- Facile route fabrication of nickel based mesoporous carbons with high catalytic performance towards 4-nitrophenol reduction
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Novel nickel based mesoporous carbons are firstly in situ fabricated via pyrolysis of CTAB-chitosan-nickel supramolecular aggregates, which are pre-constructed by CTAB-directed self-assembly of 8-quinolinol modified chitosan and nickel acetate under basic conditions. This facile route fabrication method renders smart and homogeneously dispersed Ni nanoparticles (NPs) on the mesoporous carbonaceous framework without using any stabilizer and additional reductant, verified by high-energy X-ray diffraction, TEM, X-ray absorption fine structure, N2 adsorption/desorption and Raman spectroscopy. Moreover, it is found that the morphology of Ni NPs, the textural property of carbonaceous supports, and the corresponding catalytic performance towards 4-nitrophenol reduction vary with the pyrolysis temperature. It is suggested that the nickel based mesoporous carbon pyrolyzed at 750 °C (Ni/MC-750) simultaneously possessing uniform spherical Ni NPs (24.5 nm) and bottle-neck mesopores exhibits the largest activity factor of 20.9 s-1 g -1 of any nickel catalysts. the Partner Organisations 2014.
- Yang, Ying,Ren, Yang,Sun, Chengjun,Hao, Shijie
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- Rational design of 5-((1H-imidazol-1-yl)methyl)quinolin-8-ol derivatives as novel bromodomain-containing protein 4 inhibitors
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Bromodomain-containing protein 4 (BRD4), an epigenetic reader of acetyl lysine, has emerged as a promising therapeutic target for many diseases including cancer, inflammation and heart failure. Our previous study reported that nitroxoline, an FDA approved antibiotic, showed potential BRD4 inhibitory activity and antiproliferation activity against leukemia cell lines. In this study, we further explored the structure-activity relationship (SAR) around nitroxoline and employed our previously developed machine learning based activity scoring function BRD4LGR for further analysis. To improve the cellular level activity, physico-chemical properties were optimized using computational approaches. Then the candidates were tested for their ADME/T profiles. Finally, based on this rational hit-to-lead optimization strategy, 3 drug-like BRD4 inhibitors were obtained, with different profiles on cell line selectivity for multiple myeloma, leukemia and triple negative breast cancer. Further mechanism study showed these compounds could down-regulate c-Myc to inhibit cancer cell growth. This work illustrates the application of multiple computer-aided drug design techniques in a hit-to-lead optimization scenario, and provides novel potent BRD4 inhibitors with different phenotype propensities for future cancer treatment.
- Xing, Jing,Zhang, Rukang,Jiang, Xiangrui,Hu, Tianwen,Wang, Xinjun,Qiao, Gang,Wang, Junjian,Yang, Fengling,Luo, Xiaomin,Chen, Kaixian,Shen, Jingshan,Luo, Cheng,Jiang, Hualiang,Zheng, Mingyue
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- Experimental investigation on the corrosion inhibition of carbon steel by 5-(chloromethyl)-8-quinolinol hydrochloride in hydrochloric acid solution
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5-(chloromethyl)-8-quinolinol hydrochloride (Cl-QH) was synthesized and characterized. Thus, its inhibition effect on XC38 steel corrosion in 1 M HCl medium was investigated using weight loss and electrochemical measurements. Polarization measurements indicated that, the studied compound acts as a mixed type inhibitor, the inhibition efficiency depends on its concentration and reaches 97% at 10- 3 M. Electrochemical impedance spectroscopy showed that the Cl-QH acts by the formation of a protective film at the metallic surface. The adsorption of the studied compound followed the Langmuir isotherm. So, scanning electronic microscopy (SEM) confirms the performance of Cl-QH against corrosion. In addition, quantum chemical calculations using DFT at the B3LYP/6-31G?level of theory was further used to calculate and discussed some electronic properties of the studied molecule. The theoretical and experimental results are in good agreement.
- El Faydy,Galai,El Assyry,Tazouti,Touir,Lakhrissi,Ebn Touhami,Zarrouk
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- Synthesis and photophysics of novel 8-hydroxyquinoline aluminum metal dye with hole transfer groups
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A novel luminescent dye metal complex, (CZHQ)3Al, with 8-hydroxyquinoline aluminum and hole-transporting carbazole units was designed and synthesized. The (CZHQ)3Al optical properties were carefully investigated by UV-vis absorption and fluorescence spectra in diluent solution. The results showed that the luminescent quantum yield of (CZHQ)3Al was 0.62 in DMSO and it emitted red-light with the band gap of 2.89 eV estimated from the onset absorption. In addition, the light-emission of (CZHQ)3Al can be quenched by electron acceptor (dimethylterephalate), where the process followed the Stern-Volmer equation. However, the fluorescent intensities of (CZHQ)3Al were slowly increased with the addition of electron donor (N,N-dimethylaniline). Furthermore, the molecular interactions of (CZHQ)3Al with fullerene (C60) and carbon nanotubes (CNTs) were also respectively investigated, which indicated the metal dye can be used as new fluorescent probe.
- Wang, Xiaoju,Feng, Liheng,Chen, Zhaobin
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- Coordination polymers of N, N'-di-(8-Hydroxyquinolinolyl- 5-methyl)-N, N-diethyl-1, 3-propane diamine (QEPD)
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Coordination polymers containing a novel bis(oxine) bidentate ligand, namely N,N'-di(8-hydroxyquinolinolyl-5-methyl)-N,N'-diethyl-1,3- propane diamine (QEPD) have been prepared with the metal ions Zn(II), Cu(II), Ni(II), Co(II) and Mn(II). The novel bis-(bidentate) ligand was synthesized by condensation of 5-chloromethyl-8-hydroxyquinoline hydrochloride with N,N'-diethyl-1,2- propane diamine in the presence of a base catalyses. All of these coordination polymers and the parent ligand were characterized by elemental analyses, IR spectral and diffuse reflectance spectral studies. The thermal stability and number- average molecular weights (Mn) of all of the coordination polymers were determined by thermogravimetric analyses and non-aqueous conductometric titrations, respectively. In addition, all of the coordination polymers have been characterized by their magnetic susceptibilities.
