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RESEARCH ON CHEMICAL INTERMEDIATES · 2017 ·Vol. 44 ·期 1 ·491-502 · IF 1.369

A off–on pH fluorescence probe derived from phenanthro[9,10-d]imidazol-fluorescein based on ESIPT and ICT

Li Shaoxin,Zhao Bing,Kan Wei,Wang Liyan,Song Bo,Chen Shuwen

A novel pH fluorescence probe (PIF), derived from phenanthro[9,10- d ]imidazole bound to the fluorescein, is designed and synthesized based on the intramolecular hydrogen bond and then its spectra properties are investigated. Probe PIF exhibits negligible fluorescence intensity at acidic pH condition due to ESIPT quenching caused by the formation of the intramolecular hydrogen bonds, and a significant fluorescence enhancement in neutral and weak alkaline environments because of the strengthened ICT process arose from the fracture of the intramolecular hydrogen bonds. The studies of UV–Vis and fluorescence spectra mean that probe PIF is able to respond linearly and reversibly over pH from 6.5 to 9.0 with p K a of 7.0. Moreover, the pH responses of probe PIF are stable and not disturbed by the common cations and anions. The possible response mechanism has been proposed according to the analysis of 1 H NMR and DFT calculations.

研究领域: 分析化学 · 生物化学
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ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY · 2023 · IF 6.8

A highly selective and sensitive ICT-based Cu2+ fluorescent probe and its application in bioimaging

Xina Liu,Taozhong Shi,Chenyang Xu,Meiqing Zhu,Yi Wang

Cu 2+ is an essential trace element for the organism, but its excess can also cause irreversible damage to the organism. As such, a “Turn-Off” fluorescent probe DPAP for the specific detection of Cu 2+ was successfully constructed. DPAP exhibits large Stokes shift (120 nm), fast reaction speed (1 min), low detection limit (15.2 nM), low toxicity, and good cell permeability. Cu 2+ quenches the fluorescence of DPAP by blocking its intramolecular charge transfer process to achieve the detection of Cu 2+ and has been confirmed by HRMS, 1 H NMR and DFT calculations. Excitingly, the five-cycle detection of Cu 2+ and the successful recovery of trace Cu 2+ in environmental water samples fully demonstrate the potential of DPAP for practical applications. In particular, DPAP can observe the distribution and translocation patterns of exogenous Cu 2+ in HeLa cells and zebrafish in real-time. This research concept has offered important theoretical support for the study of the environmental behavior of heavy metal ions.

研究领域: 生物化学 · 分析化学 · 环境科学
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SENSORS AND ACTUATORS B-CHEMICAL · 2015 · IF 4.097

A turn on fluorescent sensor for cyanide based on ICT off in aqueous and its application for bioimaging

Fangjun Huo,Jin Kang,Caixia Yin,Jianbin Chao,Yongbin Zhang

A turn on fluorescent probe for cyanide has been rationally constructed based on an intramolecular charge transfer (ICT) mechanism. Upon treatment with cyanide, probe 1 exhibited a strong fluorescence emission based on blocking ICT. The emission showed good linearity with the cyanide concentration in the range of 0–1.8   μM, and the detection limit measured to be as low as 0.05   μM. The NMR experiments confirmed that the ratiometric response of probe 1 to cyanide is due to the electrophilic addition reaction, which results in the inhibition of the ICT process in the probe. Furthermore, the qualitative determination of exogenous cyanide in HepG2 cells demonstrated that the probe can be employed to detect exogenous cyanide in real biological samples.

研究领域: 分析化学 · 生物医学 · 分子生物学
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Analytical Methods · 2019 ·Vol. 11 ·期 19 ·2579-2584 · IF 2.378

Modulation of ICT and PET processes in boranil derivatives: a ratiometric fluorescent probe for imaging of cysteine

Dongjian Zhu,Xiaowei Yan,Aishan Ren,Wen Cai,Zhenhua Duan,Yanghe Luo

A novel ratiometric fluorescent probe 1 based on boranil derivatives modulated by ICT and PET processes was designed and synthesized for the first time. Upon addition of Cys, the emission peak of 1 changed from 461 nm to 474 nm, accompanied by a fluorescence color change from dark blue to blue under illumination with a 365 nm UV lamp. 1 exhibited a fast response (within 9 min), high sensitivity (detection limit of 95.1 nM) and excellent selectivity toward Cys over Hcy and GSH owing to a specific conjugate addition–cyclization reaction between Cys and the acrylate moiety. Furthermore, 1 was successfully implemented for monitoring Cys in living cells.

