Preparation of HOPO-containing lariate ethers based on the diaza-18-crown-6 scaffold-Reference-Cited by-同舟云学术

Preparation of HOPO-containing lariate ethers based on the diaza-18-crown-6 scaffold

Published:2024-03-14 Issue:7 Volume:78 Page:4157-4164
ISSN:0366-6352
Container-title:Chemical Papers
language:en
Short-container-title:Chem. Pap.

Author:

Paßler Florian,Belke Linda,Reissig Falco,Kopka Klaus,Mamat Constantin^ORCID

Abstract

AbstractCyclic and acyclic ligands containing the hydroxypyridinone (HOPO) moiety as donor group are known as strong coordinating compounds for a wide variety of metal ions. Based on the diaza-crown[18]ether Kryptofix K22, five different tendentate ligands were prepared using 1,2-HOPO, 1,2,3-HOPO and 2,3-Me-HOPO as additional binding moieties. The diaza-crown ether basic skeleton was furnished with two primary amine functions and subsequently reacted with the respective HOPO acids or the HOPO acid chlorides to obtain the desired HOPO derivatives in two synthesis steps after final deprotection. All compounds were evidenced by NMR and MS analyses.

Funder

Helmholtz-Zentrum Dresden - Rossendorf e. V.

Publisher

Springer Science and Business Media LLC

Link

https://link.springer.com/content/pdf/10.1007/s11696-024-03376-8.pdf

Reference28 articles.

1. Abergel RJ, Raymond KN (2006) Synthesis and thermodynamic evaluation of mixed hexadentate linear iron chelators containing hydroxypyridinone and terephthalamide units. Inorg Chem 45:3622–3631. https://doi.org/10.1021/ic052111a

2. Carter KP, Deblonde GJ-P, Lohrey TD, Bailey TA, An DD, Shield KM, Lukens W Jr, Abergel RJ (2020) Developing scandium and yttrium coordination chemistry to advance theranostic radiopharmaceuticals. Commun Chem 3:61. https://doi.org/10.1038/s42004-020-0307-0

3. Chaves S, Mendonça AC, Marques SM, Prata MI, Santos AC, Martins AF, Geraldes CFGC, Santos MA (2011) A gallium complex with a new tripodal tris-hydroxypyridinone for potential nuclear diagnostic imaging: solution and in vivo studies of 67Ga-labeled species. J Inorg Biochem 105:31–38. https://doi.org/10.1016/j.jinorgbio.2010.09.012

4. Clevette DJ, Lyster DM, Nelson WO, Rihela T, Webb GA, Orvig C (1990) Solution chemistry of gallium and indium 3-hydroxy-4-pyridinone complexes in vitro and in vivo. Inorg Chem 29:667–672. https://doi.org/10.1021/ic00329a021

5. Datta A, Raymond KN (2009) Gd−hydroxypyridinone (HOPO)-based high-relaxivity magnetic resonance imaging (MRI) contrast agents. Acc Chem Res 42:938–947. https://doi.org/10.1021/ar800250h