- A Smart Molecule for Selective Sensing of Nitric Oxide: Conversion of NO to HSNO; Relevance of Biological HSNO Formation
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A smart molecule, QT490, containing thiosemicarbazide moiety acts as a highly selective turn-on in vitro NO sensor through the unprecedented NO-induced transformation of thiosemicarbazide moiety to 1,3,4-oxadiazole heterocycle with the concomitant release of HSNO, thereby eliminating any interference from various endogenous biomolecules including dehydroascorbic acid, ascorbic acid, etc. The kinetic studies of the reactions between QT490 and NO provide a mechanistic insight into formation of HSNO/RSNO from the reaction between H2S/RSH and NO in the biological system. This novel probe is non-cytotoxic, cell permeable, water-soluble, and appropriate for intracellular cytoplasmic NO sensing with the possibilities of in vivo applications.
- Islam, Abu Saleh Musha,Bhowmick, Rahul,Pal, Kaberi,Katarkar, Atul,Chaudhuri, Keya,Ali, Mahammad
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- A novel ratiometric fluorescent probe for detection of Fe3+ by rhodamine-quinoline conjugate
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In this study, we have developed a novel ratiometric fluorescence probe (HL) which contains rhodamine and quinoline moiety. In the absence of Fe3+, the sensor displays fluorescence emission at 425 nm, in the presence of Fe3+, the sensor shows a large fluorescence enhancement at 550 nm in methanol. More importantly, the reversibility of the recognition process of HL is performed by adding a Fe3+ bonding agent Na2EDTA.
- Qin, Jing-Can,Yang, Zheng-Yin,Wang, Guan-Qun
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- Both visual and ratiometric fluorescent sensor for Zn2+ based on spirobenzopyran platform
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A ratiometric fluorescent Zn2+ chemosensor, SPQH, based on spirobenzopyran platform, was synthesized. In aqueous HEPES 7.4 buffer solution, upon chelation with Zn(II), SPQH demonstrates high selectivity and subnanomolar sensitivity for zinc ion with 36-fold enhancement in the NIR fluorescence output.
- Zhu, Jian-Fa,Chan, Wing-Hong,Lee, Albert W.M.
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- New N-(Aryl)-5-((quinolin-8-yloxy)methyl)-1,3,4-oxa/Thiadiazol-2-amines and 4-Aryl-5-((quinolin-8-yloxy)methyl)-2H-1,2,4-triazole-3(4H)-thiones, synthesis and characterization
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Figure presented In this study, methyl 2-(quinolin-8-yloxy) acetate (2) obtained by reaction of 8-hydroxyquinoline (1) with methyl chloroacetate was condensed with hydrazine hydrate to afford the carbohydrazide (3). Thio/semicarbazide derivatives (4a-g) w
- Saeed, Aamer,Abbas, Naeem,Ibrar, Aliya,Bolte, Michael
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- Synthesis of some novel 3,4,5-trisubstituted triazole derivatives bearing quinoline ring and evaluation of their antimicrobial activity
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Some new 3,4,5-trisubstituted 1,2,4-triazole derivatives were synthesized and studied for their antimicrobial activity. The lead compounds were obtained starting from 8-hydroxyquinoline and ethyl 2-chloroacetate. The obtained ester compound (1) first reac
- Yurtta?, Leyla,Kubilay, Asl?han,Evren, Asaf Evrim,K?sac?k, ?pek,Karaca Gen?er, Hülya
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- Synthesis, characterization and molecular docking of novel quinoline and pyridine derivatives
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A new series of substituted quinoline and pyridine derivatives 6a-h are synthesized by the coupling of hydrazide derivatives 4a-b with substituted carboxylic acids 5a-c in the presence of N,N,N’,N’-tetramethyl-o-(benzotriazol-1-yl) uranium tetrafluoroborate TBTU as a coupling agent and lutidine as a base. The newly synthesized compounds 6a–l is characterized by analytical NMR and mass spectral data. The newly synthesized compounds were subjected to molecular docking studies for the inhibition of human Aurora A kinase target to evaluate their potential value for the treatment of cancers.
- Saleh, Suheb,Al-Timari, Usama,Al-Fahdawi, Aeed,El-Khatatneh, Nasseem,Chandra,Mahendra,Al-Ghorbani6, Mohammed
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- Nitric Oxide Sensing through 1,2,3,4-Oxatriazole Formation from Acylhydrazide: A Kinetic Study
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A simple molecular probe displays highly selective turn-on response toward NO by the unprecedented NO-induced formation of a 1,2,3,4-oxatriazole ring exhibiting no interference from various endogenous biomolecules including DHA, AA, etc. Kinetics of the reactions between NO and the probe provide a mechanistic insight into the formation of 1,2,3,4-oxatriazole which showed that, though initially 1,2,3,4-oxatriazole is formed and extractable in solid form, it exists in equilibrium with the ring opened azide form which ultimately hydrolyzed and converted to carboxylic acid and nitrate. The reaction displays second-order dependence on [NO] and first-order on [Probe]. The probe is water-soluble, cell permeable, and noncytotoxic and appropriates for live cell imaging. This constitutes the first report where there is a direct evidence of NO-induced ring closing reaction of an acyl hydrazide moiety leading to the formation of 1,2,3,4-oxatriazole.
