TALANTA
·
2017
·
IF 4.162
Qianqian Wu,Kangnan Wang,Zian Wang,Yatong Sun,Duxia Cao,Zhiqiang Liu,Ruifang Guan,Songfang Zhao,Xueying Yu
Two 3-hydroxyflavone derivatives as one- and two-photon fluorescent chemosensors for cysteine (Cys) and homocysteine (Hcy) were synthesized. The recognition properties and mechanism of the chemosensors for Cys and Hcy were investigated systematically. The experiment results indicate that 3-hydroxyflavone compound 1 (6-bromo-2-(9-ethyl-9 H -carbazol-3-yl)-3-hydroxy-chromen-4-one) after the addition of nickel ions exhibits good recognition properties for Cys and Hcy with fluorescence enhancement and 65 nm absorption peak blue shift based on nickel displacement reaction mechanism. The detection limits (DL) with fluorescence as detected signal are 4.06 × 10 −3 µM (Cys, linear range of 10–80 µM) and 5.8 × 10 −3 µM (Hcy, linear range of 10–100 µM), respectively. But acrylate substituted 3-hydroxyflavone compound 2 (4-oxo-2-(4-diethylamino-phenyl)-4 H -chromen-3-yl acrylate) can specially identify Cys with fluorescence turn-on (DL = 1.87 × 10 −3 µM, linear range of 4–22 µM) based on Cys leading to acrylate hydrolysis mechanism and succedent excited-state intramolecular proton transfer process of 3-hydroxyflavone compound. Then Cys and Hcy biological thiols can be recognized at one time by these two 3-hydroxyflavone derivatives. The bioimaging experiment indicates that both the compounds can be successfully applied to the detection of Cys/Hcy in living cells and compound 2 also can be applied to bioimaging Cys in zebrafish by one- and two-photon fluorescence mode. Then these two compounds have a potential in the application of biological sample analysis.
研究领域:
生物化学
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分子生物学
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医学影像学
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高影响因子
JOURNAL OF MOLECULAR STRUCTURE
·
2026
·
IF 4.9
Changhai Sun,Mengxin Xiao,Biyue Cui,Shiyuan Sun,Shushuang Shen,Shuting Zhang,Xinran Zhang,Liting Mu
Based on the current state of research, the identification of flavonoid isomers still faces certain difficulties and challenges, and developing liquid chromatography separation conditions requires substantial resources. Therefore, this study constructed a quantitative structure-retention relationship (QSRR) model for anthoxanthins in reverse-phase chromatography by exploring quantitative relationships between chromatographic retention time (t R ) and implicit solvent model solvation free energy and hydrogen bonding energies in the mobile phase. A database was compiled by calculating the molecular descriptors of 1023 hydroxy-substituted flavonoids. When using UHPLC-HRMS technology combined with a database to identify unknown anthoxanthins, this model provides auxiliary identification to enhance the accuracy of the identification results. The model was constructed using 11 modeling compounds and two molecular descriptors to achieve the goal of predict compound retention times. The chromatographic retention time of anthoxanthins exhibited a linear correlation with their solvation free energy in the mobile phase. Furthermore, the feasibility of calculating the hydrogen bonding energies between anthoxanthins and the mobile phase using quantum chemical methods based on electron density was demonstrated. This study provides novel insights into the reverse-phase chromatographic separation of structurally similar compounds, while the constructed database offers extensive data support for isomer research.
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高影响因子
INORGANIC CHEMISTRY COMMUNICATIONS
·
2021
·
IF 2.495
Qian-Qian Huang
A novel tetranuclear nickel(II)-flavonolate complex [Ni II 4 (fla) 4 (CH 3 O) 4 (H 2 O) 4 ] (flaH: 3-Hydroxyflavone, flavonol) was synthesized. Its crystal structure and spectroscopic features have been investigated in details by physicochemical methods and single crystal X-ray diffraction. Different from other mononuclear metal-flavonolate complexes, this complex demonstrates a cluster molecular structure which has four Ni II centers, and each Ni II centre is coordinated by a bidentate flavonolate, three methanol and a water molecule. The crystal of this complex is tetragonal crystal system: space group I 41/a, a = 24.4361(14), b = 24.4361(14), c = 12.7972 (14), α = β = γ = 90 ° , V = 7641.5 (12), Z = 4. The complex can react with O 2 , in other words, it has enzymatic reactivity just like enzyme-substrate model of quercetin 2,3-dioxygenase, and the reaction products are similar with the other reported enzyme-substrate models.
