子生物学 · 生物分析化学 · 转化医学
✓ 已验证 DOI 高影响因子
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JOURNAL OF FLUORESCENCE · 2025 · IF 3.1

Visual Detection of Cadmium and Glutathione by Dicyanoisophorone Fluorescent Probe and its Portable Application

Zu Panru,Yu Yanchao,Li Bolin,You Jun,Wu Wenju,Wu Mianyuan

A novel fluorescent probe XL derived from dicyanoisophorone was designed and synthesized, achieving successful sequential detection of Cd 2+ and GSH. As probe XL interacted with Cd 2+ , the emission wavelength redshifted from 565 nm to 650 nm, accompanied by enhanced red fluorescence, which realising a fluorescence turn-on response in the near-infrared region. A large Stokes shift (121 nm) combined with low detection limit (0.484 µmol/L) were key advantages of the detection process. However, due to high affinity of GSH for Cd 2+ , as addition of GSH to complex XL-Cd 2+ , fluorescence response in NIR region was switched off and emission peak was blue-shifted back to 565 nm. Detection limit for GSH was calculated as 0.784 µmol/L, a value significantly lower than its normal intracellular concentration, and the assay process with good sensitivity. Notably, probe XL showed an immediate response (3 s) to Cd 2+ and GSH, with a clear visual detection in natural light. In addition, XL could be used to detect Cd 2+ and GSH in real samples and achieve linked applications with smartphones.

研究领域: 分析化学 · 生物传感 · 环境科学 · 材料科学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2023 · IF 4.4

A dicyanoisophorone-based long-wavelength fluorescent probe for detection of cysteine in vitro and in vivo

Hui Zhou,Yang Li,Ru Fang,Jinghua Li,Chen Hong,Wen Luo

In this research, an “off–on” long-wavelength fluorescent probe (DCMN-Cl) based on (E)-2-(3-(2-(6-hydroxynaphthalen-2-yl)vinyl)-5,5-dimethylcyclohex-2-en-1-ylidene) malononitrile (DCMN) is designed and synthesized for cysteine (Cys) detection. DCMN-Cl exhibits a large Stokes shift (211 nm) and shows rapid response and high specificity to Cys. The fluorescence initensity at 635 nm reveals a good linear relationship with Cys concentration in the 0 to 50 μM range, and the detection limit is as low as 159 nM. The probe is also used for fluorescence imaging of Cys in cells and mice. Moreover, the probe provided visual evidence of Cu 2+ and curcumin-induced intracellular Cys fluctuations.

研究领域: 生物化学 · 医学检测 · 分子生物学
✓ 已验证 DOI 高影响因子
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SENSORS AND ACTUATORS B-CHEMICAL · 2019 · IF 6.393

A highly sensitive fluorescent probe for hydrogen sulfide based on dicyanoisophorone and its imaging in living cells

Junping Wang,Ying Wen,Fangjun Huo,Caixia Yin

Due to the importance of hydrogen sulfide (H 2 S) in physiology and pathology, the development of fluorescence probes for the detection of H 2 S has attracted extensive attention of researchers. We developed a H 2 S fluorescence probe ( DCN-S ) based on dicyanoisopentanone using dithioether and ester groups as the reaction sites. Under the nucleophilic substitution of H 2 S, disulfide bond of DCN-S was broken. Then the probe changed into dicyanoisophorone derivative and emitted an orange fluorescence band from 530 nm to 700 nm (centred 580 nm). Upon response for H 2 S, DCN-S exhibited high sensitivity (88 nM detection limit) and large stokes shift (155 nm). Importantly, the probe also was successfully used for endogenous and exogenous imaging of living cells.