- Islam, Abu Saleh Musha,Bhowmick, Rahul,Chandra Garain, Bidhan,Katarkar, Atul,Ali, Mahammad
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- β-Hydroxy-α-naphthaldehyde [2-(quinolin-8′-yloxy) acetyl] hydrazone as an efficient fluorescent chemosensor for Mg2+
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An efficient fluorescent sensor based on β-hydroxy-α-naphthaldehyde [2-(quinolin-8′-yloxy) acetyl] hydrazone (HL) for Mg2+ has been designed and synthesized. The receptor showed "off-on" fluorescent responses toward Mg2+ in acetonitrile. The reasons for this phenomenon is that the addition of Mg2+ to the solution of HL induce the formation of a 1:1 ligand-metal complex which inhibit excited-state intramolecular proton transfer (ESIPT).
- Qin, Jing-Can,Yang, Zheng-Yin,Fan, Long,Wang, Bao-Dui
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- Synthesis of indole–quinoline–oxadiazoles: their anticancer potential and computational tubulin binding studies
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Abstract: Small hybrid molecules with two or more structural pharmacores having different biological functions and distinct activity have gained a significant role in cancer drug development to combat various types of malignancies. The present study describes an efficient, clean and strategic synthesis of 12 new substituted quinoline–indole–oxadiazole hybrids from substituted 2-(quinolin-8-yloxy)acetohydrazides and indole-3-carboxylic acids by employing T3P as a green catalyst. Structures of the newly synthesized compounds were established by IR, 1H NMR, 13C NMR, DEPT C-NMR and MS spectroscopic evidence, as well as CHN analysis data. All indole–quinoline–oxadiazoles were tested for their in vitro cytotoxic potential in breast adenocarcinoma (MCF7) and normal kidney (vero) cell lines using MTT assay. 8-((5-(3-(1H-indol-3-yl)propyl)-1,3,4-oxadiazol-2-yl)methoxy)quinoline (3d) exhibited a low IC50 value and a high selectivity index to MCF7 cells and also displayed a mitotic block in flow cytometric cell cycle progression analysis. Microtubule disruption can induce G2/M phase cell cycle arrest leading to abnormal mitotic spindle formation. Ligand 3d demonstrated its capability of being a probable tubulin inhibitor when docked in the colchicine domain of tubulin. Graphical Abstract: New series of 8-((5-((1H-indol-3-yl)methyl)-1,3,4-oxadiazol-2-yl)methoxy)quinolines were synthesized using T3P as a green catalyst and screened for their cytotoxic and antimitotic potential. The most active 8-((5-(3-(1H-indol-3-yl)propyl)-1,3,4-oxadiazol-2-yl)methoxy)quinoline?3d, displayed good binding interactions with the colchicine binding cavity of microtubule.[Figure not available: see fulltext.]
- Kamath, Pooja R.,Sunil, Dhanya,Ajees, Abdul A.
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- Novel Pyrazoline-based Organometallic Compounds Containing Ferrocenyl and Quinoline units: Synthesis, Characterization and Microbial susceptibilities
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Some novel pyrazoline-based organometallic compounds were synthesized as new leads in antimicrobial chemotherapy. The structures of compounds were elucidated by different spectroscopic techniques and elemental analyses. All compounds were investigated for in vitro antimicrobial studies against fifteen ATTC bacterial and fungal strains. The microbial susceptibility of these compounds revealed that all the tested compounds gave good minimum inhibitory concentration (MIC) values against the tested organisms that are either similar or even better than the reference drugs amoxicillin and fluconazole, which gave MIC values 8-64?μg/ml against bacterial and 64?μg/ml against fungal strains, respectively. Among all compounds, compound (4d). 1-(5-(4-chlorophenyl)-3-ferrocenyl-4,5-dihydropyrazol-1-yl)-2-quinolin-8-yloxy) ethanone, emerged out the most promising antimicrobial organometallic derivative with MIC values against all the strains ranging from 8-32?μg/ml. Other compounds gave a range of MIC values between 16-64?μg/ml against S. bovis, 16-32?μg/ml against E. coli, and C. tropicalis except compound (4d) which gave MIC 8?μg/ml against S. bovis and E. coli, whereas 32?μg/ml against C. tropicalis. Collectively, these compounds gave a lower MIC value between 32-64?μg/ml against both of the biofilm forming strains namely, P. aeruginosa and S. mutans. The results of microbial susceptibility concluded that these novel organometallic compounds are new leads in antimicrobial chemotherapy and can be very useful for further optimization work on microbial chemotherapy.
- Parveen, Humaira,Alatawi, Raedah Aiyed Suliman,Alsharif, Meshari A.,Alahmdi, Mohammed Issa,Mukhtar, Sayeed,Khan, Salman Ahmad,Hasan, Sadaf,Khan, Asad U.
