57709-62-3Relevant articles and documents
Synthesis, characterization, second and third order non-linear optical properties and luminescence properties of 1,10-phenanthroline-2,9-di(carboxaldehyde phenylhydrazone) and its transition metal complexes
Prasad, G. Krishna,Prashanth,Srivastava,Nageswara Rao,Babu, D. Rajesh
, p. 283 - 292 (2017)
The requirement for materials which exhibit good second and third order non-linear optical properties and also for materials which could sense metals in trace quantities has kindled renewed investigations. Organometallics and coordination compounds show a
Construction of a luminescent sensor based on a lanthanide complex for the highly efficient detection of methyl parathion
Hu, Xuan,Wang, Fengyi,Peng, Qianqian,Hu, Jing,Peng, Huaqiao,Li, Lin,Zheng, Baozhan,Du, Juan,Xiao, Dan
, p. 13048 - 13053 (2019)
A highly sensitive and selective luminescent sensor for the detection of methyl parathion (MP) pesticide was described in this study. The target molecule HL was synthesized by modifying the structure of 4-hydroxybenzlidene imidazolinone (HBI) with nitrogen-containing heterocyclic 1,10-phenanthroline. In the presence of Eu3+, a HL-Eu3+ complex was formed which could emit strong red fluorescence due to the removal of coordinated water molecules and an intramolecular energy transfer from HL to Eu3+. Addition of MP into the strongly fluorescent solution of HL-Eu3+ induced quenching of the complex's fluorescence, and this quenching behavior occurred because of the competition coordination of MP and HL for Eu3+. A calibration curve was developed that related the extent of fluorescence quenching to MP concentration, making the HL-Eu3+ system a sensitive and selective fluorescent sensor for MP. Under the experimental conditions, the detection limit for MP was down to 95 nM based on LOD = 3σ/S. Moreover, the fluorescence assay developed here allowed the detection of MP in two different types of real samples including pond water and pear juice, and satisfactory results demonstrate that this fluorescent sensor based on HL-Eu3+ has potential application in environment and food analysis.
Potential cytotoxic and amoebicide activity of first row transition metal compounds with 2,9-bis-(2′,5′-diazahexanyl)-1,1-phenanthroline (L1)
García-Ramos, Juan Carlos,Toledano-Maga?a, Yanis,Talavera-Contreras, Luis Gabriel,Flores-álamo, Marcos,Ramírez-Delgado, Vanessa,Morales-León, Emmanuel,Ortiz-Frade, Luis,Gutiérrez, Anllely Grizett,Vázquez-Aguirre, Adriana,Mejía, Carmen,Carrero, Julio César,Laclette, Juan Pedro,Moreno-Esparza, Rafael,Ruiz-Azuara, Lena
, p. 10164 - 10174 (2012)
A new synthetic pathway was reported to obtain N6 donor ligand 2,9-bis-(2′,5′-diazahexanyl)-1,10-phenanthroline (L1) and its coordination compounds of essential divalent metal ions Mn, Fe, Co, Ni, Cu and Zn. Complete characterization of all compounds was done with the conventional techniques. Crystal structures of [NiL1](PF6)2 and [ZnL1](PF6)2·H2O were also reported. Electrochemical studies have shown an active participation of the aromatic moiety of the ligand in redox reactions. The in vitro tests of the cytotoxic activity against human tumour cell lines HeLa (cervix) and CHP-212 (neuroblastoma) showed that all coordination compounds that involve redox active metal ions exhibit noteworthy antiproliferative activity, superior in all cases to cisplatin. [CuL1]2+ showed the lower IC50 value in the HeLa cell line with 1.84 μM, meanwhile, [CoL1]2+ showed the lower value in neuroblastoma CHP-212 with IC50 = 45.28 μM. None of these compounds were active against the SK-N-SH neuroblastoma cell line. In Entamoeba histolytica cultures, remarkable nanomolar IC50 values were found for [NiL1]2+ and [MnL1]2+ with 60 nM and 80 nM respectively, improving the antiproliferative activity more than 1000 times compared with the first choice drug for clinical treatments of human amoebiasis, metronidazole. On the other hand, a free ligand does not show antiproliferative activity either on human tumor cell lines or on Entamoeba histolytica trophozoites, highlighting the role played by metal ions to produce cytotoxicity in tumor cells and protozoa systems.