研究领域: 分析化学 · 生物化学 · 细胞生物学
✓ 已验证 DOI 高影响因子
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JOURNAL OF MOLECULAR LIQUIDS · 2026 · IF 5.2

Dually responsive fluorescence probe based on dicyanoisophorone for sensing polarity/pH in living systems and environmental systems

Jianchao Hou,Wen Zhang,Zhonglong Wang,Xiaoqin Yang,Xiaoping Rao,Ping Zhao,Qian Jiang

Polarity serves as a vital parameter in assessing diagnosing diseases, reflecting quality in cellular metabolic status. In this work, two novel dicyanoisophorone-based fluorescence probes ( DCIV-1 and DCIV-2 ) have designed and synthesized, capable of detecting pH levels and polarity fluctuation effectively. A detailed analysis of the probe's optical properties reveals that DCIV-1 and DCIV-2 exhibit distinct fluorescence and colorimetric responses under varying pH conditions. Meanwhile, DCIV-1 and DCIV-2 exhibit excellent responsiveness to polarity change respectively. Biological application reveals that both probes are successfully applied for distinguishing between cancer cells and normal cells. Furthermore, DCIV-1 and DCIV-2 enable rapid pH values in real water samples. As a convenient detection method, probe-based test strips have developed for detecting pH changes. This work highlights the potential of DCIV-1 and DCIV-2 for pH levels and polarity monitoring in biological and environmental fields.

✓ 已验证 DOI 高影响因子
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JOURNAL OF MOLECULAR STRUCTURE · 2025 · IF 4.7

A dicyanoisophorone-based highly selective fluorescent probe with a large stokes shift for cysteine detection in lipid droplets

Yang Zhang,Shan Zhao,Huayu Wang,Chunpo Ge

Cysteine (Cys), a pivotal biothiol involved in protein synthesis, metabolism, and detoxification, plays essential roles in various physiological and pathological processes. Dysregulation of Cys levels is associated with diseases such as Parkinson's, Alzheimer's, cardiovascular conditions, and hepatic pathologies. Despite advancements in Cys detection, probes specifically designed for lipid droplet (LD)-targeted Cys monitoring remain scarce. Here, we report the development of a fluorescent probe, DCI-HBT-Cys , for the selective detection of Cys within LDs. The probe features an acrylate-based recognition unit for specific nucleophilic cyclization with Cys and a hydrophobic DCI-HBT-OH fluorophore enabling efficient LD localization. DCI-HBT-Cys exhibits remarkable properties, including high selectivity, a large Stokes shift (240 nm), excellent photostability, and pH stability in the physiological range (pH 6–9). In vitro and cellular assays demonstrate the probe's ability to sensitively detect endogenous and exogenous Cys with minimal interference from related biothiols (e.g., Hcy, GSH). Furthermore, DCI-HBT-Cys enables real-time imaging of Cys upregulation in various cell lines, including HeLa and HepG2 cells, in response to ginseng polysaccharide stimulation. Co-localization studies confirm the probe’s LD-targeting specificity, while quantitative fluorescence analysis highlights its potential for precise Cys monitoring. These findings underscore the utility of DCI-HBT-Cys as a powerful tool for elucidating the intricate interplay between Cys metabolism, oxidative stress, and LD-associated cellular processes, paving the way for novel diagnostic and therapeutic strategies.

研究领域: 分析化学 · 生物化学 · 细胞生物学 · 荧光成像 · 医学诊断 · 分子生物学 · 药理学
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JOURNAL OF MOLECULAR STRUCTURE · 2025 · IF 4.7

A novel fluorescent probe based on dicyanoisophorone for the detection of tetracycline antibiotics and its application to water samples

Linxiu Zhao,Yue Zhao,Yuqi Wu,Taisheng Zhu,Yuxin Miao,Tongtong Zhang,Shengling Li,Jianlan Cui

