A Bispidol Chelator with a Phosphonate Pendant Arm: Synthesis, Cu(II) Complexation, and (64)Cu Labeling - Archive ouverte HAL Access content directly
Journal Articles Inorganic Chemistry Year : 2017

A Bispidol Chelator with a Phosphonate Pendant Arm: Synthesis, Cu(II) Complexation, and (64)Cu Labeling

(1) , (1) , (1) , (2, 3) , (4) , (4) , (1) , (1)
1
2
3
4

Abstract

Here we present the synthesis and characterization of a new bispidine (3,7-diazabicyclo[3.3.1]nonane) ligand with N-methanephosphonate substituents (L2). Its physicochemical properties in water, as well as those of the corresponding Cu(II) and Zn(II) complexes, have been evaluated by using UV-visible absorption spectroscopy, potentiometry, (1)H and (31)P NMR, and cyclic voltammetry. Radiolabeling experiments with (64)Cu(II) have been carried out, showing excellent radiolabeling properties. Quantitative complexation was achieved within 60 min under stoichiometric conditions, at room temperature and in the nanomolar concentration range. It was also demonstrated that the complexation occurred below pH 2. Properties have been compared to those of the analogue bispidol bearing a N-methanecarboxylate substituent (L1). Although both systems meet the required criteria to be used as new chelator for (64/67)Cu in terms of the kinetics of formation, thermodynamic stability, selectivity for Cu(II), and kinetic inertness regarding redox- or acid-assisted decomplexation processes, substitution of the carboxylic acid function by the phosphonic moiety is responsible for a significant increase in the thermodynamic stability of the Cu(II) complex (+2 log units for pCu) and also leads to an increase in the radiochemical yields with (64)Cu(II) which is quantitative for L2.
Fichier principal
Vignette du fichier
IC phosphonate_revised3 _ic-2017-01731e.pdf (1.33 Mo) Télécharger le fichier
Origin : Files produced by the author(s)
Loading...

Dates and versions

hal-01617953 , version 1 (01-12-2017)

Identifiers

Cite

Raphaël Gillet, Amandine Roux, Jérémy Brandel, Sandrine Huclier-Markai, Franck Camerel, et al.. A Bispidol Chelator with a Phosphonate Pendant Arm: Synthesis, Cu(II) Complexation, and (64)Cu Labeling. Inorganic Chemistry, 2017, 56 (19), pp.11738-11752. ⟨10.1021/acs.inorgchem.7b01731⟩. ⟨hal-01617953⟩
361 View
249 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More