- Synthesis of DPA-triazole structures and their application as ligand for metal catalyzed organic reactions
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In this work, the use of DPA-triazole (DPA = dipicolylamine) molecules as ligands for metal catalyzed organic reactions has been investigated. A small library of ligands has been prepared by a CuAAC (click reaction) between propargyl-DPA and different azi
- Colombo Dugoni, Greta,Sacchetti, Alessandro,Urra Mancilla, Carolina
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- Fluconazole analogues with metal-binding motifs impact metal-dependent processes and demonstrate antifungal activity in Candida albicans
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Abstract: Azole antifungals are an important class of antifungal drugs due to their low cost, ability to be administered orally, and broad-spectrum activity. However, their widespread and long-term use have given rise to adaptation mechanisms that render these compounds less effective against common fungal pathogens, including Candida albicans. New antifungals are desperately needed as drug-resistant strains become more prevalent. We recently showed that copper supplementation potentiates the activity of the azole antifungal fluconazole against the opportunistic fungal pathogen C. albicans. Here, we report eight new azole analogues derived from fluconazole in which one triazole group has been replaced with a metal-binding group, a strategy designed to enhance potentiation of azole antifungal activity by copper. The bioactivity of all eight compounds was tested and compared to that of fluconazole. Three of the analogues showed activity against C. albicans and two had lower levels of trailing growth. One compound, Flu-TSCZ, was found to impact the levels, speciation, and bioavailability of cellular metals. Graphic abstract: [Figure not available: see fulltext.]
- Franz, Katherine J.,Hunsaker, Elizabeth W.,McAuliffe, Katherine J.
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- Molecular Recognition by Zn(II)-Capped Dynamic Foldamers
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Two α-aminoisobutyric acid (Aib) foldamers bearing Zn(II)-chelating N-termini have been synthesized and compared with a reported Aib foldamer that has a bis(quinolinyl)/mono(pyridyl) cap (BQPA group). Replacement of the quinolinyl arms of the BQPA-capped foldamer with pyridyl gave a BPPA-capped foldamer, then further replacement of the linking pyridyl with a 1,2,3-triazole gave a BPTA-capped foldamer. Their ability to relay chiral information from carboxylate bound to Zn(II) at the N-terminus to a glycinamide-based NMR reporter of conformational preference at the C-terminus was measured. The importance of the quinolinyl arms became readily apparent, as the foldamers with pyridyl arms were unable to report on the presence of chiral carboxylate in acetonitrile. Low solubility, X-ray crystallography and 1H NMR spectroscopy suggested that interfoldamer interactions inhibited carboxylate binding. However changing solvent to methanol revealed that the end-to-end relay of chiral information could be observed for the Zn(II) complex of the BPTA-capped foldamer at low temperature.
- Clayden, Jonathan,Eccles, Natasha,Le Bailly, Bryden A. F.,Webb, Simon J.,Whitehead, George F. S.,della Sala, Flavio
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p. 338 - 345
(2020/04/15)
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- Ligand, preparation method thereof, fluorescent probe, and preparation method and application of fluorescent probe
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The invention discloses a preparation method of a ligand, a fluorescent probe, and a preparation method and an application of the fluorescent probe. The ligand is DATP, and is obtained by reacting a compound 1, NaN3, tetrabutylammonium hydrogen sulfate, bis(2-pyridylmethyl)amine, propargyl bromide, CuI, and a CH2Cl2 and CF3COOH mixed solvent. The fluorescent probe adopts DATP and Ni as cores,Eu and Ni are linked with the ligand through a Ni-N coordination bond, and Tb is linked with the ligand trough Tb-O and Tb-N coordination bonds. The fluorescent probe of the invention is prepared with DATP as the core, and a Eu/Tb complex can be used in time-resolved fluorescence detection to effectively eliminate interference from samples and short-lived fluorescence such as scattered light, so the prepared fluorescent probe has the advantages of good water solubility, extremely high sensitivity, excellent selectivity to histidine, simple preparation method and mild conditions, and is suitable for detecting histidine in biological systems.