Multifunctional 1,10-phenanthroline derivative and its metal complexes as an anti-Alzheimer’s agent: structure-based drug design, synthesis, characterization and pharmacological studies
Gladis, E. H. Edinsha,Nagashri,Suman,Joseph
, p. 3267 - 3290 (2020)
N-Heterocycles are structural constituents of pharmaceuticals based on FDA approved therapeutic agents with more than 60% of drugs containing N-heterocycles as building blocks. In the present study, a 1,10-phenanthroline derivative with metal acetates forms metal chelates of the type [MIIL], where L?=?1,10-phenanthroline derivative and M = Co(II), Zn(II), Cu(II) and Ni(II). They were characterized by analysis, spectra [IR, UV–vis, (1H and 13C) NMR, mass, ESR] and magnetism as well as thermal analysis for the structural elucidation. Spectroscopic and analytical measurements confirmed an octahedral geometry for the Co(II), Zn(II), Cu(II) and Ni(II) chelates. The antimicrobial efficacy of the prepared complexes was assessed against Bacillus subtilis, Escherichia coli, Staphylococcus aureus, Aspergillus flavus, Candida albicans and Aspergillus niger. The antimycobacterial efficacy of the 1,10-phenanthroline derivative and its chelates was assessed against H37Rv using Microplate Alamar Blue Assay approach and compared with a standard. The acetylcholinesterase (AChE) inhibitory effect of the ligand was examined to find the therapeutic efficiency of compound in the treatment of neurodegenerative diseases. The synthesized ligand exhibited selective inhibition against AChE and butyryl-cholinesterase with IC50 values of 0.20 and 3.20 μM as compared to standards, rivastigmine and galantamine. Further, the in?vitro anti-inflammatory efficiency of metal chelates was examined with the help of egg albumin method. The α-glucosidase inhibition activity was also carried out for the prepared metal complexes.
1,10-Phenanthroline-based hexacatenar LCs with complex self-assembly, photophysical and binding selectivity behaviors
Liu, Xiaotong,Shen, Baoyu,Zuo, Rongzhou,Hong, Shijun,Xiao, Yulong
, (2021)
A novel series of V-shaped phenanthroline-based hexacatenars containing a 1,10-phenanthroline which was substituted on 2,9- positions with two cyanovinyl units were synthesized using oxidation and Knoevenagel reactions. The self-assembly, photophysical pr
A novel and fast responsive turn-on fluorescent probe for the highly selective detection of Cd2+ based on photo-induced electron transfer
Huang, Meng-Xia,Lv, Cai-Hua,Huang, Qing-Da,Lai, Jia-Ping,Sun, Hui
, p. 36011 - 36019 (2019)
A novel, highly sensitive and fast responsive turn-on fluorescence probe, 2,2′-((1E,1′E)-((1,10-phenanthroline-2,9-diyl)bis(methanylylidene)) bis(azanylylidene)) diphenol (ADMPA), for Cd2+ was successfully developed based on 2,9-dimethyl-1,10-p
A novel O-phenanthroline-based bis(half-salamo)-like chemical sensor: For rapid and efficient continuous recognition of Cu2+, HPO42? and H2PO4?