- Patel, Asha D.,Patel, Rignesh S.,Patel, Ganpat R.
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- Design, Synthesis, and Evaluation of Orally Bioavailable Quinoline-Indole Derivatives as Innovative Multitarget-Directed Ligands: Promotion of Cell Proliferation in the Adult Murine Hippocampus for the Treatment of Alzheimer's Disease
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A novel series of quinoline-indole derivatives were synthesized and evaluated as multitarget-directed ligands for the treatment of Alzheimer's disease (AD). Biological evaluation revealed that the derivatives had multifunctional profiles including antioxidant effects, blood-brain barrier (BBB) penetration, biometal chelation, Aβ aggregation modulation, neurotrophic and neuroprotective properties. Moreover, several representative target derivatives demonstrated hippocampal cell proliferation in living adult mice by intracerebroventricular (icv) injection or oral administration. Further drug-like property analysis demonstrated that the optimized compound, 8d (WI-1758), had liver microsomal metabolic stability, was well tolerated (>2000 mg/kg), and had a rational pharmacokinetic profile, as well as an oral bioavailability of 14.1% and a positive log BB (-0.19) to cross the BBB in vivo. Pharmacodynamics studies demonstrated that chronic oral administration of 8d·HCl substantially ameliorated the cognitive and spatial memory deficits in APP/PS1 AD mice and noticeably reduced overall cerebral β-amyloid deposits.
- Wang, Zhiren,Hu, Jinhui,Yang, Xiaoping,Feng, Xing,Li, Xingshu,Huang, Ling,Chan, Albert S. C.
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- Synthesis and characterization of novel Cu (II) and Zn (II) complexes of 5-{[(2-Hydroxyethyl) sulfanyl] methyl}-8-hydroxyquinoline as effective acid corrosion inhibitor by experimental and computational testings
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Two new complexes were synthesized, characterized and tested as inhibitors for mild steel corrosion in 1.0 M HCl. The anticorrosive effect has been studied using the potentiodynamic polarization (PDP) and impedance spectroscopy (EIS). The inhibitory efficiency increases with increasing concentration to reach 96.0percent for Q-Cu and 94.6percent for Q-Zn at 10?3 M. The two inhibitors are mixed type and follows the Langmuir isotherm adsorption. The surface of the mild steel has been examined by SEM/EDS and the corrosive solution by ICP-OES. DFT calculations and molecular dynamic simulation (MD) show a good correlation with the experimental results for both complexes.
- Abousalem, Ashraf S.,Benhiba, F.,Ebn Touhami, M.,Galai, M.,Jama, C.,Lai, Chin-Hung,Lakhrissi, B.,Ouakki, M.,Rbaa, M.,Warad, I.,Zarrouk, A.
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- Spectroscopic, photophysical, solution thermodynamics and computational study of europium and terbium complexes with a flexible quinolinol-based symmetric tripodal chelator
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Coordination behaviour and photonic properties of a flexible tripodal multidentate ligand, 5,5′,5′'-(Cyclohexane-1,3,5-triyltris(oxy))tris(methylene)triquinolin-8-ol (CYTOM5OX), with Eu and Tb ions were explored through potentiometric, UV-visible and fluorescence spectrophotometric methods. The interaction of tripod towards the lanthanides has been examined for thermodynamic equilibrium, photophysical behavior, and time-resolved luminescence measurements. Besides, a theoretically empirical method followed by quantum mechanical treatment of these chelates has also been summarized. A noticeable change in the electronic spectra of these complexes disclose CYTOM5OX as a pH-sensitive optical sensor for lanthanides detection; also, a strong green fluorescence allows simultaneous sensing in the visible region in a competitive medium. The intense fluorescence intermittently gets quenched under acidic and basic conditions due to photoinduced intramolecular electron transfer from the excited 8-hydroxyquinoline (8-HQ) moiety to the metal ion. The thermodynamically stable Ln3+ complexes in aqueous solution show stability constants in the range log β110 = 33–35 and pLn3+ in the range of 21–22. The hydration number that was predicted by the coordination scan was substantiated by lifetime measurements reveal presence of coordinated water molecules in Eu(CYTOM5OX) and Tb(CYTOM5OX) complexes. Theoretical spectra were also calculated by ZINDO/s methodology at single excitations (CIS) level on PM7 as sparkle energy-minimized geometries.
- Akbar, Rifat,Baral, Minati,Kanungo, B. K.
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- Design and Synthesis of Nanosensor Based on CdSe Quantum Dots Functionalized with 8-Hydroxyquinoline: a Fluorescent Sensor for Detection of Al3+ in Aqueous Solution
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A novel nanosensor based on CdSe quantum dots (QDs) capped with 8-hydroxyqunoline (HQ) was developed for Al3+ ions determination in aqueous solutions. The method is based on the fluorescence enhancement of the HQ functionalized QDs in the presence of Al3+ ions, due to the strong interaction between Al3+ and HQ. Prepared nanosensor exhibited an acceptable selectivity and sensitivity for Al3+ ions in the presence of other metal ions. Plot of Log(I/I0) against Log[Al3+] shows a good linearity in the range of 0.02–3.0?mM, and the method could be used for detection of Al3+ ions concentration in aqueous solutions.
- Eftekhari-Sis, Bagher,Samadneshan, Khadijeh,Vahdati-Khajeh, Saleh
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- Sample synthesis, characterization, experimental and theoretical study of the inhibitory power of new 8-hydroxyquinoline derivatives for mild steel in 1.0 M HCl
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Some new compounds which are derived from 8-hydroxyquinoline were both prepared and characterized by IR, NMR spectroscopy and elemental analysis. After the successful synthesis, we tested these products as corrosion inhibitors of mild steel (MS) in 1.0 M HCl at 298 K ± 1. The anticorrosive property was achieved by electrochemical and theoretical methods such as potentiodynamic polarization (PDP), the spectroscopy impedance (EIS), density functional theory (DFT) calculations and the Monte Carlo simulation (MC). The experimental and theoretical results obtained show that these products have an excellent anticorrosive property for the MS. The thermodynamic parameters show that all the compounds adsorb to the metal surface by chemical bonds according to the Langmuir adsorption isotherm. The surface morphology was investigated using scanning electron spectroscopy (SEM) coupled with energy dispersive spectroscopy (EDS) and the FT-IR analysis. The gravimetric solutions after 6 h of immersion were analyzed by the UV–Visible spectrometry.