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- The synthesis and study of the fluorescent probe for sensing Cu 2+ based on a novel coumarin Schiff-base
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A novel, fluorescent probe was synthesized from 2,4-dihydroxybenzaldehyde and 8-hydroxyquinoline for sensing Cu2+ by the naked eye. The structure was confirmed by IR, MS, 1H NMR, 13C NMR and the spectral properties of the probe were investigated. It exhibited strong fluorescence responses toward Cu2+ and high selectivity over other metal ions. The binding constant between the probe and Cu2+ was calculated using Benesi-Hildebrand equation.
- Duan, Yu-Wei,Tang, Hao-Yang,Guo, Yuan,Song, Zhan-Ke,Peng, Meng-Jiao,Yan, Yong
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- New oxadiazole derivatives: Synthesis and appraisal of their potential as antimicrobial agents
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Introduction: The escalating threat due to dwindling effect of antibiotics and challenge of tackling rising drug-resistant infections has gathered high focus in current medicinal research. Methods: In an attempt to find new molecules that can defeat microbial resistance, two new series of 2-[2-substituted ethenyl]-5-(substituted methoxy)-1,3,4-oxadiazole derivatives were synthesized. Various aromatic hydrazides were allowed to undergo cyclization to substituted oxadiazole-2- amines in the presence of cyanogen bromide and further condensed with different heterocyclic aldehydes to give new oxadiazole derivatives. The synthesized molecules were fully characterized by various spectral techniques and tested for antimicrobial activity. Results: Almost all the newly synthesized compounds especially (5g-5l) displayed remarkable growth inhibition against three bacterial strains: M. smegmatis, S. aureus, E. coli and fungi C. albicans. The antimicrobial activity was further confirmed by MIC assay against the same microorganisms. Oxadiazole 5g displayed promising activity with a MIC value of 0.025 mM for two bacteria and fungi, whereas MIC of this compound for E. coli was 0.1 mM. Other active compounds (5h-5l) also exhibited good MIC ranging between 0.313 to 5.0 mM against the selected microorganisms. Docking simulations were generated to explore the potential binding approaches of ligand 5g at the D-alanine:d-alanine ligase (Ddl) protein of E. coli and S. aureus. Conclusion: Molecule 5g was active even at a lower concentration and could probably act as a prospective lead molecule for targeting the drug resistant microorganisms.
- Dhara, Deboleena,Sunil, Dhanya,Kamath, Pooja R.,Ananda,Shrilakshmi,Balaji
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- New Schiff bases of 2-(quinolin-8-yloxy)acetohydrazide and their Cu(ii), and Zn(ii) metal complexes: Their in vitro antimicrobial potentials and in silico physicochemical and pharmacokinetics properties
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The purpose of this work was to prepare Schiff base ligands containing quinoline moiety and using them for preparing Cu(ii) and Zn(ii) complexes. Four bidentate Schiff base ligands (SL1-SL4) with quinoline hydrazine scaffold and a series of mononuclear Cu(ii) and Zn(ii) complexes were successfully prepared and characterized. The in vitro antibacterial and antifungal potential experimentation revealed that the ligands exhibited moderate antibacterial activity against the Gram-positive bacterial types and were inactive against the Gram-negative bacteria and the fungus strains. The metal complexes showed some enhancement in the activity against the Gram-positive bacterial strains and were inactive against the Gram-negative bacteria and the fungus strains similar to the parent ligands. The complex [Cu(SL1)2] was the most toxic compound against both Gram-positive S. aureus and E. faecalis bacteria. The in silico physicochemical investigation revealed that the ligand SL4 showed highest in silico absorption (82.61percent) and the two complexes [Cu(SL4)2] and [Zn(SL4)2] showed highest in silico absorption with 56.23percent for both compounds. The in silico pharmacokinetics predictions showed that the ligands have high gastrointestinal (GI) absorption and the complexes showed low GI absorption. The ligands showed a good bioavailability score of 0.55 where the complexes showed moderate to poor bioavailability.
- Althobiti, Hanan A.,Zabin, Sami A.
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- A novel 8-hydroxyquinoline-pyrazole based highly sensitive and selective Al(III) sensor in a purely aqueous medium with intracellular application: Experimental and computational studies
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A new 8-hydroxyquinoline-pyrazole based highly sensitive and selective Al3+ sensor, 8Q-NH-Pyz (H2L3), was found to exhibit a turn-on fluorescence enhancement (FE) as high as 157 fold with Kd = (1.76 ± 0.06) × 10-5 M. The 1:1 binding stoichiometry was revealed from the linear fit of (Fmax - F0)/(F - F0) vs. 1/[Al3+] of the fluorescence titration data which was further substantiated by Job's method and HRMS studies. The LOD determined by 3σ methods was found to be 4.29 nM and quantum yields were determined to be 0.002 and 0.28 for the ligand and its Al3+ complex, respectively. The tentative coordination environment in the [Al(L3)(H2O)]+ complex was delineated by DFT calculations. TDDFT calculations reveal spectral features comparable to the experimental ones. This constitutes the first report on the fluorescence sensing of Al3+ and hence F- in a purely aqueous medium.
