- Self-assembly of novel molecular complexes of 1,10-phenanthroline and 5-amino-1,10-phenanthroline and evaluation of their in vitro antitumour activity
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Novel molecular complexes of 1,10-phenanthroline (phen) and 5-amino-1,10-phenanthroline (5-NH2-phen) [(5-NH2-phen) 2(phen) (H2O)3 (1), (phen) 2(imidazole) (H+) (BF4-) (2), (phen)2(benzimidazole) (H+) (BF4-) (3), (5-NH2-phen)4(H2O)3 (4), and (phen)3 (indole) (H+) (BF4-) (5)] were synthesized via self-assembly processes and their in vitro anticancer activity was investigated. The structures of the compounds were confirmed by UV, FTIR, CIMS(CH4) and elemental analysis. The crystal structure of 2 was determined by X-ray diffraction. Cytotoxicity of the substances was measured using the cultivated human tumour cell lines HepG2, HEp-2, and 8-MB-GA. The tested substances showed different activity depending on the cell line and amount used. Substances 2 and 3 were not toxic to the non-tumour cells (Lep-3), but significantly toxic to all tumour ones. This is not the case with compounds 4 and 5, which are non-toxic towards carcinogenic cell lines, but even stimulate both HepG2 and HEp-2.
- Kaloyanov, Nikolay,Alexandrova, Radostina,Wesselinova, Diana W.,Mayer-Figge, Heike,Sheldrick, William S.,Dimitrov, Georgi D.
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- The oxime bond formation as an efficient tool for the conjugation of ruthenium complexes to oligonucleotides and peptides
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A convenient method for the conjugation of ruthenium complex on oligonucleotides and peptides through chemoselective oxime linkage is reported. Novel Ru(II) complexes sustaining an aminooxy containing ligand were prepared and efficiently coupled with the oligonucleotides and peptides functionalized with the complementary reactive aldehyde group. The method described herein could be a useful tool for preparing a broad range of metal complex-oligonucleotide and peptide conjugates.
- Villien, Mathilde,Deroo, Stéphanie,Gicquel, Etienne,Defrancq, Eric,Moucheron, Cécile,Kirsch-De Mesmaeker, Andrée,Dumy, Pascal
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- Organic-inorganic hybrid nanomaterial as a new fluorescent chemosensor and adsorbent for copper ion
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Functionalized silica nanotube (FSNT) possessing the phenanthroline moiety as a fluorescent receptor was fabricated by sol-gel reaction, and the binding ability of FSNT with metal ions was evaluated by fluorophotometry. The Royal Society of Chemistry 2006.
- Lee, Soo Jin,Lee, Shim Sung,Lah, Myoung Soo,Hong, Jae-Min,Jung, Jong Hwa
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- Synthesis and biological activity of novel heavy metal complexes of 5-amino-1, 10-phenanthroline and 1,10-phenanthroline
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Novel heavy metal complexes: Sr(5-NH2-phen)4(NO 3)(OH)(H2O)2 (1) (synthesized via a static self-assembly process) and Sn(phen) (NO3)(OH)(H2O) (2), Sn(5-NH2-phen)(OH)(Cl)(H2O) (3), Pb(5-NH 2-phen)(NO3)2(H2O) (4) (obtained via metal competitive reactions under mild conditions) were reported. The coordination compounds were characterized by elemental analysis, FTIR-spectroscopy and FAB-mass spectrometry. Their cytotoxicity was measured by MTS-test towards human tumour (MDA-MB-231, HT-29, HeLa, HepG2) and non-tumour diploid (Lep-3) cell lines. The most pronounced cytotoxic effect on all cancer lines showed 1 and 4 at their high concentrations as well as 1 at its lower ones (≤ 4×10-2 mg). Therefore, strontium complex of 5-amino-o-phenanthroline (1) exhibited the widest antitumour spectrum activity, having no toxicity to non-tumour cells at quantities ≤ 4×10 -2 mg. The computed EC50 values of 1-4 against MDA-MB-231, HT-29, HeLa, HepG2 varied from 1.40×10-3 to 6.31×10 -6 M. Towards Lep-3 substances 2-4 showed IC50 7.52×10-4 - 0.44 M. Substance 1 possess EC50=1. 26×10-7 M to the non-tumour cells. Versita Sp. z o.o.
- Kaloyanov, Nikolay,Neykov, Mihail,Wesselinova, Diana W.,Dimitrov, Georgi D.
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- Interaction of sulfonated ruthenium(ii) polypyridine complexes with surfactants probed by luminescence spectroscopy
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Novel anionic [RuL2L′]2- complexes, where L stands for (1,10-phenanthroline-4,7-diyl)bis(benzenesulfonate) (pbbs; 3a) or (2,2′-bipyridine)-4,4′-disulfonate (bpds; 3b), and L′ is N-(1,10-phenanthrolin-5-yl)tetradecanamide (pta; 2a) or N-(1,10-phenanthrolin-5-yl)acetamide (paa; 2b), were synthesized, and their interaction with the prototypical surfactants sodium dodecylsulfate (SDS), cetyl trimethyl ammonium bromide (CTAB), and Triton X-100 (TX-100) was investigated by electronic absorption, luminescence spectroscopy, emission-lifetime determinations, and O2-quenching measurements. [Ru(bpds)2(pta)]2- (5a) displayed cooperative self-aggregation in aqueous medium at concentrations above 1.3 μM; the observed association was enhanced in the presence of either β-cyclodextrin or NaCl. This amphiphilic Ru11 compound showed the strongest interaction with all the detergents tested: nucleation of surfactant molecules around the luminescent probe was observed below their respective critical micellar concentrations. As much as a 12-fold increase of the emission intensity and a 3-fold rise in the lifetime were measured for 5a bound to TX-100 micelles; the other complexes showed smaller variations. The O2-quenching rate constants decreased up to 1/8 of their original value in H2O (e.g., for [Ru(bpds)2(pta)]2- (6a) bound to CTAB micelles). Luminescence-lifetime experiments in H2O/D2O allowed the determination of the metal-complex fraction exposed to solvent after binding to surfactant micelles. For instance, such exposure was as low as 25% for pta complexes · CTAB aggregates. The different behaviors observed were rationalized in terms of the Ru11 complex structure, the electrostatic/hydrophobic interactions, and the probe environment.
