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JOURNAL OF ORGANIC CHEMISTRY · 2022 · IF 4.198

Gold(I)-Catalyzed Tandem Cyclization/Hydroarylation of o-Alkynylphenols with Haloalkynes

Jiawen Wu,Cunbo Wei,Fen Zhao,Wenqian Du,Zhishuai Geng,Zhonghua Xia

A convenient and mild protocol for the gold-catalyzed intermolecular coupling of o-alkynylphenols with haloalkynes to give vinyl benzofurans is reported. In this work, the gold catalyst SIPrAuCl and the co-catalyst NaBARF would corporately promote the intramolecular cyclization of the o-alkynylphenol to benzofuran, and then a selective hydroarylation of benzofuran to haloalkyne was catalyzed by the same catalysts. Computational studies suggest that the hydroarylation process takes place via a concerted nucleophilic attack pathway of the benzofuran to the C2 carbon of the activated haloalkyne, and reveal the original driving force of this hydroarylation process.

研究领域: 有机化学 · 催化 · 合成化学
✓ 已验证 DOI PubMed 高影响因子
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SENSORS AND ACTUATORS B-CHEMICAL · 2017 · IF 5.401

Exonuclease I assisted fluorometric aptasensor for adenosine detection using 2-AP modified DNA

Haiyan Liu,Yunfeng Bai,Jun Qin,Haiyan Wang,Yuzhen Wang,Zezhong Chen,Feng Feng

A novel sensitive fluorescence method was developed for adenosine detection by using adenosine aptamer, Exo I and a 2-aminopurine-modified DNA (2-AP probe). 2-AP probe was completely complementary to adenosine aptamer. This strategy took advantage of the high binding affinity of adenosine aptamer and the susceptibility of 2-aminopurine (2-AP) to the local base stacking environment. In the absence of the adenosine, the formation of double-stranded DNA (dsDNA) through the hybridization of the aptamer with the 2-AP probe prevented the digestion of 2-AP probe by Exo I. The fluorescence of 2-AP was significantly quenched due to the base-stacking interaction. In the presence of adenosine, the binding of adenosine with the aptamer prevented the hybridization between aptamer and 2-AP probe, leading to the digestion of 2-AP probe by Exo I and the release of 2-AP. The fluorescence was recovered. A limit of detection of 0.30   μM and a linear range from 10   μM to 600   μM ( R 2   =   0.9933) were achieved by this assay. Moreover, adenosine analogs did not produce any significant change in the fluorescence intensity response, indicating good selectivity of this sensor for adenosine detection. Finally, it was used for the diluted serum sample.

研究领域: 分析化学 · 分子生物学 · 生物技术
✓ 已验证 产品关联 DOI 高影响因子
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JOURNAL OF ORGANIC CHEMISTRY · 2020 · IF 4.335

Synthesis of Allenyl-Bdan via the Cu(I)-Catalyzed Borylation of Propargylic Alcohols with the Unsymmetric Diboron Reagent (Bpin-Bdan)

Lujia Mao,Chunlei Li,Libo Xiang,Dejun Fu,Wangyang Ma,Qing Ye

The synthesis of allenyl-Bdan has been realized via the Cu(I)-catalyzed borylation of propargylic alcohols. This methodology offers a facile and efficient pathway toward allenyboronates with diverse functional groups due to the simple access to the substrates. The substrates bearing ester groups are well-tolerated in the synthesis of allenyl-Bdan under the Lewis acidic conditions. The structures of two allenyl-Bdan were further confirmed via single-crystal X-ray diffraction.

研究领域: 有机化学 · 合成化学
✓ 已验证 DOI PubMed 高影响因子
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INORGANICA CHIMICA ACTA · 2021 · IF 2.545

Synthesis, structures, DFT studies and luminescent properties of copper(I)-diimine complexes and application in yellow-green light-emitting diode

Tian-Cheng Wu,Qiao-Long Hu,Ting-Hong Huang,Yi-Shun Cui,Dan Zheng,Changyan Ji,Cheng Luo

