- Synthesis and electrochemical study of a new chiral tris- catecholamide analogue of enterobactin
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The comparison of siderophore complex redox potentials with those of physiological reductants may aid in the clarification of the mechanism of iron metabolism. In this paper, a new chiral tris-catecholamide compound N,N',N''-tris-(2,3-dihydroxybenzoyl)-1,
- Cheraiti,Brik,Gaudemer,Kunesh
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- Triamidetriamine bearing macrobicyclic and macrotricyclic ligands: Potential applications in the development of copper-64 radiopharmaceuticals
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A versatile and straightforward synthetic approach is described for the preparation of triamide bearing analogues of sarcophagine hexaazamacrobicyclic cage ligands without the need for a templating metal ion. Reaction of 1,1,1-tris(aminoethyl)ethane (tame) with 3 equiv of 2-chloroacetyl chloride, yields the tris(α-chloroamide) synthetic intermediate 6, which when treated with either 1,1,1-tris(aminoethyl)ethane or 1,4,7-triazacyclononane furnished two novel triamidetriamine cryptand ligands (7 and 8 respectively). The Co(III) and Cu(II) complexes of cryptand 7 were prepared; however, cryptand 8 could not be metalated. The cryptands and the Co(III) complex 9 have been characterized by elemental analysis, 1H and 13C NMR spectroscopy, and X-ray crystallography. These studies confirm that the Co(III) complex 9 adopts an octahedral geometry with three facial deprotonated amido-donors and three facial amine donor groups. The Cu(II) complex 10 was characterized by elemental analysis, single crystal X-ray crystallography, cyclic voltammetry, and UV-visible absorption spectroscopy. In contrast to the Co(III) complex (9), the Cu(II) center adopts a square planar coordination geometry, with two amine and two deprotonated amido donor groups. Compound 10 exhibited a quasi-reversible, one-electron oxidation, which is assigned to the Cu2+/3+ redox couple. These cryptands represent interesting ligands for radiopharmaceutical applications, and 7 has been labeled with 64Cu to give 64Cu-10. This complex showed good stability when subjected to L-cysteine challenge whereas low levels of decomplexation were evident in the presence of L-histidine.
- Tan, Kel Vin,Pellegrini, Paul A.,Skelton, Brian W.,Hogan, Conor F.,Greguric, Ivan,Barnard, Peter J.
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supporting information
p. 468 - 477
(2014/01/23)
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- Synthesis of tris(N,N-dimethylthiocarbamoyl)-1,1,1-tris-(methylaminomethyl) ethane and its application as ligand for Pauson-Khand reaction
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Tris(N,N-dimethylthiocarbamoyl)-1,1,1-tris(methylaminomethyl)ethane ligand was prepared from very cheap and commercially availably tris-1,1,1- (hydroxymethyl)ethane in five steps and applied as ligand in 1:1 coordination to cobalt in a catalytic Pauson-Kh
- Petrovski, Zeljko,Romao, Carlos C.,Afonso, Carlos A. M.
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experimental part
p. 2761 - 2767
(2009/04/11)
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- Highly selective ratiometric fluorescence determination of Ag+ based on a molecular motif with one pyrene and two adenine moieties
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(Chemical Equation Presented) A highly selective ratiometric fluorescence sensor for Ag+ was developed with a molecular motif containing one pyrene and two adenine moieties.
- Liu, Lei,Zhang, Deqing,Zhang, Guanxin,Xiang, Junfeng,Zhu, Daoben
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supporting information; scheme or table
p. 2271 - 2274
(2009/05/26)
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- Peptide-based compounds
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The invention relates to new peptide-based compounds for use as diagnostic imaging agents or as therapeutic agents wherein the agents comprise a targeting vector which binds to receptors associated with integrin receptors.
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- Azetidines as intermediates in polyamine synthesis - Structure and reactions of a quadridentate ligand incorporating an azetidine ring
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Reaction of the tris(benzene sulfonate) of 1,1,1-tris-(hydroxymethyl)ethane with neat 1,2-ethanediamine under relatively mild conditions leads to formation in good yield (60%) of a quadridentate amine incorporating a four-membered, azetidine ring, the nature of the tetramine being established by determination of the crystal structures of two of its cobalt(III) complexes and the reactivity of the azetidine ring being explored in further reactions with 1,2-ethanediamine.
- Harrowfield, Jack M.,Gyu, Hwan Jang,Kim, Yang,Thuery, Pierre,Vicens, Jacques
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p. 1241 - 1243
(2007/10/03)
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- Synthesis of the smallest tris-(catecholamide) siderophore analogue
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The tris-(catecholamide) (H6L) (8) was synthesised in six steps and characterized. This is the smallest analogue of naturally occurring siderophores structurally related to an approved enterobactin and protochelin model, known up to now.
- Cheraiti,Brik,Kunesch,Gaudemer
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p. 149 - 152
(2007/10/03)
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