- Garcia-Fresnadillo, David,Orellana, Guillermo
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- An efficient synthesis of enantiomerically pure Δ- and Λ-ruthenium(II)-labelled oligonucleotides
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The synthesis of a novel tris(bidentate ligand)ruthenium(II) complex 7 and its efficient tethering to the 5'-end of oligonucleotides is described. The resulting Δ- and Λ-isomeric ruthenium(II)-labelled oligonucleotides 10a-c and 11a-d were separated either by reversed-phase HPLC or by polyacrylamide gel electrophoresis. The diastereoisomerically pure isomers were fully characterized by UV/VIS and CD spectroscopy, mass spectrometry, and enzymatic digestion with base analysis. We also investigated the thermal denaturation of the hybridized double strands.
- Meggers, Eric,Kusch, Dirk,Giese, Bernd
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- N-Phenanthroline glycosylamines: Synthesis and copper(II) complexes
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A series of novel N-(1,10-phenanthrolin-5-yl)-β-glycopyranosylamines was obtained with excellent stereoselectivity and synthetically useful yields by treatment of 5-amino-1,10-phenanthroline with different unprotected monosaccharides, using (NH4)2SO4 as an efficient promoter. Copper(II) complexes having a 2:1 mole ratio of the bidentate ligand phenanthroline N-glycoside and the metal were also prepared.
- Duskova, Katerina,Gude, Lourdes,Arias-Pérez, María-Selma
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- Selective fluorescent sensing of chloride
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The urea functionalised phenanthroline sensor 1, which was characterised by several methods, including X-ray crystallography, gives rise to large changes in the fluorescence emission spectra upon interaction with several anions such as acetate, phosphate,
- dos Santos, Cidália M.G.,McCabe, Thomas,Gunnlaugsson, Thorfinnur
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- Metal coordination as a tool for controlling the self-assembling and gelation properties of novel type cholic amide-phenanthroline gelating agent
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(3α,7α,12α)-Trihydroxy-N-[1,10-phenanthrolin-5-yl]- 5β-cholan-24-amide was found to be a powerful gelating agent for methanol-water in gelator to solvent ratio starting from 0.1% in absence of metal ion. Formation of phenanthroline-zinc (II) 2:1 complex changes dramatically gelating properties; when stored, it dissolves into clear solution without Tyndall effect and this solution, when heated to ca. 70°C reversibly forms a gel again, without chemical change as proven by NMR spectrometry. Structures of the gels of cholic amide-phenanthroline and its Zn2+ complex were studied by SEM.
- Dukh,?aman,Kroulík,?erny,Pouzar,Král,Dra?ar
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- Different morphological organic-inorganic hybrid nanomaterials as fluorescent chemosensors and adsorbents for CuII ions
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Functionalized silica nanotubes (FSNT), functionalized mesoporous silica (FMS), and functionalized silica nanoparticles (FSNP-15) with an immobilized phenanthroline moiety as a fluorescent receptor were fabricated by a sol-gel reaction, and their binding abilities with metal ions were evaluated by fluorophotometry in water/acetonitrile (8:2, v/v) at pH 7. They selectively recognized Cu2+ ions among other metal cations such as Co 2+, Cd2+, Hg2+, Ni2+, Fe 3+, Ag+, Pb2+, and Zn2+, because the Cu2+ ion selectively binds to the nitrogen atoms of the phenanthroline moiety. Among the three silica nanomaterials with the immobilized receptor 1, the sensitivity of FSNT for Cu2+ ions is better than those of FMS and FSNP-15, indicating that the adsorption capacity for metal ions is dependent on the shape and surface area of the supporting nanomaterials. FSNT (10 mg) adsorb 75% of the Cu2+ ions (2.0 × 10-4 mM) while FSNP-15 (10 mg) adsorb only 36%. The detection limit of FSNT for Cu2+ ions was ca. 3.0 × 10-8 M. FSNT and FMS can be easily renewed by treatment with a solution of HCl and tetrabutylammonium hydroxide. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Soo, Jin Lee,Doo, Ri Bae,Won, Seok Han,Shim, Sung Lee,Jong, Hwa Jung
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- pH responsive Eu(III)-phenanthroline supramolecular conjugate: Novel off-on-off luminescent signaling in the physiological pH range
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The formation of luminescent supramolecular ternary complexes in water: delayed luminescence sensing of aromatic carboxylates using coordinated unsaturated cationic heptadenatate lanthanide ion complexes. Copyright
- Gunnlaugsson, Thorfinnur,Leonard, Joseph P.,Senechal, Katell,Harte, Andrew J.
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- Ionic iridium (III) complex containing viologen units and preparation method and application thereof
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The invention discloses an ionic iridium (III) complex containing viologen units, the iridium (III) complex is composed of a metal center iridium atom, different counter anions, different C^N ligandsand N^N ligands, the structural formula is as follows: the excellent photophysical characteristics of the ionic iridium (III) complex containing viologen units are utilized, and a memristor is prepared through device structure optimization. The memristor has a good application effect in the aspect of nerve synapse electronic bionics.
