- 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
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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
- Prasad, G. Krishna,Prashanth,Srivastava,Nageswara Rao,Babu, D. Rajesh
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- Construction of a luminescent sensor based on a lanthanide complex for the highly efficient detection of methyl parathion
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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.
- Hu, Xuan,Wang, Fengyi,Peng, Qianqian,Hu, Jing,Peng, Huaqiao,Li, Lin,Zheng, Baozhan,Du, Juan,Xiao, Dan
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- Potential cytotoxic and amoebicide activity of first row transition metal compounds with 2,9-bis-(2′,5′-diazahexanyl)-1,1-phenanthroline (L1)
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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.
- 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
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- Multifunctional 1,10-phenanthroline derivative and its metal complexes as an anti-Alzheimer’s agent: structure-based drug design, synthesis, characterization and pharmacological studies
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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.
- Gladis, E. H. Edinsha,Nagashri,Suman,Joseph
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- 1,10-Phenanthroline-based hexacatenar LCs with complex self-assembly, photophysical and binding selectivity behaviors
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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
- Liu, Xiaotong,Shen, Baoyu,Zuo, Rongzhou,Hong, Shijun,Xiao, Yulong
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- A novel and fast responsive turn-on fluorescent probe for the highly selective detection of Cd2+ based on photo-induced electron transfer
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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
- Huang, Meng-Xia,Lv, Cai-Hua,Huang, Qing-Da,Lai, Jia-Ping,Sun, Hui
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- A novel O-phenanthroline-based bis(half-salamo)-like chemical sensor: For rapid and efficient continuous recognition of Cu2+, HPO42? and H2PO4?
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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
- Bian, Ruo-Nan,Xu, Xin,Feng, Tao,Dong, Wen-Kui
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- Lanthanide clusters of phenanthroline containing a pyridine-pyrazole based ligand: magnetism and cell imaging
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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.
- 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
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- Design and synthesis of a neutral fluorescent macrocyclic receptor for the recognition of urea in chloroform
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(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.
- Goswami, Shyamaprosad,Mukherjee, Reshmi,Ray, Jayanta
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- Probing the difference in covalence by enthalpy measurements: A new heterocyclic N-donor ligand for actinide/lanthanide separation
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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.
- Yang, Yanqiu,Liu, Jun,Yang, Liang,Li, Kun,Zhang, Huabei,Luo, Shunzhong,Rao, Linfeng
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- Tritopic phenanthroline and pyridine tail-tied aza-scorpiands
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The synthesis of two new tritopic double-scorpiand receptors in which two equivalent 5-(2-aminoethyl)-2,5,8-triaza[9]-(2,6)-pyridinophane moieties have been linked with 2,6-dimethylpyridine (L1) or 2,9-dimethylphenanthroline (L2) units is reported for the
- Gonzalez, Jorge,Llinares, Jose M.,Belda, Raquel,Pitarch, Javier,Soriano, Concepcion,Tejero, Roberto,Verdejo, Begona,Garcia-Espana, Enrique
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- Synthesis of phenanthroline and indole based hybrid cyclophane derivatives via ring-closing metathesis
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Here, we report new phenanthroline-based cyclophane derivatives via Fischer indolization and ring-closing metathesis (RCM) as key steps. Addition of Grignard reagent to 1,10-phenanthroline-2,9-dicarbaldehyde 2 and subsequent autoxidation gave the bis-alkene dione derivative 3. Further, Fischer indolization 3 followed by RCM under mild reaction conditions gave indole and containing hybrid cyclophanes such as 6a and 6b.
- Kotha, Sambasivarao,Shirbhate, Mukesh E.,Chinnam, Ajay Kumar,Sreevani, Gaddamedi
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- A new tetradentate mixed aza-thioether macrocycle and its complexation behavior towards Fe(II), Ni(II) and Cu(II) ions
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A new tetradentate mixed aza-thioether macrocyclic ligand 2,6-dithia[7](2,9)-1,10-phenanthrolinophane ([13]ane(phenN2)S2) was successfully synthesized. Reacting metal precursors [Fe(CH3CN)2(OTf)2], Ni(ClO4)2·6H2O, and Cu(ClO4)2·6H2O with one equivalent of [13]ane(phenN2)S2 afforded [Fe([13]ane(phenN2)S2)(OTf)2] (1), [Ni([13]ane(phenN2)S2)](ClO4)2 (2(ClO4)2), and [Cu([13]ane(phenN2)S2)(OH2)](ClO4)2 (3(ClO4)2), respectively. The structures of [13]ane(phenN2)S2 and all of its metal complexes were investigated by X-ray crystallography. The [13]ane(phenN2)S2 was found to behave as a tetradentate ligand via its donor atoms N and S.
- Chan, Siu-Chung,Ng, Sze-Wing,Wong, Chun-Yuen,Yeung, Chi-Fung,Yiu, Shek-Man
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- Design, synthesis, characterization, DNA binding, acetyl and butyryl cholinesterase activities of metal chelates with 1,10-Phenanthroline derivative
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Metal chelates comprised of highly conjugated planar 1,10-Phenanthroline derivative, [ML] where L is ligand (1,10-Phenanthroline derivative); M = Cu2+, Co2+, Ni2+ & Zn2+, were prepared. They were subjected to the composition measurement and different spectroscopic techniques for structural elucidation. Based on spectroscopic and analytical measurements confirmed that a distorted square planar arrangement for the Cu2+, Co2+, Ni2+ & Zn2+ chelates. The antimicrobial efficacy of prepared complexes were assessed against C. albicans, E. coli, B. subtilis, A. flavus, S. aureus, and A. niger. The anti-mycobacterial efficacy of ligand title chelates was evaluated against H37Rv and related to standard with the aid of MABA assay. The acetylcholinesterase (AChE) inhibitory effect of the ligand was examined to find out the beneficial efficiency of compound in the management of neurodegenerative syndromes. The synthesized ligand exhibited selective inhibition (AChE & BuChE), IC50 values of 0.20 and 3.20 μM as compared to standard, Rivastigmine and Galantamine. Further, the in vitro anti-inflammatory efficiency of metal chelates were performed with the help of egg albumin method. The α-glucosidase inhibition activity was also carried out for the prepared metal chelates. The inherent binding constants of metal chelates with DNA was calculated based molar extinction coefficient (Kb), 4.11, 3.62, 3.85 and 2.9 × 105 mol?1 for Cu2+, Co2+, Ni2+ & Zn2+ chelates, respectively, demonstrating that the metal chelates intensely bound to DNA. Studies of DNA cleavage were also conducted on pUC 18 DNA.