- Abousalem, Ashraf S.,Benhiba, F.,Galai, M.,Lakhrissi, B.,Oudda, H.,Rbaa, M.,Rouifi, Z.,Warad, I.,Zarrouk, A.
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- Comparative studies of the electronic, binding and photophysical properties of a new nona-dentate hemi-cage tripodal HQ pendant trizaza-macrocycle with unfilled, half-filled and completely filled lanthanide ions
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The present paper describes the comparative studies of the electronic, photophysical and binding properties of a new C3-symmetric polydentate ligand, 1,4,7-tris-{(5-methylene-8-hydroxyquinoline)-1,4,7-triazacyclononane} (9N3Me5Ox), and its complexes with 4f0, 4f7, and 4f14 metal ions (La3+, Gd3+, and Lu3+) by experimental and theoretical methods using DFT, TDDFT, TDDFTB, ETS-NOCV, NBO and Ligand Field DFT (LFDFT). The ligand and the complexes were synthesized and characterized through elemental analysis, molar conductance, TGA, FT-IR, FT-NMR, 1H-1H COSY and ESI-mass spectrometry techniques. The spectral data and structural studies revealed the formation of nine-coordinate compounds with the general formula [Ln(9N3Me5Ox)(H2O)3], in which the nonadentate chelator acted as a trinegative hexadentate ligand coordinating to the metal ions through three sets of O,N-donors of 8-hydroxyquinoline groups and three coordinated water molecules. The molecular modeling studies suggest that the metal ion can be easily encapsulated in its central cavity forming hemi-cage complexes without altering the basic metal-ligand coordination sphere. The nature of the bonding between the lanthanide ions and 9N3Me5Ox3?, elucidated by means of the natural bond orbital (NBO), Morokuma-Ziegler energy decomposition analysis (ETS-NOCV) scheme, suggests that the Ln-L bonds are more electrostatic (~82percent) than covalent (~18percent). The covalent character of the complexes increases in the order Lu > La > Gd. The photoluminescence spectral studies of the metal complexes revealed that the observed luminescence of the compounds in the solid state and solution is of different origin. The vibrational, 1H and 13C NMR spectral data obtained from the DFT optimized structures showed good agreement with the experimental results. The excitation and emission behaviours of the ligand and the complexes were established by molecular orbital analysis of the ground state DFT geometry as well as of the excited state optimized geometry using TD-DFT and TD-DFTB orbital analysis, excitation and emission properties.
- Baral, Minati,Kanungo, B. K.,Rohini
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- A dual-functional metallogel of amphiphilic copper(II) quinolinol: Redox responsiveness and enantioselectivity
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A dual-functional metallogel, which was based on the copper(II) complex of quinolinol-substituted L-glutamide, showed both redox-responsive and enantioselective properties; moreover, the metallogels collapsed into a sol after reduction and could be revived upon subsequent oxidation. The supramolecular chirality and morphology also reversible changed with the gel-sol transition. Furthermore, the metallogels showed new enantioselective recognition towards chiral aromatic amino acids. A new emission band in the blue-light region at around 393 nm appeared when the metallogels encountered L-aromatic amino acids, whereas no new emission band was observed for the corresponding D-aromatic amino acids. Such enantioselectivity only occurred in the gel state. No similar phenomenon could be observed in solution. This result suggested that, during the gel formation, the gelator molecules self-assembled into ordered, chiral supramolecular structures and enhanced the enantiorecognition of the L-aromatic amino acids. Double or quits: A dual-functional metallogel that was based on the copper(II) complex of quinolinol-substituted L-glutamide was developed to show redox-responsive and enantioselective properties. Moreover, these metallogels showed a reversible gel-sol transition and obvious enantioselective recognition towards chiral aromatic amino acids, with an on/off emission band at around 393 nm (see scheme). Copyright
- Miao, Wangen,Zhang, Li,Wang, Xiufeng,Cao, Hai,Jin, Qingxian,Liu, Minghua
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- Enhanced photoluminescence and the self-assembled fibrillar nanostructure of 5-(cholesteryloxy)methyl-8-hydroxyquinoline lithium in a gel state
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Soluble 5-(cholesteryloxy)methyl-8-hydroxyquinoline lithium(i) (LiChQ) was synthesized through the modification of 8-hydroxyquinoline lithium (LiQ) with cholesterol, and showed about 3 times more enhanced luminescence than pristine LiQ. When increasing the concentration of LiChQ up to 1 wt% in non-protic solvents, nanoscale fibers of 30-100 nm diameter were formed through self-assembly in a super-gel state. There was a red shift in the absorption of the gel in comparison to the solution, which indicates that LiChQ tends to form a J-aggregate in the gel state. We also investigated the gelation process of LiChQ using the Lippert-Mataga equation. We suggest that LiChQ has potential applications in luminescent devices and/or as a template for nanostructured optoelectronic materials.
- Kong, Sheng,Xiao, Lixin,Chen, Zhijian,Yan, Xingzhong,Qu, Bo,Wang, Shufeng,Gong, Qihuang
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- Novel potential neuroprotective agents with both iron chelating and amino acid-based derivatives targeting central nervous system neurons
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Antioxidants and iron chelating molecules are known as neuroprotective agents in animal models of neurodegenerative disorders such as Alzheimer's disease (AD) and Parkinson's disease (PD). In this study, we designed and synthesized a novel bifunctional molecule (M10) with radical scavenging and iron chelating ability on an amino acid carrier likely to be a substrate for system L, thus targeting the compound to the central nervous system (CNS). M10 had a moderate iron affinity in HEPES buffer (pH 7.4) with log K3 = 12.25 ± 0.55 but exhibited highly inhibitory action against iron-induced lipid peroxidation, with an IC50 value (12 μM) comparable to that of desferal (DFO). EPR studies indicated that M10 was a highly potent .OH scavenger with an IC50 of about 0.3 molar ratio of M10 to H2O2. In PC12 cell culture, M10 was at least as potent as the anti-Parkinson drug rasagiline in protecting against cell death induced by serum-deprivation and by 6-hydroxydopamine (6-OHDA). These results suggest that M10 deserves further investigation as a potential agent for the treatment of neurodegenerative disorders such as AD and PD.
