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Collect. Czech. Chem. Commun. 2005, 70, 1909-1942
https://doi.org/10.1135/cccc20051909

Thermodynamic and Kinetic Studies of Lanthanide(III) Complexes with H5do3ap (1,4,7,10-Tetraazacyclododecane-1,4,7-triacetic-10-(methylphosphonic Acid)), a Monophosphonate Analogue of H4dota

Petr Táborskýa, Přemysl Lubala,*, Josef Havela, Jan Kotekb, Petr Hermannb,* and Ivan Lukešb

a Department of Analytical Chemistry, Masaryk University, Kotlářská 2, 611 37 Brno, Czech Republic
b Department of Inorganic Chemistry, Charles University, Hlavova 2030, 128 40 Prague 2, Czech Republic

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  • Baranyai Zsolt, Tircsó Gyula, Rösch Frank: The Use of the Macrocyclic Chelator DOTA in Radiochemical Separations. Eur J Inorg Chem 2020, 2020, 36. <https://doi.org/10.1002/ejic.201900706>
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  • Huclier-Markai S., Alliot C., Sebti J., Brunel B., Aupiais J.: A comparative thermodynamic study of the formation of scandium complexes with DTPA and DOTA. RSC Adv. 2015, 5, 99606. <https://doi.org/10.1039/C5RA16736A>
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  • Lima Luís M. P., Delgado Rita, Hermann Petr, Ševčík Radek, Lubal Přemysl, Carvalho Henrique F., Martins André F., Tóth Éva, Geraldes Carlos F. G. C.: Tris(phosphonomethyl)cyclen Derivatives: Thermodynamic Stability, Kinetics, Solution Structure, and Relaxivity of Ln3+ Complexes. Eur J Inorg Chem 2012, 2012, 2548. <https://doi.org/10.1002/ejic.201101335>
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  • Amatori Stefano, Ambrosi Gianluca, Fanelli Mirco, Formica Mauro, Fusi Vieri, Giorgi Luca, Macedi Eleonora, Micheloni Mauro, Paoli Paola, Pontellini Roberto, Rossi Patrizia: Synthesis, Basicity, Structural Characterization, and Biochemical Properties of Two [(3-Hydroxy-4-pyron-2-yl)methyl]amine Derivatives Showing Antineoplastic Features. J. Org. Chem. 2012, 77, 2207. <https://doi.org/10.1021/jo202270j>
  • Lima Luís M. P., Delgado Rita, Plutnar Jan, Hermann Petr, Kotek Jan: A New Tris(phosphonomethyl) Monoacetic Acid Cyclam Derivative: Synthesis, Acid‐Base and Metal Complexation Studies. Eur J Inorg Chem 2011, 2011, 527. <https://doi.org/10.1002/ejic.201000919>
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  • Drahoš Bohuslav, Kubíček Vojtěch, Bonnet Célia S., Hermann Petr, Lukeš Ivan, Tóth Éva: Dissociation kinetics of Mn2+ complexes of NOTA and DOTA. Dalton Trans 2011, 40, 1945. <https://doi.org/10.1039/c0dt01328e>
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  • Svobodová I., Piskula Z., Lubal P., Lis S., Hermann P.: Dissociation kinetics study of Ce(III) complexes with H8dotp (H8dotp = 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis (methylphosphonic acid)). Journal of Alloys and Compounds 2008, 451, 42. <https://doi.org/10.1016/j.jallcom.2007.04.052>
  • Försterová Michaela, Jandurová Zuzana, Marques Fernanda, Gano Lurdes, Lubal Přemysl, Vaněk Jakub, Hermann Petr, Santos Isabel: Chemical and biological evaluation of 153Sm and 166Ho complexes of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methylphosphonic acid monoethylester) (H4dotpOEt). Journal of Inorganic Biochemistry 2008, 102, 1531. <https://doi.org/10.1016/j.jinorgbio.2008.02.002>
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  • Hermann Petr, Kotek Jan, Kubíček Vojtěch, Lukeš Ivan: Gadolinium(iii) complexes as MRI contrast agents: ligand design and properties of the complexes. Dalton Trans. 2008, 3027. <https://doi.org/10.1039/b719704g>
  • Kubíček Vojtěch, Kotek Jan, Hermann Petr, Lukeš Ivan: Aminoalkylbis(phosphonates): Their Complexation Properties in Solution and in the Solid State. Eur J Inorg Chem 2007, 2007, 333. <https://doi.org/10.1002/ejic.200600615>
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  • Mamedov Ilgar, Mishra Anurag, Angelovski Goran, Mayer Hermann A., Pålsson Lars-Olof, Parker David, Logothetis Nikos K.: Synthesis and characterization of lanthanide complexes of DO3A-alkylphosphonates. Dalton Trans. 2007, 5260. <https://doi.org/10.1039/b711351j>
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