14510-06-6Relevant articles and documents
A novel cysteine fluorescent probe based on benzothiazole and quinoline with a large stokes shift and application in living cell and mice
Cai, Yonghong,Gu, Xin,Mei, Huihui,Wang, Minghui,Xu, Kuoxi
, (2021)
A novel fluorescent probe based on hydroxyquinoline conjugated with benzothiazolyl unit dye Doc-Ac was prepared. The results of fluorescent and absorption spectroscopic responses towards amino acids showed that the probe had a capability of rapidly and selectively detecting cysteine over other amino acids with a large stokes shift in aqueous solution. The sensing mechanism was proved by the proton NMR and high resolution mass spectrometry analysis. The fluorescence images indicated that this probe could discriminate the exogenous/endogenous cysteine in living cells and mice.
Rhombus-shaped tetranuclear [Ln4] complexes [Ln = Dy(III) and Ho(III)]: Synthesis, structure, and SMM behavior
Chandrasekhar, Vadapalli,Hossain, Sakiat,Das, Sourav,Biswas, Sourav,Sutter, Jean-Pascal
, p. 6346 - 6353 (2013)
The reaction of a new hexadentate Schiff base hydrazide ligand (LH 3) with rare earth(III) chloride salts in the presence of triethylamine as the base afforded two planar tetranuclear neutral complexes: [{(LH)2Dy4}(μ2
Novel lavendamycin analogues as antitumor agents: Synthesis, in vitro cytotoxicity, structure-metabolism, and computational molecular modeling studies with NAD(P)H:quinone oxidoreductase 1
Hassani, Mary,Cai, Wen,Holley, David C.,Lineswala, Jayana P.,Maharjan, Babu R.,Ebrahimian, G. Reza,Seradj, Hassan,Stocksdale, Mark G.,Mohammadi, Farahnaz,Marvin, Christopher C.,Gerdes, John M.,Beall, Howard D.,Behforouz, Mohammad
, p. 7733 - 7749 (2005)
Novel lavendamycin analogues with various substituents were synthesized and evaluated as potential NAD(P)H:quinone oxidoreductase (NQO1)-directed antitumor agents. Pictet-Spengler condensation of quinoline- or quninoline-5,8-dione aldehydes with tryptamin
Synthesis and biological evaluation of novel 8-substituted quinoline-2-carboxamides as carbonic anhydrase inhibitors
Thacker, Pavitra S.,Shaikh, Pirpasha,Angeli, Andrea,Arifuddin, Mohammed,Supuran, Claudiu T.
, p. 1172 - 1177 (2019)
A series of novel 8-substituted-N-(4-sulfamoylphenyl)quinoline-2-carboxamides was synthesised by the reaction of 8-hydroxy-N-(4-sulfamoylphenyl) quinoline-2-carboxamide with alkyl and benzyl halides. The compounds were assayed for carbonic anhydrase (CA)
Linear and nonlinear optical properties of Ln-Zn heteronuclear complexes from a Schiff base ligand containing 8-hydroxyquinoline moiety
Chen, Ling,Yan, Cheng,Du, Bin-Bin,Wu, Kai,Zhang, Lu-Yin,Yin, Shao-Yun,Pan, Mei
, p. 13 - 16 (2014)
Starting from a Schiff base ligand containing 8-hydroxyquinoline moiety, namely, 3,3′-(1E,1′E)-(propane-1,3-diylbis(azan-1-yl-1-ylidene)) bis(methan-1-yl-1-ylidene) diquinolin-8-ol (H2PBIQ), five heteronuclear Ln(III)-Zn(II) complexes (([Eu2Zn(PBIQ) 2(NO3)4]·CH2Cl2, 1), ([Tb2Zn(PBIQ)2(NO3)4] ·CH2Cl2, 2), ([Gd2Zn(PBIQ) 2(NO3)4]·CH2Cl2, 3), ([Nd2Zn(PBIQ)2(NO3)4] ·CH2Cl2, 4)), and ([Yb2Zn(PBIQ) 2(NO3)4]·CH2Cl2, 5) were obtained. Due to the low energy level resided in the excited state, the Schiff base ligand can sensitize near infrared emitting Ln(III) ions (Nd and Yb), while visible light emitting Eu and Tb ions cannot be excited. Instead, nonlinear optical properties were observed in Eu/Tb-Zn heteronuclear complexes.