- Zheng, Hailin,Youdim, Moussa B.H.,Weiner, Lev M.,Fridkin, Mati
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- Synthesis and biological evaluation of selective survivin inhibitors derived from the MX-106 hydroxyquinoline scaffold
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The survivin (BIRC5) expression is very low in normal differentiated adult tissues, but it is one of the most widely upregulated genes in tumor cells. The overexpression of survivin in many cancer types has been positively correlated with resistance to chemotherapy, tumor metastasis, and poor patient survival. Survivin is considered to be a cancer specific biomarker and serves as a potential cancer drug target. In this report, we describe the design and syntheses of a series of novel selective survivin inhibitors based on the hydroxyquinoline scaffold from our previously reported lead compound MX-106. The best compound identified in this study is compound 12b. In vitro, 12b inhibited cancer cell proliferation with an average IC50 value of 1.4 μM, using a panel of melanoma, breast, and ovarian cancer cell lines. The metabolic stability of 12b improved over MX-106 by 1.7-fold (88 vs 51 min in human microsomes). Western blot analyses demonstrated that treatments with 12b selectively decreased survivin protein levels, but negligibly affected other closely related members in the IAP family proteins, and strongly induced cancer cell apoptosis. In vivo, compound 12b effectively inhibited melanoma tumor growth when tested using a human A375 melanoma xenograft model. Further evaluation using an aggressive, orthotopic ovarian cancer mouse model showed that 12b was highly efficacious in suppressing both primary tumor growth in ovaries and tumor metastasis to multiple peritoneal organs. Collectively, results in this study strongly suggest that the hydroxyquinoline scaffold, represented by 12b and our earlier lead compound MX-106, has abilities to selectively target survivin and is promising for further preclinical development.
- Albadari, Najah,Chen, Hao,Deng, Shanshan,Li, Wei,Miller, Duane D.,Wu, Zhongzhi,Yue, Junming,Zhang, Sicheng,Zhao, Guannan
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- Synthesis, bioinformatics and biological evaluation of novel pyridine based on 8-hydroxyquinoline derivatives as antibacterial agents: DFT, molecular docking and ADME/T studies
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The present study aims to first explore the relationship between the chemical structure of the organic compounds (pyridine based on 8-hydroxyquinoline) and the antibacterial activities, as well as the impact of substituent effects on their antibacterial properties. These compounds were synthesized by efficient methods, and their structures confirmed by the spectral methods (IR, 1H NMR, 13C NMR and elemental analysis). The antibacterial activities of synthesized the compounds were checked with five Gram-positive and Gram-negative strains such as Enterobacter cloacae (ATCC29893),Escherichia coli (ATCC35218), Klebsiella pneumoniae (ATCC13883), Staphylococcus aureus (ATCC29213) and Acinetobacter baumannii (ATCC19606). The results of the antibacterial activities of four synthesized compounds were compared with three standard antibiotics [Penicillin G, Erythromycin and Norfloxacin (quinoline type)]. The minimum inhibitory concentrations (MICs) of active compounds were calculated and discussed. The chemical and biological activities of hydroxyquinoline derivatives were compared with theoretical methods. The chemical activities of hydroxyquinoline derivatives were contrasted with the important quantum chemical parameters using the HF/6–31++g (d, p) basis sets. Besides, biological activities of hydroxyquinoline derivatives against cancer proteins that are respectively protein of the BRCT repeat region of breast cancer that is ID: 1JNX, crystal structure of liver cancer protein that is ID: 3WZE, and crystal structure of lung cancer protein that is ID: 5ZMA, were compared. ADME/T (Adsorption, Distribution, Metabolism, Excretion, and Toxicity) analysis was studied for molecules with high biological activity to become efficient drugs in the future.
- Ajana, Mohammed Aziz,Anouar, El Hassane,Berdimurodov, Elyor,Hajji, Halima,Hichar, Abdelhadi,Lakhrissi, Brahim,Oubihi, Asmaa,Rbaa, Mohamed,Tüzün, Burak,Zarrouk, Abdelkader
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- Quinoline tryptamine heterozygote and application thereof in preparation of medicines for treating Alzheimer's disease
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The invention belongs to the technical field of medicines, and particularly relates to a quinoline tryptamine heterozygote and application thereof in preparation of medicines for treating and/or preventing Alzheimer's disease. Specifically disclosed are a compound represented by formula (I) and a pharmaceutically acceptable salt thereof. The quinoline tryptamine heterozygote disclosed by the invention has excellent oxygen free radical scavenging capacity, a protective effect on hydrogen peroxide induced SH-SY5Y cell oxidative damage, good blood-brain barrier passive dialysis capacity, an A[beta] self-aggregation inhibiting effect and metal ion chelating capacity, and is a multi-target anti-Alzheimer disease active molecule. The compound is expected to be used as a clinical medicine for treating and/or preventing Alzheimer's disease.
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Paragraph 0085-0088
(2020/10/04)
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- Corrosion inhibition performance of newly synthesized 5-alkoxymethyl-8-hydroxyquinoline derivatives for carbon steel in 1 M HCl solution: Experimental, DFT and Monte Carlo simulation studies
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Three new organic compounds primarily based on 8-hydroxyquinoline have been successfully synthesized and characterized via different spectroscopic methods (FTIR, 1H, and 13C NMR). The synthesized compounds, namely 5-propoxymethyl-8-hydroxyquinoline (PMHQ), 5-methoxymethyl-8-hydroxyquinoline (MMHQ) and 5-hydroxymethyl-8-hydroxyquinoline (HMHQ), were evaluated as corrosion inhibitors for carbon steel in 1 M HCl solution using electrochemical impedance spectroscopy, potentiodynamic polarization and weight loss measurements at 298 K. Electrochemical measurements confirmed that the newly synthesized 5-alkoxymethyl-8-hydroxyquinoline derivatives are mixed type corrosion inhibitors and confirmed maximum protection efficiencies of 94, 89 and 81% for PMHQ, MMHQ, and HMHQ, respectively, at the optimum concentration of 10-3 M. The EIS spectra confirmed a slightly depressed semi-circle profile with a single time constant in Bode diagrams for the three organic compounds over the whole concentration and temperature ranges studied. The adsorption of PMHQ, MMHQ, and HMHQ on the carbon steel surface followed the Langmuir adsorption isotherm. In addition, the kinetic and thermodynamic parameters for carbon steel corrosion and inhibitor adsorption, respectively, were determined and discussed. Scanning electron microscopy (SEM) and X-ray photoelectron spectroscopy (XPS) analyses supported the formation of a protective film on carbon steel in the presence of PMHQ, MMHQ, and HMHQ. Density functional theory calculations (DFT) showed that the effectiveness of the inhibitive actions of the studied compounds correlates well with their electron donating ability, whilst Monte Carlo simulations revealed that the extent and favourability of adsorption of inhibitor molecules on the carbon steel surface establish their corrosion inhibition performances.