- Edinsha Gladis, E. H.,Joseph, J.,Nagashri, K.
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- A simple strategy for the visual detection and discrimination of Hg2+and CH3Hg+species using fluorescent nanoaggregates
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Fluorescent nanoaggregates (FNAs) based on phenanthroline-based amphiphiles show changes in solution color from colorless to yellow upon addition of both Hg2+(LOD ～4 ppb) and CH3Hg+(LOD ～18 ppb). However, the extent of flu
- Dey, Nilanjan,Dey, Nilanjan
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- Utilizing electronic effects in the modulation of BTPhen ligands with respect to the partitioning of minor actinides from lanthanides
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Effects of bromine substitution at the 5 and 5,6-positions of the 1,10-phenanthroline nucleus of BTPhen ligand on their extraction properties for Ln(iii) and An(iii) cations have been studied. Compared to C5-BTPhen, electronic modulation in BrC5-BTPhen and Br2C5-BTPhen enabled these ligands to be fine-tuned in order to enhance the separation selectivity of Am(iii) from Eu(iii). The Royal Society of Chemistry 2013.
- Afsar, Ashfaq,Laventine, Dominic M.,Harwood, Laurence M.,Hudson, Michael J.,Geist, Andreas
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- Synthesis and structural properties of hexaaza[5]helicene containing two [1,2,3]triazolo[1,5-a]pyridine moieties
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We have synthesized a novel hexaaza[5]helicene in a straightforward way from neocuproine. The crystal structure has been elucidated with direct-space strategy TALP which demonstrates the power of the powder X-ray diffraction technique. In this crystal structure it is possible to see an interplanar angle of 33(1) between the two triazolopyridine rings. The centrosymmetric crystal structure is a racemic mixture, but the resolution was not possible due to a ring-chain isomerization in a solution that produces a dynamic racemization.
- Adam, Rosa,Ballesteros-Garrido, Rafael,Vallcorba, Oriol,Abarca, Belén,Ballesteros, Rafael,Leroux, Frédéric R.,Colobert, Fran?oise,Amigó, José M.,Rius, Jordi
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- A sweet toothed saccharide (PET) sensor
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A novel phenanthroline diboronic acid 1 has been synthesised which can detect a range of saccharides at neutral pH in aqueous media. The binding events are sensitively monitored by changes in the fluorescence intensity.
- Linnane, Patrick,James, Tony D.,Imazu, Sachiko,Shinkai, Seiji
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- Designer ligands. VII. Synthesis of biomimetic Schiff-base ligands
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The preparation of a series of novel acyclic and macrocyclic Schiff-base ligands, designed to model the tyrosinase receptor, is described.
- Kaye,Wellington
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- Europium (III) complexes of amino acid-derived bis-imine-substituted phenanthroline ligands for phosphate recognition
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Phenanthroline-based chiral hexadentate ligands L1, L2 and L3, as well as their europium (III) complexes 1–3 are synthesized and characterized. The coordination compounds show strong red emission typical for europium (III) derivatives. Various anionic spe
- Hu, Yanfang,Subramanian,Albrecht, Markus
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- Selective separation of americium from europium using 2,9-bis(triazine)-1,10-phenanthrolines in ionic liquids: a new twist on an old story
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Bis-triazine phenanthrolines have shown great promise for f-block metal separations, attributable to their highly preorganized structure, nitrogen donors, and more enhanced covalent bonding with actinides over lanthanides. However, their limited solubility in traditional solvents remains a technological bottleneck. Herein we report our recent work using a simple 2,9-bis(triazine)-1,10-phenanthroline (Me-BTPhen) dissolved in an ionic liquid (IL), demonstrating the efficacy of IL extraction systems for the selective separation of americium from europium, achieving separation factors in excess of 7500 and selectively removing up to 99% of the americium. Characterization of the coordination environment was performed using a combination of X-ray absorption fine structure spectroscopy (XAFS) and density functional theory (DFT) calculations.
- Williams, Neil J.,Dehaudt, Jérémy,Bryantsev, Vyacheslav S.,Luo, Huimin,Abney, Carter W.,Dai, Sheng
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- Tuning the solubilities of bis-triazinylphenanthroline ligands (btphens) and their complexes
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A series of bis-triazinylphenanthroline ligands (BTPhens) was synthesized by modifying the triazine substituents. It was found that varying these substituents altered the solubilities of the ligands in a number of non-polar solvents. Thus C5-BTPhen showed
- Laventine, Dominic M.,Afsar, Ashfaq,Hudson, Michael J.,Harwood, Laurence M.
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- Polyoxometalate-Based Frameworks as Adsorbents for Drug of Abuse Extraction from Hair Samples
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The linkage of molecular components into functional heterogeneous framework materials has revolutionized modern materials chemistry. Here, we use this principle to design polyoxometalate-based frameworks as high affinity adsorbents for drugs of abuse, leading to their application in solid-phase extraction analysis. The frameworks are assembled by the reaction of a Keggin-type polyanion, [SiW12O40]4-, with lanthanoids Dy(III), La(III), Nd(III), and Sm(III) and the multidentate linking ligand 1,10-phenanthroline-2,9-dicarboxylic acid (H2PDA). Their reaction leads to the formation of crystalline 1D coordination polymers. Because of the charge mismatch between the lanthanoids (+3) and the dodecasilicotungstate (-4), we observe incorporation of the PDA2- ligands into crystalline materials, leading to four polyoxometalate-based frameworks where Keggin-type heteropolyanions are linked by cationic {Lnn(PDA)n} groups (Ln = Dy (1), La (2), Nd (3), and Sm (4)). Structural analysis of the polyoxometalate-based frameworks suggested that they might be suitable for surface binding of common drugs of abuse via supramolecular interactions. To this end, they were used for the extraction and quantitative determination of four model drugs of abuse (amphetamine, methamphetamine, codeine, and morphine) by using micro-solid-phase extraction (D-μSPE) and high-performance liquid chromatography (HPLC). The method showed wide linear ranges, low limits of detection (0.1-0.3 ng mL-1), high precision, and satisfactory spiked recoveries. Our results demonstrate that polyoxometalate-based frameworks are suitable sorbents in D-μSPE for molecules containing amine functionalities. The modular design of these networks could in the future be used to expand and tune their substrate binding behavior.