A series of copper(I) - diimine complexes, [Cu(bdpp)(bpy)]BF 4 ( 1 ), [Cu(bdpp) (pen)]BF 4 ( 2 ), [Cu(bdpp)(damp)]BF 4 ( 3 ), [Cu(bdpp)(pen)]BF 4 ( 4 ) (bdpp  =  4,6-bis-(biphenyl phosphino) phenoxazine, bpy = 2,2′-bipyridine, phen = 1,10-Phenanthroline, dmp = 2,9-dimethyl-1,10-phenanthroline, bphen = 4,7-diphenyl-1,10-phenanthroline), have been synthesized and characterized by IR, 1 H NMR, 31 P NMR, XRD and X-ray crystal structure analysis. Structural analysis reveals that each Cu + in 1 – 4 is four-coordinated by two N atoms and two P atoms and adopts a distorted tetrahedral geometry. DFT calculations show that the HOMOs in 1 – 4 are mainly comprised of bdpp and copper d–orbitals, while the LUMOs are mainly dominated by diimine ligands. Calculation of atomic charges indicates that the charges of the central Cu atoms in 1 – 4 are less than + 1, and the diimine ligands may be the key to the metal charge transfer to the coordinated atom. In 1 – 4 , the maximum phosphorescent lifetimes and quantum yields are up to 349 μs and 22%, respectively. Moreover, complex 3 is used for fabricating the LED device, showing a decent performance with the maximum EQE of 11%.

研究领域: 化学 · 材料科学
✓ 已验证 DOI 高影响因子
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2025 · IF 6.2

Rethinking the Cucurbitane-Type Triterpenoid Profile of Bitter Gourd (Momordica charantia L.): The Chemical Transformation of Momordicine I in Solution

Xueyi Cai,Ziqiang Lin,Lang Liu,Wangwang Yan,Zi Wang,Yang Zhang,Xiao Chen,Dong Liang

Momordica charantia L., commonly known as bitter gourd, is a popular vegetable and medical herb in many countries. The most characteristic phytochemical profile of bitter gourd is its high content of cucurbitane-type triterpenoids, which are responsible for its bitter taste and therapeutic potential. More than 260 cucurbitane-type triterpenoids, including at least 11 5,19-hemiacetals, 40 5,19-methyl acetals, 46 methyl ethers, 6 5,19-ethyl acetals, and 7 ethyl ethers, have been identified from bitter gourd. In this work, by studying the chemical transformation of momordicine I, one of the most abundant cucurbitane-type triterpenoids in bitter gourd, we showed that under acidic conditions, 5,19-hemiacetals of cucurbitane-type triterpenoids could be formed from the intramolecular nucleophilic addition between the C-19 aldehyde and the C-7 hydroxyl group; furthermore, 5,19-acetals and methyl ethers could be generated if methanol was available. Using a UPLC-MS/MS quantification method, we showed that these momordicine I derivatives could not be detected from bitter gourd fruits when extracted with a nonmethanolic solution but could be detected when extracted with methanol after thermal treatment. Moreover, these momordicine I derivatives were detected in two of eight brands of bitter gourd dietary supplements. This might be concerning because these derivatives were not the natural components of bitter gourd, and their safety and efficacy profiles were unknown. Besides, the transformation reactions reported herein should apply widely to other cucurbitane-type triterpenoids as well. Therefore, we believe all 40 5,19-acetals, 46 methyl ethers, 6 5,19-ethyl acetals, and 7 ethyl ethers were the extraction and isolation artifacts and should not be regarded as the natural components of bitter gourd. This work will help to clarify the current misunderstanding of the real cucurbitane-type triterpenoid profile of bitter gourd.

CAS / MDL: 631-61-8 64-19-7 64-18-6
研究领域: 植物化学 · 食品科学 · 药物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ACS Sustainable Chemistry & Engineering · 2016 · IF 5.267

New Copper(I)/DBU Catalyst System for the Carboxylative Cyclization of Propargylic Amines with Atmospheric CO2: An Experimental and Theoretical Study

Yuling Zhao,Jikuan Qiu,Li Tian,Zhiyong Li,Maohong Fan,Jianji Wang

Carbon dioxide (CO2) is an abundant and renewable feedstock for the production of high-value chemicals. Herein, CuI and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were employed as an efficient catalyst system to synthesize 2-oxazolidinones through the coupling reaction of CO2 and propargylic amines. It was found that this cost-competitive catalyst system could efficiently catalyze the reaction within only 4 h at atmospheric pressure CO2, and a wide range of substrates were suitable for this reaction. Various target products were obtained in excellent yields. Furthermore, the catalytic mechanism of the CuI/DBU system was investigated by using density functional theory. It was shown that copper(I) and DBU played synergistic roles in activating both the C≡C triple bond and the amino group of propargylic amines in the reaction.

