894-93-9Relevant articles and documents
Synthesis, spectroscopic characterization and in vitro studies of new heteroleptic copper (II) complexes derived from 2-hydroxy napthaldehyde Schiff's bases and N, N donor ligands: Antimicrobial, DNA binding and cytotoxic investigations
Kiran, Tummalapalli,Prasanth, Vuppalapati Giri,Balamurali,Vasavi,Munusami, Punnagai,Sathiyanarayanan, Kulathu Iyer,Pathak, Madhvesh
, p. 26 - 34 (2015)
A series of eight new copper (II) complexes of types [Cu(HL1)(B)] (4a-4d) and [Cu(HL2)(B)] (4e-4h), where HL1 is N-(2-hydroxy-1-naphthalidene)-2-aminophenol, HL2 is N-(2-hydroxy-1-naphthylidene)-2-mercaptoaniline and B is N, N donor ligands viz bipyridyl (bpy), 1,10-phenanthroline (phen), dipyridoquinoxaline (dpq) and dipyridophenazine (dppz) have been synthesized and characterized by elemental analysis as well as by spectroscopic techniques (IR, UV, ESI mass and EPR spectra). The DNA-binding properties of these copper complexes (4a-4h) have been investigated by electronic absorption, viscosity measurements and docking analyses. The results obtained indicated that the complexes get bonded with DNA via an intercalation binding mode with an intrinsic binding constant, Kb (1.116 ± 0.21 to 7.227 ± 0.21) × 104 M-1. The antimicrobial activity assays with the Schiff's bases and their heteroleptic copper (II) complexes of 4a and 4b exhibited profound activity against gram positive bacteria, gram negative bacteria and fungi. Further, complexes 4d and 4h displayed significant cytotoxicity when examined in vitro on a panel of cancerous cell line - human liver cancer cell line - HepG-2 cells (IC50 = 40.82 and 29.74 μg/ml).
Three novel Ni(II), VO(II) and Cr(III) mononuclear complexes encompassing potentially tridentate imine ligand: Synthesis, structural characterization, DNA interaction, antimicrobial evaluation and anticancer activity
Abdel-Rahman, Laila H.,Abu-Dief, Ahmed M.,Basha, Maram,Hassan Abdel-Mawgoud, Azza A.
, (2017)
Three novel Cr(III),VO(II) and Ni(II) imine complexes derived from the condensation of 2-aminophenol (AP) with 2-hydroxynaphthaldehyde (HN) were synthesized. The prepared HNAP imine ligand and its complexes were investigated via various physicochemical tools. The results suggest that the parent ligand behaves as a dibasic tridentate ONO ligand, when coordinated to Cr(III) in octahedral and to Ni(II) in tetrahedral geometry. In the case of VO(II), it coordinates in distorted square pyramidal geometry. Also, the prepared compounds were screened for their antimicrobial activities against pathogenic bacteria, Escherichia coli (?ve), Bacillus subtilis (+ve) and Staphylococcus aureus (+ve), and some types of fungi, Aspergillus niger, Candida glabrata and Trichophyton rubrum. The results indicate that the complexes show a stronger antimicrobial efficiency compared to the pro-ligand. The interaction of the prepared complexes with calf thymus DNA was investigated using spectral, viscosity and gel electrophoresis measurements. The obtained results clearly demonstrate that the binding affinity with calf thymus DNA follows the order HNAPCr > HNAPV > HNAPNi. The cytotoxic activity of the prepared compounds on human colon carcinoma cells (HCT-116 cell line), hepatic cellular carcinoma cells (HepG-2cell line) and breast carcinoma cells (MCF-7cell line) was examined. From these results it is found that the investigated complexes have potent cytotoxicity against growth of carcinoma cells compared to the corresponding imine pro-ligand.
Spectroscopic and computational study of a naphthalene derivative as colorimetric and fluorescent sensor for bioactive anions
Sharma, Darshna,Sahoo, Suban K.,Bera, Rati Kanta,Kamal, Raj
, p. 387 - 392 (2013)
The anion recognition property of a naphthalene based receptor (L) was investigated by naked-eye, UV-Vis, fluorescence, 1H NMR and computational methods. The receptor L showed fluoride selective naked-eye detectable colorimetric and UV-Vis spectral changes over other tested anions due to the formation of hydrogen bonding complex in 1:1 stoichiometry and/or deprotonation between fluoride and the receptor. Interestingly, the fluorescence of L was quenched by fluoride but enhanced by acetate.
The arginine detection and cytotoxicity of fluorescent probes based on naphthalene derivatives
Shang, Xuefang,Li, Congshu,Li, Jie,Chen, Yanmei,Chen, Hongli,Wang, Tianyun
, (2018)
From a biological point of view, Schiff base probes containing fluorescent groups are chemically modified to provide an effective method for the detection of amino acids. According to this method, three molecular probes containing Schiff base and hydroxyl group have been designed and synthesized. UV-Vis and fluorescent data indicated that compound 2 showed strong sensitivity and high selectivity for arginine (Arg) among normal twenty kinds of amino acids. In addition, compound 2 displayed high combining ability with Arg and low cytotoxicity in MCF-7 cell from 0 to 150?μg/mL. The above results showed the synthesized probes also can be used a biosensor for the Arg detection in vivo.
Reinforcement of ‘imine-hydroxyl chelation pocket’ by encapsulating into the β-CD cavity for the sterically protective detection of Al3+
Bharathi, A.,Chakravarty, Sujay,Krishnan, M. Murali,Parinamachivayam, G.,Premkumar, K.,Ragavendran, V.,Sivakumar, K.,Stalin, T.
, (2021)
The effect of encapsulating a schiff base probe; o-phenolnaphthylimine (pni) into β-cyclodextrin (β-CD) and its impact on the detection of Al3+ was investigated using the spectrofluorometric technique. The impact of imine moiety and the neighbouring hydroxyl groups of pni in the sensing of Al3+ were assessed through the experimental and computational procedure. The role of ‘imine-hydroxyl chelation pocket’ of pni in the detection of Al3+ was estimated, correlated and demonstrated. FTIR, NMR and mass spectral techniques were used for the investigations in solid state. Stoichiometry of the complexes was estimated using UV–visible and fluorescence spectral techniques in liquids state. Molecular modeling and steric maps were obtained using 3D structural data of compounds. Linearity range, LOD and LOQ were estimated from the selectivity and sensitivity studies. The proposed work demonstrates the impact of additional binding centers that has to be considered while designing a chemosensor for metal cations.
Compound with aggregation-induced emission function and preparation method and application thereof
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Paragraph 0071; 0072, (2021/03/13)
The invention relates to a compound with an aggregation-induced emission function, the chemical structure of the compound is shown as a general formula I, 2-hydroxy-1-naphthaldehyde and 2-aminothiophenol (or 2-aminophenol) react in organic solvents to obtain Schiff base structure intermediates; and recrystallizing and purifying are carried out to obtain the intermediate, and the intermediate is reacted with an oxidant in an organic solvent to obtain the compound with the aggregation-induced emission function. Further the compound is modified to obtain series of functionalized aggregation-induced emission compounds. The synthesis method of the compounds is simple, the reaction conditions are mild, the synthesis is easy, the post-treatment operation is convenient, the yield is high, and theheating reaction shortens the reaction time. The obtained aggregation-induced emission compound has an excited state intramolecular proton transfer effect. Intramolecular weak acting force hydrogen bonds exist between hydroxyl hydrogen atoms on a naphthalene ring and nitrogen atoms on an ortho-benzothiazole ring, an excited state intramolecular proton transfer effect is achieved, and large Stokesshift is shown.