- Derakhshanrad, Shadi,Mirzaei, Masoud,Streb, Carsten,Amiri, Amirhassan,Ritchie, Chris
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- Synthesis, characterization, theoretical studies and biological activity of coordination compounds with essential metals containing N4-donor ligand 2,9-di(ethylaminomethyl)-1,10-phenanthroline
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The work shows the synthesis and characterization of N4-donor L: 2,9-di(ethylaminomethyl)-1,10-phenanthroline and its coordination compounds with some divalent essential metals (Mn, Fe, Co, Ni Cu and Zn). L was obtained as the hydrochloride derivative H3LCl3. The complexes were synthesized by two routes: 1) using L as hydrochloride for Mn, Fe, Co and Zn complexes and 2) from L as a free base for Cu and Ni ones. [Co(HL)Cl2]NO3 and [Zn(HL)Cl2]Cl were crystallized and reveal that L is bound to metallic nuclei by only three nitrogen atoms. Cyclic voltammetry studies showed that L alone is capable of being reduced and in complexes, the potential of the coordinated compound process is lower. DFT calculations explain the observable redox behavior regarding HOMO-LUMO orbital energies. Also, the modeling of protonated species of the ligand L suggests that the tetradentate behavior depends on pH conditions of the synthesis. The antiproliferative activity observed on Entamoeba Histolytica and HeLa human tumor cell cultures confirmed that even if complexes are less active than the first choice drugs (metronidazole and cisplatin respectively), it exists a correlation between the observed cytotoxicity and the compounds redox potential.
- Hernández-Ayala, Luis Felipe,Flores-álamo, Marcos,Escalante-Tovar, Sigfrido,Galindo-Murillo, Rodrigo,García-Ramos, Juan Carlos,García-Valdés, Jesús,Gómez-Vidales, Virginia,Reséndiz-Acevedo, Karen,Toledano-Maga?a, Yanis,Ruiz-Azuara, Lena
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- Synthesis and structural characterization of a novel seven-coordinate cobalt(II) complex: 2,9-Bis(ethanolamine)-1,10-phenanthrolinechlorocobalt(II) chloride
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Condensation reaction of 2,9-dicarboxaldehyde-1,10-phenanthroline with 2-aminoethanol followed by NaBH4 reduction yielded the polydentate Schiff base ligand 2,9-bis(ethanolamine)-1,10-phenanthroline in its reduced form. This ligand was characterized by elemental analysis, LC-MS, IR, UV-Vis and NMR spectroscopy. Reaction of the reduced Schiff base ligand with aqueous solution of cobalt(II) chloride affords 2,9-bis(ethanolamine)-1,10- phenanthrolinechlorocobalt(II) chloride in high yield. Single crystals of the cobalt(II) complex were obtained from the crystallization in ethanol and its structure was elucidated by X-ray structural analysis. The cobalt(II) complex ion was found to be seven-coordinated in a pentagonal bipyramidal geometry, whereby cobalt(II) ion is surrounded by the six donor atoms in the ligand molecule and a chloride ion.
- Baysal, Akin,Aydemir, Murat,Durap, Feyyaz,?zkar, Saim,Yildirim, Leyla Tatar
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- Quinoline-functionalized BODIPY dyes: Structural and photophysical properties
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BODIPYs at different positions of quinolines show similar absorption spectra but very different visible emission efficiency. Single-crystal structures show different tilting angles of quinoline groups and BODIPY core structure. The emission efficiency decreases as the torsion angle between BODIPY core and quinoline becomes smaller in the order of 4-Q-BDP > 3-Q-BDP > 2-Q-BDP ≈ 2,9-Phen-BDP. The restoration of fluorescence in the presence of methanol and theoretical calculations indicate the photoinduced electron transfer from quinoline N to BODIPY core could be responsible for such a gradual fluorescence change.
- He, Hongshan,Kukoyi, Adedayo,Wheeler, Kraig
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- Synthesis, structural elucidation, DNA binding, cleavage, AChE and BuChE cholinesterase efficiencies of metal complexes with 1,10-phenanthroline scaffold
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A series of metal complexes containing a 1,10-phenanthroline scaffold [ML] (L-1,10-Phenanthroline derivative comprises conjugated aromatic core and electron withdrawing –NO2 group); M = Cu(II), Zn(II), Co(II), and Zn(II) ions were designed and synthesized to obtain effective anti-cholinesterase efficiencies of metal chelates. Analytical and spectroscopic studies were used to determine the structural features. An octahedral structure with moderate distortion was attributed to the above metal chelates based on spectroscopic data. S. aureus, A. niger, C. albicans, B.subtilis, A. flavus, and E. coli were used to test the antibacterial efficacy of the synthesized ligands and metal complexes. Using agarose gel electrophoresis, the DNA fragmentation proficiency of prepared metal complexes was tested on pUC 18 DNA. The distorted octahedral geometry of the copper(II) complex to DNA (K b = 4.11 × 105 M?1) is stronger than that of ethidium bromide (EB) to DNA (K b = 3.3 × 105 M?1) and other metal complexes, respectively. The synthesized 1,10-phenanthroline derivative had the best inhibitory effects against acetylcholinesterase and butyrylcholinesterase, with IC50 values of 0.45 and 3.6 M, respectively, which were lower than the reference molecules. Our experimental results may contribute to the development of new drug molecules particularly in the treatment of neurological disorders including glaucoma, Alzheimer’s disease and diabetes. The actions of inhibitors on the glycosidase enzyme help to delay the breakdown and release of sugar molecules into the bloodstream, and they can be used as therapeutic factors in the treatment of diabetes.
- Gladis, E. H. Edinsha,Nagashri,Krishnendu
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p. 285 - 313
(2022/02/09)
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- Phenanthroline-derived dipyrazole extractant as well as preparation method and application thereof
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The invention discloses a double-pyrazole extracting agent derived from o-phenanthroline with the following structural general formula, and a preparation method and application of the double-pyrazoleextracting agent. In the formula, R is any one selected from n-octyl, n-butyl, isobutyl, ethyl, pyridyl and phenyl. The double-pyrazole extracting agent derived from the o-phenanthroline provided by the invention has a unique rigid structure and an alkyl chain for improving the solubility, and simultaneously only four elements of C, H, O and N are contained, so that the extraction kinetics of a separation extraction system can be greatly increased, the extraction capacity of an organic phase can be increased, secondary pollutants cannot be produced, and thus the environmental protection is facilitated. The extraction agent can be used to separate Ans (actinide elements)/Lns (lanthanide elements), and can not only form a separation extraction system of the Ans/Lns, but also can be used to form a separation reverse extraction system of the Ans/Lns.
