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    Picolinate-Containing Macrocyclic Mn2+ Complexes as Potential MRI Contrast Agents
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    † Departamento de Química Fundamental, Facultade de Ciencias, Universidade da Coruña, Campus da Zapateira-Rúa da Fraga 10, 15008 A Coruña, Spain
    ‡ Dipartimento di Scienze e Innovazione Tecnologica, Università del Piemonte Orientale “Amedeo Avogadro”, Viale T. Michel 11, 15121 Alessandria, Italy
    § Université de Bretagne Occidentale, UMR-CNRS 6521, UFR des Sciences et Techniques, 6 avenue Victor le Gorgeu, C.S. 93837, 29238 BREST Cedex 3, France
    ∥ Department of Inorganic and Analytical Chemistry, Faculty of Science and Technology, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary
    *E-mail: [email protected]
    *E-mail: [email protected]
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    Inorganic Chemistry

    Cite this: Inorg. Chem. 2014, 53, 10, 5136–5149
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    https://doi.org/10.1021/ic500231z
    Published April 28, 2014
    Copyright © 2014 American Chemical Society
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    Abstract

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    We report the synthesis of the ligand Hnompa (6-((1,4,7-triazacyclononan-1-yl)methyl)picolinic acid) and a detailed characterization of the Mn2+ complexes formed by this ligand and the related ligands Hdompa (6-((1,4,7,10-tetraazacyclododecan-1-yl)methyl)picolinic acid) and Htempa (6-((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)picolinic acid). These ligands form thermodynamically stable complexes in aqueous solution with stability constants of logKMnL = 10.28(1) (nompa), 14.48(1) (dompa), and 12.53(1) (tempa). A detailed study of the dissociation kinetics of these Mn2+ complexes indicates that the decomplexation reaction at about neutral pH occurs mainly following a spontaneous dissociation mechanism. The X-ray structure of [Mn2(nompa)2(H2O)2](ClO4)2 shows that the Mn2+ ion is seven-coordinate in the solid state, being directly bound to five donor atoms of the ligand, the oxygen atom of a coordinated water molecule and an oxygen atom of a neighboring nompa– ligand acting as a bridging bidentate carboxylate group (μ–η1-carboxylate). Nuclear magnetic relaxation dispersion (1H NMRD) profiles and 17O NMR chemical shifts and transverse relaxation rates of aqueous solutions of [Mn(nompa)]+ indicate that the Mn2+ ion is six-coordinate in solution by the pentadentate ligand and one inner-sphere water molecule. The analysis of the 1H NMRD and 17O NMR data provides a very high water exchange rate of the inner-sphere water molecule (kex298 = 2.8 × 109 s–1) and an unusually high value of the 17O hyperfine coupling constant of the coordinated water molecule (AO/ℏ = 73.3 ± 0.6 rad s–1). DFT calculations performed on the [Mn(nompa)(H2O)]+·2H2O system (TPSSh model) provide a AO/ℏ value in excellent agreement with the one obtained experimentally.

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    Supporting Information

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    X-ray crystal structure of [Mn2(nompa)2(H2O)2](ClO4)2 in cif format, dependence of the pseudo-first-order rate constants on Cu2+ ion concentration and the nature and the concentration of the buffers applied in the study, 1H NMR spectra and chemical shifts of Htempa recorded as a function of pH, temperature and pH dependence of r1p for [Mn(nompa)(H2O)]+, equations used for the analysis of the 1H NMRD and 17O NMR data, optimized Cartesian coordinates obtained with DFT calculations, potentiometric titration curves, absorption spectra of the Cu2+–dompa system, pH-potentiometric titration curve of the [Cu(dompa)]+ complex and additional pseudo-first-order rate constants obtained for the [Mn(nompa)]+ complex (pseudo-first-order rate as a function of the nature and the concentration of the buffers applied in the study). This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: Inorg. Chem. 2014, 53, 10, 5136–5149
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    https://doi.org/10.1021/ic500231z
    Published April 28, 2014
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