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-
Paragraph 0042; 0056; 0067-0074
(2019/10/23)
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- An alternative modular 'click-SNAr-click' approach to develop subcellular localised fluorescent probes to image mobile Zn2+
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Zn2+ is involved in a number of biological processes and its wide-ranging roles at the subcellular level, especially in specific organelles, have not yet been fully established due to a lack of tools to image it effectively. We report a new and
- Fang, Le,Trigiante, Giuseppe,Crespo-Otero, Rachel,Philpott, Michael P.,Jones, Christopher R.,Watkinson, Michael
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supporting information
p. 10013 - 10019
(2019/12/23)
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- Alkane oxidation catalysed by a self-folded multi-iron complex
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A preorganised ligand scaffold is capable of coordinating multiple Fe(II) centres to form an electrophilic CH oxidation catalyst. This catalyst oxidises unactivated hydrocarbons including simple, linear alkanes under mild conditions in good yields with selectivity for the oxidation of secondary CH bonds. Control complexes containing a single metal centre are incapable of oxidising unstrained linear hydrocarbons, indicating that participation of multiple centres aids the CH oxidation of challenging substrates.
- Mettry, Magi,Moehlig, Melissa Padilla,Gill, Adam D.,Hooley, Richard J.
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p. 120 - 128
(2016/11/09)
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- A bioinspired heterogeneous catalyst based on the model of the manganese-dependent dioxygenase for selective oxidation using dioxygen
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A hybrid bioinspired material with manganese(ii) complexes grafted on the surface of a mesostructured porous silica is investigated. The Mn sites mimic the manganese-dependent dioxygenase (MndD), which is an enzyme that catalyses the oxidation of catechol derivatives. The metal complexes were introduced in the silica using a dinuclear complex [Mn2L2(Cl)2(μ-Cl)2] as a precursor with a clickable ligand N,N′-bis[(pyridin-2-yl)methyl]prop-2-yn-1-amine (L). Azide moieties covalently grafted on MCM-41 type mesoporous silica were utilised to anchor the manganese complex through Huisgen cycloaddition using CuBr(PPh3)3 as a catalyst. A second functional group-trimethylsilyl or pyridine—was grafted on the silica to bring, together with nanopore size confinement, a similar metal environment as in MndD. The mesostructure of the materials was maintained after incorporation of the Mn complex. Catalytic oxidation of 3,5-di-t-butyl-catechol (3,5-DTBC) into quinone occurred without the need of an additional base when the metal complex was confined in the porous solid. In comparision, the oxidation of 4-t-butyl-catechol (4-TBC) that always required a basic media led to a total oxidation into the ortho-quinone, contrary to the molecular analogue.
- Chaignon, Jérémy,Gourgues, Marie,Khrouz, Lhoussain,Moliner, Nicolás,Bonneviot, Laurent,Fache, Fabienne,Castro, Isabel,Albela, Belén
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p. 17336 - 17345
(2017/03/29)
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- Surfactant-modulated discriminative sensing of HNO and H2S with a Cu2+-complex-based fluorescent probe
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Recent investigations revealed the close relationship between H2S and HNO in biological systems. It is significant to develop an efficient fluorescent sensor to realize the discriminative sensing of HNO and H2S. Herein, we designed and synthesized a novel fluorescent sensor (CuHCD) with hemicyanine-carbazole as fluorophore and bipyridine-triazole-Cu2+complex as receptor, which enabled the selective recognition of HNO and H2S, respectively via the non-covalent modulation of surfactant assemblies. The CuHCD/surfactant sensor system exhibited excellent selectivity for H2S at 5?mM SDS in HEPES buffer, and displayed high specificity for HNO at 1?mM SDS in HEPES buffer over other common anions and reactive species. Different detection mechanisms in sensing H2S and HNO were deeply investigated. The results showed that H2S seized Cu2+from the complex to recover the fluorescence of HCD, while HNO reduced Cu2+to Cu+in the complex to turn on the fluorescence. In different SDS micellar systems, HCD possessed different dispersity and binding capacity with Cu2+, which led to the selective detection of H2S and HNO, respectively. The hypothesis was further confirmed by replacing SDS micelles with liposome under the same conditions.
- Lv, Hai-juan,Ma, Rong-fang,Zhang, Xiao-tai,Li, Mei-han,Wang, Yu-tong,Wang, Shu,Xing, Guo-wen
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p. 5495 - 5501
(2016/08/04)
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- Copper-catalyzed regioselective hydroboration of terminal alkynes in aqueous medium
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A mild and environment-friendly copper-catalyzed hydroboration of terminal alkynes in aqueous medium was reported. Regioselectivity control was achieved in the presence of cyclodextrin-bispyridine ligand (CD-1). This protocol was successfully applied to inactivated terminal alkynes. Moreover, the ligand was recovered and reused without any loss of activity over five cycles.