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Paragraph 0047-0051; 0061-0065; 0070-0074; 0097-0101
(2021/04/03)
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- New 2,9-disubstituted-1,10-phenanthroline derivatives with anticancer activity by selective targeting of telomeric G-quadruplex DNA
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Fifteen new 1,10-phenanthrolines disubstituted at positions 2 and 9 via amide bonds with different heterocycles have been designed and synthesized as G-quadruplex DNA stabilizers. Ten compounds were evaluated for the in vitro anticancer activity against 60 human tumor cell lines panel, four of them showing a very good inhibitory activity on several cell lines. To assess the ability of the most active compounds to interact with G-quadruplex DNA (G4-DNA), circular dichroism experiments were performed. The potency of the compounds to stabilize the G4-DNA has been shown from the thermal denaturation experiments. The mechanism of compounds binding to DNA and to G4-DNA was theoretically investigated by molecular docking studies. The experimental results demonstrated excellent capacity of the two compounds bearing two pyridin-3-yl residues (methylated and non-methylated) to act as selective G-quadruplex binders with promising anticancer activity.
- Craciun, Anda-Mihaela,Rotaru, Alexandru,Cojocaru, Corneliu,Mangalagiu, Ionel I.,Danac, Ramona
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- Lithium halide ion-pair recognition with halogen bonding and chalcogen bonding heteroditopic macrocycles
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A series of halogen bonding and chalcogen bonding phenanthroline containing heteroditopic macrocyclic receptors exhibit cooperative recognition of lithium halide (LiX) ion-pairs. Quantitative 1H NMR ion-pair titration experiments in CDCl3?:?CD3CN (1?:?1,
- Tse, Yuen Cheong,Docker, Andrew,Zhang, Zongyao,Beer, Paul D.
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supporting information
p. 4950 - 4953
(2021/06/03)
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- Hybrid bis-histidine phenanthroline-based ligands to lessen aβ-bound cu ros production: An illustration of cu(i) significance
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We here report the synthesis of three new hybrid ligands built around the phenanthroline scaffold and encompassing two histidine-like moieties: phenHH, phenHGH and H’phenH’, where H correspond to histidine and H’ to histamine. These ligands were designed to capture Cu(I/II) from the amyloid-β peptide and to prevent the formation of reactive oxygen species produced by amyloid-β bound copper in presence of physiological reductant (e.g., ascorbate) and dioxygen. The amyloid-β peptide is a well-known key player in Alzheimer’s disease, a debilitating and devasting neurological disorder the mankind has to fight against. The Cu-Aβ complex does participate in the oxidative stress observed in the disease, due to the redox ability of the Cu(I/II) ions. The complete characterization of the copper complexes made with phenHH, phenHGH and H’phenH’ is reported, along with the ability of ligands to remove Cu from Aβ, and to prevent the formation of reactive oxygen species catalyzed by Cu and Cu-Aβ, including in presence of zinc, the second metal ions important in the etiology of Alzheimer’s disease. The importance of the reduced state of copper, Cu(I), in the prevention and arrest of ROS is mechanistically described with the help of cyclic voltammetry experiments.
- Drommi, Marielle,Esmieu, Charlène,Hureau, Christelle,Rulmont, Clément
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supporting information
(2021/12/24)
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- Bis-(1,2,4-triazin-3-yl) ligand structure driven selectivity reversal between Am3+and Cm3+: solvent extraction and DFT studies
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Selectivity between Am3+and Cm3+was investigated after their aqueous complexation with three structurally tailored hydrophilic bis-(1,2,4-triazin-3-yl) ligands followed by their extraction withN,N,N′N′-tetraoctyl diglycolamide (TODGA) dissolved in an ionic liquid (C4mim·Tf2N). The three hydrophilic ligands used were SO3PhBTP, SO3PhBTBP, and SO3PhBTPhen. It was evident from the solvent extraction studies that SO3PhBTP formed a stronger complex with Cm3+than with Am3+, but SO3PhBTPhen showed better complexation ability for Am3+than for Cm3+, and SO3PhBTBP showed no selectivity for the two actinide ions. DFT calculations indicated that the coordinating ‘N’atoms in BTP were more co-planar in the complex and this co-planarity was higher in the Cm3+complex as compared to that in Am3+. In the case of BTBP and BTPhen ligands, on the other hand, the co-planarity was more pronounced in the Am3+complexes. Mayer's bond order calculations of M-N bonds in the complexes also indicated a reversal of the complexation ability of the BTP and BTPhen ligands for Am3+and Cm3+. Calculations of the complexation energies further supported the higher selectivity of the BTP ligand for Am3+by ?52.0 kJ mol?1, and better selectivity of the BTPhen ligand for Cm3+by ?24.7 kJ mol?1
- Ansari, S. A.,Bhattacharyya, Arunasis,Karthikeyan, N. S.,Mohapatra, P. K.,Rao, T. S.,Ravichandran, C.,Seshadri, H.,Venkatachalapathy, B.
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supporting information
p. 7783 - 7790
(2021/06/16)
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- Selective Separation of Am(III)/Eu(III) by the QL-DAPhen Ligand under High Acidity: Extraction, Spectroscopy, and Theoretical Calculations
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Although 1,10-phenanthroline-based ligands have recently shown vast opportunities for the separation of trivalent actinides (Ans(III)) from lanthanides (Lns(III)), the optimization and design of the extractant structure based on the phenanthroline framework remain hotspots for further improving the separation. Following the strategy of hard and soft donor atom combination, for the first time, the quinoline group was attached to the 1,10-phenanthroline skeleton, giving a lipophilic ligand, 2,9-diacyl-bis((3,4-dihydroquinoline-1((2H)-yl)-1),10-phenanthroline (QL-DAPhen)), for Am(III)/Eu(III) separation. In the presence of sodium nitrate, the ligand can effectively extract Am(III) over Eu(III) in HNO3 solution, with the separation factor (SFAm/Eu) ranging from 29 to 44. The coordination chemistry of Eu(III) with QL-DAPhen was investigated by slope analysis, NMR titration, UV–vis titration, Fourier transform infrared spectroscopy, electrospray ionization-mass spectrometry, and theoretical calculations. The experimental results unanimously confirm that the ligand forms both 1:1 and 1:2 complexes with Eu(III), and the stability constants (log β) of each of the two complexes were obtained. Density functional theory calculations show that the Am–N bonds have more covalent characteristics than the Eu–N bonds in the complexes, which reveals the reason why the ligand preferentially bonds with Am(III). Meanwhile, the thermodynamic analysis reveals that the 1:1 complex is more thermodynamically stable than the 1:2 complex. The findings of this work have laid a solid theoretical foundation for the application of phenanthroline-based ligands in the separation of An(III) from practical systems.