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高影响因子
DYES AND PIGMENTS
·
2019
·
IF 4.018
Xiaojun He,Wei Xiong,LileiZhang,Chuchu Xu,Jinyi Fan,Yuna Qian,Jinsheng Wen,Feng Ding,Jianliang Shen
Gallium , aluminum , and indium belong to Group IIIA of the periodic table with similar chemical properties, which were a double-edged sword for living organisms. Therefore, it's particularly important to detect the content of Group IIIA in organisms. Obviously, the fluorescent probe method has become a mainstream method for detecting metal ions with advantages of convenience and high efficiency. Unfortunately, fluorescent probes that can simultaneously detect these three metal ions are rarely reported. 3-hydroxyflavone ( 3-HF ) is a highly focused molecule with chemical and photochemical properties and have great potential for bioimaging applications as sensors with excited-state intramolecular proton transfer (ESIPT). Here, 3-HF as ratiometric fluorescence probes have been developed for responding to Group IIIA ions including Ga(III), Al(III) and In(III) ions with ESIPT-based mechanism. 3-HF displayed highly specific sensing for Group IIIA ions over other cations with a green fluorescence transformation into blue fluorescence by the formation of 2:1 complexes. However, rapid response toward Group IIIA ions was developed using ratiometric fluorescence with wide pH range and good reversibility , and the response mechanism of 3-HF toward Group IIIA ions was annotated by density functional theory (DFT). Furthermore, the biological applicability of 3-HF has shown that 3-HF were able to detect and image Group IIIA ions in cells. Additionally, using a zebrafish model, we exhibited the capability of this 3-HF probe for detecting and imaging Group IIIA ions in zebrafish. This work achieves the detection and imaging of Group IIIA simultaneously by 3-HF probe in living cells and zebrafish and provides another example for “ESIPT OFF”.
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高影响因子
FOOD RESEARCH INTERNATIONAL
·
2025
·
IF 8
Li-Feng Li,Meng-Di Wang,Chen-Yang Zhang,Meng-Yao Jin,Hua-Lei Chen,Huan Luo,Tian-Yu Hou,Zhi-Jun Zhang,He Li
Advanced glycation end products (AGEs) generated from the Maillard reaction (MR) during food processing in the human physiological environment, have been proven to be significantly associated with various chronic metabolic diseases. In this study, 18 flavonoids were investigated to study their effects on AGEs formation during MR within a glucose-lysine-arginine model system. Five AGEs— N ε -carboxymethyl-lysine (CML), N ε -carboxyethyl-lysine (CEL), pyrraline, pentosidine, and argpyrimidine—were determined by high-performance liquid chromatography-mass spectrometry, with inhibitory rates ranging between 0 % and 71.35 %. Isorhamnetin and naringenin exhibited the strongest inhibitory effect on the formation of CML and CEL, respectively, whereas myricetin exhibited the strongest inhibitory effect on pyrraline, pentosidine, and argpyrimidine formation. In addition, each flavonoid was reacted with glyoxal (GO) and methylglyoxal (MGO) to investigate their trapping activities and adducts. The results showed that the 18 flavonoids could effectively clear GO and MGO, with clearance rates of 1.03 %–71.42 % and 0.93 %–69.37 % for GO and MGO, respectively. Six flavonoids—chrysin, naringenin, apigenin, luteolin, diosmetin, and kaempferol—could form adduct products with mono-/di-MGO, with flavonoid to mono-/di-MGO adduct ratios of approximately 6:1, 2:1, 8:1, 23:1, 10:1, and 3:1, respectively. The number and site of phenolic hydroxyl groups, as well as methoxy substitution on the B-ring in flavonoids, had little effect, but phenolic hydroxyl groups at the C-3 position in the C-ring impeded adduct formation. The flavonoids lowered the degradation of glucose itself, and decreased ammonia-induced degradation and Amadori rearrangement product oxidation due to their antioxidant activities, and they trapped the reactive 1,2-di‑carbonyl species via nucleophilic addition reaction to form AGEs.
