69146-58-3Relevant articles and documents
Total synthesis and structure revision of mirubactin, and its iron binding activity
Kishimoto, Shinji,Nishimura, Shinichi,Kakeya, Hideaki
, p. 1303 - 1305 (2015)
Dechloro-chlorocatechelin A (3), a deschloro-derivative of a microbial siderophore chlorocatechelin A (2), was synthesized from 2,3-dihydroxybenzoic acid, D-arginine, and 1-benzyl Dglutamate. The spectral data were unambiguously identical with those of mi
Optimization of Artificial Siderophores as 68Ga-Complexed PET Tracers for in Vivo Imaging of Bacterial Infections
Peukert, Carsten,Langer, Laura N. B.,Wegener, Sophie M.,Tutov, Anna,Bankstahl, Jens P.,Karge, Bianka,Bengel, Frank M.,Ross, Tobias L.,Br?nstrup, Mark
, p. 12359 - 12378 (2021/09/02)
The diagnosis of bacterial infections at deep body sites benefits from noninvasive imaging of molecular probes that can be traced by positron emission tomography (PET). We specifically labeled bacteria by targeting their iron transport system with artificial siderophores. The cyclen-based probes contain different binding sites for iron and the PET nuclide gallium-68. A panel of 11 siderophores with different iron coordination numbers and geometries was synthesized in up to 8 steps, and candidates with the best siderophore potential were selected by a growth recovery assay. The probes [68Ga]7 and [68Ga]15 were found to be suitable for PET imaging based on their radiochemical yield, radiochemical purity, and complex stability in vitro and in vivo. Both showed significant uptake in mice infected with Escherichia coli and were able to discern infection from lipopolysaccharide-triggered, sterile inflammation. The study qualifies cyclen-based artificial siderophores as readily accessible scaffolds for the in vivo imaging of bacteria.
PEPTOID-BASED CHELATING LIGANDS FOR SELECTIVE METAL CHELATION
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, (2020/04/29)
The present disclosure provides peptoid-based chelating ligands, corresponding cyclic peptoids, and methods of making thereof. Functional groups may be tailored for high metal binding affinity and selectivity. The side chains of a cyclic peptoid according to the present disclosure may be selected based on, for example, high affinity for actinide or other metal ions, selectivity for actinide or other metal ions, the ability to recover a metal once it is bound to the peptoid, and whether the overall peptoid should be hydrophobic or hydrophilic. Unlike siderophores, peptoid-based chelating ligands of the present disclosure are not readily hydrolyzed under physiological conditions. Therefore, peptoid-based chelating ligands may be, for example, used to treat actinide (e.g., iron and lead) poisoning in vivo. Moreover, peptoid-based chelating ligands of the present disclosure may be used for medical imaging, chelation therapy, drug delivery, and separation technologies, for example.
Peptoid-based siderophore mimics as dinuclear Fe3+chelators
Costabile, Chiara,D'Amato, Assunta,De Riccardis, Francesco,Della Sala, Giorgio,Ghosh, Pritam,Izzo, Irene,Maayan, Galia
, p. 6020 - 6029 (2020/05/25)
A practical synthesis of preorganized tripodal enterobactin/corynebactin-type ligands (consisting of aC3-symmetric macrocyclic peptoid core, three catecholamide coordinating units, and C2, C4, and C6spacers) is
ANTIBACTERIAL SIDEROMYCINS
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, (2016/03/13)
A compound, comprising: an Fe(III)-binding and/or Fe(III)-bound siderophore; one or more optional linker covalently bound to the siderophore; and daptomycin covalently bound to the linker, or, if no linker is present, then to the siderophore; or pharmaceu
Catechol-based matrix metalloproteinase inhibitors with additional antioxidative activity
Tauro, Marilena,Laghezza, Antonio,Loiodice, Fulvio,Piemontese, Luca,Caradonna, Alessia,Capelli, Davide,Montanari, Roberta,Pochetti, Giorgio,Di Pizio, Antonella,Agamennone, Mariangela,Campestre, Cristina,Tortorella, Paolo
, p. 25 - 37 (2016/12/22)
New catechol-containing chemical entities have been investigated as matrix metalloproteinase inhibitors as well as antioxidant molecules. The combination of the two properties could represent a useful feature due to the potential application in all the pa
Symmetrical 1,3-dicarbonyl biscatecholamide ligands as sequestering agents for uranyl decorporation
Zhang, Qingchun,Jin, Bo,Peng, Rufang,Lei, Shan,Chu, Shijin
, p. 417 - 423 (2015/02/05)
The synthesis of a series of new symmetrical 1,3-dicarbonyl biscatecholamide ligands CH2[COX(CH2)nCAM; X = O, NH; n = 2, 3, 4]2 [CAM = 2,3-Ph(OH)2CONH] is presented. 1H NMR, 13C
EDTA and DTPA modified ligands as sequestering agents for uranyl decorporation
Leydier, Antoine,Lin, Yi,Arrachart, Guilhem,Turgis, Rapha?l,Lecerclé, Delphine,Favre-Reguillon, Alain,Taran, Frédéric,Lemaire, Marc,Pellet-Rostaing, Stéphane
, p. 1163 - 1170 (2012/02/15)
Synthesis of modified EDTA and DTPA ligands and determination of their binding affinities for the uranyl cation are described. Thanks to a screening method, based on a chromophoric complex displacement procedure, chelating properties were studied in aqueous media under various pH conditions for evaluation of their in vivo uranyl-removal efficacy. Each ligand showed a more or less pronounced affinity for uranium. Specific ligands based on EDTA or DTPA analogues containing sulfocatecholamide (CAMS) were found to exhibit a significant affinity towards uranyl ion in acidic, neutral or basic conditions.
Sequestering agent for uranyl chelation: New binaphtyl ligands
Leydier, Antoine,Lecerclé, Delphine,Pellet-Rostaing, Stéphane,Favre-Reguillon, Alain,Taran, Frédéric,Lemaire, Marc
experimental part, p. 3973 - 3977 (2011/09/12)
The synthesis of phosphonate, sulfocatecholamide (CAMS) and hydroxypyridinone (HOPO) binaphtyl ligands is presented. Their binding abilities for uranyl cation were determined by UV spectrophotometry in aqueous media versus pH. These titrations showed that
Synthesis and investigation of a chiral enterobactin analogue based on a macrocyclic peptide scaffold
Pinter, Aron,Haberhauer, Gebhard
scheme or table, p. 11061 - 11068 (2009/11/30)
A chiral C3-symmetric enterobactin analogue (1) has been synthesized by attachment of three 2,3-dihydroxybenzoyl units to a chiral oxazole-containing macrocyclic peptide scaffold. Complex formation kinetics and stoichiometry with various metal ions were investigated by spectrophotometric methods. In the cases of AlIII, InIII and FeIII complexes, UV absorption and CD kinetics showed nonlinearity, which results from slow conformational changes of the octahedral complexes. Virtual binding constants were determined from UV absorption data and showed selective binding of GaIII in preference to FeIII, by two orders of magnitude. CD spectroscopy revealed highly diastereoselective binding of Al III, GaIII, InIII, FeIII and Ge IV ions at room temperature, corresponding to the helical chirality opposite to that of the analogous enterobactin complexes. Ab initio calculations confirmed the energetic stabilization of the A isomers relative to the A isomers.