- Wang, Shuai,Wang, Cui,Yang, Xiao-Fan,Yu, Ji-Pan,Tao, Wu-Qing,Yang, Su-Liang,Ren, Peng,Yuan, Li-Yong,Chai, Zhi-Fang,Shi, Wei-Qun
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p. 19110 - 19119
(2021/12/13)
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- Highly selective and potent anti-cancer agents based on 2,9-substituted-1,10-phenanthroline derivatives
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A study concerning on in-vitro anticancer evaluation of structurally tuned 1,10-phenanthroline at 2,9 positions with different functional groups such as –CH3 (S1), >C[dbnd]O (S2), –COOH (S3), –COOCH3 (S4) and –CONHNH2 (S5) were described. The solubility data revealed that all ligands were completely soluble in dimethyl sulphoxide (DMSO) and moderately soluble in water. The photo-physical properties of these ligands revealed that a common absorption peak appeared in the region of 270–300 nm and emission spectra in the region of 330–510 nm with a large Stokes shift of 85 nm. The binding constant of ligands (S1-S5) with calf-thymus deoxyribonucleic acid (CT-DNA) and bovine serum albumin (BSA) were found to be 105 M?1 and 104 M?1 respectively. The fluorescence quenching of ethidium bromide (EtBr) from DNA upon addition of ligand was confirmed from binding affinity values KSV (104 M?1) and Kapp (106 M?1). The mode of interaction of ligand with DNA is either by intercalation or groove binding this is further supported by viscosity and in-silico studies. The gel electrophoresis studies exhibited that S4 and S5 have cleaved plasmid DNA completely within 60 min while rest of the ligands took more than 60 min. The cytotoxicity study of these ligands (S1-S5) were conducted with two different cancer cell lines (MDA-MB-231 and HeLa) and their performance were compared with normal HEK-293 cells. The study revealed that ligands S5 and S4 were found to be least inhibitory concentration (IC50) and high selectivity factor values of 7.66 μM/12.97 and 13.35 μM/6.19 with respect to HeLa and MDA-MB-231 cell lines while ligands S1-S3 showed high IC50 values compare to doxorubicin. However, both S5 and S4 ligands have been displayed higher cytotoxicity effect than doxorubicin and least effect on normal cell HEK-293.
- Ashok Kumar, S. K.,De, Sourav
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- Functionalized chitosan adsorbents allow recovery of palladium and platinum from acidic aqueous solutions
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Platinum (Pt) and palladium (Pd) are precious metals considered critical in our society and are needed in a variety of sustainable technologies. Their scarcity urges the increase of recycling from secondary waste streams through new and efficient recovery techniques. Adsorption is an established recovery method for liquid streams, where chitosan shows promising results as a low-cost adsorbent, derived from biomass. This biopolymer is able to capture metals, but suffers from a low stability under acidic conditions and poor adsorbing properties. In this study, three new chitosan derivatives were synthesized and employed for Pd(ii) and Pt(iv) recovery from acidic solutions. Specific and simple modifications were selected based on their known affinities for these metal ions and taking into account the principles of green chemistry. The prepared derivatives consist of 1,10-phenanthroline-2,9-dicarbaldehyde cross-linked chitosan (Ch-PDC), [2,2′-bipyridine]-5,5′-dicarbaldehyde cross-linked chitosan (Ch-BPDC) and glutaraldehyde cross-linked chitosan grafted with 8-hydroxyquinoline-2-carbaldehyde (Ch-GA-HQC). For all derivatives, the adsorption occurred fast and equilibrium reached within 30 min. The Langmuir isotherms revealed a maximum adsorption capacity for Pd(ii) and Pt(iv) of respectively 262.6 mg g-1 and 119.5 mg g-1 for Ch-PDC, 154.7 mg g-1 and 98.3 mg g-1 for Ch-BPDC and 340.3 mg g-1 and 203.9 mg g-1 for Ch-GA-HQC. Such adsorption capacities are considerably higher compared to the biosorbents reported in the literature. Excellent physical properties in homo- and heterogeneous systems and high regeneration performances demonstrate that chitosan-based adsorbents are very promising for Pd(ii) and Pt(iv) recovery from acidic solutions.
- Mincke, Stein,Asere, Tsegaye Grima,Verheye, Ivar,Folens, Karel,Vanden Bussche, Flore,Lapeire, Linsey,Verbeken, Kim,Van Der Voort, Pascal,Tessema, Dejene A.,Fufa, Fekadu,Du Laing, Gijs,Stevens, Christian V.
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supporting information
p. 2295 - 2306
(2019/05/21)
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- A multifunctional catenated host for the efficient binding of Eu3+ and Gd3+
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A new multifunctional [2]catenane is synthesized by using a phenanthroline-based heteroditopic wheel and Axle, which acts as a receptor for the efficient binding of lanthanide ions such as Eu3+ and Gd3+.
- Nandi, Mandira,Bej, Somnath,Ghosh, Tamal Kanti,Ghosh, Pradyut
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supporting information
p. 3085 - 3088
(2019/04/05)
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- Development of the Smartphone-Assisted Colorimetric Detection of Thorium by Using New Schiff's Base and Its Applications to Real Time Samples
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In this paper, a new Th4+ ion-selective chromogenic sensor (L) was developed by reacting 1,10-phenanthroline-2,9-dicarbohydrazide with 2-hydroxy naphthaldehyde. The sensing ability of L toward Th4+ was investigated in solution and paper strips loaded with L using spectrophotometric and colorimetric methods. The selective interaction of L was examined with various f-metal ions and other selected metal ions from s-block and d-block elements. Results show that by the colorimetric method in solution-phase dimethyl sulfoxide/H2O (7:3, v/v) and paper strip methods, the naked-eye detectable color change of L occurred from colorless solution to yellow-orange and pale yellow colour upon interacting with Th4+ and Al3+, respectively, whereas other metal ions did not interfere. The ligand L exhibits two absorbance bands at 320 and 375 nm because of ligand-to-ligand charge transfer. Upon interaction with Th4+, L undergoes red shift of both absorption bands and the formation of a new UV-vis band at 335 and 440 nm. The UV-visible spectral studies indicate the formation of a 1:1 host-guest complex between L and Th4+ with an association constant of 4.7 × 103 M-1. The limit of quantification and limit of detection of L for the analysis of Th4+ are found to be 167 and 50 nM, respectively. The visually detectable color change of L has been well integrated with a smartphone RGB color value to make it an analytical signal for real-time analysis of Th4+ with the detection limit down to 116 nM. Besides, L was applied for the analysis of Th4+ content present in various real water samples, monazite, and lantern mantle samples by spectrophotometry and RGB color values. The binding mode of L with Th4+ is investigated by 1H NMR, electrospray ionization-mass, and theoretical studies.