- Yao, Zi-Jian,Hong, Shibin,Zhang, Wei,Liu, Mengyan,Deng, Wei
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supporting information
p. 910 - 913
(2016/02/05)
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- DENDRIMER COMPOSITIONS, METHODS OF SYNTHESIS, AND USES THEREOF
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The disclosure relates to novel dendrimer conjugates and the methods of synthesizing the same, as well as systems and methods utilizing the dendrimer conjugates (e.g., in diagnostic and/or therapeutic settings (e.g., for the delivery of therapeutics, imaging, and/or targeting agents (e.g., in disease diagnosis and/or therapy, etc.))).
- -
-
Paragraph 0149; 0150
(2016/11/09)
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- Synthesis and characterization of copper(ii) complexes with multidentate ligands as catalysts for the direct hydroxylation of benzene to phenol
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Four copper(ii) complexes with multidentate ligands, 1 ([CuL1Cl2]), 2 ([Cu(HL2)Cl2]), 3 ([Cu2(L2)2](ClO4)2) and 4 ([CuL3(HOCH3)ClO4]) {L1 = N,N-bis((pyridin-2-yl)methyl) prop-2-yn-1-amine, HL2 = 2-((((1-methyl-1H-imidazol-2-yl)methyl)(pyridin-2-ylmethyl)amino)methyl)phenol and HL3 = 2-((((1-methyl-1H-imidazol-2-yl)methyl)(pyridin-2-ylmethyl)amino)methyl)-2-t-butyl-phenol} are reported. The complexes were characterized by UV-vis spectroscopy, elemental analysis and electrochemical analysis. Complexes 1 and 3 were further characterized by X-ray single crystal diffraction analysis. The catalytic performances of these complexes were evaluated in the direct hydroxylation of benzene to phenol with hydrogen peroxide as an oxidant in aqueous acetonitrile media. Under optimized reaction conditions, complex 4 with the most negative reduction potential exhibited the highest conversion without considering the dinuclear complex 3. A correlation between the catalytic efficiency and the reduction potentials of these complexes was observed, that is the more negative the reduction potential, the higher the benzene conversion. A radical mechanism for the catalysis was confirmed by the fact that addition of radical scavengers such as TEMPO into the reaction mixture could severely suppress the catalysis.
- Wu, Li,Zhong, Wei,Xu, Beibei,Wei, Zhenhong,Liu, Xiaoming
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p. 8013 - 8020
(2015/05/05)
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- INHIBITORS OF METALLO-BETA-LACTAMASE (MBL) COMPRISING A ZINC CHELATING MOIETY
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The invention provides compounds according to formula I: A - L - B wherein A represents a lipophilic chelating moiety which is selective for Zn2+ ions; L is a covalent bond or a linker; and B is a vector which is either a moiety capable of interacting with one or more biological structures found in a bacterium (preferably in a bacterial cell wall), for example a penicillin-binding protein such as a metallo-β- lactamase or DD-transferase, or a moiety capable of enhancing transport of the compound across a bacterial cell membrane. Such compounds find use in a method of treating and/or preventing a bacterial infection in a human or non-human mammal. In such a method, the compound of formula I may be administered in combination with (either simultaneously, separately, or sequentially) a β-lactam antibiotic.
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Page/Page column 23
(2015/04/22)
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- Synthesis of a phenazine-based 1,2,3-triazole from naturally occurring naphthoquinone designed as a probe for Cd2+ ions
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The synthesis of a phenazine-based 1,2,3-triazole luminescent probe was successfully accomplished from the available natural product lapachol, which was easily extracted from the heartwood of Tabebuia sp. (Tecoma). Photophysics and fluorescence studies were conducted by using the probe in the presence of metal ions (Cd2+, Ca2+, Co2+, Cu2+, Fe3+, Hg2+, Mg2+, Na+, Ni2+, Ag+, Pb2+, Zr2+, and Zn2+ as their chloride salts with the exceptions of silver and lead that were used as acetates). The probe was able to detect Cd2+ ions in H2O/CH3CN (8.5:1.5 v/v) medium. Studies performed with the sensor in a solution of cadmium chloride resulted in a green color after ultraviolet excitation, but for most metals blue color was observed, which could be detected by the naked eye. This is the first report of a lapachol, an accessible naphthoquinoidal compound, having been used to prepare a probe to detect the heavy metal cadmium.