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PubMed
高影响因子
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
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2024
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IF 4.3
Qinli Ye,Miaomiao Wu,Qian Xu,Shuwen Zeng,Tao Jiang,Wei Xiong,Songyin Fu,Muhammad Danang Birowosuto,Chenjie Gu
The Surface-enhanced Raman scattering (SERS) is an attractive optical detecting method with high sensitivity and detectivity, however challenges on large-area signal uniformity and complex spectra analysis methods always retards its wide application. Herein, a highly sensitive and uniform SERS detection strategy supported by porous carbon film/WO 3-x nanosheets (PorC/WO 3-x ) based noble-metal-free SERS substrate and deep learning algorithm are reported. Experimentally, the PorC/WO 3-x substrate was prepared by high-temperature annealing the PorC/WO 3 films under the argon atmosphere. The defect density of the WO 3 was controlled by tuning the reducing reaction time during the annealing process. The SERS performance was evaluated by using R6G as the Raman reporter, it showed that the SERS intensity obtained on the substrate with the optimal annealing time of 3 h was about 8 times as high as that obtained on the PorC/WO 3 substrate without annealing treatment. And detection limit of 10 -7 M and Raman enhancement factor of 10 6 could be achieved. Moreover, the above optimal SERS substrate was utilized to detect flavonoids of quercetin, 3-hydroxyflavone and flavone, and a deep learning algorithms was incorporated to identify the quercetin. It revealed that quercetin can be accurately detected within the above flavonoids, and lowest detectable concentration of 10 -5 M can be achieved.
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PubMed
高影响因子
Food Frontiers
·
2025
·Vol. 6
·期 2
·1058-1078
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IF 6.9
Haolin Zhang,Jingjing Zhang,Hui Cao,Petra Högger,Randolph Arroo,Mohamed A. Farag,Avi Shpigelman,Jianbo Xiao,Chunlin Li
A class of flavonoid aminated derivatives that had been consistently overlooked in literature was shown to be formed as artefacts in cell culture medium. In this study, 34 flavonoids from different subclasses were incubated in Dulbecco's modified Eagle's Medium (DMEM) at 37°C for 2 h to identify the reaction mechanism behind aminated derivatives formation from flavonoids. Baicalein, scutellarein, dihydromyricetin, (−)-gallocatechin (GC), (−)-epigallocatechin (EGC), (−)-GC gallate, and (−)-EGC gallate were found to yield corresponding nitrogenous derivatives in both DMEM and amino acid solution. The nitrogen source of these seven flavonoid -aminated derivatives was revealed to be amino acids in DMEM. The pyrogallol group of the flavonoids was a key structural motif, being first oxidized into quinone and then further reacting with amino acids (Strecker degradation) to yield aminated flavonoids and corresponding aldehydes. A slightly alkaline environment accelerated the amination of flavonoids, possibly via the formation of flavonoid quinone. These results provide the mechanistic evidence for the in vitro generation of flavonoid -aminated derivatives, yet to be tested using in vivo assays.
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高影响因子
ACS Applied Polymer Materials
·
2025
·
IF 4.7
Boying Wang,Jin Liu,Wenfei Shen,Yao Wang,Jun Li,Yan Zhang,Qiao Wang,Christopher D. Snow,Matt J. Kipper,Soo Wohn Lee,Laurence A. Belfiore,Jianguo Tang
Facing the significant challenges of information security, this work proposes an information encoding system based on the fluorescence properties of metal-ion-induced polystyrene-block-poly(acrylic acid) (PS–PAA) nanoaggregates (MIPAs), in which Eu3+, Tb3+, and Al3+ ions are embedded. By adding poly(vinylpyrrolidone) (PVP), red, green, and blue primary color inks are obtained. By precisely adjusting the ratio of cations, the control of photoluminescence (PL) intensity at different emission wavelengths is achieved, thereby obtaining a full-color fluorescent ink. Under the potential driving force in the nozzle of an electrofluidic inkjet printer, the ink can be printed onto a paper substrate and exhibit multiple fluorescent colors under ultraviolet (UV) irradiation. The printed fine image structures can carry encoded data. In these images, the multiple emission modes of fluorescent nanoaggregates induced by metal ions (Eu3+, Tb3+, and Al3+) can be combined with multiple quenching mechanisms. This will hopefully further improve the security of encoded information and the efficiency of information retrieval.
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高影响因子
危险品化学品经营许可证（带存储）