Approaching the Kinetic Inertness of Macrocyclic Gadolinium(III)-Based MRI Contrast Agents with Highly Rigid Open-Chain Derivatives

Gyula Tircsõ, Martín Regueiro-Figueroa, Viktõria Nagy, Zoltán Garda, Tamás Garai, Ferenc Krisztián Kálmán, David Esteban-Gõmez, Éva Tõth, Carlos Platas-Iglesias

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15 Citations (Scopus)

Abstract

A highly rigid open-chain octadentate ligand (H4cddadpa) containing a diaminocylohexane unit to replace the ethylenediamine bridge of 6,6′-[(ethane-1,2 diylbis{(carboxymethyl)azanediyl})bis(methylene)]dipicolinic acid (H4octapa) was synthesized. This structural modification improves the thermodynamic stability of the Gd3+ complex slightly (log KGdL=20.68 vs. 20.23 for [Gd(octapa)]-) while other MRI-relevant parameters remain unaffected (one coordinated water molecule; relaxivity r1=5.73 mm-1 s-1 at 20 MHz and 295 K). Kinetic inertness is improved by the rigidifying effect of the diaminocylohexane unit in the ligand skeleton (half-life of dissociation for physiological conditions is 6 orders of magnitude higher for [Gd(cddadpa)]- (t1/2=1.49×105 h) than for [Gd(octapa)]-. The kinetic inertness of this novel chelate is superior by 2-3 orders of magnitude compared to non-macrocyclic MRI contrast agents approved for clinical use.

Original languageEnglish
Pages (from-to)896-901
Number of pages6
JournalChemistry - A European Journal
Volume22
Issue number3
DOIs
Publication statusPublished - Jan 18 2016

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Keywords

  • NMR imaging
  • contrast agents
  • coordination compounds
  • gadolinium
  • lanthanides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Tircsõ, G., Regueiro-Figueroa, M., Nagy, V., Garda, Z., Garai, T., Kálmán, F. K., Esteban-Gõmez, D., Tõth, É., & Platas-Iglesias, C. (2016). Approaching the Kinetic Inertness of Macrocyclic Gadolinium(III)-Based MRI Contrast Agents with Highly Rigid Open-Chain Derivatives. Chemistry - A European Journal, 22(3), 896-901. https://doi.org/10.1002/chem.201503836