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- A shining proposal for the detection of dissolved O2 in aqueous medium: Self-calibrated optical sensing via a covalent hybrid structure of carbon-dots&Ru
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O2 is a life-supporting gas and has been widely recognized as an important analyte in life science, medical care and environmental science. Optical sensing for gaseous oxygen has been widely reported owing to the simple, cost-effective and easy-to-go procedure. On the other hand, optical sensors for dissolved oxygen in aqueous media have been rarely reported, since most of them are incompatible with water, leading to poor sensitivity and linearity. In this effort, we tried the combination of Ru(II)-bpy complex and carbon dots (CDs) via covalent bonds, where bpy = bipyridine. A hybrid structure, named as Ru@CD, was constructed for the detection of dissolved oxygen, using Ru(II)-bpy as sensing probe and CDs as water-compatible supporting matrix. Ru@CD was carefully characterized to confirm its hybrid structure. Detailed analysis suggested that its emission showed self-calibrated sensing signals for dissolved oxygen. A good linearity of 99.1% was realized. Its sensitivity (3.18) was higher than most literature values for dissolved oxygen detection. Its working equation was confirmed as a corrected Stern-Volmer equation (Lehrer mode). Good selectivity and signal stability were observed.
- Jiang, Yuanyuan,Liu, Liang,Liu, Xuelian,Mao, Li,Wang, Hongjun,Zhao, Yanping
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- Meta Selective C-H Borylation of Sterically Biased and Unbiased Substrates Directed by Electrostatic Interaction
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An electrostatically directed meta borylation of sterically biased and unbiased substrates is described. The borylation follows an electrostatic interaction between the partially positive and negative charges between the ligand and substrate. With this strategy, it has been demonstrated that a wide number of challenging substrates, especially 4-substituted substrates, can selectively be borylated at the meta position. Moreover, unsubstituted substrates also displayed excellent meta selectivity. The reaction employs a bench-stable ligand and proceeds at a milder temperature, precluding the need to synthesize a bulky and sophisticated ligand/template.
- Chaturvedi, Jagriti,Haldar, Chabush,Bisht, Ranjana,Pandey, Gajanan,Chattopadhyay, Buddhadeb
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p. 7604 - 7611
(2021/05/26)
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- Molecular engineering for optical properties of 5-substituted-1,10-phenanthroline-based Ru(ii) complexes
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A series of homo- and heteroleptic Ru(ii) complexes[Ru(phen)3?n(phen-X)n](PF6)2(n= 0-3, X = CN, epoxy, H, NH2) were prepared and characterized. The influence of electron-withdrawing or electron-releasing substituents of the 1,10-phenanthroline ligands on the photo-physical properties was evaluated. It reveals fundamental interests in the fine tuning of redox potentials and photo-physical characteristics, depending both on the nature of the substitution of the ligand, and on the symmetry of the related homo- or heteroleptic complex. These complexes exhibit linear absorption and two-photon absorption (2PA) cross-sections over a broad range of wavelength (700-900 nm) due to absorption in the intra-ligand charge transfer (ILCT) and the metal-to-ligand charge transfer (MLCT) bands. These 2PA properties were more particularly investigated in the 700-1000 spectral range for a family of complexes bearing electro-donating ligands (phen-NH2).
- Beley, Marc,Blanchard-Desce, Mireille,Chevreux, Sylviane,Gros, Philippe C.,Lawson-Daku, Latévi Max,Lemercier, Gilles,Mongin, Olivier,Moreau, Juliette,Rousset, Elodie
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p. 10119 - 10132
(2021/08/03)
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- Memristors Based on an Iridium(III) Complex Containing Viologen for Advanced Synaptic Bionics
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Memristors with nonvolatile memory properties are expected to open the era of neuromorphic computing. However, it remains a huge challenge to develop memristors with high uniformity, high stability, and low power consumption for advanced synaptic bionics. Herein, an electroactive iridium(III) complex Ir-vio was designed and synthesized by incorporating a viologen moiety into its N?N ligand. Complex Ir-vio showed multiple redox states and high sensitivity to an electrical stimulus. Importantly, two-terminal memristors with Ag/Ir-vio/W structure were successfully fabricated by the solution-processable method, which exhibited multilevel storage characteristics with a low switching threshold voltage of 0.5 V and high ON1/ON2/ON3/OFF current ratio of 105/103/102/1 at a low reading bias of 0.05 V. Moreover, the memristors can mimic synaptic plasticity, indicating that they can act as artificial synapses to construct brain-inspired neural networks. The memristive mechanisms can be ascribed to the interconversion among different charge-transfer and redox states under various electrical stimulus. To the best of our knowledge, this work is the first experimental demonstration of memristors based on iridium(III) complexes, opening a new era for the development of synaptic bionic devices based on organometallic compounds.
- Zhuang, Yanling,Wang, Yu,Deng, Yongjing,Li, Feiyang,Chen, Xintong,Liu, Shujuan,Tong, Yi,Zhao, Qiang
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p. 13021 - 13028
(2021/09/03)
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- Synthesis and characterization of luminescent SiO2@Eu(phen–Si) core–shell nanospheres
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Four core–shell structured nanometre luminescent composites with different kernel sizes and different shell layer thicknesses (SiO2(500)@Eu (phen–Si)(50), SiO2(500)@Eu (phen–Si)(15), SiO2(250)@Eu (phen–Si)(5) and SiO2(250)@Eu (phen–Si)(10)) were made by changing synthesis conditions. Here, initial subscript numbers in parentheses refer to the particle size of the SiO2 core, whereas the final subscript numbers in parentheses refer to shell layer thickness. In these composites, silica spheres of 500?nm or 250?nm were identified as the core. The shell layer was composited of silicon, 1,10-phenanthroline and europium perchlorate, abbreviated as Eu(phen–Si); the chemical formula of phen–Si was phen-N-(CONH (CH2)Si(OCH2CH3)3)2. The composites were characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), and infrared spectroscopy. The monodispersed spherical SiO2 showed characteristics of a regular microstructure and a smooth surface, as well as the advantage of dispersity, shown by SEM. The Eu(phen–Si) complex was able to self-assemble into monodispersed SiO2 spheres, as seen using TEM. Fluorescence spectra indicated that the four composites had excellent luminescence properties. Furthermore, composites composed of a SiO2 core and a 250?nm kernel size exhibited stronger fluorescence than 500?nm kernel-sized composites. Fluorescence properties were affected by shell thickness: the thicker the shell, the greater the fluorescence intensity. For the four composites, quantum yield values and fluorescence lifetime corresponded to fluorescence emission intensity data as quantum yield values and fluorescence lifetime were higher, and luminescence properties increased.