- El Faydy,Touir,Ebn Touhami,Zarrouk,Jama,Lakhrissi,Olasunkanmi,Ebenso,Bentiss
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p. 20167 - 20187
(2018/08/16)
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- Benzofuran quinolone derivative and application of benzofuran quinolone derivative in preparation of medicine for treating Alzheimer's disease
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The invention discloses a benzofuran quinolone derivative and application of the benzofuran quinolone derivative in preparation of a medicine for treating Alzheimer's disease. The benzofuran quinolone derivative is a multiple target point active molecule for resisting the Alzheimer's disease, has inhibitory activity of phosphodiesterase 4D and also has functions of resisting oxidation, inhibiting A beta aggregation and depolymerizing; animal experimental results show that the benzofuran quinolone derivative disclosed by the invention has efficacies of improving cognitive ability and spatial memory of rats with the Alzheimer's disease, protecting brain hippocampal neuronal cells of the rats with the Alzheimer's disease, and inhibiting the loss and necrosis of neuronal cells.
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Paragraph 0035-0039
(2016/10/10)
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- Design, synthesis, and evaluation of orally available clioquinol-moracin M hybrids as multitarget-directed ligands for cognitive improvement in a rat model of neurodegeneration in Alzheimer's disease
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A novel series of clioquinol-moracin hybrids were designed and synthesized by fusing the pharmacophores of clioquinol and moracin M, and their activities as multitarget-directed ligands against Alzheimer's disease were evaluated. Biological activity results demonstrated that these hybrids possessed significant inhibitory activities against phosphodiesterase 4D (PDE4D) and Aβ aggregation as well as remarkable antioxidant effects and excellent blood-brain barrier permeability. The optimal compound, 18d (WBQ5187), exhibited excellent PDE4D inhibitory potency (IC50 = 0.32 μM), significant antioxidant effects, appropriate biometal chelating functions, and interesting properties that modulated self- and metal-induced Aβ aggregation. Two-dimensional NMR studies revealed that 18d had significant interactions with Aβ1-42 at the R5, H6, H14, Q15, and F20 residues. Furthermore, this typical hybrid possessed preeminent neuroprotective effects against inflammation in microglial cells. Most importantly, oral administration of 18d·HCl demonstrated marked improvements in cognitive and spatial memory in a rat model of Alzheimer's disease and protected hippocampal neurons from necrosis.
- Wang, Zhiren,Wang, Yali,Wang, Bo,Li, Wenrui,Huang, Ling,Li, Xingshu
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p. 8616 - 8637
(2015/11/25)
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- Design, synthesis and structure-activity relationship studies of novel survivin inhibitors with potent anti-proliferative properties
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The anti-apoptotic protein survivin is highly expressed in most human cancer cells, but has very low expression in normal differentiated cells. Thus survivin is considered as an attractive cancer drug target. Herein we report the design and synthesis of a series of novel survivin inhibitors based on the oxyquinoline scaffold from our recently identified hit compound UC-112. These new analogs were tested against a panel of cancer cell lines including one with multidrug-resistant phenotype. Eight of these new UC-112 analogs showed IC50 values in the nanomole range in anti-proliferative assays. The best three compounds among them along with UC-112 were submitted for NCI-60 cancer cell line screening. The results indicated that structural modification from UC-112 to our best compound 4g has improved activity by four folds (2.2 μM for UC-112 vs. 0.5 μM for 4g, average GI50 values over all cancer cell lines in the NCI-60 panel).Western blot analyses demonstrated the new compounds maintained high selectivity for survivin inhibition over other members in the inhibition of apoptosis protein family. When tested in an A375 human melanoma xenograft model, the most active compound 4g effectively suppressed tumor growth and strongly induced cancer cell apoptosis in tumor tissues. This novel scaffold is promising for the development of selective survivin inhibitors as potential anticancer agents.
- Xiao, Min,Wang, Jin,Lin, Zongtao,Lu, Yan,Li, Zhenmei,White, Stephen W.,Miller, Duane D.,Li, Wei
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- COMPOUNDS THAT TRAP ALPHA-OXOALDEHYDES AND ALPHA-BETA-UNSATURATED ALDEHYDES, META-COMPOUNDS CONTAINING SUCH COMPOUNDS, AND USE OF SAID COMPOUNDS IN TREATING ILLNESSES RELATED TO THE ACCUMULATION OF AGES AND ALES
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The present invention relates to a series of molecules derived from 2,3-diaminopropionic acid (DAP), comprising or not comprising an 8-hydroxyquinoline (8-HQ) motif, and to the use of said molecules for trapping an alpha-oxoaldehyde resulting particularly from the degradation of the glucose or for trapping an alpha-beta-unsaturated aldehyde, resulting particularly from the oxidative degradation of fatty acids. These molecules can have a further application in the fields of cosmetics, food processing, and pharmaceuticals.