- Islam, Abu Saleh Musha,Bhowmick, Rahul,Mohammad, Hasan,Katarkar, Atul,Chaudhuri, Keya,Ali, Mahammad
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- Two similar Schiff-base receptor based quinoline derivate: Highly selective fluorescent probe for Zn(II)
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As is known, Zn2+ plays a vital role in a variety of biological processes but excessive exposure of Zn2+ to human beings can cause toxicity, inducing a series of overt poisoning symptoms and neurodegenerative disorders. Thus, we designed and synthesized two quinoline-derived Schiff-bases HL1 and HL2, and investigated the fluorescence emission responses of these two Schiff-bases to various metal ions. A significant enhancement in fluorescence emission band centered at 450 nm was observed in the ethanolic solution of HL1 with addition of Zn2+, while remarkably lower fluorescence emission enhancement was obtained in the case of HL2 in which one methyl group was introduced to the azomethine carbon. In addition, HL1 showed good selectivity and high sensitivity towards Zn2+ in the existence of other various interfering metal ions, and the reversibility and regeneration of HL1 were also perfect for extending its applications in environmental and biological systems. Therefore, HL1 could be identified as a fluorescent probe for sensing Zn2+ environmentally and biologically.
- Fan, Long,Li, Chao-rui,Qin, Jing-can,Yang, Zheng-yin
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- Synthesis and application of new acetohydrazide derivatives as a corrosion inhibition of mild steel in acidic medium: Insight from electrochemical and theoretical studies
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Abstract Corrosion inhibition of mild steel in 15% HCl solutions by synthesized acetohydrazides namely, N′-[(1Z)-phenylmethylene]-2-(quinolin-8-yloxy) acetohydrazide (PQA) and N′-[(1Z)-4-chlorophenylmethylene]-2-(quinolin-8-yloxy) acetohydrazide (CPQA) wa
- Yadav,Sinha,Kumar,Bahadur,Ebenso
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- Synthesis, crystal structure, Hirshfeld surface analysis, spectral characterization, reduced density gradient and nonlinear optical investigation on (E)-N'-(4-nitrobenzylidene)-2-(quinolin-8-yloxy) acetohydrazide monohydrate: A combined experimental and DFT approach
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In this work, (E)-N'-(4-nitrobenzylidene)-2-(quinolin-8-yloxy) acetohydrazide monohydrate (NBQA) crystal was synthesized and its structural characterization was carried out by single-crystal X-ray diffraction. The intermolecular interactions in the crystal were investigated through the Hirshfeld surface analysis and the 2D-fingerprint plot. In the solid phase, the spectroscopic characterization was also carried out using FT-IR, 1H NMR, and 13C NMR experimental spectroscopies. To support experimental results, DFT calculations have been accomplished on the NBQA molecule in the ground state. First, theoretical calculations were performed using BPV86 and GGA-PBE functionals with the 6-311G(d,p) basis set to obtain the stable conformer of the molecule. Likewise, harmonic vibrational frequencies, 1H and 13C chemical shifts, and NBO analysis were also calculated using the same level of theory and compared to available experimental data. Furthermore, the molecular electrostatic potential (MEP), frontier molecular orbitals (FMO) analysis, HOMO-LUMO energies, energy band gap, density of state (DOS), global chemical reactivity descriptors, and some thermodynamic functions were studied and discussed. UV–Vis spectrum was predicted by the TD-DFT method in chloroform solvent and compared with the experimental spectrum for displaying the involved electronic transitions in the compound. The repulsive, attractive, and Van der Waals strong and weak interactions in NBQA were investigated via the RDG analysis. The NLO properties of NBQA have also investigated in different available solvents by DFT and compared to the most important compounds in the field. The first hyperpolarizability values of NBQA have been increased with increasing solvent polarity and decreasing the energy band gap.
- Belkafouf, Nour El Houda,Benhalima, Nadia,Chouaih, Abdelkader,Daran, Jean-Claude,Djafri, Ahmed,Djafri, Ayada,Kourat, Oumeria,Megrouss, Youcef,Rahmani, Rachida
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- Development of a simple pyrazine-derived "turn on" Al3+ fluorescent sensor with high selectivity and sensitivity
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Abstract In this article, a novel pyrazine-derived hydrazone Schiff-base ligand bearing the quinoline unit (1) has been designed, synthesized and evaluated as a "turn on" fluorescent chemosensor for Al3+ based on the photoinduced electron-transfer (PET) mechanism and the chelation-enhanced fluorescence (CHEF) phenomenon. The sensor 1 showed remarkably enhanced fluorescence intensity at 488 nm in the presence of Al3+ ion and it also showed high selectivity and sensitivity towards Al3+ ion over a wide range of metal ions in ethanol, for the detection limit of 1 for Al3+ could reach at 10-7 mol/L.
- Li, Chao-Rui,Qin, Jing-Can,Wang, Guan-Qun,Wang, Bao-Dui,Fu, An-Kun,Yang, Zheng-Yin
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- A naphthalimide-quinoline based probe for selective, fluorescence ratiometric sensing of trivalent ions
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A new naphthalimide-quinoline based probe (NAQ) is designed and synthesized and its structure is confirmed through single crystal analysis. It detects the trivalent ions (Fe3+ or Al3+ or Cr3+) selectively among other alkali and transition metal ions studied. NAQ shows a distinct ratiometric fluorescence behavior upon addition of trivalent metal ions in CH3CN-HEPES buffer solution (40/60, v/v, pH = 7.4). This fluorogenic sensing of NAQ to M3+ (M3+ = Fe3+ or Al3+ or Cr3+) can be observed by the naked eye, when illuminated under the UV light.