- Li, Wen-Xian,Zheng, Yu-Shan,Zhang, Hong-Bo,Bao, Jin-Rong,Li, Yi-Lian,Ma, Yang-Yang,Feng, Li-Na,Feng, Shu-Yan
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p. 250 - 259
(2019/11/25)
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- A self-calibrating phosphorescent polymeric probe for measuring pH fluctuations in subcellular organelles and the zebrafish digestive tract
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The precise regulation of pH in biological systems, including intracellular organelles and tissues, is essential to the normal functions of vital movement. Accurate pH determination will contribute to a better understanding of related physiological processes and the effective monitoring of physiologic derangements. Luminescence imaging and sensing are useful tools for biological study. However, the conventional intensity-based detection method suffers from low signal-to-noise ratio. Herein, we report a water-soluble ratiometric phosphorescent probe (P-pH) for measuring pH fluctuations in biological samples based on ratiometric photoluminescence imaging and photoluminescence lifetime imaging. P-pH consists of a pH-responsive iridium(iii) complex, pH-inert iridium(iii) complex, and hydrophilic poly(N-vinyl-2-pyrrolidone). Owing to its dual emission, P-pH was successfully used to monitor the pH variation in mitochondria and lysosomes based on the ratiometric readout. Using P-pH, the reliable evaluation of three types of pH modifiers in the zebrafish digestive tract was also realized with a distinguishable long emission lifetime. This is the first example of assessing pH modifiers in real animal models using a luminescent approach.
- Chen, Zejing,Guo, Song,Jiang, Jiayang,Liu, Shujuan,Meng, Xiangchun,Shi, Yuxiang,Xie, Mingjuan,Zhao, Qiang,Zou, Liang
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p. 2265 - 2271
(2020/03/04)
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- A Click Chemistry Approach to Developing Molecularly Targeted DNA Scissors
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Nucleic acid click chemistry was used to prepare a family of chemically modified triplex forming oligonucleotides (TFOs) for application as a new gene-targeted technology. Azide-bearing phenanthrene ligands—designed to promote triplex stability and copper binding—were ‘clicked’ to alkyne-modified parallel TFOs. Using this approach, a library of TFO hybrids was prepared and shown to effectively target purine-rich genetic elements in vitro. Several of the hybrids provide significant stabilisation toward melting in parallel triplexes (>20 °C) and DNA damage can be triggered upon copper binding in the presence of added reductant. Therefore, the TFO and ‘clicked’ ligands work synergistically to provide sequence-selectivity to the copper cutting unit which, in turn, confers high stabilisation to the DNA triplex. To extend the boundaries of this hybrid system further, a click chemistry-based di-copper binding ligand was developed to accommodate designer ancillary ligands such as DPQ and DPPZ. When this ligand was inserted into a TFO, a dramatic improvement in targeted oxidative cleavage is afforded.
- Carell, Thomas,Crisp, Antony L.,Kellett, Andrew,Lauria, Teresa,Müller, Markus,McKee, Vickie,Slator, Creina,Stazzoni, Samuele
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p. 16782 - 16792
(2020/11/30)
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- Cell-responsive ruthenium complex anticancer drug and preparation method thereof
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The invention relates to the technical field of anticancer drugs, in particular to a ruthenium complex anticancer drug and a preparation method thereof. The ruthenium complex anticancer drug is activated through redox, inserted into tumor cell DNA, and coordinated with DNA to undergo a crosslinking reaction, so as to prevent DNA replication and DNA breakage. Due to the introduction of a planar structure ligand, namely, 1,8-naphthalic anhydride, the binding capacity of the drug to DNA is enhanced by 14.17 times, and the stability and anti-tumor activity of the anticancer drug are greatly improved.
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- Probing anion and cation with novel salicylidene Schiff base receptor appended with 1, 10-phenanthroline: Mimicking INHIBIT molecular logic gate
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A novel tailor-made 1, 10-phenanthroline based Schiff base, 2-((E)-(1, 10-phenanthroline -5-ylimino) methyl) phenol, (1) receptor has been designed, synthesized and reported as multi-ion responsive scaffolds for the sensing of both anions and cations via chromogenic methods. In CH3CN, receptor 1 displayed excellent selectivity for F? ions amongst anions and for Al3+ and Hg2+ ions amongst cations. Moreover, the colorless solution of 1 turned yellow only with F? ions due to new absorption band in visible region. Receptor 1 formed 1:1 complex with F? ions while 1:2 with the Hg2+/Al3+ ions as revealed by the separate Job's plot analysis. Receptor 1 can also mimic the functioning of “TRANSFER” and INHIBIT molecular logic gate with chemical inputs from Al3+ and F? ions.
- Alreja, Priya,Kaur, Navneet
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p. 127 - 131
(2018/05/28)
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- Dual mechanism of action of 5-Nitro-1,10-phenanthroline against mycobacterium tuberculosis
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New chemotherapeutic agents with novel mechanisms of action are urgently required to combat the challenge imposed by the emergence of drug-resistant mycobacteria. In this study, a phenotypic whole-cell screen identified 5-nitro-1,10-phenanthroline (5NP) as a lead compound. 5NP-resistant isolates harbored mutations that were mapped to fbiB and were also resistant to the bicyclic nitroimidazole PA-824. Mechanistic studies confirmed that 5NP is activated in an F420-dependent manner, resulting in the formation of 1,10-phenanthroline and 1,10-phenanthrolin-5-amine as major metabolites in bacteria. Interestingly, 5NP also killed naturally resistant intracellular bacteria by inducing autophagy in macrophages. Structure-activity relationship studies revealed the essentiality of the nitro group for in vitro activity, and an analog, 3-methyl-6-nitro-1,10-phenanthroline, that had improved in vitro activity and in vivo efficacy in mice compared with that of 5NP was designed. These findings demonstrate that, in addition to a direct mechanism of action against Mycobacterium tuberculosis, 5NP also modulates the host machinery to kill intracellular pathogens.