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Paragraph 0183-0185
(2015/02/19)
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- Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized tripodal molecular switch as a highly selective sequential pH sensor in aqueous solution
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The development and photophysical properties of a biomimetic analogue of microbial siderophore from quinolobactin have been described. The putative analogue, 5,5′-(2(((8-hydroxyquinolin-5-yl)methylamino)methyl)2-methylpropane-1,3-diyl)-bis(azanediyl)-bis(methylene)diquinolin-8-ol (TAME5OX), was synthesized with three bidentate 8-hydroxyquinoline (8HQ) groups, connected to a 1,1,1-tris(aminomethyl)ethane framework, and was selected for its potential applications in chemical and biological fields. A combination of absorption and emission spectrophotometry, potentiometry, electrospray mass spectrometry, NMR, IR and theoretical investigation was used to fully characterize TAME5OX. The intense fluorescence from TAME5OX is quenched intermittently under acidic and basic conditions due to the photoinduced intramolecular electron transfer from excited N-pyridyl to hydroxyl moiety of 8HQ units. This renders the ligand an OFF-ON-OFF type of pH-dependent fluorescent sensor. DFT was employed for optimization and evaluation of vibrational modes, excitation and emission properties of the protonated, neutral, deprotonated states of the analogue. Anomalous enhancement observed in the fluorescence spectra of the neutral form of the sensor can be attributed to subtle structural differences from its cationic and anionic forms. Plausible explanations for low fluorescence of the acidic as well as basic form are provided. This journal is
- Akbar, Rifat,Baral, Minati,Kanungo
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p. 16207 - 16222
(2015/03/04)
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- N-methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine, a new cholinesterase and monoamine oxidase dual inhibitor
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On the basis of N-((5-(3-(1-benzylpiperidin-4-yl)propoxy)-1-methyl-1H-indol-2-yl)methyl)-N-methylprop-2-yn-1-amine (II, ASS234) and QSAR predictions, in this work we have designed, synthesized, and evaluated a number of new indole derivatives from which we have identified N-methyl-N-((1-methyl-5-(3-(1-(2-methylbenzyl)piperidin-4-yl)propoxy)-1H-indol-2-yl)methyl)prop-2-yn-1-amine (2, MBA236) as a new cholinesterase and monoamine oxidase dual inhibitor.
- Bautista-Aguilera, Oscar M.,Samadi, Abdelouahid,Chioua, Mourad,Nikolic, Katarina,Filipic, Slavica,Agbaba, Danica,Soriano, Elena,De Andrés, Lucía,Rodríguez-Franco, María Isabel,Alcaro, Stefano,Ramsay, Rona R.,Ortuso, Francesco,Ya?ez, Matilde,Marco-Contelles, José
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supporting information
p. 10455 - 10463
(2015/02/19)
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- Neuroprotective multi-target directed drugs
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A new family of multitarget molecules able to interact with acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), as well as with monoamino oxidase (MAO) A and B, has been synthesized. Novel compounds have been designed using a conjunctive approach that combines the benzylpiperidine moiety of the AChE inhibitor donepezil, connected through an oligomethylene linker, to a central nitrogen atom substituted with the propargyl moiety responsible for the MAO inhibition, and a 8-hydroxy-5-methylaminoquinoline functional group, the biometal pro-chelator motif. Overall, the results suggest that the new compounds are promising multitarget drug candidates with potencial impact for AD therapy.
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Paragraph 0092-0093
(2014/05/20)
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- Enhanced alkenes epoxidation reactivity of discrete bis(8-quinolinol) oxovanadium(IV) or bis(8-quinolinol)dioxomolybdenum(VI) tethered to graphene oxide by a metal-template/metal-exchange method
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A series of imprinted catalysts were obtained by covalent attachment of discrete bis(8-quinolinol)oxovanadium(IV) or bis(8-quinolinol) dioxomolybdenum(VI) complex onto graphene oxide (GO) through the metal-template/metal-exchange method to control the distribution of covalently attached independent ligands, which were examined as catalysts in the epoxidation of alkenes using t-butylhydroperoxide (TBHP) or H2O 2 as oxidant in comparison with their homogeneous counterparts and materials synthesized by random grafting of the ligand. The prepared catalysts were characterized by XRD, N2 adsorption/desorption, TEM, FT-IR, diffusion reflection UV-visible, ICP-AES, TG, Raman, EPR, N element analysis and XPS. FT-IR, diffusion reflection UV-visible, ICP-AES, TG, N element analysis, Raman and XPS results showed that oxovanadium(IV) or dioxomolybdenum(VI) complexes were successfully grafted on GO. XRD, N2 adsorption/desorption and TEM results indicated that the structures of the samples were well preserved. EPR results revealed that the materials synthesized by the metal-template method had better site-isolation compared with conventional materials. Furthermore, these imprinted oxovanadium(IV) or dioxomolybdenum(VI) complex catalysts are efficient and recyclable, which exhibit higher activity and higher selectivity to target product than either their homogeneous ones or randomly grafted analogues due to better site-isolation.
- Li, Zhifang,Wu, Shujie,Zheng, Dafang,Liu, Heng,Hu, Jing,Su, Hailiang,Sun, Jian,Wang, Xu,Huo, Qisheng,Guan, Jingqi,Kan, Qiubin
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p. 104 - 114
(2013/12/04)
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- Facile fabrication of composition-tuned Ru-Ni bimetallics in ordered mesoporous carbon for levulinic acid hydrogenation
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Bimetallic catalysts are of great importance due to their unique catalytic properties. However, their conventional synthesis requires tedious multistep procedures and prolonged synthetic time, and the resulting bimetallics usually disperse unevenly and show poor stability. It is challenging to develop a facile and step-economic synthetic methodology for highly efficient bimetallic catalysts. In this study, we report an elegant metal complex-involved multicomponent assembly route to highly efficient Ru-Ni bimetallics in ordered mesoporous carbons (OMC). The fabrication of composition-tuned Ru-Ni bimetallics in OMC (RuxNi1-x-OMC, x = 0.5-0.9) was facilely realized via in situ construction of CTAB-directed cubic Ia3d chitosan-ruthenium-nickel- silica mesophase before pyrolysis and silica removal. The resulting Ru xNi1-x-OMC materials are in-depth characterized with X-ray diffraction, N2 adsorption-desorption, transmission electron microscopy, infrared spectrum, and X-ray absorption fine structure. This facile fabrication method renders homogeneously dispersed Ru-Ni bimetallics embedded in the mesoporous carbonaceous framework and creates a highly active and stable Ru0.9Ni0.1-OMC catalyst for the hydrogenation of levulinic acid (LA) to prepare γ-valerolactone (GVL), a biomass-derived platform molecule with wide application in the preparation of renewable chemicals and liquid transportation fuels. A high TOF (>2000 h-1) was obtained, and the Ru0.9Ni0.1-OMC catalyst could be used at least 15 times without obvious loss of its catalytic performance.