- Jardim, Guilherme A. M.,Calado, Hllen D. R.,Cury, Luiz A.,Da Silva, Eufrnio N.
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p. 703 - 709
(2015/01/30)
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- Iron(iii) complexes of multidentate pyridinyl ligands: Synthesis, characterization and catalysis of the direct hydroxylation of benzene
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Three multidentate ligands, L1-L3, derived from bis(pyridin-2-ylmethyl)amine (L1) were synthesized. Reaction of these ligands with FeCl3·6H2O in methanol led to the formation of the iron complexes Fe1-Fe3 (Fe1: [FeL1Cl3]; Fe2: [FeL2Cl3]; Fe3: [FeL3Cl3]) in good yields. These complexes have been fully characterized. The structures of complexes Fe1-Fe3 have been determined using X-ray single crystal diffraction analysis. Electrochemical investigation revealed that complex Fe3 partially converts to Fe4 ([FeL3Cl2]PF6) by the replacement of one of its three chlorides with its pendant triazolyl group in solution. Fe4 was also synthesized by dechlorination using AgPF6 as the Cl- abstractor and its composition was further confirmed by both elemental analysis and X-ray single crystal diffraction analysis. All four complexes catalyze the direct hydroxylation of benzene to phenol with hydrogen peroxide as an oxidant in a mixed medium of water and acetonitrile. The reactivity of the complexes correlates well with their reduction potentials. The more negative the potential, the more reactive (high conversion rate) the catalysts. These complexes catalyze not only the oxidation of benzene, but also the further oxidation of the product, phenol. In the oxidation, a radical mechanism is certainly involved but an alternative pathway may also exist. This journal is
- Xu, Beibei,Zhong, Wei,Wei, Zhenhong,Wang, Hailong,Liu, Jian,Wu, Li,Feng, Yonggang,Liu, Xiaoming
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p. 15337 - 15345
(2015/01/09)
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- Two multidentate ligands utilizing triazolyl, pyridinyl and phenolate groups as donors for constructing dinuclear copper(II) and iron(III) complexes: Syntheses, structures, and electrochemistry
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Two multidentate ligands 2,2′-(1,1′-(pyridine-2,6-diylbis(methylene))bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene)bis((pyridin-2-ylmethyl)azanediyl)bis(methylene)diphenol (H2LI) and N,N′-((1,1′-(pyridine-2,6-diylbis(methylene))bis(1H-1,2,3-triazole-4,1-diyl))bis(methylene))bis(1-(pyridin-2-yl)-N-(pyridin-2-ylmethyl)methanamine) (LII) containing triazolyl, phenolate and pyridinyl groups were prepared by click reaction between diazide and terminal alkynes in the presence of catalyst CuI. Both ligands were reacted with Cu2+and Fe3+salts to give three dinuclear complexes [LICu2](BPh4)2·2DMF (1), [LII(DMF)2Cu2](ClO4)4·H2O (2) and [LII(FeCl2)2](PF6)2(3). All complexes were characterized by IR, UV-Vis spectra and element analysis. X-ray analysis revealed that the Cu2+centers in complexes 1 and 2 adopted the distorted trigonal bipyramidal geometry, and the Fe3+center in complex 3 chose an octahedral geometry. In addition, the electrochemistry of complexes 1-3 was investigated.
