共查询到20条相似文献,搜索用时 15 毫秒
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Baogang Wang Prof. Shichong Yu Dr. Xiaoyun Chai Prof. Tiejun Li Prof. Qiuye Wu Prof. Ting Wang 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(16):5649-5656
The requirement for nitric oxide (NO) of lysosomes has motivated the development of a sophisticated fluorescent probe to monitor the distribution of this important biomolecule at the subcellular level in living cells. A near‐infrared (NIR) fluorescent Si‐rhodamine (SiRB)‐NO probe was designed based on the NO‐induced ring‐opening process of Si‐rhodamine. The probe exhibits fast chromogenic and fluorogenic responses, and high sensitivity and selectivity toward trace amounts of NO. Significantly, the spirolactam in Si‐rhodamine exhibits very good tolerance to H+, which in turn brings extremely low background fluorescence not only in the physiological environment but also under acidic conditions. The stability of the highly fluorescent product in acidic solution provides persistent fluorescence emission for long‐term imaging experiments. To achieve targeted imaging with improved spatial resolution and sensitivity, an efficient lysosome‐targeting moiety was conjugated to a SiRB‐NO probe, affording a tailored lysosome‐targeting NIR fluorescent Lyso‐SiRB‐NO probe. Inheriting the key advantages of its parent SiRB‐NO probe, Lyso‐SiRB‐NO is a functional probe that is suited for monitoring lysosomal NO with excellent lysosome compatibility. Imaging experiments demonstrated the monitoring of both exogenous and endogenous NO in real time by using the Lyso‐SiRB‐NO probe. 相似文献
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Dong‐Hao Li Cynthia L. Schreiber Bradley D. Smith 《Angewandte Chemie (International ed. in English)》2020,59(29):12154-12161
The near‐infrared window of fluorescent heptamethine cyanine dyes greatly facilitates biological imaging because there is deep penetration of the light and negligible background fluorescence. However, dye instability, aggregation, and poor pharmacokinetics are current drawbacks that limit performance and the scope of possible applications. All these limitations are simultaneously overcome with a new molecular design strategy that produces a charge balanced and sterically shielded fluorochrome. The key design feature is a meso‐aryl group that simultaneously projects two shielding arms directly over each face of a linear heptamethine polyene. Cell and mouse imaging experiments compared a shielded heptamethine cyanine dye (and several peptide and antibody bioconjugates) to benchmark heptamethine dyes and found that the shielded systems possess an unsurpassed combination of photophysical, physiochemical, and biodistribution properties that greatly enhance bioimaging performance. 相似文献
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Construction of a Near‐Infrared Fluorescent Turn‐On Probe for Selenol and Its Bioimaging Application in Living Animals 下载免费PDF全文
Hua Chen Baoli Dong Yonghe Tang Prof. Weiying Lin 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(33):11696-11700
As selenocysteine (Sec) carries out the majority of the functions of the various Se‐containing species in vivo, it is of high importance to develop reliable and rapid assays with biocompatibility to detect Sec. Herein, an NIR fluorescent turn‐on probe for highly selective detection of selenol was designed and synthesized. The probe exhibits large turn‐on signal upon treatment with selenocysteine (R‐SeH), and it was further demonstrated that the new NIR fluorescent probe can be employed to image selenol in living animals. 相似文献
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Georg M. Fischer Dipl.‐Chem. Magnus Isomäki‐Krondahl Inigo Göttker‐Schnetmann Dr. Ewald Daltrozzo Prof. Dr. Andreas Zumbusch Prof. Dr. 《Chemistry (Weinheim an der Bergstrasse, Germany)》2009,15(19):4857-4864
NIRer there : Pyrrolopyrrole cyanine (PPCys) dyes, a new class of near‐infrared (NIR) fluorophores, are obtained by condensation of heteroarylacetonitrile and diketopyrrolopyrrole compounds (see picture). Complexation with BF2 or BPh2 yields strongly fluorescent, photostable NIR dyes that show high absorption cross‐sections and fluorescence quantum yields. Furthermore, alteration of the heterocycle can tune the main absorption between λ = 684 and 864 nm.