- Yang, Ying,Gao, Guang,Zhang, Xin,Li, Fuwei
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p. 1419 - 1425
(2014/05/20)
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- New 2,3-diaminopropionic acid inhibitors of AGE and ALE formation
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Novel 2,3-diaminopropionic acid-based molecules were synthesised and tested successfully as glyoxal/methylglyoxal scavengers and as AGE inhibitors. Addition of an 8-hydroxyquinoline moiety led to an increase of the overall activity. The compounds tested in this study were also proved to be efficient in trapping ALE precursor malondialdehyde. The Royal Society of Chemistry 2013.
- Audic, Nicolas,Potier, Guy,Sasaki, N. André
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p. 773 - 780
(2013/03/13)
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- IRON CHELATORS AND USES THEREOF
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8-Hydroxy-quinoline derivatives and 8-ethers, 8-esters, 8-carbonates, 8- acyloxymethyl, 8-phosphates, 8(phosphoryloxy)methyl, and 8-carbamates derivatives thereof substituted at the 5-position are described as useful for iron chelation and neuroprotective therapies.
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Page/Page column 19
(2013/08/15)
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- NEUROPROTECTIVE AND NEURO-RESTORATIVE IRON CHELATORS AND MONOAMINE OXIDASE INHIBITORS AND USES THEREOF
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8-Hydroxy-quinoline derivatives and 8-ethers, 8-esters, 8-carbonates, 8-acyloxymethyl, 8- phosphates, (phosphoryloxy)methyl, and 8-carbamates derivatives thereof are described that exhibit iron chelation, neuroprotective, neurorestorative, apoptotic and/or selective MAO-AB inhibitory activities.
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Page/Page column 22
(2012/03/09)
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- A novel ditopic ligand derived from 8-hydroxyquinoline: Synthesis, characterisation, and its coordination chemistry with selected metal ions
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A novel multidentate ligand, 5-(bis(pyridin-2-ylmethyl)amino)quinolin-8-ol (HL) was synthesised and characterised. Its coordination modes with a variety of metal ions (Mg2+, Co2+, Cu2+, Zn2+, and Hg2+) were investigated using UV-Vis spectroscopic titration. Among the examined metal ions, coordination ratios (M2+: HL) between the metal ion and the ligand at 1:2, 1:1, and 3:2 were observed due to the ditopic nature of the ligand. In acetonitrile, Mg2+ showed relatively strong fluorescent response upon binding to the ligand among the examined metal ions, Li+, K+, Mg2+, Ca2+, Al 3+, Cu2+, Fe3+, Cr3+, Zn 2+, Co2+, Ni2+, and Hg2+.
- Xie, Xiang,Jiang, Xiujuan,Liu, Jian,Ren, Xingye,Wang, Hongming,Liu, Xiaoming
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experimental part
p. 132 - 136
(2012/05/04)
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- Discovery of 4-(4-(2-((5-Hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl) amino)ethyl)piperazin-1-yl)quinolin-8-ol and its analogues as highly potent dopamine D2/D3 agonists and as iron chelator: In vivo activity indicates potential application in symptomatic and neuroprotective therapy for Parkinson's disease
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The role of iron in the pathogenesis of Parkinson's disease (PD) has been implicated strongly because of generation of oxidative stress leading to dopamine cell death. In our overall goal to develop bifunctional/multifunctional drugs, we designed dopamine D2/D3 agonist molecules with a capacity to bind to iron. Binding assays were carried out with HEK-293 cells expressing either D2 or D3 receptor with tritiated spiperone to evaluate inhibition constants (K i). Functional activity of selected compounds was carried out with GTPyS binding assay. SAR results identified compounds (+)-19a and (-)-19b as two potent agonists for both D2 and D3 receptors (EC50 (GTPyS); D2 = 4.51 and 1.69 nM and D3 = 1.58 and 0.74 nM for (-)-19b and (+)-19a, respectively). In vitro complexation studies with 19b demonstrated efficient chelation with iron. Furthermore, the deoxyribose assay with 19b demonstrated potent antioxidant activity. In PD animal model study, (-)-19b exhibited potent in vivo activity in reversing locomotor activity in reserpinized rats and also in producing potent rotational activity in 6-OHDA lesioned rats. This reports initial development of unique lead molecules that might find potential use in symptomatic and neuroprotective treatment of PD.
- Ghoshs, Balaram,Antonio, Tamara,Reith, Maarten E. A.,Dutta, Aloke K.
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experimental part
p. 2114 - 2125
(2010/08/20)
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- Synthesis, spectroscopic and in-vitro antifungal studies of drug based mixed ligand complexes
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The mixed-ligand complexes of various metal(ll) with 5-chloro-7-iodo-8- hydroxyquinoline (Clioquinol) and 5-(methoxymethyl-8-quinolinol) (MMQ) were prepared. The structure of mixed-ligand complexes was investigated using spectral, physicochemical, elemental analyses and thermal studies. Magnetic moment and reflectance spectral studies reveal that an octahedral geometry has been assigned to all the prepared complexes. The ligands, metal salts, complexes, control and standard drug were tested for their in-vitro antifungal.The metal complexes exhibit good activity against fungal strains compared with parental compounds and moderate compared with the standard drug (Clioquinol).
- Chauhan,Kharadi,Patel
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experimental part
p. 1431 - 1436
(2011/10/12)
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- Microwave assisted synthesis of a small library of substituted N, N ′-Bis((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ethers
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Figure presented. N,N′-Bis-((8-hydroxy-7-quinolinyl)methyl)-1,10- diaza-18-crown-6 ether 1a and its analogue 1c are known as fluorescent sensors of magnesium in living cells. With the aim to investigate the effects of the substitution pattern on the photophysical properties of ligands 1 and their metal complexes, we developed an efficient microwaves enhanced one-pot Mannich reaction to double-armed diaza-crown ligands 1 carrying a variety of substituents. This new protocol is characterized by shorter reaction times, enhanced yields, and improved product purities with respect to the use of conventional conductive heating.