- Goswami, Shyamaprosad,Aich, Krishnendu,Das, Avijit Kumar,Manna, Abhishek,Das, Sangita
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- Synthesis, crystal structure, spectroscopic characterization and nonlinear optical properties of (Z)-N'-(2,4-dinitrobenzylidene)-2-(quinolin-8-yloxy) acetohydrazide
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New organic compound of (Z) -N'- (2, 4-dinitrobenzylidene) -2- (quinolin-8-yloxy) acetohydrazide (DBQA) was synthesized for the first time and its structural characterization was performed by single crystal X-ray diffraction method. The compound crystallizes in the triclinic system with space group P-1. The spectroscopic characterization was also performed by the applying of FT-IR, UV–Vis, 1H and 13C NMR spectroscopies. In order to support experimental results, density functional theory (DFT) calculations have been performed using B3LYP functionnal with 6–311++G(d, p) basis set. All of the obtained theoretical results are in a perfect agreement with the experimental ones. Furthermore, nonlinear optical (NLO) behavior of DBQA has been investigated by determining of electric dipole moment (μ), polarizability (α) and hyperpolarizability (β) using the same basis set. Finally, the molecular electrostatic potential (MEP) surface of DBQA molecule was simulated and discussed.
- Boukabcha,Djafri,Megrouss,Tamer,Avc?,Tuna,Dege,Chouaih,Atalay,Hamzaoui
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- Simple quinoline-based "turn-on" fluorescent sensor for imaging copper (II) in living cells
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In this work, a novel fluorescent sensor based on a quinoline derivative was designed and synthesized for detecting copper ions in a near-aqueous media. According to its extra-nuclear structure, copper (II) normally exhibits effectiveness for quenching the singlet excited state of organic chromophores through a fast electron transfer mechanism. However, this molecule displayed a strong fluorescence "turn-on" phenomenon upon addition of Cu2+, which was rarely reported in previous research. In addition, density functional theory calculations were adopted to investigate the molecular orbitals as well as the spatial structure. Furthermore, this sensor was applied into living SGC-7901 cells to extend its application in biological systems.
- Zhou, Chen,Xiao, Ning,Li, Yapeng
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- Single sensor for multiple analytes: Fluorogenic detection of Al 3+ in aqueous media and AcO- in organic media
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A simple novel receptor, designed to have a combination of both oxygen and nitrogen-binding sites for metal ion and hydrogen bond donor sites for anion, was synthesised. The receptor has been explored for the selective detection of cation Al3+ over the other interfering metal ions and anion AcO - against a range of physiologically relevant anions in the fluorescence spectroscopy. The receptor shows a different response to aluminium and acetate in the emission spectra. The binding isotherm and detection limit demonstrate that the receptor is an excellent fluorometric probe for Al 3+ and AcO-.
- Goswami, Shyamaprosad,Das, Avijit Kumar,Aich, Krishnendu,Manna, Abhishek,Fun, Hoong-Kun,Quah, Ching Kheng
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- A new ICT and CHEF based visible light excitable fluorescent probe easily detects in vivo Zn2+
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A new chelator and ICT donor based visible light excitable Zn2+ sensor was designed and developed by integrating quinoline and 2-hydroxy-3-(hydroxymethyl)-5-methylbenzaldehyde. The probe is sensitive towards Zn2+ in absorbance as well as in fluorescence experiments in 90% aqueous medium. The sensor demonstrates Zn2+-specific emission enhancement due to the ICT and CHEF process with the LOD in the range of 10-8 M. The fluorescence quantum yield of the chemosensor is only 0.02, and it increases almost 11-fold (0.22) after complexation with Zn2+. Interestingly, the introduction of other metal ions causes the fluorescence intensity to remain almost unchanged. Moreover, the ability of the probe (BQ) to sense Zn2+ in living cells has been explored.
- Aich, Krishnendu,Goswami, Shyamaprosad,Das, Sangita,Mukhopadhyay, Chitrangada Das
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- Synthesis, structure analysis, DFT calculations and energy frameworks of new coumarin appended oxadiazoles, to regress ascites malignancy by targeting VEGF mediated angiogenesis
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Ascites malignancy is a frequent cause of morbidity and presents significant management problems which occur in many cancers. Angiogenesis plays a major role in the prognosis of ascites tumor through Vascular Endothelial Growth Factor (VEGF). Inhibition o
- Banumathi,Jyothi, Mahima,Khamees, Hussien Ahmed,Khanum, Shaukath Ara,Prabhakar, B. T.,Sherapura, Ankith,Zabiulla
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- Molecular docking and synthesis of caffeic acid analogous and its anti-inflammatory, analgesic and ulcerogenic studies
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A series of caffeic acid (CA) derivatives 7a-j were synthesized via etherification and coupling action and their chemical structures were elucidated spectroscopically. Motivated by the various biological activities displayed by CA derivatives such as anti-inflammatory, antiviral, anticancer and antioxidant and also based on its extensively consumption in the human diet. In the present work, the newly synthesized compounds 7a-j were evaluated for anti-inflammatory and analgesic action and most of them exerted comparable activity to the reference compound celecoxib. Further, ulcer indexes for the most active compounds were calculated and most of them showed less ulcerogenic effect than the reference drug. Among the title series 7a-j, compounds 7f and 7g with electron withdrawing bromo and chloro group respectively, at the para position of the phenoxy ring was showed good activity compared to all other compounds. Interestingly, the COX-I/COX-II activity ratio of potent compounds 7f and7g showed an almost equal inhibitory effect on both isoenzymes. Further, molecular docking studies have been performed for the potent compounds which showed statistically significant result.