研究领域: 分析化学 · 生物医学
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Micromachines · 2023 ·Vol. 14 ·期 3 ·500 · IF 3.4

Enantioselective Recognition of L-Lysine by ICT Effect with a Novel Binaphthyl-Based Complex

Shi Tang,Zhaoqin Wei,Jiani Guo,Xiaoxia Sun,Yu Hu

A novel triazole fluorescent sensor was efficiently synthesized using binaphthol as the starting substrate with 85% total end product yield. This chiral fluorescence sensor was proved to have high specific enantioselectivity for lysine. The fluorescence intensity ofR-1was found to increase linearly when the equivalent amount of L-lysine (0–100 eq.) was gradually increased in the system. The fluorescence intensity of L-lysine toR-1was significantly enhanced, accompanied by the red-shift of emission wavelength (389 nm to 411 nm), which was attributed to the enhanced electron transfer within the molecular structure, resulting in anICTeffect, while the fluorescence response of D-lysine showed a decreasing trend. The enantioselective fluorescence enhancement ratio for the maximum fluorescence intensity was 31.27 [ef = |(IL−I0)/(ID−I0)|, 20 eq. Lys], thus it can be seen that this fluorescent probe can be used to identify and distinguish between different configurations of lysine.Keywords:enantioselective recognition;ICT effect;intermolecular hydrogen bond

研究领域: 化学 · 生物化学
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Frontiers in Bioengineering and Biotechnology · 2022 · IF 6.064

An ICT-Based Coumarin Fluorescent Probe for the Detection of Hydrazine and Its Application in Environmental Water Samples and Organisms

Liu Xina,Zhu Meiqing,Xu Chenyang,Fan Fugang,Chen Panpan,Wang Yi,Li Dongyang

As an inorganic small molecule pollutant, the toxicity and potential carcinogenicity of hydrazine (N2H4) are of increasing concern. In this work, A water-soluble fluorescent probe (OCYB) based on the intramolecular charge transfer (ICT) mechanism for the detection of hydrazine was designed and synthesized. Taking the advantage of 4-bromobutyryl as the recognition group, the high selectivity of OCYB to N2H4 was confirmed by steady-state fluorescence spectroscopy. The limit of detection (LOD) was calculated to be 78 nM in the DMSO-HEPES (pH 7.4) system. The detection mechanism was verified by NMR, HRMS and density functional theory (DFT) calculations. In addition, OCYB exhibits strong anti-interference ability and an “Off-On” fluorescence enhancement effect. Importantly, OCYB can be used to effectively monitor the fluorescence distribution of N2H4 in environmental water samples and organisms.

CAS / MDL: 121-44-8
研究领域: 分析化学 · 环境科学 · 生物化学
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TETRAHEDRON · 2019 · IF 2.379

A near-infrared large Stokes shift probe based enhanced ICT strategy for F- detection in real samples and cell imaging

Qinghua Hu,Qiuxiang Huang,Yu Mao,Xinlin Liu,Fangrong Tan,Yuyuan Wang,Qiang Yin,Xumeng Wu,Hongqing Wang

In view of the few reports of the near-infrared emissive probe for fluorine ions , we herein designed and synthesized a new easy-to-get colorimetric and near-infrared emissive fluorescent probe ( IS-NR-F ) with a large Stokes shift (>127 nm). Based on specific F − triggered desilylation reaction induced enhanced ICT strategy involving the donor phenolate anion and the acceptor malononitrile , the probe exhibited dual colorimetric and fluorescent turn-on responses, and provided excellent selectivity for fluoride ions. The fluorescent response at 665 nm displayed very good linear relationship in the wide concentration range and deduced a low detection limit of 0.09 ppm. The detection mechanism was confirmed by 1 H NMR, ESI-MS, and TLC calculation. Moreover, probe IS-NR-F has been successfully employed to detect F − in tap water, toothpaste samples, and fluorescent imaging of F − in HeLa cells.

研究领域: 分析化学 · 生物医学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2022 · IF 4.831

A dual-site multifunctional fluorescent probe for selective detection of endogenous H2O2 and SO2 derivatives based on ICT process and its bioimaging application

Xue-Liang Liu,Mengdi Yan,Zhi-guo Chen,Bingxin Zhang,Ningcong Yao,Shan Zhao,Xiaoxia Zhao,Tao Zhang,Guangfan Hai

In this paper, we reported a coumarin-based fluorescent probe for selective detection of H 2 O 2 /SO 2 derivatives via ICT process. To the best of our knowledge, it was few reported with the same probe to enable visual detection of H 2 O 2 /SO 2 derivatives in vivo and in vitro. H 2 O 2 and SO 3 2− were selectively sensed over other analytes, and the probe displayed 20-fold and 220-fold relative fluorescence intensity respectively, as well as the good linear relationship and the excellent detection limits of 2.7 * 10 3 nM and 19.3 nM. Furthermore, the probe was successfully used for fluorescence imaging of the HeLa cells and the mice to monitor exogenous and endogenous H 2 O 2 and SO 3 2− , suggesting its potential biomedical application for investigation and detection the intermediate indicator of oxidative stress in vitro and in vivo.

