3281-08-1Relevant articles and documents
A Smart Molecule for Selective Sensing of Nitric Oxide: Conversion of NO to HSNO; Relevance of Biological HSNO Formation
Islam, Abu Saleh Musha,Bhowmick, Rahul,Pal, Kaberi,Katarkar, Atul,Chaudhuri, Keya,Ali, Mahammad
, p. 4324 - 4331 (2017)
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.
Both visual and ratiometric fluorescent sensor for Zn2+ based on spirobenzopyran platform
Zhu, Jian-Fa,Chan, Wing-Hong,Lee, Albert W.M.
, p. 2001 - 2004 (2012)
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.
Synthesis of some novel 3,4,5-trisubstituted triazole derivatives bearing quinoline ring and evaluation of their antimicrobial activity
Yurtta?, Leyla,Kubilay, Asl?han,Evren, Asaf Evrim,K?sac?k, ?pek,Karaca Gen?er, Hülya
, p. 767 - 773 (2020)
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
Nitric Oxide Sensing through 1,2,3,4-Oxatriazole Formation from Acylhydrazide: A Kinetic Study
Islam, Abu Saleh Musha,Bhowmick, Rahul,Chandra Garain, Bidhan,Katarkar, Atul,Ali, Mahammad
, p. 13287 - 13295 (2018)
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.
Synthesis of indole–quinoline–oxadiazoles: their anticancer potential and computational tubulin binding studies
Kamath, Pooja R.,Sunil, Dhanya,Ajees, Abdul A.
, p. 5899 - 5914 (2016)
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.]
The synthesis and study of the fluorescent probe for sensing Cu 2+ based on a novel coumarin Schiff-base
Duan, Yu-Wei,Tang, Hao-Yang,Guo, Yuan,Song, Zhan-Ke,Peng, Meng-Jiao,Yan, Yong
, p. 1082 - 1086 (2014)
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.
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
Althobiti, Hanan A.,Zabin, Sami A.
, p. 591 - 607 (2020)
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.
Two similar Schiff-base receptor based quinoline derivate: Highly selective fluorescent probe for Zn(II)
Fan, Long,Li, Chao-rui,Qin, Jing-can,Yang, Zheng-yin
, (2020)
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.
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
Belkafouf, Nour El Houda,Benhalima, Nadia,Chouaih, Abdelkader,Daran, Jean-Claude,Djafri, Ahmed,Djafri, Ayada,Kourat, Oumeria,Megrouss, Youcef,Rahmani, Rachida
, (2020)
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.
A naphthalimide-quinoline based probe for selective, fluorescence ratiometric sensing of trivalent ions
Goswami, Shyamaprosad,Aich, Krishnendu,Das, Avijit Kumar,Manna, Abhishek,Das, Sangita
, p. 2412 - 2416 (2013)
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.
Simple quinoline-based "turn-on" fluorescent sensor for imaging copper (II) in living cells
Zhou, Chen,Xiao, Ning,Li, Yapeng
, p. 1092 - 1097 (2014)
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.
A new ICT and CHEF based visible light excitable fluorescent probe easily detects in vivo Zn2+
Aich, Krishnendu,Goswami, Shyamaprosad,Das, Sangita,Mukhopadhyay, Chitrangada Das
, p. 31189 - 31194 (2015)
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.
Molecular docking and synthesis of caffeic acid analogous and its anti-inflammatory, analgesic and ulcerogenic studies
Al-Ostoot, Fares Hezam,Ara Khanum, Shaukath,Grisha, S.,Mohammed, Yasser Hussein Eissa,Vivek, H. K.,Zabiulla
, (2020/12/25)
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.
A New Series of 1,3,4-Oxadiazole Linked Quinolinyl-Pyrazole/Isoxazole Derivatives: Synthesis and Biological Activity Evaluation
Basavanna, V.,Bhadraiah, U. K.,Chandra,Chandramouli, M.,Doddamani, Shridevi,Kempaiah, C.,Lingegowda, N. S.,Ningaiah, S.
, p. 2257 - 2266 (2021/12/23)
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.