A Rhodamine-based fluorescent sensor for chromium ions and its application in bioimaging
Li, Xue-Mei,Zhao, Rui-Rui,Yang, Yan,Lv, Xue Wei,Wei, Yu-Ling,Tan, Rui,Zhang, Jun-Feng,Zhou, Ying
, p. 1258 - 1261 (2017)
A rhodamine-based sensor (1) has been developed for the detection of chromium ions. Cr3+-induced opening of the rhodamine spirocycle in sensor (1) led to the distinct colorimetric and fluorescence responses. Among all the tested ions, only Cr3+ generated a significant fluorescence enhancement of up to 13-fold, which indicated the high selectivity of 1. Sensor (1) was successfully applied in the in vivo fluorescence imaging of Cr3+ in C. elegans. The results provided solid evidences for the future estimation of Cr3+ in environmental applications and tobacco samples.
Reaction-based bi-signaling chemodosimeter probe for selective detection of hydrogen sulfide and cellular studies
Guria, Uday Narayan,Maiti, Kalipada,Ali, Syed Samim,Samanta, Sandip Kumar,Mandal, Debasish,Sarkar, Ripon,Datta, Pallab,Ghosh, Asim Kumar,Mahapatra, Ajit Kumar
, p. 5367 - 5375 (2018)
A new quinoline-indolium-based chemical probe (DPQI) was synthesized and characterized for selective detection of hydrogen sulphide (H2S). Probe DPQI displays highly selective and sensitive detection of hydrogen sulphide over other allied anions and thiol-containing amino acids in aqueous-DMSO at physiological pH. The probe DPQI acts as a bi-signaling fluorescent chemodosimeter for selective detection of hydrogen sulphide when excited at different wavelengths. The selectivity was guaranteed by the use of the unique nucleophilicity of HS- for nucleophilic addition to the most electrophilic positively charged centre followed by thiolysis of the dinitrophenyl ether to yield DNB-SH and a fluorescent phenoxide moiety, which led to the fluorescence emission 'turn on' and characteristic visual fluorescent color change behavior of the sensing system. This is why the probe DPQI showed different optical properties at varying concentrations of hydrogen sulphide. The structural and electronic properties of the probe (DPQI) and its thiolysis product have been demonstrated using ab initio density functional theory (DFT) combined with time-dependent density functional theory (TDDFT) calculations. Utilizing this probe, we have successfully detected hydrogen sulphide in live cells.
S-shaped decanuclear heterometallic [Ni8Ln2] complexes [Ln(iii) = Gd, Tb, Dy and Ho]: Theoretical modeling of the magnetic properties of the gadolinium analogue
Hossain, Sakiat,Das, Sourav,Chakraborty, Amit,Lloret, Francesc,Cano, Joan,Pardo, Emilio,Chandrasekhar, Vadapalli
, p. 10164 - 10174 (2014)
The reaction of 8-quinolinol-2-carboaldoxime (LH2) with Ni II and LnIII salts afforded the heterometallic decanuclear compounds [Ni8Dy2(μ3-OH) 2(L)8(LH)2(H2O)6] (ClO4)2·16H2O (1), [Ni 8Gd2(μ3-OH)2(L) 8(LH)2(H2O)4(MeOH) 2](NO3)2·12H2O (2), [Ni 8Ho2(μ3-OH)2(L) 8(LH)2(H2O)4(MeOH) 2](ClO4)2·2MeOH·12H2O (3) and [Ni8Tb2 (μ3-OH)2(L) 8(LH)2(MeOH)4(OMe)2]·2CH 2Cl2·8H2O (4). While compounds 1-3 are dicationic, compound 4 is neutral. These compounds possess an S-shaped architecture and comprise a long chain of metal ions bound to each other. In all the complexes, the eight NiII and two LnIII ions of the multimetallic ensemble are hold together by two μ3-OH, eight dianionic (L2-) and two monoanionic oxime ligands (LH-) whereas compound 4 has two μ3-OH, eight dianionic (L 2-), two monoanionic oxime ligands (LH-) and two terminal methoxy (MeO-) ligands. The central portion of the S-shaped molecular wire is made up of an octanuclear NiII ensemble which has at its two ends the LnIII caps. Magnetic studies on 1-4 reveal that the magnetic interactions between neighboring metal ions are negligible at room temperature. On the other hand, at lower temperatures in all the compounds anti-ferromagnetic interactions seem to be dominated. Analysis of the magnetic data for the GdIII derivative indicates NiII-Ni II anti-ferromagnetic interactions and GdIII-Ni II ferromagnetic interactions at low temperatures. A theoretical density functional study on the magnetic behavior of the GdIII derivative suggests that while the weak ferromagnetic interaction between GdIII and NiII is in line with the expectation of the magnetic interactions between orthogonal d and f orbitals, antiferromagnetic NiII-NiII interactions are related to the wide Ni-O-Ni angles (～102°) and quasi-planar conformation of the Ni2O 2 core.
