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1.
Bioorg Chem ; 148: 107423, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38733751

ABSTRACT

Viscosity and sulfur dioxide derivatives were significant indicators for the assessment of health threat and even cancers, therefore, on-site and real time detection of viscosity and sulfur dioxide derivatives has obtained considerable attentions. An FRET-based fluorescence probe JZX was designed and synthesized based on a novel energy donor of N,N-diethyl-4-(1H-phenanthro[9,10-d]imidazol-2-yl)benzamide fluorophore. JZX exhibited a large Stokes shift (230 nm), high energy transfer efficiency, wide emission channel gap (135 nm) and excellent stability and biocompatibility. JZX detected sulfur dioxide with low detection limit (55 nM), fast responding (16 min), high selectivity and sensitivity. Additionally, JZX tend to target endoplasmic reticulum of which normal metabolism will be disturbed by the abnormal levels of viscosity and sulfur dioxide derivatives. Prominently, JZX could concurrently detect viscosity and sulfur dioxide derivatives depending on different fluorescence signals in living cells for the screening of cancer cells. Hence, probe JZX will be a promising candidate for the detection of viscosity and sulfur dioxide derivatives, and even for the diagnosis of liver cancers.


Subject(s)
Fluorescence Resonance Energy Transfer , Fluorescent Dyes , Sulfites , Fluorescent Dyes/chemistry , Fluorescent Dyes/chemical synthesis , Humans , Viscosity , Sulfites/analysis , Molecular Structure , Sulfur Dioxide/analysis , Optical Imaging , HeLa Cells
2.
Molecules ; 28(24)2023 Dec 05.
Article in English | MEDLINE | ID: mdl-38138429

ABSTRACT

A Ag@AuNP-functionalized capillary-based surface-enhanced Raman scattering (SERS) sensing platform for the interference-free detection of glucose using SERS tags with a built-in nitrile signal has been proposed in this work. Capillary-based SERS capture substrates were prepared by connecting 4-mercaptophenylboronic acid (MBA) to the surface of the Ag@AuNP layer anchored on the inner wall of the capillaries. The SERS tags with a built-in interference-free signal could then be fixed onto the Ag@AuNP layer of the capillary-based capture substrate based on the distinguished feature of glucose, which can form a bidentate glucose-boronic complex. Thus, many "hot spots" were formed, which produced an improved SERS signal. The quantitative analysis of glucose levels was realized using the interference-free SERS intensity of nitrile at 2222 cm-1, with a detection limit of about 0.059 mM. Additionally, the capillary-based disposable SERS sensing platform was successfully employed to detect glucose in artificial urine, and the new strategy has great potential to be further applied in the diagnosis and control of diabetes.


Subject(s)
Glucose , Metal Nanoparticles , Capillaries , Spectrum Analysis, Raman , Gold
3.
JACS Au ; 1(8): 1208-1216, 2021 Aug 23.
Article in English | MEDLINE | ID: mdl-34467359

ABSTRACT

Hard carbons (HCs) as an anode material in sodium ion batteries present enhanced electrochemical performances in ether-based electrolytes, giving them potential for use in practical applications. However, the underlying mechanism behind the excellent performances is still in question. Here, ex situ nuclear magnetic resonance, gas chromatography-mass spectrometry, and high-resolution transmission electron microscopy were used to clarify the insightful chemistry of ether- and ester-based electrolytes in terms of the solid-electrolyte interphase (SEI) on hard carbons. The results confirm the marked electrolyte decomposition and the formation of a SEI film in EC/DEC but no SEI film in the case of diglyme. In situ electrochemical quartz crystal microbalance and molecular dynamics support that ether molecules have likely been co-intercalated into hard carbons. To our knowledge, these results are reported for the first time. It might be very useful for the rational design of advanced electrode materials based on HCs in the future.