- Selva Kumar,Kumar, S. K. Ashok,Vijayakrishna, Kari,Sivaramakrishna, Akella,Brahmmananda Rao,Sivaraman,Sahoo, Suban K.
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supporting information
p. 15270 - 15279
(2019/01/03)
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- Towards understanding the correlation between UO22+ extraction and substitute groups in 2,9-diamide-1,10-phenanthroline
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2,9-Diamide-1,10-phenanthroline (DAPhen) ligands represent a new family of tetradentate extractants given their strong affinity to actinides and the CHON principle. Among this family, N,N′-diethyl-N,N′-ditolyl-2,9-diamide-1,10-phenanthroline (Et-Tol-DAPhen), initially reported by us, exhibits excellent selectivity towards actinides (U, Th, Am, Pu) over lanthanides and thus can be potentially applied in the group actinide extraction (GANEX) process for the group separation of actinides. In this article, by tailoring the lengths of alkyl chains, we synthesized other four DAPhen ligands with different substitute groups in the diamide moieties, and characterized the relationship between properties and substitute groups of DAPhen ligand. The extraction results show that three of the ligands exhibit high performance in UO22+ extraction from an acidic solution and the extracted UO22+ can be easily stripped by only using ultrapure water. Spectrophotometry titration confirms that UO22+ combined with all the four ligands in 1:1 mode. The extended X-ray absorption finestructure (EXAFS) study shows that six donor atoms comprise the first equatorial shell of the UO22+ ions bonded by the DAPhen ligands, among which two nitrogen and two oxygen atoms are from the DAPhen ligand, while other two oxygen atoms are from one nitrate ions. This article promises to provide basic data for assessing the feasibility of this kind of DAPhen ligands applied in actinides separation from nuclear wastes.
- Chai, Zhifang,Shi, Weiqun,Yuan, Liyong,Zhang, Xinrui
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p. 1285 - 1292
(2018/10/08)
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- Metallo-Organozymes with Specific Proteolytic Activity
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Metallopeptides that show efficiency and selectivity in peptide bond cleavage in water at room temperature and neutral conditions are presented. These small and versatile organozymes take advantage of metal-coordinating building blocks that are strategica
- Embaby, Ahmed M.,Lelieveldt, Lianne P. W. M.,Diness, Frederik,Meldal, Morten
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supporting information
p. 17424 - 17428
(2018/11/03)
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- Highly Efficient Trivalent Americium/Europium Separation by Phenanthroline-Derived Bis(pyrazole) Ligands
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The synthesis, Eu3+ complexation, and solvent extraction of Am3+ and Eu3+ from nitric acid solutions by tetradentate phenanthroline-derived bis(pyrazole) (BPPhen) ligands were described. By using meta-nitrobenzotrifluoride as diluent, BPPhen ligands in combination with 2-bromohexanoic acid extracted Am3+ and Eu3+ with remarkably high efficiency, excellent selectivity, and fast extraction kinetics. Stripping posed no issues. The ligands also showed excellent hydrolytic stability and acid tolerance. 2-Bromohexanoic anion neutralized the charge and increased the lipophilicity of the extracted ion pair. The extraction conformed to a cation exchange model. Slope analysis demonstrated the extraction of 1:2 metal/ligand complexes. Analyses by electrospray ionization mass spectrometry, time-resolved laser-induced fluorescence spectroscopy, Raman, and Fourier transform infrared techniques indicated that the composition of the extracted species is [Eu(nOct-BPPhen)2(H2O)]3+. The formation of 1:2 complexes was also confirmed by UV-vis spectroscopic titration and microcalorimetric titration methods. Meanwhile, the stability constants (K) and the thermodynamic parameters (ΔH, ΔS, ΔG) for the complexation of Eu3+ with nOct-BPPhen were presented too.
- Liu, Ying,Yang, Xiuying,Ding, Songdong,Wang, Zhipeng,Zhang, Lirong,Song, Lianjun,Chen, Zhili,Wang, Xueyu
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p. 5782 - 5790
(2018/05/28)
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- A highly selective fluorescent probe for Fe3+ in living cells: a stress induced cell based model study
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A rhodamine-phenanthroline dyad based fluorescent probe 4 has been designed and synthesized which selectively monitors Fe3+ ions among the various metal ions tested. Furthermore, probe 4 has been explored for monitoring of dynamic changes in the Fe3+ ion level under aggressive Fenton reaction conditions using a cell based model study. More significantly, probe 4 has also been utilized for real time imaging of endogenous Fe3+ ions in living C6 cell lines, the results of which demonstrated that probe 4 acts as an efficient fluorescent tool for Fe3+ ion detection in biological systems.
- Sharma, Neetu,Reja, Shahi Imam,Gupta, Neha,Bhalla, Vandana,Kaur, Davinder,Arora, Saroj,Kumar, Manoj
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supporting information
p. 1006 - 1012
(2017/02/05)
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- Pd-Ce nanoparticles supported on functional Fe-MIL-101-NH2: An efficient catalyst for selective glycerol oxidation
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Metal organic framework Fe-MIL-101-NH2 was prepared at different reaction time. The morphology of the Fe-MIL-101-NH2 slightly changed following a longer reaction time; the crystal structure remained. Neocuproine ligand coordinating palladium complex has demonstrated high activity in selective glycerol oxidation towards 1,3-dihydroxyacetone (DHA). Neocuproine ligand was attached to MOF Fe-MIL-101-NH2 by forming an amide (CO[sbnd]NH) bond in this work. The functional Fe-MIL-101-NH2 was used as catalyst supports to hold palladium and cerium nanoparticles. The resulting composite of the Pd-Ce/Fe-MIL-101[sbnd]N[dbnd]CHNeocuproine was found to be a high efficient catalyst in the selective oxidation conversion of glycerol to dihydroxyacetone in comparison with catalysts Pd/Fe-MIL-101[sbnd]N[dbnd]CHNeocuproine and Pt-Bi/C. The catalysts and products were analyzed by FT-IR, XRD, SEM, TEM and 1H, 13C NMR spectroscopy. In addition, the supported catalyst is recyclable with sustainable activity.