Antibiotics play an irreplaceable role in controlling bacterial infections and safeguarding human health. However, the misuse of antibiotics in animal husbandry and aquaculture has caused widespread ecological contamination. Specifically, tetracycline antibiotics (Tetracyclines, TCs), as one of the most prevalent antibiotic residues, pose significant risks to environmental sustainability and food safety. To address this issue, we developed a novel dicyanoisophorone-based fluorescent probe, ( E )-2-(3-(2-(5-formyl-6-hydroxy-2-naphthalenyl)vinyl)-5,5-dimethylcyclohex-2-en-1-yl)malononitrile ( ZHP ), enabling rapid and selective detection of TCs. Notably, ZHP exhibited distinct fluorescence responses toward different TCs: fluorescence quenching upon binding to chlortetracycline (CTE) (detection limit: 9.6 µM) and fluorescence enhancement in the presence of doxycycline (DOX), oxytetracycline (OXY), and tetracycline (TET) (detection limits: 0.23 µM, 0.24 µM, and 0.39 µM). This differential response mechanism, potentially attributed to structural variations among TCs. The probe demonstrated excellent pH tolerance (pH 6 - 12) and high selectivity over 6 common interfering antibiotics. A paper-based colorimetric assay achieved visual TCs detection within 5 seconds, highlighting its field-deployable potential. Furthermore, the probe ZHP was successfully applied to quantify TCs in different water samples with recoveries of 96.33 - 103.00%. This work provides a sensing platform for TCs monitoring, offering critical insights into the design of multifunctional probes for environmental applications.

CAS / MDL: 10026-22-9
研究领域: 环境科学 · 分析化学
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ANALYTICA CHIMICA ACTA · 2024 · IF 5.7

Novel pyrrolidine-alkylamino-substituted dicyanoisophorone derivatives as near-infrared fluorescence probe for imaging β-amyloid in vitro and in vivo

Hui Zhou,Jihang Zhai,Huiyuan Gong,Ru Fang,Yongmei Zhao,Wen Luo

Background The formation of amyloid-β (Aβ) plaques is one of the key neuropathological hallmarks of Alzheimer's disease (AD). Near-infrared (NIR) probes show great potential for imaging of Aβ plaques in vivo and in vitro. Dicyanoisophorone (DCIP) based Aβ probes have attracted considerable attention due to their exceptional properties. However, DCIP probes still has some drawbacks, such as short emission wavelength (<650 nm) and low fluorescence intensity after binding to Aβ. It is clear that further modification is needed to improve their luminescence efficiency and sensitivity. Results We designed and synthesize four novel pyrrolidine-alkylamino-substituted DCIP derivatives ( 6a - d ) as imaging agents for β-amyloid (Aβ) aggregates. Compound 6c responds better to Aβ aggregates than the other three compounds ( 6a , 6b and 6d ) and its precursor DCIP. The calculated detection limit is to be as low as 0.23 μM. Compound 6c shows no cytotoxicity in the tested concentration for SH-SY5Y and HL-7702 cells. Additionally, compound 6c is successfully applied to monitor Aβ aggregates in live SH-SY5Y cells and APP/PS1 transgenic mice . The retention time in the transgenic mice brain is much longer than that of age-matched wild-type mice. Significance The results indicates that compound 6c had an excellent ability to penetrate the blood-brain barrier and it could effectively distinguish APP/PS1 transgenic mice and wide-type mice. This represents its promising applications for Aβ detection in basic and biomedical research .

研究领域: 神经生物学 · 医学影像学 · 药物化学
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TALANTA · 2022 · IF 6.556

Dicyanoisophorone-based fluorescent probe with large Stokes shift for ratiometric detection and imaging of exogenous/endogenous hypochlorite in cell and zebrafish

Xiang-yu Kong,Shao-Min Shuang,Yue-tao Zhang,Yu Wang,Chuan Dong

A novel dicyanoisophorone-based red-emissive fluorescence probe (YT) with large Stokes shift (230 nm) was synthesized for rapid (<20 s) and selective detection of hypochlorite ions in nearly 100% aqueous medium. YT responded to hypochlorite ions via the ClO − -promoted oxidative deprotection of thioacetal , leading to a red shift in its fluorescence maximum from 590 nm to 640 nm accompanied by naked-eye color change from orange to red. The emission response of the probe toward ClO − presented a good linear relationship in the 5–160 μM concentration range, with the LOD of 4.64 μM. Further, the probe YT was successfully employed in exogenous and LPS-induced endogenous imaging of ClO − in live cells and zebrafish, demonstrating its potential applications in biological science.

研究领域: 分析化学 · 生物化学 · 生物成像
✓ 已验证 产品关联 DOI PubMed 高影响因子
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