4.
Anal Chim Acta ; 1137: 47-55, 2020 Nov 15.
Article in English | MEDLINE | ID: mdl-33153608

ABSTRACT

A deep-red emission and lipid droplets-targeted fluorescence probe (named ZFPy) for effective bioimaging of bisulfite was developed from flavone moiety and benzoindole derivative based on intramolecular charge transfer (ICT) and Förster resonance energy transfer (FRET) platform. ZFPy displayed promising fluorescence parameters including bright deep red fluorescence (615 nm), large Stokes shift (205 nm), extended emission window gap (140 nm), high absolute fluorescence quantum yield (4.1%) and stable emission signal output. In addition, ZFPy realized ratiometric fluorescence monitoring for SO2 derivatives with low detection limit (30 nM), preferable linearity, high sensitivity and selectivity. Interestingly, dual fluorophores (i.e. the donor moiety and 1,1,2,3-tetra-substituent-1H-benzo[e]indol-3-ium iodide moiety) released the same emission band about 475 nm to enhance the emission signal when ZFPy reacted with SO2 derivatives, to the best of our knowledge, this is the first synergetic FRET/ICT platform for fluorescence probe, which might effectively offer ZFPy a high sensitivity and low detection limit in the detection of SO2 derivatives. More importantly, ZFPy could image exogenous and endogenous SO2 derivatives in living HeLa, HepG2 and L-O2 cells with good biocompatibility and photostability. ZFPy also preferred to load on lipid droplets with high Pearson's coefficient (0.95).


Subject(s)
Fluorescence Resonance Energy Transfer , Lipid Droplets , Fluorescent Dyes , Humans , Sulfites
5.
Analyst ; 145(8): 2937-2944, 2020 Apr 14.
Article in English | MEDLINE | ID: mdl-32104823

ABSTRACT

A unique fluorescent probe (ZACA) for the monitoring of SO2 derivatives was developed from coumarin and benzoindoles based on FRET and ICT. ZACA exhibited an active emission signal, large Stokes shift, wide emission window distance, and high photostability. It also possessed many advantages in the ratiometric detection of HSO3-/SO32- including low detection limit and high selectivity and sensitivity. Importantly, ZACA was successfully applied in the ratiometric detection of endogenous HSO3-/SO32- in living cells with excellent cellular imaging capability (1 µM) and mitochondria-targeting ability (co-localization coefficient: 0.91).


Subject(s)
Fluorescent Dyes/chemistry , Mitochondria/metabolism , Sulfites/analysis , Cell Line, Tumor , Coumarins/chemical synthesis , Coumarins/chemistry , Fluorescent Dyes/chemical synthesis , Humans , Indoles/chemical synthesis , Indoles/chemistry , Limit of Detection , Microscopy, Fluorescence
6.
J Mater Chem B ; 7(42): 6585-6591, 2019 11 14.
Article in English | MEDLINE | ID: mdl-31589220

ABSTRACT

A promising near-infrared emissive and mitochondria-targeted fluorescence probe (SNB) for the ratiometric detection of sulfur dioxide derivatives with a novel reaction mechanism was developed on the basis of FRET and the ICT platform. Probe SNB showed favorable fluorescence properties, including an active NIR emission signal (671 nm), ultra-large Stokes shift (251 nm) and an ultra-broad emission band gap (193 nm). Furthermore, SNB was applied to detect sulfur dioxide derivatives with a low detection limit (17 nM), excellent sensitivity and exceptional selectivity. Of greater significance, SNB also successfully implemented the real-time and ratiometric surveillance for exogenous or endogenous sulfur dioxide derivatives in living HeLa, L-O2 and HepG2 cells. Interestingly, SNB possessed a subcellular organelle targeting ability with a preferred co-localization coefficient of 0.91 for mitochondria, which revealed its promising potential in the detection of subcellular sulfur dioxide derivatives.


