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Highly Stable and Inert Complexation of Indium(III) by Reinforced Cyclam Dipicolinate and a Bifunctional Derivative for Bead Encoding in Mass Cytometry
Author(s) -
Grenier Laura,
Beyler Maryline,
PlatasIglesias Carlos,
Closson Taunia,
Gómez David Esteban,
Seferos Dwight S.,
Liu Peng,
Ornatsky Olga I.,
Baranov Vladimir,
Tripier Raphaël
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201903969
Subject(s) - bifunctional , cyclam , chemistry , dota , diethylenetriamine , mass cytometry , chelation , inert , polystyrene , covalent bond , combinatorial chemistry , polymer chemistry , nuclear chemistry , metal , polymer , organic chemistry , catalysis , biochemistry , gene , phenotype
H 2 cb‐te2pa, a cross‐bridged cyclam functionalized by two picolinate arms, was used for the formation of an incredible inert In III chelate. The inertness of the complex was evaluated by UV/Vis experiments in several competitive media and was highlighted by the comparison with [In(dota)] − and [In(dtpa)] 2− (H 4 dota = 1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid, H 5 dtpa = diethylenetriamine pentaacetic acid), which are currently used in biological applications. For the first time, a bifunctional analogue of H 2 cb‐te2pa was prepared by C‐functionalization to keep its coordination properties intact. However, this strategy leads to the formation of two diastereoisomers as evidenced and studied by NMR experiments and DFT calculations. Kinetic studies proved nevertheless that both isomers of the complex are equally inert. They were therefore used without distinction for their covalent grafting on polystyrene beads. The so‐called metal‐encoded beads were tested for imaging mass cytometry. The detection of 115 In allows the generation of images with high quality, proving the great potential of the bifunctional [In(cb‐te2pa)] + derivatives for single‐cell analysis by mass cytometry.