Chelation in One Fell Swoop: Optimizing Ligands for Smaller Radiometal Ions
Choudhary, Neha,Guadalupe Jaraquemada-Peláez, Mar?a De,Kubeil, Manja,Orvig, Chris,Radchenko, Valery,Stephan, Holger,Wang, Xiaozhu,Zarschler, Kristof
, p. 5728 - 5741 (2020)
[44/47Sc]Sc3+, [68Ga]Ga3+, and [111In]In3+ are the three most attractive trivalent smaller radiometalnuclides, offering a wide range of distinct properties (emission energies and types) in the toolbox of nuclear medicine. In this study, all three of the metal ions are successfully chelated using a new oxine-based hexadentate ligand, H3glyox, which forms thermodynamically stable neutral complexes with exceptionally high pM values [pIn (34) > pSc (26) > pGa (24.9)]. X-ray diffraction single crystal structures with stable isotopes revealed that the ligand is highly preorganized and has a perfect fit to size cavity to form [Sc(glyox)(H2O)] and [In(glyox)(H2O)] complexes. Quantitative radiolabeling with gallium-68 (RCY > 95%, [L] = 10-5 M) and indium-111 (RCY > 99%, [L] = 10-8 M) was achieved under ambient conditions (RT, pH 7, and 15 min) with very high apparent molar activities of 750 MBq/μmol and 650 MBq/nmol, respectively. Preliminary quantitative radiolabeling of [44Sc]ScCl3 (RCY > 99%, [L] = 10-6 M) was fast at room temperature (pH 7 and 10 min). In vitro experiments revealed exceptional stability of both [68Ga]Ga(glyox) and [111In]In(glyox) complexes against human serum (transchelation 3glyox exhibits enhanced fluorescence, which was employed to determine the stability constants for Sc(glyox) in addition to the in-batch UV-vis spectrophotometric titrations; as a proof-of-concept these complexes were used to obtain fluorescence images of live HeLa cells using Sc(glyox) and Ga(glyox), confirming the viability of the cells. These initial investigations suggest H3glyox to be a valuable chelator for radiometal-based diagnosis (nuclear and optical imaging) and therapy.
Design, synthesis, spectroscopic, photophysical and computational studies of a C3-symmetric hydroxyquinoline based tripod: TREN2OX and its interaction with Fe(III) and Al(III)
Thakur, Monika,Baral, Minati,Kanungo
, (2021/09/20)
A new tripodal chelator 2,2′,2′′-((1E,1′E,1′'E)-(nitrilotris(ethane-2,1-diyl)tris(azanylylidene))-tris(methanylylidene))tris(quinolin-8-ol), TREN2OX, containing three 8-hydrixyquinoline (8-HQ) units appended to a tris(2-aminoethyl)amine (TREN) skeleton has been synthesized and characterized through elemental analysis (CHN), FT-IR, NMR (1H, 13C) and ESI mass spectrometry. The interaction of the ligand with the proton, Fe3+ and Al3+ was studied by potentiometric and spectrophotometric methods. The solution thermodynamic formation constants could be evaluated in an aqueous solution at 298±1 K. Six protonation constants were evaluated with formation constants ranging from 1.50 to 9.86, corroborating three nitrogen atoms of the 8-hydroxyquinoline ring and three phenolate groups. With iron and aluminium, the ligand forms [FeL], [FeLH2], [FeLH3] and [AlL], [AlLH3] complexes having log β as 43.64, 24.92, 53.82, and 29.20, 52.85 respectively. The absorbance spectra of TREN2OX and its complexes showed variation in spectral behavior with a change in pH. In the aqueous solution, the ligand showed an enhancement in emission at 460 nm at neutral pH 7.0, while in acidic and basic pH, the fluorescence was quenched with bathochromic shift implying its utility as an OFF-ON-OFF pH molecular sensor. Interestingly, the fluorescence of TREN2OX showed enhancement in the presence of Al3+, while a reverse phenomenon (quenching) was observed for Fe3+, indicating that the ligand can behave as a metal sensor for both the metal ions, one as “ON” type and the other as “OFF” type. The DFT was used to predict molecular geometry, IR, NMR, absorbance, emissions spectra for all possible species for the ligand and its ligand-proton and ligand-metal complexes. The structure, bonding, and electronic behavior, including the electronic transitions, were evaluated by studying FMO, EDA, ETS-NOCV, and NTO in the ground and excited state geometry.
Nitric oxide-donating and reactive oxygen species-responsive prochelators based on 8-hydroxyquinoline as anticancer agents
Zhang, Yuxia,Yang, Jiaxin,Meng, Tingting,Qin, Yajuan,Li, Tingyou,Fu, Junjie,Yin, Jian
, (2021/01/19)
Metal ion chelators based on 8-hydroxyquinoline (8-HQ) have been widely explored for the treatment of many diseases. When aimed at being developed into potent anticancer agent, a largely unmet issue is how to avoid nonspecific chelation of metal ions by 8