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FRET‐Based Mitochondria‐Targetable Dual‐Excitation Ratiometric Fluorescent Probe for Monitoring Hydrogen Sulfide in Living Cells 下载免费PDF全文
Hydrogen sulfide (H2S) is connected with various physiological and pathological functions. However, understanding the important functions of H2S remains challenging, in part because of the lack of tools for detecting endogenous H2S. Herein, compounds Ratio‐H2S 1/2 are the first FRET‐based mitochondrial‐targetable dual‐excitation ratiometric fluorescent probes for H2S on the basis of H2S‐promoted thiolysis of dinitrophenyl ether. With the enhancement of H2S concentration, the excitation peak at λ≈402 nm of the phenolate form of the hydroxycoumarin unit drastically increases, whereas the excitation band centered at λ≈570 nm from rhodamine stays constant and can serve as a reference signal. Thus, the ratios of fluorescence intensities at λ=402 and 570 nm (I402/I570) exhibit a drastic change from 0.048 in the absence of H2S to 0.36 in the presence of 180 μM H2S; this is a 7.5‐fold variation in the excitation ratios. The favorable properties of the probe include the donor and acceptor excitation bands, which exhibit large excitation separations (up to 168 nm separation) and comparable excitation intensities, high sensitivity and selectivity, and function well at physiological pH. In addition, it is demonstrated that the probe can localize in the mitochondria and determine H2S in living cells. It is expected that this strategy will lead to the development of a wide range of mitochondria‐targetable dual‐excitation ratiometric probes for other analytes with outstanding spectral features, including large separations between the excitation wavelengths and comparable excitation intensities. 相似文献
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Gergely Knorr Eszter Kozma Dr. András Herner Dr. Edward A. Lemke Dr. Péter Kele 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(26):8972-8979
The synthesis of a set of tetrazine‐bearing fluorogenic dyes suitable for intracellular labeling of proteins in live cells is presented. The red excitability and emission properties ensure minimal autofluorescence, while through‐bond energy‐transfer‐based fluorogenicity reduces nonspecific background fluorescence of unreacted dyes. The tetrazine motif efficiently quenches fluorescence of the phenoxazine core, which can be selectively turned on chemically upon bioorthogonal inverse‐electron‐demand Diels–Alder reaction with proteins modified genetically with strained trans‐cyclooctenes. 相似文献
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Dr. Jinping Lai An Yu Letao Yang Yixiao Zhang Dr. Birju P. Shah Prof. Dr. Ki Bum Lee 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(18):6361-6367
Photoactivatable fluorophores are essential tools for studying the dynamic molecular interactions within important biological systems with high spatiotemporal resolution. However, currently developed photoactivatable fluorophores based on conventional dyes have several limitations including reduced photoactivation efficiency, cytotoxicity, large molecular size, and complicated organic synthesis. To overcome these challenges, we herein report a class of photoactivatable fluorescent N‐hydroxyoxindoles formed through the intramolecular photocyclization of substituted o‐nitrophenyl ethanol (ONPE). These oxindole fluorophores afford excellent photoactivation efficiency with ultra‐high fluorescence enhancement (up to 800‐fold) and are small in size. Furthermore, the oxindole derivatives show exceptional biocompatibility by generating water as the only photolytic side product. Moreover, structure–activity relationship analysis clearly revealed the strong correlation between the fluorescent properties and the substituent groups, which can serve as a guideline for the further development of ONPE‐based fluorescent probes with desired photophysical and biological properties. As a proof‐of‐concept, we demonstrated the capability of a new substituted ONPE that has an uncaging wavelength of 365–405 nm and an excitation/emission at 515 and 620 nm, for the selective imaging of a cancer cell line (Hela cells) and a human neural stem cell line (hNSCs). 相似文献