Subject(s)
Fluorescent Dyes/chemistry , Mitochondria/metabolism , Sulfites/analysis , Cell Line, Tumor , Cell Survival/drug effects , Fluorescent Dyes/toxicity , Humans , Limit of Detection , Microscopy, Fluorescence/methods
7.
Chem Asian J ; 14(19): 3363-3369, 2019 Oct 01.
Article in English | MEDLINE | ID: mdl-31464079

ABSTRACT

A new fluorescent hybrid porous polymer (HPP) is synthesized by an anhydrous FeCl3 -mediated oxidative coupling reaction of octa[4-(9-carbazolyl)phenyl]silsesquioxane (OCPS). The polymer possesses a surface area of 1741 m2 g-1 and hierarchical bimodal micropores (1.41 and 1.69 nm) and mesopores (2.65 nm). The material serves as an excellent adsorbent for CO2 and dyes with high adsorption capacity for CO2 (8.53 wt %,1.94 mmol g-1 ), congo red (1715 mg g-1 ) and rhodamine B (1501 mg g-1 ). In addition, the presence of peripheral cabozolyl groups with extended π-conjugation in the crosslinked framework imparts luminescent character to the polymer and offers the detection of nitroaromatic compounds.

8.
Bioorg Med Chem ; 27(13): 2845-2856, 2019 07 01.
Article in English | MEDLINE | ID: mdl-31103402

ABSTRACT

Biological activities of a series of fluorescent compounds against human lung cancer cell line A549 were investigated. The results showed that (E)-1,3,3-trimethyl-2-(4-(piperidin-1-yl)styryl)-3H-indol-1-ium iodide (8) and (E)-2-(5,5-dimethyl-3-(4-(piperazin-1-yl)styryl)cyclohex-2-en-1-ylidene) malononitrile (11) could inhibit the growth of A549 cancer cells in a dose and time-dependent manner. Furthermore, compound 8 could trigger autophagy and apoptosis, but not obviously induce necrosis under the stimulatory condition. Therefore, 8 can be used as autophagy activator to investigate the regulatory mechanism of autophagy and may offer a new candidate for the treatment of lung cancer.


Subject(s)
A549 Cells/drug effects , Autophagy/drug effects , Lung Neoplasms/physiopathology , Humans , Molecular Structure
9.
Talanta ; 201: 330-334, 2019 Aug 15.
Article in English | MEDLINE | ID: mdl-31122431

ABSTRACT

A novel ratiometric fluorescence probe for hypochlorous acid was constructed by coumarin and pyridinium fluorophore based on the Forster resonance energy transfer (FRET) and intramolecular charge transfer (ICT) platform. In this ICT/FRET system, the energy transfer efficiency is high to 94.3%. Moreover, the probe could respond to hypochlorous acid with high selectivity and sensitivity, and exhibited a large Stokes shift. It was interesting to find that the probe could recognize hypochlorous acid via a new mechanism, in which the α-position of carbonyl group was oxidized to form a diketone derivative. More importantly, the probe was successfully applied to the ratiometric imaging of both exogenous and endogenous hypochlorous acid in living RAW 264.7 cells, with low toxicity and high photo-stability.


Subject(s)
Coumarins/chemistry , Fluorescent Dyes/chemistry , Hypochlorous Acid/analysis , Hypochlorous Acid/metabolism , Pyridinium Compounds/chemistry , Animals , Coumarins/chemical synthesis , Coumarins/radiation effects , Drug Design , Fluorescence , Fluorescence Resonance Energy Transfer/methods , Fluorescent Dyes/chemical synthesis , Fluorescent Dyes/radiation effects , Hydrogen-Ion Concentration , Light , Limit of Detection , Mice , Optical Imaging/methods , Pyridinium Compounds/chemical synthesis , Pyridinium Compounds/radiation effects , RAW 264.7 Cells
10.
Anal Chim Acta ; 1064: 87-93, 2019 Aug 08.
Article in English | MEDLINE | ID: mdl-30982522

ABSTRACT

A ratiometric fluorescence probe (named ZOC) for the fast detection of HClO/ClO- was constructed by coumarin (donor) and pyridinium (acceptor) based on Forster resonance energy transfer (FRET) and intramolecular charge transfer (ICT) platform. ZOC possessed red emission signal (610 nm), large Stocks shift (190 nm), high energy transfer efficiency (95.3%), high selectivity and sensitivity, low detection limit (25 nM), wider detection range (from 25 nM to 30 µM), rapid response (within 13 S), and good biocompatibility. It was very interesting that the recognition mechanism involved a new organic reaction in which olefin double bond reacted first with HClO/ClO- regioselectively, followed by cyclization. ZOC was successfully used to the real time detection of endogenous HClO/ClO- in RAW 264.7 cells.