CAS / MDL: 6674-22-2
研究领域: 有机化学 · 催化化学
✓ 已验证 产品关联 DOI 高影响因子
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SENSORS AND ACTUATORS B-CHEMICAL · 2016 · IF 4.758

Fluorescence “turn on-off” detection of heparin and heparinase I based on the near-infrared emission polyethyleneimine capped Ag2S quantum dots

Dan Yan,Yu He,Yili Ge,Gongwu Song

A novel fluorescence “turn on-off” method for sensitive and selective detection of heparin and heparinase I was developed based on near infrared Polyethyleneimine Capped Ag 2 S Quantum Dots (PEI-Ag 2 S QDs). The fluorescence “turn-on” arose from aggregation-induced emission enhancement (AIEE) characteristics of PEI-Ag 2 SQDs induced by electrostatic interaction between PEI-Ag 2 SQDs and heparin. Heparinase I, which can specifically hydrolyze heparin into short fragments would de-aggregate PEI-Ag 2 S QDs/heparin system and lead to fluorescence “turn-off”. Under optimal conditions described, the fluorescence enhancement at 685   nm was linearly related to the concentration of heparin and heparinase I in the range of 0.069–2.275   μM and 0–103   ng   mL −1 with the relative correlation coefficient of R 2   =   0.997 and 0.99 and detection limit as low as 6   nM and 0.5   ng   mL −1 , respectively. The activity of the heparinase I was further investigated using steady-state kinetic for the reaction. In ddition, the proposed method was successfully utilized in serum samples, which presaged more opportunities for application in related biochemical and biomedical researches.

研究领域: 生物化学 · 医学检测 · 纳米技术
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Oncologie · 2023 ·Vol. 25 ·期 3 ·233-243 · IF 0.9

Anemarrhenasaponin I suppresses ovarian cancer progression via inhibition of SHH signaling pathway

Simin Deng,Yuan Xu,Binbin Gao,Tingting Yu,Lun Kuang,Bo’ang Han,Shaolun Feng,Haodong Chi,Qing Cao,Shen Yue,Chen Liu

Objectives The Sonic hedgehog (SHH) signaling is essential in animal development and tissue homeostasis. Aberrant activation of SHH pathway has been implicated in tumorigenesis and progression of several cancers, including ovarian cancer. Therefore, targeting SHH pathway may pave the way for successful ovarian cancer treatment. Methods To identify the potential SHH inhibitors from traditional Chinese medicines, we herein employed two in vitro cell models. In addition, western blotting and quantitative real-time PCR were performed to evaluate the inhibitory activity of Anemarrhenasaponin I (An-I) on SHH signaling in ovarian cancer cells. Cell proliferation assay and transwell assay were used to assess the effect of An-I on tumorigenicity. We also applied RNA-seq to examine the potential mechanism of An-I against ovarian cancer. Results Drug screening results showed that An-I drastically inhibited SHH signaling. More importantly, An-I effectively suppressed ovarian cancer cell proliferation and aggressiveness. RNA-seq-based transcriptome data showed that An-I affected ovarian cancer cells by suppressing SHH-WNT-Matrix metalloproteinases (MMPs) pathway. Conclusions An-I suppressed ovarian cancer progression by inhibiting SHH-WNT-MMP signaling transduction, providing a new treatment strategy for ovarian cancer.

研究领域: 肿瘤学 · 药理学 · 分子生物学 · 细胞生物学
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DALTON TRANSACTIONS · 2024 · IF 3.5

Broadband blue light emissions of one-dimensional hybrid Cu(I) halides with ultrahigh anti -water stability

Na Lin,Yun-Xia Li,Yu Liu,Kai-Qi Sun,Hong-Yan Zhang,Xiao-Wu Lei,Zhi-Wei Chen

Low-dimensional organic–inorganic hybrid lead halide perovskites have attracted much interest in solid-state lighting and displays, but the toxicity and instability of lead halide are obstacles to their industrial applications, which must be overcome. As an alternative, Cu(I)-based hybrid metal halides have emerged as a new type of luminescent material owing to their diversified structure, adjustable luminescence, low toxicity and low cost. Herein, we report three one-dimensional (1D) hybrid Cu(I)-based halides with the general formula ACu2Br4 (A = [(Me)4-Pipz]2+ and [BuDA]2+ and [TMEDA]2+). These 1D hybrid Cu(I) halides display stable broadband blue emission with maximum emission peaks in the range of 445–474 nm and the highest photoluminescence quantum yield of 37.8%. Furthermore, in-depth experimental and theoretical investigations revealed that the broadband blue emissions originate from the radiative recombination of self-trapped excitons. Most importantly, there is no structural degradation and attenuation of emission intensity even after continuously soaking these halides in water for at least two months, demonstrating their ultra-high anti-water stability. Hirshfeld surface analysis shows that a large number of weak hydrogen bonds can protect the inorganic skeleton from degradation due to water. This work provides a new strategy for the design of water-stable Cu(I)-based halides with efficient blue emission and wide potential applications in humid environments.

