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Synthesis and characterisation of bismacrocyclic DO3A-amide derivatives: an approach towards metal-responsive PARACEST agents

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Cakić,  N
Department High-Field Magnetic Resonance, Max Planck Institute for Biological Cybernetics, Max Planck Society;
Max Planck Institute for Biological Cybernetics, Max Planck Society;

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Angelovski,  G
Research Group MR Neuroimaging Agents, Max Planck Institute for Biological Cybernetics, Max Planck Society;
Max Planck Institute for Biological Cybernetics, Max Planck Society;

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Cakić, N., Verbic, T., Jelić, T., Platas-Iglesias, C., & Angelovski, G. (2016). Synthesis and characterisation of bismacrocyclic DO3A-amide derivatives: an approach towards metal-responsive PARACEST agents. Dalton Transactions, 45(15), 6555-6565. doi:10.1039/C5DT04625D.


Cite as: http://hdl.handle.net/21.11116/0000-0000-79F6-3
Abstract
Three new bismacrocyclic Ln3+ chelates consisting of triamide derivatives of cyclen with glycine, methyl and tert-butyl substituents (L1-3, respectively) linked to an acyclic EGTA-derived calcium chelator were synthesised as potential MRI contrast agents (EGTA – ethylene glycol-bis(2-aminoethylether)-N,N,N′,N′-tetraacetic acid). Eu3+ and Yb3+ complexes of L1-3 were investigated as chemical exchange saturation transfer (CEST) agents. Moderate to minor CEST effects were observed for Eu2L1, Eu2L2 and Yb2L2 complexes in absence of Ca2+, with negligible changes upon addition of this metal ion. Luminescence steady-state emission and lifetime experiments did not reveal any changes in the coordination environment of the complexes, while the number of inner-sphere water molecules remained constant in absence and presence of Ca2+. The protonation constants of Eu2L1 and Eu2L2 and stability constants of their complexes with Ca2+, Mg2+ and Zn2+ were determined by means of potentiometric titrations. The results show that the charge of the complex dramatically affects the protonation constants of the EGTA-binding unit. The stability constants of the complexes formed with Ca2+, Mg2+ and Zn2+ are several orders of magnitude lower than those of EGTA. These findings indicate that the nature of Ln3+ chelates and their charge are the main reasons for the observed results and weaker response of these EGTA-derived triamide derivatives compared to their tricarboxylate analogues.