65604-89-9Relevant academic research and scientific papers
A novel strategy for the design of 8-hydroxyquinolinate-based lanthanide bioprobes that emit in the near infrared range
Comby, Steve,Imbert, Daniel,Vandevyver, Caroline,Buenzli, Jean-Claude G.
, p. 936 - 944 (2007)
A new polydentate tripodal ligand T2soxMe was synthesized to take advantage of the chelating effect of tridentate 8-hydroxyquinolinate sub-units. Potentiometric and spectrophotometric titrations reveal seven pKa values of between 3.7 and 10.2. In water, the use of T2soxMe leads to thermodynamically stable and soluble LnIII complexes at physiological pH, with conditional stability constants in the range log β11= 7.8-8.6. The chelates are resistant toward hydrolysis and show interesting photophysical proper ties, particularly in the near infrared (NIR) range. The emission lifetimes of the NdIII and YbIII complexes recorded in D2O and H2O suggest the absence of water molecules in the first coordination sphere of the metal ions. Moreover, the low energy of the triplet state allows efficient energy transfer from the ligand to the metal ions: in waterat pH 7.4, the sensitization efficacy of the NIR luminescence reaches 75 and ≈ 100% for NdIII and YbIII, respectively, leading to overall quantum yields of 0.027 and 0.13%; Er III luminescence is also detected. According to the WST-1 test, the YbIII podate at concentrations of up to 250 μM does not display sizeable cytotoxicity for Jurkat cells after 24 h of incubation. Finally, the same podate is shown to couple to human serum albumin, leading to an increase of 50% in the NIR-luminescence intensity.
Synthesis and Complexation Properties of a New Tetraazatricarboxylate Ligand
Geraldes, Carlos F. G. C.,Bruecher, Erno,Cortes, Sergio,Koenig, Seymour H.,Sherry, A. Dean
, p. 2517 - 2522 (1992)
A non-cyclic tetraazatricarboxylate ligand tris(4-carboxy-3-methyl-3-azabutyl)amine (H3L), derived from tris(2-aminoethyl)amine, was synthesised and purified.Its macroscopic and microscopic protonation behaviour was studied using potentiometry and proton
Preliminary evaluation of the cytotoxicity of a series of tris-2-aminoethylamine (Tren) based hexadentate heterocyclic donor agents
Torti, Suzy V.,Ma, Rong,Venditto, Vincent J.,Torti, Frank M.,Planalp, Roy P.,Brechbiel, Martin W.
, p. 5961 - 5967 (2005)
Tachpyridine is a cytotoxic metal chelator with potential anti-tumor activity. The synthesis and evaluation of a set of derivatives of the related hexadentate heterocyclic donor agents tris-2-aminoethylamine (tren) and tris[N-(2-pyridylmethylene)-2-aminoe
The Chloroazaphosphatrane Motif for Halogen Bonding in Solution
Li, Chunyang,Manick, Anne-Doriane,Yang, Jian,Givaudan, David,Biletskyi, Bohdan,Michaud-Chevalier, Sabine,Dutasta, Jean-Pierre,Hérault, Damien,Bugaut, Xavier,Chatelet, Bastien,Martinez, Alexandre
supporting information, p. 11964 - 11973 (2021/08/20)
Chloroazaphosphatranes, the corresponding halogenophosphonium cations of the Verkade superbases, were evaluated as a new motif for halogen bonding (XB). Their modulable synthesis allowed for synthetizing chloroazaphosphatranes with various substituents on the nitrogen atoms. The binding constants determined from NMR titration experiments for Cl-, Br-, I-, AcO-, and CN- anions are comparable to those obtained with conventional iodine-based monodentate XB receptors. Remarkably, the protonated azaphosphatrane counterparts display no affinity for anions under the same conditions. The strength of the XB interaction is, to some extent, related to the basicity of the corresponding Verkade superbase. The halogen bonding abilities of this new class of halogen donor motif were also revealed by the Δδ(31P) NMR shift observed in CD2Cl2 solution in the presence of triethylphosphine oxide (TEPO). Thus, chloroazaphosphatranes constitute a new class of halogen bond donors, expanding the repertory of XB motifs mainly based on CAr-I bonds.