研究领域: 分析化学 · 生物医学工程 · 细胞生物学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2023 · IF 4.4

A pyridine modified naphthol hydrazone Schiff base chemosensor for Al3+ via intramolecular charge transfer process

Brian Musikavanhu,Zeping Huang,Quanhong Ma,Yongdi Liang,Zhaoli Xue,Lei Feng,Long Zhao

A pyridine modified naphthol hydrazone Schiff base chemosensor, NaPy , was prepared in a two-step process to detect aluminum ion (Al 3+ ) in different samples. The probe shows a turn-off emission response towards Al 3+ at a 1:1 binding stoichiometry via intramolecular charge transfer (ICT) mechanism, as validated by density functional theory (DFT) calculations and a series of spectroscopic measurements. The response time is slightly over one minute with a limit of detection (LOD) value of 0.164 µM, demonstrating the great sensitivity of the probe. It is also found that NaPy exhibits high selectivity towards Al 3+ and resists interference from seventeen other cations. Application investigations in paper strips, water samples and HeLa cells suggest that NaPy can be used as an efficient probe for sensing Al 3+ in real environmental samples and biosystems.

研究领域: 分析化学 · 环境科学 · 生物医学
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TALANTA · 2016 · IF 4.035

An intramolecular charge transfer process based fluorescent probe for monitoring subtle pH fluctuation in living cells

Mingtai Sun,Libo Du,Huan Yu,Kui Zhang,Yang Liu,Suhua Wang

It is crucial to monitor intracellular pH values and their fluctuation since the organelles of cells have different pH distribution. Herein we construct a new small molecule fluorescent probe HBT-O for monitoring the subtle pH values within the scope of neutral to acid in living cells. The probe exhibited good water solubility, a marked turquoise to olivine emission color change in response to pH, and tremendous fluorescence hypochromatic shift of ∼50   nm (1718   cm −1 ) as well as the increased fluorescence intensity when the pH value changed from neutral to acid. Thus, the probe HBT-O can distinguish the subtle changes in the range of normal pH values from neutral to acid with significant fluorescence changes. These properties can be attributed to the intramolecular charge transfer (ICT) process of the probe upon protonation in buffer solutions at varied pH values. Moreover, the probe was reversible and nearly non-toxic for living cells. Then the probe was successfully used to detect pH fluctuation in living cells by exhibiting different fluorescence colors and intensity. These findings demonstrate that the probe will find useful applications in biology and biomedical research.

研究领域: 生物化学 · 细胞生物学 · 医学研究
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ANALYTICAL SCIENCES · 2019 ·Vol. 35 ·期 12 ·1341-1345 · IF 1.618

A New Fluorescent Turn-on Dual Interaction Position Probe for Determination of Hydrazine

Xu Wenzhi,Li Xue,Yin Jiwei,Liu Weiyan,Yang Yutao,Li Wei

Hydrazine is an important catalyst and chemical raw material. But it is highly toxic and potentially carcinogenic. We designed a new hydrazine probe based on a synergistic effect by introducing acetate and phthalimide into 2-phenylbenzimidazole (PBI). Comparative experiments proved that “the dual position interaction” had a “synergistic effect” on fluorescence enhancement. The fluorescence enhancement caused by the probe (15.0 fold) is much larger than the sum of the fluorescence enhancement of the two monomer compounds (2.6 and 1.4 folds, respectively). A theoretical calculation showed an inhibition of the PET process and a recovery of the ICT process led to a fluorescence enhancement. The probe was specific to hydrazine and showed a linear response to it in the concentrations range of 0.2–200 μM with a LOD of 0.062 μM (1.99 ppb). Moreover, the probe could detect hydrazine in tap water; the recovery of hydrazine from the tap water was between 98.86–103.28%.

研究领域: 分析化学 · 环境科学 · 毒理学
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SENSORS AND ACTUATORS B-CHEMICAL · 2018 · IF 5.667

A novel fluorescent probe for the ratiometric recognition of protein based on intramolecular charge transfer

Jianjun Du,Quanyong Gu,Jingyao Chen,Jiangli Fan,Xiaojun Peng

The quantitative recognition of proteins receives great importance in the fields of biology and biomedicine. Though the ratiometric fluorescent probe is a good choice for the quantitative recognition which is less susceptible to the environmental and instrumental interference, very few examples have been reported in the protein identification. In this work, a novel and interesting probe, MY, was developed for the quantitative recognition of serum albumin based on the intramolecular charge transfer (ICT) mechanism. By the structure regulation, the distribution between ICT and twisted ICT state was well controlled. The MY showed a fast, sensitive, and ratiometric response to the serum albumin. Besides, the accurate recognition of serum albumin in practical samples exhibited good recoveries compared with the bromocresol green-based standard method.

研究领域: 生物化学 · 分析化学 · 医学检测
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