- Al-Ostoot, Fares Hezam,Ara Khanum, Shaukath,Grisha, S.,Mohammed, Yasser Hussein Eissa,Vivek, H. K.,Zabiulla
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- Fluorescence sensor based on quinoline derivative, synthesis of fluorescence sensor and application of fluorescence sensor in detection of aluminum ions
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The invention designs and synthesizes a fluorescence sensor based on a quinoline derivative, which is prepared by the following steps of: taking 8-hydroxyquinoline and 2-ethyl bromoacetate as substrates, and reacting in an acetonitrile solvent to prepare
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Paragraph 0027-0028; 0030
(2021/08/14)
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- A New Series of 1,3,4-Oxadiazole Linked Quinolinyl-Pyrazole/Isoxazole Derivatives: Synthesis and Biological Activity Evaluation
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Abstract: A series of 1,3,4-oxadiazole bridged pyrazole/isoxazole bearing quinoline derivatives has been designed and synthesized by a clean and convenient method. Structures of the newly synthesized compounds have been confirmed by FTIR, 1H and 13C NMR, and HRMS spectral data. The titled compounds have been evaluated for their molecular docking guided antimicrobial and anti-inflammatory activity. One of 1,3,4-oxadiazole bridged quinolinyl-pyrazole derivatives has interacted efficiently with E. Coli protein (PDB file: 1KZN), and has been characterized by good antimicrobial activity against the majority of the tested pathogens. Another product has exhibited excellent anti-inflammatory activity.
- Basavanna, V.,Bhadraiah, U. K.,Chandra,Chandramouli, M.,Doddamani, Shridevi,Kempaiah, C.,Lingegowda, N. S.,Ningaiah, S.
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p. 2257 - 2266
(2021/12/23)
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- A facile AIE fluorescent probe for broad range of pH detection
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Detection of pH has received more and more attention in various fields. Currently, a hot research topic is focused on how to use a facile fluorescent dye to achieve a wide range and accurate pH detection. Herein, we reported a simple fluorescence probe for pH detection with wide range and accuracy based on the Aggregation-Induced Emission (AIE) characteristics. The probe 2-oxo-N’-(2-(quinolin-8-yloxy)acetyl)-2H-chromene-3-carbo- hydrazide (CHBQ) as comprised of coumarin and quinoline as the electron donor and acceptor, N, N′-diformylhydrazine bond as the linking group, respectively. The probe displays good AIE characteristics under water content up to 99% in mixed medium. Furthermore, it can identify acid and base as fast as 30 s by color change of the solution under UV365 nm lamp. The detection of the probe for pH was hardly interfered with other ions. What's more, the probe CHBQ can be designed to be a broad range test paper of pH detection, which has a great practical value.
- Wang, Xiaoju,Wang, Haoping,Niu, Yan,Wang, Yunxia,Feng, Liheng
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- Recognition of Al3+ through the off-on mechanism as a proficient driving force for the hydrolysis of BODIPY conjugated Schiff base and its application in bio-imaging
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Two new BODIPY azine bearing quinoline and pyrazine attached Schiff base chemosensors (R1 and R2) have been synthesized and applied for the detection of Al3+ in CH3CN/H2O medium. Intramolecular hydrogen bonding makes both the sensors rigid and helps to encapsulate Al3+ in the cavity. The pink colour of R1 and R2 has been changed to green fluorescent upon excess addition of Al3+ which is only because of the hydrolysis of imine bond to regenerate compound 8. Another nitrogen atom present in quinoline and in pyrazine moiety made R1 and R2 more efficient in sensing of Al3+ ion compare to R1D, R2B and R2D. Cell viability and fluorescence microscopic experiments showed that the chemosensors are cytocompatible and can be used as an effective fluorescent probe for detecting Al3+ ion in the living cell.
- Kashyap, Kumari Somlata,Kumar, Ashish,Hira, Sumit Kumar,Dey, Swapan
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- Aggregation-induced luminescent material containing quinoline and coumarin functional groups and preparation method of aggregation-induced luminescent material
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The invention belongs to the technical field of organic light-emitting materials, and provides an aggregation-induced luminescent material containing quinoline and coumarin functional groups. The invention aims to solve the technical problems that the structure of a current aggregation-induced luminescent material with specific functions is complicated, and raw materials for preparing the currentaggregation-induced luminescent material have high cost. The preparation method of the aggregation-induced luminescent material comprises the steps: using a quinoline derivative and a coumarin derivative as raw materials, performing ethyl bromoacetate substitution on the quinoline derivative so as to obtain quinoline functional group-containing ethyl acetate, then performing a reaction on the quinoline functional group-containing ethyl acetate and hydrazine hydrate so as to obtain quinoline functional group-containing acethydrazide, and finally performing a reaction on the quinoline functionalgroup-containing acethydrazine and the coumarin derivative so as to obtain the aggregation-induced luminescent material containing the quinoline and coumarin functional groups. The preparation methodhas simple operation and mild reaction conditions, the aggregation-induced luminescent material containing the quinoline and coumarin functional groups has a simple structure, and the raw materials for preparing the aggregation-induced luminescent material are inexpensive.