研究领域: 材料科学 · 光学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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International Journal of Nanomedicine · 2023 · IF 8

A robust and versatile signal-on fluorescence sensing strategy based on SYBR Green I dye and graphene oxide

Huazhang Qiu,Namei Wu,Yanjie Zheng,Min Chen,Shaohuang Weng,Yuanzhong Chen,Xinhua Lin

A robust and versatile signal-on fluorescence sensing strategy was developed to provide label-free detection of various target analytes. The strategy used SYBR Green I dye and graphene oxide as signal reporter and signal-to-background ratio enhancer, respectively. Multidrug resistance protein 1 (MDR1) gene and mercury ion (Hg2+) were selected as target analytes to investigate the generality of the method. The linear relationship and specificity of the detections showed that the sensitive and selective analyses of target analytes could be achieved by the proposed strategy with low detection limits of 0.5 and 2.2 nM for MDR1 gene and Hg2+, respectively. Moreover, the strategy was used to detect real samples. Analytical results of MDR1 gene in the serum indicated that the developed method is a promising alternative approach for real applications in complex systems. Furthermore, the recovery of the proposed method for Hg2+ detection was acceptable. Thus, the developed label-free signal-on fluorescence sensing strategy exhibited excellent universality, sensitivity, and handling convenience.

研究领域: 生物化学 · 分析化学 · 分子生物学
✓ 已验证 DOI PubMed 高影响因子
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ACS Applied Energy Materials · 2021 · IF 6.024

Accelerated Proton Transport Based on a p-i-n Heterostructure Membrane for Low-Temperature Solid Oxide Fuel Cells

Zheng Jiang,Jun Wang,Enyi Hu,Jingjing Liu,Lei Yu,Faze Wang

The p-i-n junction structure has garnered great interest from researchers due to its increased photoactive area and wider space charger region compared with that of the p-n junction. Herein the ultrawide bandgap (∼6.7 eV) semiconductor alumina (Al2O3) has been introduced to construct a p-i-n junction with ZnO and NiO. ZnO–Al2O3–NiO powders are suitable for electrolyte membrane material of low-temperature solid oxide fuel cells (LT-SOFCs). The insulating Al2O3 brings a doubled depletion region and more effective charge separation compared with the p-n junction consisting of ZnO and NiO. The fuel cell based on the p-i-n junction membrane material delivers an enhanced maximum power density (MPD) of 917 mW cm–2 along with a high open-circuit voltage (OCV) of 1.013 V at 550 °C. An analysis based on the space charge region and energy band alignment in the p-i-n junction is proposed to account for the appreciable cell performance and ionic conductivity, as well as the electron blocking and charge separation ability. This study presents a practical p-i-n junction design based on ZnO–Al2O3–NiO via a solution process for LT-SOFC electrolyte material and sheds light on the extensive exploration of p-i-n junctions applied in LT-SOFCs.

研究领域: 材料科学 · 能源工程
✓ 已验证 DOI 高影响因子
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JOURNAL OF POLYMER RESEARCH · 2013 ·Vol. 21 ·期 1 ·1-13 · IF 2.019

The Cu(I)-mediated azide–alkyne cycloadditions as a facile and efficient route for functionalization of waterborne polyurethane

Li Xing-Jian,Sun Dao-Xing,Zhang Yi-Heng

The Cu(I)-mediated azide–alkyne cycloaddition reaction, “click” chemistry, has been used to functionalize the waterborne polyurethane, by which a novel fluorinated waterborne polyurethane (FWPU) was synthesized. FWPU was confirmed by FT-IR and 1 H NMR. The structure and properties of FWPU were characterized by water contact angle, water absorption, surface energy, scanning electron microscope (SEM) equipped with energy dispersive X-ray spectrometry (EDS), thermogravimetric analysis (TGA) and X-ray diffraction (XRD), etc. From the research of the surface properties, it was found that the modified materials were endowed with a remarkable hydrophobicity and stain resistance. SEM results showed that the micro-phase separation of FWPU became increasingly apparent with the rise of fluorinated side chains in polyurethane backbone. XRD measurements reflected that the crystallinity of FWPU tended to decrease firstly and then increase with the change of fluorine content. TGA results demonstrated that FWPU possessed flame retardant performance to a certain extent due to the incorporated alkyne groups in the FWPU to improve the final char strongly.

研究领域: 高分子化学 · 材料科学 · 表面工程 · 有机化学 · 应用化学
✓ 已验证 DOI 高影响因子
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