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Canjia Zhai Dr. Cynthia L. Schreiber Sasha Padilla-Coley Dr. Allen G. Oliver Prof. Bradley D. Smith 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(52):23948-23955
A general synthetic method creates a new class of covalently connected, self-threaded, fluorescent molecular probes with figure-eight topology, an encapsulated deep-red fluorophore, and two peripheral peptide loops. The globular molecular shape and rigidified peptide loops enhance imaging performance by promoting water solubility, eliminating probe self-aggregation, and increasing probe stability. Moreover, the peptide loops determine the affinity and selectivity for targets within complex biological samples such as cell culture, tissue histology slices, or living subjects. For example, a probe with cell-penetrating peptide loops targets the surface of cell plasma membranes, whereas, a probe with bone-targeting peptide loops selectively stains the skeleton within a living mouse. The unique combination of bright deep-red fluorescence, high stability, and predictable peptide-based targeting is ideal for photon intense fluorescence microscopy and biological imaging. 相似文献
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A “Distorted‐BODIPY”‐Based Fluorescent Probe for Imaging of Cellular Viscosity in Live Cells 下载免费PDF全文
Hao Zhu Dr. Jiangli Fan Miao Li Jianfang Cao Dr. Jingyun Wang Prof. Dr. Xiaojun Peng 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(16):4691-4696
Cellular viscosity is a critical factor in governing diffusion‐mediated cellular processes and is linked to a number of diseases and pathologies. Fluorescent molecular rotors (FMRs) have recently been developed to determine viscosity in solutions or biological fluid. Herein, we report a “distorted‐BODIPY”‐based probe BV‐1 for cellular viscosity, which is different from the conventional “pure rotors”. In BV‐1 , the internal steric hindrance between the meso‐CHO group and the 1,7‐dimethyl group forced the boron–dipyrrin framework to be distorted, which mainly caused nonradiative deactivation in low‐viscosity environment. BV‐1 gave high sensitivity (x=0.62) together with stringent selectivity to viscosity, thus enabling viscosity mapping in live cells. Significantly, the increase of cytoplasmic viscosity during apoptosis was observed by BV‐1 in real time. 相似文献
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Reaction‐Based Fluorescent Probe for Detection of Endogenous Cyanide in Real Biological Samples 下载免费PDF全文
Dr. Lingliang Long Lin Wang Yanjun Wu Prof. Aihua Gong Dr. Zulin Da Prof. Chi Zhang Zhixiang Han 《化学:亚洲杂志》2014,9(11):3291-3298
Herein, two compounds ( 1 a and 1 b ) were rationally constructed as novel reaction‐based fluorescent probes for CN? by making use of the electron‐withdrawing ability of the cyano group that was formed from the sensing reaction. Notably, this design strategy was first employed for the development of fluorescent CN? probes. The experimental details showed that probe 1 a exhibited a fluorescence turn‐on response to CN?, whereas other anions, biological thiols, and hydrogen sulfide gave almost no interference. The detection limit of probe 1 a for CN? was found to be 0.12 μM . The sensing reaction product of 1 a with CN? was characterized by NMR spectroscopy and mass spectrometry. TD‐DFT calculations demonstrated that the formed cyano group drives the intramolecular charge transfer (ICT) process from coumarin dye to the cyano group and thus the original strong ICT from the coumarin dye to the 3‐position pyridyl vinyl ketone substituent is weakened, which results in recovery of coumarin fluorescence. The practical utility of 1 a was also examined. By fabricating paper strips, probe 1 a can be used as a simple tool to detect CN? in field measurements. Moreover, probe 1 a has been successfully applied for quantitative detection of endogenous CN? from cassava root. 相似文献
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Dr. Qingqing Miao Dr. David C. Yeo Dr. Christian Wiraja Dr. Jianjian Zhang Xiaoyu Ning Prof. Chenjie Xu Prof. Kanyi Pu 《Angewandte Chemie (International ed. in English)》2018,57(5):1256-1260