- Kidwai, Saqib,Park, Chan-Yong,Mawatwal, Shradha,Tiwari, Prabhakar,Jung, Myung Geun,Gosain, Tannu Priya,Kumar, Pradeep,Alland, David,Kumar, Sandeep,Bajaj, Avinash,Hwang, Yun-Kyung,Song, Chang Sik,Dhiman, Rohan,Lee, Ill Young,Singh, Ramandeep
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- Preparation methods and application of rare earth europium complex and fluorescent foam thereof
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The invention discloses preparation methods and application of a rare earth europium complex and fluorescent foam thereof. The preparation method of the rare earth europium complex comprises the steps that Phen is adopted as a raw material and reacts with a concentrated acid solution to generate Phen-NO2, Phen-NO2 and hydrazine hydrate react to obtain Phen-NH2, Phen-NH2 and Eu(TTA)3.2H2O are mixed and react, and then the rare earth europium complex Eu(TTA)3.Phen-NH2 is obtained. The rare earth europium complex is dissolved in a DMSO solution, anions and cations are detected through an ion titration method, and the rare earth europium complex has a good recognition function on H2PO4-, CH3COO-, F- and Cu2+. The preparation method of the fluorescent foam of the rare earth europium complex comprises the steps that Eu(TTA)3.Phen-NH2 serves as luminescent molecules to be introduced into a common foamed system of PEG600, open-loop epoxidized soybean oil polyalcohol and MDI, and the fluorescent foam of the rare earth europium complex is prepared. The preparation method of the fluorescent foam is simple, short in reaction time and environmentally friendly, and the recognition function on Cu2+ is good. Compared with a traditional product, due to the fact the amount of foam is large, the specific surface area is large, the single recognition capacity is high, the defect that a traditional fluorescence probe is quenched in an aqueous solution can be overcome, and the fluorescent foam has wide application prospects in the fields of medical treatment, agriculture, food and the like.
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Paragraph 0055
(2017/04/28)
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- A Simple and Selective Fluorescent Sensor for Zn2+ and H+ Ions in Aqueous Solution with OR Logic Gate Function
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The synthesis and properties of a new compound, viz., (N,N′-[1,10-phenanthroline-4,7-diyldi((E)methylylidene)]bis(1,10-phenanthrolin-5-amine) (1), is described. Compound 1 can be used as a selective fluorescent Zn2+ sensor in buffered solution. Furthermore, 1 induces turn on fluorogenic response to H+ ions. Finally, it is shown that an OR logic gate can be constructed with 1 by using Zn2+ and H+ as two-inputs. [Figure not available: see fulltext.]
- Algi, Melek Pamuk
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p. 1083 - 1089
(2016/05/19)
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- Equipping an adsorbent with an indicator: A novel composite to simultaneously detect and remove heavy metals from water
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A novel composite that can simultaneously detect and remove heavy metals was prepared in this study. Its adsorption ability rivals that of excellent traditional adsorbents; furthermore, it can change the color to identify the adsorbate and its concentration. The color changes are very easy to detect via the naked eye or with a photometer. This novel adsorbent can remove a large amount of heavy metal ions, and also qualitatively and quantitatively detect heavy metal ions in water. Cu(ii) and Fe(ii) were used to investigate the detection and removal properties of the composite, and SEM, BET, FTIR, zeta potential and XPS were used to physicochemically characterize it. Batch sorption experiments were conducted to study the effects of various factors such as pH, the presence of coexisting metal ions, the contact time and the initial metal concentration. The studies indicated that the adsorption process fits well to the Langmuir model, and the kinetic data could be described very well by the pseudo-second-order kinetic model. The mechanism of adsorption has been discussed in detail. This study provides a simple method for the preparation of smart adsorbents.
- Jiang, Hualin,Zhang, Weibo,Chen, Pinghua,Zhang, Weiwei,Wang, Guoyao,Luo, Xubiao,Luo, Shenglian
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p. 11897 - 11907
(2016/08/04)
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- In situ generation of self-enhanced luminophore by β-lactamase catalysis for highly sensitive electrochemiluminescent aptasensor
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This work described a new electrogenerated chemiluminescence (ECL) aptasensor for ultrasensitive detection of thrombin (TB) based on the in situ generating self-enhanced luminophore by β-lactamase catalysis for signal amplification. Briefly, a ruthenium complex (Ru-Amp), including two regions of [Ru(phen)2(cpaphen)]2+ and ampicillin (Amp), was synthesized as a self-enhanced ECL luminophore, which can produce an ECL signal through intramolecular interactions. Then, carbon nanotubes (CNTs) were used for immobilization of Ru-Amp via π-π stacking interactions to form the Ru-Amp@CNTs nanocomposite. Using poly(ethylenimine) (PEI) as a linkage reagent, Au nanocages (AuNCs), owing to their electronic property and large surface areas, were decorated to the CNTs to form the Ru-Amp@CNTs-PEI-AuNCs nanocomposites, which were further used to immobilize thrombin binding aptamer II (TBA II) to form a signal probe (Ru-Amp@CNTs-PEI-AuNCs-TBA II). Through "sandwich" tactics, TBA II bioconjugates, TB and TBA I were immobilized onto the gold nanoparticles modified electrode. Then, with the enzyme catalysis of β-lactamase, a novel self-enhanced ECL luminophore (Ru-AmpA) was in situ produced, which could exhibit a significant enhancement of ECL signal, due to the structure transformation of an amide bond into a secondary amine. A sandwich ECL assay for TB detection was developed with excellent sensitivity of a concentration variation from 1.0 fM to 1.0 pM and a detection limit of 0.33 fM. Therefore, the self-enhanced ECL luminophore, combining the further enhancement by in situ enzymatic reaction, is expected to have potential applications in biotechnology and clinical diagnosis.