- You, Xiuli,Wei, Zhenhong
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p. 332 - 339
(2015/02/19)
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- Bioinspired manganese(ii) complexes with a clickable ligand for immobilisation on a solid support
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Clickable ligands like N,N′-bis((pyridin-2-yl)methyl)prop-2-yn-1- amine (L1) and N-((1-methyl-1H-imidazol-2-yl)methyl)-N-(pyridin-2- ylmethyl)prop-2-yn-1-amine (L2) have been used to synthesise a series of manganese(ii) complexes for grafting onto appropriate solid supports. These ligands mimic the 2-His-1-carboxylate facial chelation present in the active site of the manganese-dependent dioxygenase (MndD), while the alkyne side function allows grafting of the ligand onto an azido-functionalised support using click chemistry methodologies. Such synthetic analogues of the MndD crystallise in the solid state as double halide or pseudohalide-bridged dinuclear manganese(ii) complexes of the general formula [Mn2(μ-X) 2X2L2] [L = L1 with X = Cl (1), Br (2), and N3 (3); L = L2 with X = N3 (4)]. Complexes 1-4 are characterised by a weak magnetic exchange interaction between the two high-spin MnII ions through the two X- bridges (J in the range of -0.059 to +5.30 cm-1, H = -J·S Mn1·SMn2 with SMn1 = SMn2 = 5/2). A new magneto-structural correlation of superexchange bis(μ 1,1-azido)dimanganese(ii) complexes has been proposed using both structural parameters, the Mn-N-Mn bridging angle and the Mn-Nazido distance. In MeOH-EtOH solution the dimeric species are present together with few percents of mononuclear manganese(ii) complexes as evidenced by electron paramagnetic resonance (EPR) spectroscopy. Grafting the complexes onto mesoporous silica of MCM-41 type stabilises both dimers and monomers in the nanopores of the solid.
- Chaignon, Jeremy,Stiriba, Salah-Eddine,Lloret, Francisco,Yuste, Consuelo,Pilet, Guillaume,Bonneviot, Laurent,Albela, Belen,Castro, Isabel
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p. 9704 - 9713
(2014/06/23)
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- Ruthenium complexes of tripodal ligands with pyridine and triazole arms: Subtle tuning of thermal, electrochemical, and photochemical reactivity
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Electrochemical and photochemical bond-activation steps are important for a variety of chemical transformations. We present here four new complexes, [Ru(Ln)(dmso)(Cl)]PF6 (1-4), where Ln is a tripodal amine ligand with 4-n
- Weisser, Fritz,Hohloch, Stephan,Plebst, Sebastian,Schweinfurth, David,Sarkar, Biprajit
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supporting information
p. 781 - 793
(2014/01/23)
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- Bis[N-alkyl-N N-di(2-pyridylmethyl)amine]zinc(II) perchlorates display cis-facial stereochemistry in solid state and solution
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N-Alkyl-N,N-di(2-pyridylmethyl)amines are ligands commonly used by supramolecular chemists in molecular recognition and sensing applications. The metal coordination complexes of these ligands, in particular those with 2:1 (ligand:metal) molar ratio, have
- Simmons, J. Tyler,Yuan, Zhao,Daykin, Kirsten L.,Nguyen, Brian T.,Clark, Ronald J.,Shatruk, Michael,Zhu, Lei
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p. 214 - 222
(2014/05/06)
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- Integrated and passive 1,2,3-triazolyl groups in fluorescent indicators for zinc(II) ions: Thermodynamic and kinetic evaluations
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In addition to being a covalent linker in molecular conjugation chemistry, the function of a 1,2,3-triazolyl moiety resulting from the copper(I)-catalyzed azide-alkyne cycloaddition reaction as a ligand for metal ions is receiving considerable attention. In this work, we characterize the thermodynamic and kinetic effects of incorporating a 1,2,3-triazolyl group in a multidentate ligand scaffold on metal coordination in the context of fluorescent zinc(II) indicator development. Ligands L14, BrL14, and FL14 (1,4-isomers) contain the 1,4-disubstituted-1,2,3-triazolyl group that is capable of binding with zinc(II) in conjunction with a di(2-picolylamino) (DPA) moiety within a multidentate ligand scaffold. Therefore, the 1,2,3-triazolyl in the 1,4-isomers is "integrated" in chelation. The 1,5-isomers L15, BrL15, and FL15 contain 1,2,3-triazolyls that are excluded from participating in zinc(II) coordination. These 1,2,3-triazolyls are "passive linkers". Zinc(II) complexes of 2:1 (ligand/metal) stoichiometry are identified in solution using 1H NMR spectroscopy and isothermal titration calorimetry (ITC) and, in one case, characterized in the solid state. The 1:1 ligand/zinc(II) affinity ratio of L14 over L15, which is attributed to the affinity enhancement of a 1,2,3-triazolyl group to zinc(II) over that of the solvent acetonitrile, is quantified at 18 (-1.7 kcal/mol at 298 K) using an ITC experiment. Fluorescent ligands FL14 and FL15 are evaluated for their potential in zinc(II) sensing applications under pH neutral aqueous conditions. The 1,4-isomer FL14 binds zinc(II) both stronger and faster than the 1,5-isomer FL15. Visualization of free zinc(II) ion distribution in live HeLa cells is achieved using both FL14 and FL15. The superiority of FL14 in staining endogenous zinc(II) ions in live rat hippocampal slices is evident. In summation, this work is a fundamental study of 1,2,3-triazole coordination chemistry, with a demonstration of its utility in developing fluorescent indicators.