Early detection of skin diseases is imperative for their effective treatment. However, fluorescence molecular probes that allow this are rare. The first activatable near‐infrared (NIR) fluorescent molecular probe is reported for sensitive imaging of keloid cells, skin cells from abnormal scar fibrous lesions. As keloid cells have high expression levels of fibroblast activation protein‐alpha (FAPα), the probe (FNP1) is designed to have a caged NIR dye and a FAPα‐cleavable peptide substrate linked by a self‐immolative segment. FNP1 can quickly and specifically turn on its fluorescence at 710 nm by 45‐fold in the presence of FAPα, allowing it to effectively recognize keloid cells from normal skin cells. Integration of FNP1 with a simple microneedle‐assisted topical application enables sensitive detection of keloid cells in metabolically‐active human skin tissue with a theoretical limit of detection down to 20 000 cells. 相似文献
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A Selective Near‐Infrared Fluorescent Probe for In Vivo Imaging of Thiophenols from a Focused Library 下载免费PDF全文
Yue Pan Tian‐Bing Ren Dan Cheng Dr. Ze‐Bing Zeng Dr. Lin Yuan Dr. Xiao‐Bing Zhang 《化学:亚洲杂志》2016,11(24):3575-3582
Thiophenols are highly toxic industrial materials that, once released, will accumulate in the environment, and ultimately in human bodies, thereby causing serious health problems. To achieve their selective and sensitive detection, a novel near‐infrared (NIR) fluorescent probe ( CCP‐1 ) from a focused library was developed for thiophenol species. Our studies show that CCP‐1 displays a thiophenol‐triggered 28‐fold fluorescence intensity enhancement at 706 nm, with a detection limit of 34 nm observed. It is also able to differentiate thiophenols from various other thiol‐containing analytes including hydrogen sulfide, hydrogen persulfide, and aliphatic thiols. In total, the desirable properties (e.g., excitation/emission in the NIR region, good cell‐membrane permeability, intracellular stability, and low cytotoxicity) make CCP‐1 a potential candidate for thiophenol detection both in vitro and in vivo. In addition, CCP‐1 , for the first time, successfully visualized thiophenols in mice models of thiophenol inhalation. 相似文献
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Dr. Marek Grzybowski Prof. Dr. Masayasu Taki Keiji Kajiwara Prof. Dr. Shigehiro Yamaguchi 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(35):7912-7917
A series of phosphine oxide-bridged rhodamines (P-rhodamines) bearing various acyclic and cyclic amine moieties, including dimethyl- and diethylamine, azetidine, pyrrolidine and 7-azabicyclo[2,2,1]heptane (7ABH), have been synthesized. The photophysical properties as well as chemical and photostability of these dyes have been studied in detail. Among these dyes, the 7ABH-substituted dye shows stronger fluorescence in the near-infrared (NIR) region, relative to the other P-rhodamines. This dye could be applied to live-cell imaging, wherein lysosomes were selectively stained in a pH-independent manner. It was also found that the ring fusion of the amine moieties gives rise to remarkably redshifted spectra, with absorption and emission maxima at 770 and 820 nm, respectively, spectrally close to that of indocyanine green (ICG). Importantly, the ring-fused P-rhodamines showed much higher photostability than ICG, indicative of their promising utility as the NIR-emissive dyes. 相似文献
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Keto‐benzo[h]‐Coumarin‐Based Near‐Infrared Dyes with Large Stokes Shifts for Bioimaging Applications 下载免费PDF全文
Guangle Niu Prof. Dr. Weimin Liu Prof. Dr. Hongyan Xiao Prof. Dr. Hongyan Zhang Jianhong Chen Qing Dai Prof. Dr. Jiechao Ge Prof. Dr. Jiasheng Wu Prof. Dr. Pengfei Wang 《化学:亚洲杂志》2016,11(4):498-504
Fluorescence imaging is a promising tool for the visualization of biomolecules in living systems and there is great demand for new fluorescent dyes that absorb and emit in the near‐infrared (NIR) region. Herein, we constructed three new fluorescent dyes ( NBC dyes) based on keto‐benzo[h]coumarin ( k‐BC ) and benzopyrilium salts. These dyes showed large Stokes shifts (>100 nm) and NIR emission (>800 nm). The relationship between the structures and optical properties of these dyes was further investigated by using density functional theory calculations at the B3LYP/6‐3G level of theory. Fluorescence images indicated that the fabricated dyes exhibited good photostability and low cytotoxicity and, thus, have potential applications as imaging agents in living cells and animals. 相似文献