- Gui, Guo-Feng,Zhuo, Ying,Chai, Ya-Qin,Xiang, Yun,Yuan, Ruo
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p. 5873 - 5880
(2014/07/07)
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- Recyclable porous polymer-supported copper catalysts for Glaser and Huisgen 1,3-diolar cycloaddition reactions
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A family of polymer-attached phenanthrolines was prepared from solvothermal copolymerization of divinylbenzene with N-(1,10-phenanthroline-5-yl)acrylamide in different ratios. The polymer-supported copper catalysts were obtained through typical impregnation with copper(II) salts. The polymers and supported copper catalysts have been characterized by N2 adsortion, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and thermogravimetric analysis (TG); they exhibit a high surface area, hierarchical porosity, large pore volume, and high thermal and chemical stabilities. The copper catalyst has proved to be highly active for Glaser homocoupling of alkynes and Huisgen 1,3-diolar cycloaddition of alkynes with benzyl azide under mild conditions at low catalyst loading. The heterogeneous copper catalyst is more active than commonly used homogeneous and nonporous polystyrene-supported copper catalysts. In particular, the catalyst is easily recovered and can be recycled at least ten times without any obvious loss in catalytic activity. Metal leaching was prevented due to the strong binding ability of phenanthroline and products were not contaminated with copper, as determined by ICP analysis. At the Copper, Coppercabana: Stable, porous polymer-attached phenanthrolines were successfully prepared from solvothermal copolymerization of divinylbenzene with N-(1,10-phenanthrolin-5-yl)acrylamide (PCP-Phen). After coordination with copper species, a heterogeneous copper catalyst was obtained that displayed a higher activity in Glaser and Huisgen couplings than commonly used homogeneous and nonporous polystyrene-supported copper catalysts. The copper catalyst has excellent recyclability due to the strong coordination ability of phenanthrolines. Copyright
- Sun, Qi,Lv, Zhonfei,Du, Yuyang,Wu, Qinming,Wang, Liang,Zhu, Longfeng,Meng, Xiangju,Chen, Wanzhi,Xiao, Feng-Shou
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supporting information
p. 2822 - 2827
(2013/11/19)
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- Preparation and valence tautomeric behavior of a cobaltdioxolene complex with a new TTF-functionalized phenanthroline Ligand
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In this study, a new tetrathiafulvalene-functionalized phenanthroline ligand (TTF-phen) and a mononuclear cobalt(II) complex with a redox active 3,6-di-tert-butylsemiquinonato (3,6-dtsq) ligand was synthesized. Magnetic measurementsand IR spectroscopy suggested that the Co complex [Co(3,6- dtsq)2(TTF-phen)] exhibited thermally induced valence tautomerismin the temperature range 130400 K. This complex is the first example of a valence tautomeric complex with a TTFfunctionalized ligand.
- Kanegawa, Shinji,Kang, Soonchul,Sato, Osamu
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p. 700 - 702
(2013/07/26)
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- Europium (III) complex functionalized Si-MCM-41 hybrid materials with visible-light-excited luminescence
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The synthesis of organics 9-hydroxyphenalenone (HPO), 2-methyl-9- hydroxyphenalenone (MHPO), 6-hydroxybenz[de]anthracen-7-one (HBAO), 5-amino-1,10-phenanthroline (phen-NH2) and its functionalized mesoporous MCM-41 by covalent band are reported, as well as those of Europium (III) hybrid mesoporous materials, EuL3phen-MCM-41 (L = HPO, MHPO, HBAO). The photoluminescence and microstructural properties are characterized, and the XRD and BET results revealed that all of these hybrid materials have uniformity in the mesostructure. It is worth noting that the excitation spectra of these hybrid materials have a broad absorption, which occupies from UV to visible region (250-475 nm). Upon ligand-mediated excitation with the visible light, the low efficient energy transfer exhibit between the organic ligands and europium(III) ion under visible excitation, but the maximum wavelength (456 nm/457 nm/451 nm) located at blue light region, which is in consistent with the blue LED light, then might be a feasible alternative in producing time-resolved luminescence under LED-excitation.
- Gu, Yan-Jing,Yan, Bing
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- A novel white-luminescent ternary europium hybrids with phenanthroline functionalized periodic mesoporous organosilicas (PMOs) and 2-methyl-9- hydroxyphenalenone
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The molecular linkage (phenSi) is modified from 5-amino-1,10-phenanthroline (phenNH2) by 3-(triethoxysilyl)-propyl isocyanate (TESPIC). Then phenNH2 functionalized periodic mesoporous organosilica (PMO) hybrids are synthesized by linking ternary europium complexes with phenSi linkage and 2-methyl-9-hydroxyphenalenone (MHPO), which use co-condensation method in the presence of Pluronic P123 surfactant as a template. The europium PMO hybrid system (denoted as Eu(MHPO)3phen-PMO(NO3)3) has been characterized in detail, whose results reveal that these hybrids have uniformity in the mesopore structure. It is worthy pointing out that the europium hybrids show emission of both europium ion and phen functionalized PMOs, which can be integrated into the close white luminescence. This provides us a strategy to obtain white emissive lanthanide hybrids.