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(2019/09/16)
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- Synthesis of coumarin analogs appended with quinoline and thiazole moiety and their apoptogenic role against murine ascitic carcinoma
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The synthesis and antiproliferative effect of a series of quinoline and thiazole containing coumarin analogs 12a-d and 13a-f respectively, on mice leukemic cells was performed. The chemical structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectral analysis. The result indicates that, 7-methoxy-2-oxo-2H-chromene-3-carboxylic acid [4-(4-methoxy-phenyl)-thiazol-2-yl]-amide (13f) showed potent activity against EAC and DLA cells in MTT (15.3 μM), tryphan blue (15.6 μM) and LDH (14.2 μM) leak assay with 5-fluorouracil as a standard. Further, the anti-neoplastic effect of the compound 13f was verified against Ehrlich ascites tumour by BrdU incorporation, TUNEL, FACS and DNA fragmentation assays. Experimental data showed that compound 13f induces the apoptotic cell death by activating apoptotic factors such as caspase-8 &-3, CAD, Cleaved PARP, γ-H2AX and by degrading genomic DNA of cancer cells and thereby decreasing the ascitic tumour development in mice. Besides, compound 13f was also subjected for docking studies to approve the in vitro and in vivo studies. The data revealed that the compound 13f has very good interaction with caspase 3 protein by binding with amino acid Arg 207 through hydrogen bond.
- Prashanth,Avin, B.R. Vijay,Thirusangu, Prabhu,Ranganatha, V. Lakshmi,Prabhakar,Sharath Chandra, J.N. Narendra,Khanum, Shaukath Ara
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- Design and synthesis of conjugated azo-hydrazone analogues using nano BF3·SiO2 targeting ROS homeostasis in oncogenic and vascular progression
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Disrupted redox balance is implicated in multiple pathologies including malignant progression and tumor angiogenesis. In this investigation, we report the design and development of novel and effective ROS detoxifying azo-hydrazone molecules targeting mali
- Zabiulla,Vigneshwaran,Bushra, A. Begum,Pavankumar,Prabhakar,Khanum, Shaukath Ara
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p. 419 - 428
(2017/09/02)
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- Regioselective synthesis, antitumor and antioxidant activities of some 1,2,4-triazole derivatives based on 4-phenyl-5-(quinolin-8-yloxy)methyl-4H-1,2,4-triazole-3-thiol
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Regioselective synthesis of some triazole derivatives 4–18 was achieved from the versatile, readily accessible 4-phenyl-5-(quinolin-8-yloxy)methyl-4H-1,2,4-triazole-3-thiol/thione 3. The structures of the newly synthesized products were confirmed and characterized by IR, 1H NMR, 13C NMR, and mass spectral studies. Most of the synthesized compounds were evaluated for their antitumor and antioxidant activities and demonstrated potent to weak activities.
- Behalo,Amine,Fouda
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p. 410 - 417
(2017/04/03)
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- A novel highly sensitive and selective fluorescent sensor for imaging mercury(ii) in living cells
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A novel phenothiazine-based derivative was designed and synthesized in this work, this molecule exhibited an obvious fluorescence quenching upon addition of Hg2+ due to the formation of a 1:1 metal-ligand complex. In addition to the high sensitivity toward Hg(ii), it also displayed a high selectivity for Hg2+ over other transition metal ions in a rapid response time (2+ in biological systems. the Partner Organisations 2014.
- Zhou, Chen,Song, Yan,Li, Yapeng
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p. 33614 - 33618
(2014/08/18)
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- A rhodamine-quinoline based chemodosimeter capable of recognising endogenous OCl- in human blood cells
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A rhodamine-quinoline based chemodosimeter (RHQ) has been designed, synthesized and characterized in this paper. The structure of the sensor is confirmed through single crystal X-ray study. It detects hypochlorite (OCl -) selectively among other analytes studied. It showed colorimetric and orange-red fluorescence "turn-on" upon addition of OCl -. The OCl--promoted ring opening of the rhodamine spirolactam ring in RHQ evokes a large absorbance as well as fluorescence enhancement in water-acetonitrile (1/1, v/v) medium with no significant response to other competitive analytes. Furthermore, we demonstrate here that RHQ can endogenously detect OCl- in human blood cells (peripheral blood mononuclear cells). It also exhibits excellent performance in the "dip stick" method. The optimized structure of the probe is calculated by density functional theory calculations. Moreover, the limit of detection of the probe is in the 10-8 M range.