- Farruggia, Giovanna,Iotti, Stefano,Lombardo, Marco,Marraccini, Chiara,Petruzziello, Diego,Prodi, Luca,Sgarzi, Massimo,Trombini, Claudio,Zaccheroni, Nelsi
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scheme or table
p. 6275 - 6278
(2010/12/19)
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- Selective dendritic fluorescent sensors for Zn(II)
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A series of dendritic 8-hydroxyquinoline (8-HQ) and 5-dialkyl(aryl) aminomethyl -8-HQ derivatives were synthesized and their fluoroionophoric properties toward representative alkali, alkaline earth, group IIIA and transition metal ions were investigated. Among the selected ions, Zn(II) enhanced the fluorescence of N-di-(methoxycarbonylethyl)aminoethyl-3-[4-(8- hydroxyquinolin-5-ylmethyl)piperazin-1-yl]-propanoic amide] (7) by 31-fold, while Al(III) caused enhancement to some extent. The absence of any significant fluorescence enhancement by the other ions examined renders 7 a highly useful Zn(II)-selective fluorescent sensor.
- Wang, Feng,Peng, Ruogu,Sha, Yaowu
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p. 922 - 930
(2008/09/18)
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- Synthesis of 5-dialkyl(aryl)aminomethyl-8-hydroxyquinoline dansylates as selective fluorescent sensors for Fe3+
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A series of 5-dialkyl(aryl)aminomethyl□-8-hydroxyquinoline dansylates were synthesized and their fluoroionophoric properties toward representative alkali ions, alkaline earth ions and transition metal ions were investigated. Among the selected ions, Fe3+ caused considerable quenching of the fluorescence, while Cr3+ caused quenching to some extent. The absence of any significant fluorescence quenching effects of the other ions examined, especially Fe2+, renders these compounds highly useful Fe 3+-selective fluorescent sensors.
- Peng, Ruogu,Wang, Feng,Sha, Yaowu
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p. 1191 - 1201
(2008/02/07)
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- Synthesis and photophysics of novel 8-hydroxyquinoline aluminum metal complex with fluorene units
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A novel luminescent metal complex, (MQPF)3Al2, with 8-hydroxyquinoline aluminum and 9,9-diphenylfluorene was synthesized. The optical properties were investigated by UV-vis absorption and fluorescence emission spectra. The results showed that the luminescence quantum yield of (MQPF)3Al2 was 0.612 in THF and it emitted red light with the band gap of 3.18 eV estimated from the onset absorption. The emission spectra exhibited obvious solvent effect. With the increase of polarity of solvents the fluorescence spectra changed obviously and appeared blue shift about 60 nm at room temperature. In addition, the light-emitting can be quenched by both electron donor (N,N-dimethylaniline) and electron acceptor (Fullerene), where the processes followed the Stern-Volmer equation. However, when adding 1,4-dicyanobenzene (DCB) which was a stronger electron acceptor to the solution of (MQPF)3Al2, the fluorescent intensity was increased.
- Feng, Liheng,Wang, Xiaoju,Zhao, Sanhu,Chen, Zhaobin
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p. 646 - 650
(2008/02/12)
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- Design, synthesis, and evaluation of novel bifunctional iron-chelators as potential agents for neuroprotection in Alzheimer's, Parkinson's, and other neurodegenerative diseases
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Several novel antioxidant-iron chelators bearing 8-hydroxyoxyquinoline moiety were synthesized, and various properties related to their iron chelation, and neuroprotective action were investigated. All the chelators exhibited strong iron(III) chelating and high antioxidant properties. Chelator 9 (HLA20), having good permeability into K562 cells and moderate selective MAO-B inhibitory activity (IC50 110 μM), displayed the hightest protective effects against differentiated P19 cell death induced by 6-hydroxydopamine. EPR studies suggested that Chelator 9 also act as radical scavenger to directly scavenge hydroxyl radical.
- Zheng, Hailin,Weiner, Lev M.,Bar-Am, Orit,Epsztejn, Silvina,Cabantchik, Z. Ioav,Warshawsky, Abraham,Youdim, Moussa B.H.,Fridkin, Mati
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p. 773 - 783
(2007/10/03)
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- Infrared-emitting poly(norbornene)s and poly(cyclooctene)s
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Poly(norbornene)- and poly(cyclooctene)-based copolymers, bearing carbazole and 8-hydroxy-quinoline side chains, were prepared. Upon complexation of the pendant quinoline ligands in the side chain with ytterbium followed by the addition of 2 equiv of additional quinolines, infrared-emitting copolymers that emit around 970 nm were obtained. The emission intensities increased linearly as the density of lanthanide-quinolate complexes increased in the copolymers. Finally, we were able to prove that the polymer backbones do not interfere with the optical properties of the polymers, suggesting that these polymers are outstanding materials as IR emitters.
- Meyers, Amy,Kimyonok, Alpay,Weck, Marcus
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p. 8671 - 8678
(2008/02/02)
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- Synthesis of 5-alkyl-8-quinolinol
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Synthesis of new 5-alkyl-8-quinolinol was described in order to obtain substituted copper 8-hydroxyquinolinate more soluble in organic solvents than unsubstituted one. The synthesis of copper complex is described and their solubility investigated in different solvents.
- Soulounganga,Gerardin,Loubinoux
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p. 1927 - 1935
(2007/10/03)
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- Synthesis, Characterisation and Antimicrobial Activities of Binary and Ternary Complexes of UO2II and ThIV Complexes with 5-Hydroxymethyl-8-quinolinol and 8-Formyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one with Aniline
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Synthesis of 5-hydroxymethyl-8-quinolinol and 8-formyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one (FHMB) with aniline (FHMBAnil) have been carried out to study the binary and ternary complexes of uranium and thorium. Different analytical techniques have been used to find out the structure of the complexes. They have also been tested for their antimicrobial activities. ψ Abstract of this paper was published in the Proceedings of National Symposium on Organic Reagents-Synthesis and Use in Extraction Metallurgy, held at Bombay, 1994.
- Patel,Sharma, Sangita,Vora,Joshi
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p. 287 - 288
(2007/10/03)
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