- Yan, Bing,Gu, Yan-Jing
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- Supramolecular chemosensor for selective detection of iron in aqueous medium
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We have successfully developed a 'turn-on' colorimetric chemosensor for Fe3+ based on 1,10-phenanthroline. An amide derivative of 1,10-phenanthroline 4 was developed for the selective recognition of Fe 3+ over Co2+, Cr3+, Cu2+, Mn 2+, Ni2+, Ag+ and Zn2+ and could measure Fe3+ concentration in the range of 15-210 μM by UV-vis spectroscopy. Moreover, the addition of Fe3+ to a colourless solution of 4 turned its colour to light pink, indicating that 4 is capable of detecting Fe3+ by the naked eye. Compound 4 exhibits a major absorption band centred at 268 which shifted to 278 nm after addition of Fe3+, and a shoulder band around 514 nm was also observed. The complexation of Fe 3+ with 4 was analysed at a different pH and favourable binding was observed at pH 6.2.
- Nadeem, Said,Shah, Muhammad Raza,Khan, Burhan,Hoda, Numan,Topel, Oender
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p. 798 - 805
(2014/01/06)
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- Controlled drug delivery from mesoporous silica using a pH-response release system
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Mesoporous hollow silica nanoparticles were functionalized with phenanthroline (P-MHS) to prepare a carrier for a host-guest complex. Curcumin was selected as a model drug molecule. The phenanthroline attached to the P-MHS was complexed with Cu2+ through a coordination bond. When the Cu 2+-P-MHS was exposed to ～pH 5, the curcumin was efficiently released into the aqueous phase within 120 min. This work describes a method for functionalizing the surface of the porous silica nanoparticles in a well-defined manner. The P-MHS carrier exhibited controlled release of a model drug under acidic pH conditions.
- Jin, Dalsaem,Lee, Ji Ha,Seo, Moo Lyong,Jaworski, Justyn,Jung, Jong Hwa
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supporting information; experimental part
p. 1616 - 1620
(2012/10/07)
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- Synthesis and characterization of a Eu-containing polymer precursor featuring thenoyltrifluoroacetone and 5-acrylamido-1,10-phenanthroline
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A polymerizable ligand, 5-acrylamido-1,10-phenanthroline (L), was synthesized. Its Eu(III) complex with 2-thenoyltrifluoroacetone (HTTA) was prepared and characterized by elemental analysis, IR, MS, and 1H NMR spectra. The photophysical properties of the complex were studied in detail by using UV, luminescence spectra, luminescence lifetime and quantum yield. The complex shows a remarkable luminescence quantum yield at room temperature (40.1%) upon ligand excitation and a long 5D0 lifetime (590 μs), which makes it not only a promising light-conversion molecular device but also an excellent luminescent polymer precursor.
- Xu, Cun-Jin,Li, Bo-Geng,Wan, Jin-Tao,Bu, Zhi-Yang
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p. 159 - 163
(2011/10/18)
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- Luminescent ruthenium(II) polypyridyl functionalized gold nanoparticles; Their DNA binding abilities and application as cellular imaging agents
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The synthesis and photophysical and biological investigation of Ru(II)-polypyridyl stabilized water-soluble, luminescent gold nanoparticles (AuNPs) are described. These structures bind to DNA and undergo rapid cellular uptake, being localized within the cell cytoplasm and nucleus within 4 h.
- Elmes, Robert B. P.,Orange, Kim N.,Cloonan, Suzanne M.,Williams, D. Clive,Gunnlaugsson, Thorfinnur
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p. 15862 - 15865
(2012/01/04)
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- A highly selective off-on red-emitting phosphorescent thiol probe with large stokes shift and long luminescent lifetime
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(Figure presented) An OFF-ON red-emitting phosphorescent thiol probe is designed by using the 3MLCT photophysics of Ru(II) complexes, i.e., with Ru(II) as the electron donor. The probe is non-luminescent because the MLCT is corrupted by electron transfer from Ru(II) to an intramolecular electron sink (2,4-dinitrobenzenesulfonyl). Thiols cleave the electron sink, and the MLCT is re-established. Phosphorescence at 598 nm was enhanced by 90-fold, with a 143 nm (5256 cm-1) Stokes shift and a 1.1 μs luminescent lifetime.
- Ji, Shaomin,Guo, Huimin,Yuan, Xiaolin,Li, Xiaohuan,Ding, Haidong,Gao, Peng,Zhao, Chunxia,Wu, Wenting,Wu, Wanhua,Zhao, Jianzhang
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supporting information; experimental part
p. 2876 - 2879
(2010/09/05)
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- Synthesis, photophysical properties, and theoretical studies on pyrrole-containing bromo Re(I) complex
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Two bromo rhenium(I) carbonyl complexes with the formula of [Re(CO)3(L)Br], where L = 1,10-phenanthroline (Phen-Re) and 5-(1H-pyrrol-1-yl)-1,10-phenanthroline (Pyph-Re), were successfully synthesized with the aim to analyze the effect of the pyrrole (Py) moiety on the photophysical properties of Pyph-Re. It was found that the triplet metal-to-ligand charge-transfer dπ (Re) → π*(N-N) emission of Phen-Re and Pyph-Re centered at ca. 527 nm with the luminescence quantum yield (LQY) of 0.015 and ca. 578 nm with the LQY of 0.011, respectively. At the same time, the geometrical structures of the ground state and the absorption spectral properties of Phen-Re and Pyph-Re were also calculated with the 6-31G* basis set employed on C, H, N, O, and Br atoms, and LANL2DZ adopted on Re atom. According to the experimental and theoretical analysis, the red-shift of the photoluminescent spectrum and the lower LQY of Pyph-Re should be mainly attributed to the narrower energy gap between the highest occupied molecular orbital and the lowest unoccupied molecular orbital and the more LLCT transition ration of Pyph-Re, respectively.
- Si, Zhenjun,Li, Xiaona,Li, Xiyan,Zhang, Hongjie
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scheme or table
p. 3742 - 3748
(2010/03/05)
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- LIGAND-FUNCTIONALIZED/AZO COMPOUNDS AND METHODS OF USE THEREOF
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Described herein are ligand-functionalized/azo compounds and methods of use thereof.