The influence of linkages between 1-hydroxy-2(1H)-pyridinone coordinating groups and a tris(2-aminoethyl)amine core in a novel series of synthetic hexadentate iron(III) chelators on antimicrobial activity
Brandel, Jérémy,Dover, Lynn G.,Hubscher, Véronique,Hunter, Michael,Tétard, David,Wang, Shuning,Workman, David G.
, (2019/12/24)
Resistance of pathogens to antimicrobials is a major current healthcare concern. In a series of linked studies, we have investigated synthetic iron chelators based on hydroxy-pyridinone ligands as novel bacteriostatic agents. Herein we describe our synthesis of several useful building blocks based on the 1-hydroxy-2(1H)-pyridinone moiety, including a novel formyl derivative, which were combined with a tris(2-aminoethyl)amine core to obtain a series of new high-affinity hexadentate Fe(III) chelators. The design principle examined by this series is the size and flexibility of the linker between the core and the metal ligands. Measurement of the pKa and stability constants (Fe3+ and Cu2+) of representative coordinating groups was performed to help rationalise the biological activity of the chelators. The novel chelators were tested on a panel of representative microorganisms with some effectively inhibiting microbial growth. We demonstrate that the nature and position of the linker between the hydroxypyridinone and the tris(2-aminoethyl)amine core has considerable impact upon microbial growth inhibition and that both amide or amine linkages can give efficacious chelators.
Azaphosphatranes as structurally tunable organocatalysts for carbonate synthesis from CO2 and epoxides
Chatelet, Bastien,Joucla, Lionel,Dutasta, Jean-Pierre,Martinez, Alexandre,Szeto, Kai C.,Dufaud, Veronique
supporting information, p. 5348 - 5351 (2013/06/05)
Three azaphosphatranes were used as organocatalysts for the synthesis of cyclic carbonates from CO2 and epoxides. They proved to be efficient single-component, metal-free catalysts for the reaction of simple or activated epoxides (styrene oxide, epichlorohydrin, glycidyl methyl ether) with CO 2 under mild reaction conditions, displaying high stability and productivity over several days of reaction. Substitution patterns on the catalyst were shown to affect activity and stability. Kinetic analysis allowed investigation of the reaction mechanism.
Large oligosaccharide-based glycodendrimers.
Turnbull, W Bruce,Kalovidouris, Stacey A,Stoddart, J Fraser
, p. 2988 - 3000 (2007/10/03)
Carbohydrate-based dendritic structures composed of 21 and 27 monosaccharide residues have been synthesized in a convergent manner from trisaccharide building blocks. The oligosaccharide AB2 monomers are based on a maltosyl beta(1-->6)galactose structure,
Covalently supported porphyrins as ligands for the preparation of heme a3/CuB binuclear active site analogues of heme-copper terminal oxidases and metallation under mild conditions
Baeg, Jin-Ook
, p. 571 - 572 (2007/10/03)
New covalently supported binucleating porphyrins have been prepared as potential structural and/or functional ligands for the iron-copper (heme a3/CuB) active sites of heme-copper oxidases, and the introduction of iron and copper into one porphyrin under mild reaction conditions has been developed.
Synthesis and interconversions of azagermatranes
Wan, Yanjian,Verkade, John G.
, p. 79 - 81 (2008/10/08)
The syntheses of the first examples of the title compounds, namely, ZGe(NRCH2CH2)3N (4, R = H, Z = Me; 5, R = Me, Z = Me; 6, R = H, Z = t-Bu; 7, R = Me, Z = t-Bu; 8, R = Me, Z = NMe2) are reported. Syntheses of the new compounds MeGe(NMe2)3 and t-BuGe(NMe2)3 and an improved synthesis of Ge(NMe2)4 are also recorded. The azagermatranes 5 and 7 are transformed to 4 and 6, respectively, in the presence of (H2NCH2CH2)3N. This reaction was not found to be reversible, however. Azagermatranes 4 or 5 and 6 or 7 in the presence of (HOCH2CH2)3N easily react to give MeGe(OCH2CH2)3N and t-BuGe(OCH2CH2)3N, respectively. Because of steric factors, one or more of compounds 6-8 may display weakened transannular Ge←N bonding or even an absence of this bonding.