- Li, Xinhang,Tjiptoputro, Adrian Kaizen,Ding, Jun,Xue, Jun Min,Zhu, Yinghuai
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- Selective separation of trivalent f-ions using 1,10-phenanthroline-2,9-dicarboxamide ligands in ionic liquids
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1,10-Phenanthroline-2,9-dicarboxamide complexants decorated with alkyl chains and imidazolium cations have been studied for extraction of trivalent f-ions into imidazolium ionic liquids. The dicationic complexants are shown to extract Am over Eu with separation factors >50 and high extraction efficiencies. The different size selectivities for lanthanide ions were observed for these two types of complexants, highlighting the importance of the positive charge in controlling both extraction efficiencies and extraction selectivities.
- Dehaudt, Jérémy,Williams, Neil J.,Shkrob, Ilya A.,Luo, Huimin,Dai, Sheng
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supporting information
p. 11624 - 11627
(2016/07/28)
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- Synthesis of Bis-1,2,4-triazines via Telescoped Condensation of [1,10]-Phenanthroline-2,9-dicarbonitrile with Aromatic 1,2-Dicarbonyls
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(Chemical Equation Presented) Efficient separation of minor actinides from spent nuclear fuel remains a formidable challenge. As part of ongoing efforts to identify effective ligands for separation of toxic radionuclides, a series of bis-1,2,4-triazines, three novel, have been prepared from [1,10]-phenanthroline-2,9-dicarbonitrile in two-telescoped steps without additives, complicated workups, prolonged reaction times, or additional purification.
- Tai, Serene,Williams, Neil J.,Carrick, Jesse D.
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p. 307 - 312
(2015/01/30)
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- A phenanthroline-derived ligand and its complexation with Pd(II): From ligand design, synthesis and Pd(II) complexes structures to its application
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A novel phenanthroline-derived bis-opened-triazine ligand for selective complexation with Pd(ii) over 19 typical metals from HNO3 media was designed based on cavity modulation strategy. Structures of the three species of the Pd(ii) complexes of with the ligand were elucidated by 1H NMR titration isothermal titration calorimetry (ITC) and density functional theory (DFT) studies. ITC test and binding energy calculations demonstrated that the asymmetrical 1:1 Pd(ii)-ligand complex with a monodentate nitrate anion was the most stable among these three species of the Pd(ii) complexes. The excellent kinetics of Pd(ii) extraction with the ligand is due to its optimal conformation completely ready for metal ligation. The enhanced special extraction selectivity and fast extraction rate towards Pd(ii) achieved by the phenanthroline-derived ligand demonstrated that the effective separation of some radionuclides with smaller radius in HLW through cavity modulation strategy is a feasible approach.
- Xu, Lei,Zhang, Anyun,Lu, Yanchao,Yang, Hua,Liu, Ziyang
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p. 99859 - 99866
(2016/11/09)
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- Nature-inspired design of tetraindoles: Optimization of the core structure and evaluation of structure–activity relationship
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Building on the initial successful optimization of a novel series of tetraindoles, a second generation of the compounds with changes in the core phenyl ring was synthesized to improve anticancer properties. 17 new compounds with different rigidity, planarity, symmetry and degree of conjugation of their core structures to 5-hydroxyindole units were synthesized. All the compounds were fully characterized and tested against breast cancer cell line (MDA-MB-231). The results revealed that the core structure is required for activity and it should be aromatic, rigid, planar, symmetrical and conjugated for optimal activity. Compound 29, which has strong anticancer activity against various tumor-derived cell lines, including Mahlavu (hepatocellular), SK-HEP-1 (hepatic), HCT116 (colon), MIA PaCa-2 (pancreatic), H441 (lung papillary), A549 (lung), H460 (non-small cell lung) and CL1-5 (lung carcinoma) with IC50values ranging from 0.19 to 3.50?μM, was generated after series of successive optimizations. It was found to induce cell cycle arrest and apoptosis in vitro and inhibit tumor growth in the non-obese diabetic-severe combined immunodeficiency (NOD/SCID) mice bearing xenografted MIA PaCa-2 human pancreatic cancer.
- Abdu-Allah, Hajjaj H.M.,Huang, Shih-Ting,Chang, Tzu Ting,Chen, Chia-Ling,Wu, Han-Chung,Li, Wen-Shan
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p. 4497 - 4503
(2016/08/25)
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- Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines
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A new, regioselective synthesis of V-shaped 2,9-bis(6-(4-halophenyl)-1,2,4-triazin-3-yl)-1,10-phenanthrolines (4XPhBTPhen) ligands was developed, creating access to a simple and reliable synthesis of precursors for future supramolecular actinide complexing systems. Described is a reactant-directed regioselective synthetic method, which was found to be high yielding and reliable and yields exclusively 6,6′-phenyl BTPhen derivatives (including 4-chloro and 4-bromo) in five simple steps. Molecular and crystal structures of PhBTP and PhBTPhen products are fully determined and both were found to be in space group C2/c. Additionally, molecular and crystal structures of Z and E isomers of 2-hydrazono-2-phenylacetaldehyde oxime, a reagent in the synthetic route, reveal existence of strong intramolecular N-H?O hydrogen bonding in the Z isomer explaining its lower solubility in water.
- Coogan, Niall T.,Chimes, Michael A.,Raftery, James,Mocilac, Pavle,Denecke, Melissa A.
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p. 8684 - 8693
(2015/09/15)
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- Dynamic stereoisomerization in inherently chiral bimetallic [2]catenanes
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Stereoisomerization and the unprecedented phenomenon of metal translocation in the absence of redox processes were probed in two inherently chiral bimetallic [2]catenanes by using a combination of variableerature 1H NMR and CD spectroscopies, X-ray crystallography, and DFT calculations.
- Prakasam, Thirumurugan,Lusi, Matteo,Nauha, Elisa,Olsen, John-Carl,Sy, Mohamadou,Platas-Iglesias, Carlos,Charbonnière, Lo?c J.,Trabolsi, Ali
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supporting information
p. 5840 - 5843
(2015/03/31)
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- A novel 1,10-phenanthroline based chemosensor for differential metal ion sensing and constructing molecular logic gates
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A simple tailor-made amidic functionality based on 1,10-phenanthroline unit (1) gave differential absorption changes with only metal ions viz. Cd2+, Zn2+, and Cu2+ ions. In CH3CN solution of 1, addition of Cd2+ and Zn2+ ions resulted in bathochromic shift of ～65 nm, whereas Cu2+ ions resulted in hyperchromic effect with only ～15 nm bathochromic shift. These differential changes observed with Cd2+ and Cu2+ ions addition enabled chemosensor 1 to construct 'IMLICATION' and 'TRANSFER' logic gates. The observed binding constant values were found to be in order of Cd2+ > Zn2+ > Cu2+.