Subject(s)
Fluorescent Dyes/chemistry , Hypochlorous Acid/analysis , Optical Imaging , Animals , Mice , Molecular Structure , RAW 264.7 Cells
11.
Chempluschem ; 84(10): 1630-1637, 2019 Oct.
Article in English | MEDLINE | ID: mdl-31943923

ABSTRACT

Methylation of TPA-DCM (2-(2,6-bis-4-(diphenylamino)stryryl-4H-pyranylidene)malononitrile) that exhibits aggregation-caused quenching (ACQ) results in the fluorophore M-TPA-DCM (2-(2,6-bis((E)-4-(di-p-tolylamino)-styryl)-4H-pyran-4-ylidene]malononitrile) that shows aggregation-induced emission (AIE) and NIR fluorescence and has a conjugated "D-π-A-π-D" electronic configuration. Friedel-Crafts reaction of TPA-DCM and octavinylsilsesquioxane (OVS) resulted in a family of porous materials (TPAIEs) that contain the M-TPA-DCM motif and show large Stokes shifts (180 nm), NIR emission (670 nm), tunable porosity (SBET from 160 to 720 m2 g-1 , pore volumes of 0.13-0.55 cm3 g-1 ), as well as high thermal stability (400 °C, 5 % mass loss, N2 ). As a simple test case, one of TPAIE materials was used to sense Ru3+ ions with high selectivity and sensitivity.

12.
Se Pu ; 32(6): 623-8, 2014 Jun.
Article in Chinese | MEDLINE | ID: mdl-25269261

ABSTRACT

To achieve accurate, fast and sensitive detection of phenolic endocrine disruptors in small volume of environmental water samples, a method of dispersive liquid-liquid microextraction (DLLME) coupled with fluorescent derivatization was developed for the determination of bisphenol A, nonylphenol, octylphenol and 4-tert-octylphenol in environmental water samples by high performance liquid chromatography-fluorescence detection (HPLC-FLD). The DLLME and derivatization conditions were investigated, and the optimized DLLME conditions for small volume of environmental water samples (pH 4.0) at room temperature were as follows: 70 microL chloroform as extraction solvent, 400 microL acetonitrile as dispersing solvent, vortex mixing for 3 min, and then high-speed centrifugation for 2 min. Using 2-[2-(7H-dibenzo [a, g] carbazol-7-yl)-ethoxy] ethyl chloroformate (DBCEC-Cl) as precolumn derivatization reagent, the stable derivatives of the four phenolic endocrine disruptors were obtained in pH 10.5 Na2CO3-NaHCO3 buffer/acetonitrile at 50 degrees C for 3 min, and then separated within 10 min by HPLC-FLD. The limits of detection (LODs) were in the range of 0.9-1.6 ng/L, and the limits of quantification (LOQs) were in the range of 3.8-7.1 ng/L. This method had perfect linearity, precision and recovery results, and showed obvious advantages and practicality comparing to the previously reported methods. It is a convenient and validated method for the routine analysis of phenolic endocrine disruptors in waste water of paper mill, lake water, domestic wastewater, tap water, etc.


Subject(s)
Endocrine Disruptors/analysis , Water Pollutants, Chemical/analysis , Water/analysis , Benzhydryl Compounds , Carbazoles , Chloroform , Chromatography, High Pressure Liquid , Environmental Monitoring , Fluorescence , Fresh Water , Limit of Detection , Liquid Phase Microextraction , Phenols , Solvents
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