65604-89-9Relevant articles and documents
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.
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 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.
