5683-78-3Relevant articles and documents
Photodynamic fluorescent metal ion sensors with parts per billion sensitivity
Winkler, Jeffrey D.,Bowen, Corinne M.,Michelet, Veronique
, p. 3237 - 3242 (1998)
We report herein the synthesis and spectroscopic study of the first spiropyrandinolines that function as sensors for metal ions in the parts per billion range. These systems operate by either photochemically or chemically induced reversible formation of merocyanine metal ion complexes. The application of this novel photodynamic sensing material to sensor technology is discussed.
DNA-binding and anti-oxidation properties of binuclear lanthanide(III) complexes of 8-hydroxyquinoline-7-carbaldehyde-(isonicotinyl)hydrazone
Liu, Yongchun,Zhang, Kejun,Lei, Ruixia,Liu, Jianning,Zhou, Tianlin,Yang, Zheng-Yin
, p. 2041 - 2054 (2012)
Binuclear complexes [LnL(NO3)(H2O)2] 2 were prepared from the Schiff base 8-hydroxyquino-line-7- carbaldehyde-(isonicotinyl)hydrazone (H2L) and equivalent molar amounts of Ln(NO3)3 · 6H2O (Ln = La 3+, Nd3+, Sm3+, Eu3+, Gd 3+, Dy3+, Ho3+, Er3+, Yb 3+), respectively. The ligand is dibasic tetradentate and the dimerization occurs through the phenolate oxygen atoms leading to a central four-membered (LnO)2-ring. The ligand and all the Ln(III) complexes can bind to calf thymus DNA through intercalation with binding constants of 105-106 (molL-1)-1, and they show strong scavenging abilities on hydroxyl radicals and superoxide radicals. The values of SC50 of Ln(III) complexes for HO? and O2-. are 2.344-13.33 and 4.459-28.48 μmolL -1, respectively. Ln(III) complexes present stronger binding abilities to DNA and stronger anti-oxidation properties than ligand. Complex containing hydroxyl unit shows stronger scavenging abilities on hydroxyl radical, while complex containing N-heteroaromatic substituent shows stronger scavenging abilities on superoxide radicals. Furthermore, earlier rare metal complexes show stronger scavenging abilities on both hydroxyl radicals and superoxide radicals.
Synthesis, electrochemical and spectroscopic characterization of selected quinolinecarbaldehydes and their Schiff base derivatives
Wantulok, Jakub,Szala, Marcin,Quinto, Andrea,Nycz, Jacek E.,Giannarelli, Stefania,Sokolová, Romana,Ksi??ek, Maria,Kusz, Joachim
, (2020/05/16)
A new approach to the synthesis of selected quinolinecarbaldehydes with carbonyl groups located at C5 and/or in C7 positions is presented in this paper in conjunction with spectroscopic characterization of the products. The classical Reimer-Tiemann, Vilsmeier-Haack and Duff aldehyde synthesis methods were compared due to their importance. Computational studies were carried out to explain the preferred selectivity of the presented formylation transformations. A carbene insertion reaction based on Reimer-Tiemann methodology is presented for making 7-bromo-8-hydroxyquinoline-5-carbaldehyde. Additionally, Duff and Vilsmeier-Haack reactions were used in the double formylation of quinoline derivatives and their analogues benzo[h]quinolin-10-ol, 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde, 8-(dimethylamino) quinoline-5,7-dicarbaldehyde and 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde. Four Schiff base derivatives of 2,6-diisopropylbenzenamine were prepared from selected quinoline-5-carbaldehydes and quinoline-7-carbaldehyde by an efficient synthesis protocol. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, FTIR, electronic absorption spectroscopy and multinuclear NMR. The electrochemical properties of 8-hydroxy-quinoline-5-carbaldehyde, 6-(dimethylamino)quinoline-5-carbaldehyde and its methylated derivative were investigated, and a strong correlation between the chemical structure and obtained reduction and oxidation potentials was found. The presence of a methyl group facilitates oxidation. In contrast, the reduction potential of methylated compounds was more negative comparing to non-methylated structure. Calculations of frontier molecular orbitals supported the finding. The structures of 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde and four Schiff bases were determined by single-crystal X-ray diffraction measurements.
Nano cuboids: Impact of 8-hydroxyquinoline on tryptophan properties and its applications
Sharma, Poonam,Singh, Prabhpreet
supporting information, (2020/02/13)
N-terminal tryptophan residues can be labeled with fluorophore by chemical reaction. Here in we report conjugation of 8-hydroxyquinoline (as fluorophore) with tryptophan using Schiff-base condensation reaction to decipher the impact of 8-hydroxyquinoline on the fluorescence and self-assembly properties of tryptophan in water. This water-soluble hydroxyquinoline–tryptophan (HQ-W1) conjugate has been demonstrated to have Aggregation Induced Emission (AIE) phenomena in water. HQ-W1 undergo spontaneous self-assembly to form nano cuboidal superstructures having 200–500 nm diameter and 300–650 nm length. In metal-ion binding studies this HQ-W1 shows selective fluorescence enhancement (14.5-fold) in the presence of Al3+ ions. The detection limit is 3.0 nM (UV method) and 3.53 nM (FI method). The AIE utility of HQ-W1 has been demonstrated by developing latent fingerprints.