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- Synthesis of 5-isothiocyanato-1,10-phenanthroline
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Reduction of 5-nitro-1,10-phenanthroline with hydrogen over Pd/C, followed by the treatment of 1,10-phenanthrolin-5-amine with thiophosgene in the presence of sodium acetate, gave 5-isothiocyanato-1,10-phenanthroline which is a thermally stable highly reactive ligand capable of quantitatively forming covalently bonded nanohybrid structures in a system transition metal complex-silica under mild conditions. Pleiades Publishing, Inc., 2006.
- Khimich,Obrezkov,Koptelova
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p. 555 - 557
(2007/10/03)
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- Solid-phase peptide synthesis using non-covalent attachment of the growing peptide chain
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A method for solid phase synthesis of peptides, characterized by a non-covalent attachment of the growing peptide chain to the solid phase during the synthesis cycles.
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- CROWN ETHER-DERIVATISED PERYLENES
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Perylenes of formula (I) wherein R is (a), (b), unsubstituted quinolyl, anthrolinyl or phenanthrolinyl or substituted quinolyl, anthrolinyl or phenanthrolinyl, wherein m is an integer from 0 to 4 and n is an integer from 1 to 9, and the radicals R t
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- Synthesis of an oxyamino-containing phenanthroline derivative for the efficient preparation of phenanthroline oligonucleotide oxime conjugates
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A phenanthroline derivative bearing an oxyamino linker was efficiently prepared from commercial 5-nitro-1,10-phenanthroline. The subsequent reaction with an oligonucleotide containing an aldehyde either at the 5′ end or the 3′ end afforded, in good yield, the phenanthroline-oligonucleotide conjugates through oxime bond formation.
- Deroo, Stéphanie,Defrancq, Eric,Moucheron, Cécile,Kirsch-De Mesmaeker, Andrée,Dumy, Pascal
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p. 8379 - 8382
(2007/10/03)
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- Fluorescent group-containing carbodiimide compound
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Using the fluorescent group-containing carbodiimide compound represented-by the following formula (I) as the label and the like in the nucleic acid detection method, immunoassay, or chemiluminescence assay, labeling can be made efficiently for a short time, a nucleic acid derived from nature can be labelled, and highly sensitive assay is enabled. wherein F represents a fluorescent group; A represents a moiety selected from the group consisting of --CH2 --, --NHCO--, --CONH--, --O--, --S--, --NR-- wherein R is an alkyl group, --COO--, --OCO--, --NHSO2 --, and --SO2 NH--; n is 0 or 1; W represents a direct bond or a quaternary ammonium group; Y1, Y2 and Y3 each represents an alkylene group which may have a functional group in its main chain; and B represents H or a monovalent organic group which may be the same as or different from that represented by --W--Y1 --?A!n --F.
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- CAP-phenanthroline conjugate for DNA cleavage
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A class of site-specific DNA cleavage agents comprising a sequence-specific DNA binding protein and a nucleolytic moiety attached thereto at an amino acid that is close to DNA in the specific protein-DNA complex, but that is not close to DNA in the non-specific protein DNA complex. These site-specific DNA cleavage agents cleave DNA at specific DNA recognition sites and have little or no non-specific DNA cleavage activity.
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- Synthesis and Characterisation of a New DNA-binding Bifunctional Ruthenium(II) Complex
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A new DNA-binding molecule, Ru(tap)2POQ(2+), in which a polypyridylruthenium(II) complex is linked to an aminochloroquinoline by a flexible chain, has been prepared and characterised (tap = 1,4,5,8-tetraazaphenanthrene and POQ corresponds to a 1,10-phenanthroline linked to an aminochloroquinoline by an aliphatic chain).This complex is regarded as bifunctional because it contains two moieties of different binding modes and photoreactivities vs.DNA.The (1)H NMR data of this compound indicate the presence of an equilibrium between two molecular species.The spectroscopic properties of Ru(tap)2POQ(2+) in absorption and luminescence are examined and compared with those of the corresponding ruthenium(II) complex which does not contain the aminochloroquinoline moiety: Ru(tap)2phen(2+).Luminescence relative quantum yields and lifetimes show that the MLCT excited-state behaviour is influenced by the presence of the linked quinoline.An intramolecular photoinduced electron transfer in one of the two species in equilibrium, is considered to be responsible for a quenching of the ruthenium(II) complex luminescence.Preliminary results on the binding characteristics of Ru(tap)2POQ(2+) to DNA and )>2 from luminescence and thermal denaturation studies are reported.The intramolecular quenching of luminescence in Ru(tap)2POQ(2+) is inhibited when it interacts with nucleic acids.Consequently, the resulting emission is more substantially enhanced in the presence of the polynucleotide relative to the luminescence increase observed with the reference complex, Ru(tap)2phen(2+).
- Lecomte, J-P.,Mesmaeker, A. Kirsch-De,Demeunynck, M.,Lhomme, J.
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p. 3261 - 3269
(2007/10/02)
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- Mixed ligand complexes and uses thereof as binding agents and probes to DNA
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This invention concerns a coordination complex or salt thereof which is spectroscopically or photoactively determinable when bound to DNA having the formula STR1 wherein M is a suitable transition metal and each of R1, R2 and R3 is ethylenediamine, bipyridine, phenanthroline, diazafluorene-9-one or a substituted derivative thereof, or phenanthrenequinonediimine or a substituted derivative thereof, dypyridophenazine or a substituted derivative thereof; wherein R1, R2 and R3 are bound to M by coordination bonds; provided that at least one of R1, R2 or R3 is dypyridophenazine or a substituted derivative thereof. The invention also concerns a labeled DNA probe which comprises the complex covalently bound to the DNA probe. Further the invention concerns a method of detecting the presence in a sample a target DNA of interest which comprises contacting the sample containing the target DNA with a complementary labeled DNA probe under hybridizing conditions and measuring the resulting luminescense emitted from the labeled DNA probe, a change in the luminescense as compared with the luminescense in the absence of the sample indicating the presence of the target DNA.
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