- Simmons, J. Tyler,Allen, John R.,Morris, Deborah R.,Clark, Ronald J.,Levenson, Cathy W.,Davidson, Michael W.,Zhu, Lei
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supporting information
p. 5838 - 5850
(2013/07/05)
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- Visualization of nitroxyl in living cells by a chelated copper(II) coumarin complex
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The coumarin-based probe Cu(II)-COT1 was successfully developed for the detection of HNO on the basis of the reduction reaction. In addition, highly selective "turn on" type fluorogenic behavior upon the addition of Angeli's salt (Na2N2O3) was also applied to bioimaging in A375 cells.
- Zhou, Yi,Liu, Ke,Li, Ju-Ying,Fang, Yuan,Zhao, Tian-Chu,Yao, Cheng
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supporting information; experimental part
p. 1290 - 1293
(2011/05/15)
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- Efficient and tunable synthesis of new polydentate bifunctional chelating agents using click chemistry
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Two novel bifunctional chelating agents, which are bistriazole-based polyaminocarboxylic acids, have been designed and synthesised in high yields. An elegant synthetic approach using the Cu-catalysed azide-alkyne cycloaddition has been developed. This convenient route could be employed for the synthesis of a variety of polydentate bifunctional chelators.
- Camp, Clément,Dorbes, Sandra,Picard, Claude,Benoist, Eric
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p. 1979 - 1983
(2008/09/19)
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- Highly sensitive fluorescent probes for zinc ion based on triazolyl-containing tetradentate coordination motifs
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Two new 1,2,3-triazolyl-containing N4-tetradentate ligands show nanomolar affinity for Zn2+ under physiological conditions. Furthermore, they are easily derivatizable to afford fluorescent probes suitable for sensitive Zn2+ detection
- Huang, Sha,Clark, Ronald J.,Zhu, Lei
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p. 4999 - 5002
(2008/03/28)
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- A metal-complex-tolerant CuAAC 'click' protocol exemplified through the preparation of homo- and mixed-metal-coordinated [2]rotaxanes
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A series of mono- and bis-metallated [2]rotaxanes has been prepared using a CuAAC 'click' protocol that is compatible with metal-coordinated building blocks and ligands; the methodology provides a general means for appending a metal ion or complex to an organic scaffold via Cu(i)-catalysed 'click' chemistry, even when the molecule contains redox-active or kinetically labile metals or vacant ligand sites. The Royal Society of Chemistry.
- Gonzalez Cabrera, Diego,Koivisto, Bryan D.,Leigh, David A.
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p. 4218 - 4220
(2008/03/18)
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- Self-separating homogeneous copper (I) catalysts
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A heptane-soluble polyisobutylene (PIB)-Cu(I) catalyst was synthesized in a heptane/ethanol latent biphasic solvent system. The addition of water to this initially homogeneous solution produced a biphasic solvent system that separates the PIB-Cu(I) complex from the reaction mixture as a heptane solution. This heptane solution can be used in reactions such as "click" chemistry where the PIB-Cu(I) catalyst is again separated from the reaction mixture as a heptane solution with the products of the reaction mixture being separated in the ethanol phase of the latent biphasic solvent system. This PIB-Cu(I) complex can also be used in an atom transfer radical polymerization (ATRP) of polystyrene. Using the differential solubilities of PIB and polystyrene in heptane, a PIB-complexed Cu(I) species can be separated and recycled for multiple uses in further polymerization reactions with good control over molecular weight and molecular weight distribution. Copyright
- Bergbreiter, David E.,Hamilton, Patrick N.,Koshti, Nirmal M.
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p. 10666 - 10667
(2008/03/11)
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