- Goswami, Shyamaprosad,Das, Sangita,Aich, Krishnendu,Nandi, Prasanta Kumar,Ghoshal, Kakali,Quah, Ching Kheng,Bhattacharyya, Maitree,Fun, Hoong-Kun,Abdel-Aziz, Hatem A.
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p. 24881 - 24886
(2014/07/07)
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- Development of a novel fluorescent probe for copper ion in near aqueous media
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In this work, we have successfully provided a new fluorescent probe based on coumarin and quinoline (CQ) for detecting copper ion. This system utilizes such a chemical process, which responses instantaneously at room temperature with linear proportionality to the amount of copper ion. The receptor can be applied to monitoring of Cu2+ ion in aqueous solution with a pH span 5e11. The chemosensor CQ has a high fluorescence on/off ratio of over 48 and exhibits a high selectivity and sensitivity toward Cu2+ over other common metal ions in near aqueous media. And the compound CQ can easily stain living cells, having potential application in biology.
- Chen, Fengjuan,Hou, Fengping,Huang, Liang,Cheng, Ju,Liu, Hongyan,Xi, Pinxian,Bai, Decheng,Zeng, Zhengzhi
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p. 146 - 152
(2013/07/11)
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- Synthesis, characterization, antiamoebic activity and cytotoxicity of novel series of pyrazoline derivatives bearing quinoline tail
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The cyclization of chalcones (1a-1j) with 2-(quinolin-8-yloxy) acetohydrazide (2) under basic condition led to the formation of new compounds, pyrazoline derivatives (3a-3j). In vitro antiamoebic activity was performed against HM1: IMSS strain of Entamoeba histolytica. The results showed that the compounds 3d, 3g, 3h, and 3j exhibited promising antiamoebic activity (IC 50 = 0.05 μM, 0.31 μM, 0.06 μM, 0.29 μM) respectively than the standard drug metronidazole (IC50 = 1.84 μM). The toxicological studies of these compounds on human breast cancer MCF-7 cell line showed that all the compounds 3d, 3g, 3h, 3j and metronidazole were nontoxic at the concentration range of 1.56-50 μM.
- Hayat, Faisal,Salahuddin, Attar,Umar, Sadiq,Azam, Amir
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scheme or table
p. 4669 - 4675
(2010/10/19)
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- Synthesis, characterization, antiamoebic activity and cytotoxicity of novel 2-(quinolin-8-yloxy) acetohydrazones and their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives)
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A series of 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives were synthesized by the cyclization of novel 2-(quinolin-8-yloxy) acetohydrazones. In vitro antiamoebic activity was performed against HM1: IMSS strain of Entamoeba histolytica. The results showed that all the 2-(quinolin-8-yloxy) acetohydrazones were more active than their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives). SAR showed that the compounds having quinoline ring and hydrazone linkage with free N-H group are responsible for higher antiamoebic activity. The cytotoxic studies of these compounds on human breast cancer MCF-7 cell line showed that all the compounds were nontoxic at the concentration range of 1.56-50 μM.
- Hayat, Faisal,Salahuddin, Attar,Zargan, Jamil,Azam, Amir
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scheme or table
p. 6127 - 6134
(2011/01/13)
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- Synthesis and biological activity test of some new five membered heterocycles
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A new series of 1,3,4-oxadiazoles, 1,2,4-triazoles, 1,3,4-thiadiazoles were synthesized using alkylhydrazides as the starting materials, and then 1,2,4-triazoles were used to synthesize [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles. All the compounds were evaluated for in vitro antibacterial activity and antitumor activity. A new series of five membered heterocyclic compounds were synthesized using alkylhydrazides as the starting materials. All the compounds were evaluated for in vitro antibacterial activity and antitumor activity.
- Xia, Qingchun,Xu, Dongfang,He, Qizhuang,Li, Xingyu,Sun, Dazhi
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body text
p. 2433 - 2440
(2011/10/05)
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- Synthesis and pharmacological studies on some phthalimidoxy substituted quinoline derivatives
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Synthesis of novel N′-[2-(4-substitutedphenyl)-3-N-ethoxyphthalimido- 5-oxoimldazolidene-1-yl]-2-(quinoline-8-yloxy)acetamide derivatives (6a-e) with potential biological activities were carried out by adopting the reaction scheme given below. Compound et
- Bhambi, Dinesh,Sain, Devendra K.,Salvi, Vijay K.,Sharma, Chirag,Talesara
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experimental part
p. 1072 - 1078
(2011/06/20)
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- Synthesis of new 8-(5-substituted amino-1,3,4-oxadiazol-2-yl) and 8-(5-substitued amino-1,3,4-thiadiazol-2-yl) methoxyquinolines with antibilharzial activity
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Several 5-substituted amino-1,3,4-oxadiazol-2-yl and 5-substituted amino-1,3,4-thiadiazol-2-yl derivatives with different 8-hydroxyquinoline moieties in the 2-position were prepared and tested for their antiparasitic activity. Preliminary biological tests on mice experimentally infested with Schistosoma mansoni revealed that the new compounds show moderate schistosomicidal activity.
- Soliman,Mokhtar,El Sadany
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p. 403 - 405
(2007/10/02)
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