- Kaur, Navneet,Alreja, Priya
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p. 182 - 186
(2015/02/18)
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- Re(i) derivatives functionalised with thioether crowns containing the 1,10-phenanthroline subunit as a new class of chemosensors
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A series of luminescent fac-[Re(CO)3(L)(NN)]+ complexes, where L is a pyridine or an imidazole and NN is the 1,10-phenanthroline subunit of mixed donor pentadentate thioether crowns have been synthesised and their luminescence properties have been analysed. Then, heterometallic Re(i)/Au(i) complexes, with the Au(i) fragment bonded directly to the imidazole ligand, and heterometallic Re(i)/Ag(i) complexes, with the silver fragment coordinating the S-donor thioether linker of the rings have also been prepared. Analysis of their luminescence properties showed a considerable blue shift of the emission maxima for the Re(i)/Ag(i) derivatives, upon coordination of the silver centre to the S-donor atoms of the aliphatic chain of the macrocyclic units.
- Casula, Arianna,Nairi, Valentina,Fernández-Moreira, Vanesa,Laguna, Antonio,Lippolis, Vito,Garau, Alessandra,Gimeno, M. Concepción
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p. 18506 - 18517
(2015/11/09)
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- Template synthesis and spectral characterization of new Lead(II)-Schiff base macrocyclic complexes incorporating phenanthroline and/or bipyridine units
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Lead(II) complexes of Schiff-bases containing phenanthroline and/or bipyridine units were synthesized by the template reaction between new diamine compound, 6,6'-bis(2-aminophenoxymethyl)-2,2'-bipyridine and 2,2-bipyridine-6,6-dicarboxaldehyde or 1,10-phenanthroline- 2,9-dicarboxaldehyde in the presence of metal ions. These complexes, [PbL1]( ClO4)2and [PbL2](NO3)2, were characterized and investigated by using; MALDI-TOF and Q-TOF-MS spectroscopy, FTIR, UV/Visible spectroscopy, 1H NMR, Elemental analyses (CHN), magnetic susceptibility and molar conductivity measurements.
- Beynek,Tan,Beynek
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p. 4141 - 4144
(2015/12/23)
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- Excellent selectivity for actinides with a tetradentate 2,9-diamide-1,10-phenanthroline ligand in highly acidic solution: A hard-soft donor combined strategy
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In this work, we reported a phenanthroline-based tetradentate ligand with hard-soft donors combined in the same molecule, N,N′-diethyl-N,N′- ditolyl-2,9-diamide-1,10-phenanthroline (Et-Tol-DAPhen), for the group separation of actinides over lanthanides. The synthesis and solvent extraction as well as complexation behaviors of the ligand with actinides and lanthanides are studied experimentally and theoretically. The ligand exhibits excellent extraction ability and high selectivity toward hexavalent, tetravalent, and trivalent actinides over lanthanides in highly acidic solution. The chemical stoichiometry of Th(IV) and U(VI) complexes with Et-Tol-DAPhen is determined to be 1:1 using X-ray crystallography. The stability constants of some typical actinide and lanthanide complexes of Et-Tol-DAPhen are also determined in methanol by UV-vis spectrometry. Density functional theory (DFT) calculations reveal that the An-N bonds of the Et-Tol-DAPhen complexes have more covalent characters than the corresponding Eu-N bonds, which may in turn lead to the selectivity of Et-Tol-DAPhen toward actinides. This ligand possesses merits of both alkylamide and 2,9-bis-(5,6-dialkyl-1,2,4-triazin-3-yl)-1,10-phenanthroline (R-BTPhen) extractants for efficient actinide extraction and the selectivity toward minor actinides over lanthanides and hence renders huge potential opportunities in high-level liquid waste (HLLW) partitioning.
- Xiao, Cheng-Liang,Wang, Cong-Zhi,Yuan, Li-Yong,Li, Bin,He, Hui,Wang, Shuao,Zhao, Yu-Liang,Chai, Zhi-Fang,Shi, Wei-Qun
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p. 1712 - 1720
(2014/03/21)
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- Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors
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Among 18 human chemokine receptors, CCR1, CCR4, CCR5, and CCR8 were activated by metal ion Zn(II) or Cu(II) in complex with 2,2′-bipyridine or 1,10-phenanthroline with similar potencies (EC50 from 3.9 to 172 μM). Besides being agonists, they acted as selective allosteric enhancers of CCL3. These actions were dependent on a conserved glutamic acid at TM-7 (VII:06/7.39). A screening of 20 chelator analogues in complex with Zn(II) identified compounds with increased potencies, with 7 reaching highest potency at CCR1 (EC50 of 0.85 μM), 20 at CCR8 (0.39 μM), and 8 at CCR5 (1.0 μM). Altered selectivity for CCR1 and CCR8 over CCR5 (11, 12) and a receptor-dependent separation of allosteric from intrinsic properties were achieved (20). The pocket similarities of CCR1 and CCR8, contrary to CCR5 as proposed by the ligand screen, were elaborated by computational modeling. These studies facilitate exploration of chemokine receptors as possible targets for therapeutic intervention.
- Thiele, Stefanie,Malmgaard-Clausen, Mikkel,Steen, Anne,Rummel, Pia C.,Rosenkilde, Mette M.,Engel-Andreasen, Jens,Nielsen, Mads C.,Ulven, Trond,Gloriam, David E.,Frimurer, Thomas M.
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p. 8164 - 8177,14
(2020/09/15)
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- Synthesis and characterization of 1,10-Phenanthroline-2,9- dicarbaldehyde-bis-(thiosemicarbazone)
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In this work, 1,10-phenanthroline-2,9-dicarbaldehyde-bis- (thiosemicarbazone) having N and S donor atoms has been synthesized and characterized by 1H NMR, IR and mass spectroscopy. Having bis- (thiosemicarbazone) on phenanthroline ring, it should be considered as a useful ligand in coordination chemistry.
- Shabaan, Samira,Letafat, Bahram,Esmati, Nasim,Shafiee, Abbas,Foroumadi, Alireza
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experimental part
p. 2819 - 2820
(2012/08/28)
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- Inhibiting copper(i) iodide aggregate assembly in the solid state via macrocyclic encapsulation
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Three CuI complexes of diimine-bearing macrocyclic ligands are described. Reaction of CuI with macrocycles of different ring size gives rise to differing degrees of aggregation of (CuI)n in the solid state. X-Ray diffraction studies reveal that
- Smith, David J.,Blake, Alexander J.,Wilson, Claire,Champness, Neil R.
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p. 12257 - 12264
(2012/01/31)
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