Bian, Ruo-Nan,Xu, Xin,Feng, Tao,Dong, Wen-Kui
, (2021)
A novel O-phenanthroline-based bis(half-salamo)-like fluorescent chemical sensor LPOV with two N3O coordination sites was synthesized. These N3O coordination sites were used for binding to specific metal ions. The sensor L
Lanthanide clusters of phenanthroline containing a pyridine-pyrazole based ligand: magnetism and cell imaging
De, Avik,Bala, Sukhen,Saha, Sayan,Das, Krishna Sundar,Akhtar, Sohel,Adhikary, Amit,Ghosh, Arijit,Huang, Guo-Zhang,Chowdhuri, Srijita Paul,Das, Benu Brata,Tong, Ming-Liang,Mondal, Raju
, p. 3593 - 3609 (2021)
In this contribution, we report the synthesis, characterization and luminescence-magnetic properties of Ln-clusters (Ln = Gd3+, Eu3+and Tb3+) using a new pyridine-pyrazole functionalized ligand fitted with a chromophoric phenanthroline backbone. The unorthodox N-rich ligand forms isostructural trinuclear lanthanide complexes with a topology that closely resembles two interdigitating hairpins. The clusters crystallize in chiral space groups and also exhibit chirality for bulk samples, which were further confirmed using solid state CD spectra. Magnetic studies on the complexes reveal their interesting features while the Gd cluster shows a significant cryogenic magnetic cooling behaviour with a moderately high magnetic entropy change of ?23.42 J kg?1K?1at 7 T and 2 K. On the other hand, Eu and Tb complexes exhibit interesting fluorescence properties. The compounds were subsequently used as fluorescent probes for the imaging of human breast adenocarcinoma (MCF7) cells. Live cell confocal microscopy images show that the complexes penetrate beyond the usual cytoplasm region and can be useful in imaging the nucleus region of MCF7 cells.
Design and synthesis of a neutral fluorescent macrocyclic receptor for the recognition of urea in chloroform
Goswami, Shyamaprosad,Mukherjee, Reshmi,Ray, Jayanta
, p. 1283 - 1285 (2005)
(Chemical Equation Presented) An artificial macrocyclic fluorescent receptor 1 has been designed and synthesized for the recognition of urea. 1 shows significant fluorescence quenching on complexation with urea and thiourea in chloroform and thus may be used as a synthetic fluorescent molecular sensor for their determination in a nondegradative way.
Probing the difference in covalence by enthalpy measurements: A new heterocyclic N-donor ligand for actinide/lanthanide separation
Yang, Yanqiu,Liu, Jun,Yang, Liang,Li, Kun,Zhang, Huabei,Luo, Shunzhong,Rao, Linfeng
, p. 8959 - 8970 (2015)
Complexation of Am(iii), Nd(iii), and Eu(iii) with a new heterocyclic nitrogen-donor ligand, 2,9-di(quinazolin-2-yl)-1,10-phenanthroline (denoted as BQPhen in this paper), was studied by thermodynamic measurements and theoretical computations. The stability constants of two successive complexes in dimethylformamide, ML3+ and ML23+ where M stands for Nd, Eu, or Am while L stands for the BQPhen ligand, were determined by absorption spectrophotometry. The enthalpy of complexation was determined by microcalorimetry. Results show that BQPhen forms ten times stronger complexes with Am(iii) than Eu(iii) or Nd(iii) under identical conditions, suggesting that BQPhen could be used as an efficient extractant for the separations of trivalent actinides from lanthanides. The higher binding strength of BQPhen towards Am(iii) than Nd(iii) or Eu(iii) is mainly due to the more favourable enthalpy of complexation for Am(iii)/BQPhen complexes, implying a higher degree of covalence in the Am(iii)/BQPhen complexes than the lanthanide(iii)/BQPhen complexes. The thermodynamic trend was corroborated with computational results and validated by solvent extraction experiments that demonstrated BQPhen preferably extracted Am(iii) more than Eu(iii), with a separation factor of about 10. Discussions have been made to compare BQPhen with other phenanthroline derivatives such as CyMe4-BTPhen, a bis-triazine-phenanthroline derivative that was reported in the literature. Data suggest that, under identical conditions, BQPhen would form stronger complexes with Am(iii), Eu(iii), and Nd(iii) than CyMe4-BTPhen.
