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

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

Research output: Contribution to journalArticle

12 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

Fingerprint

ethylenediamine
Gadolinium
Magnetic resonance imaging
Contrast Media
Ligands
Derivatives
Kinetics
Ethane
Thermodynamic stability
Molecules
Acids
Water
dipicolinic acid
N,N'-((6-carboxylato)pyridin-2-yl)methyl)-N,N'-diacetic acid-1,2-diaminoethane

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Approaching the Kinetic Inertness of Macrocyclic Gadolinium(III)-Based MRI Contrast Agents with Highly Rigid Open-Chain Derivatives. / Tircsó, G.; Regueiro-Figueroa, Martín; Nagy, Viktõria; Garda, Zoltán; Garai, Tamás; Kálmán, Ferenc Krisztián; Esteban-Gõmez, David; Tõth, Éva; Platas-Iglesias, Carlos.

In: Chemistry - A European Journal, Vol. 22, No. 3, 18.01.2016, p. 896-901.

Research output: Contribution to journalArticle

Tircsó, G, Regueiro-Figueroa, M, Nagy, V, Garda, Z, Garai, T, Kálmán, FK, 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, vol. 22, no. 3, pp. 896-901. https://doi.org/10.1002/chem.201503836
Tircsó, G. ; Regueiro-Figueroa, Martín ; Nagy, Viktõria ; Garda, Zoltán ; Garai, Tamás ; Kálmán, Ferenc Krisztián ; Esteban-Gõmez, David ; Tõth, Éva ; Platas-Iglesias, Carlos. / Approaching the Kinetic Inertness of Macrocyclic Gadolinium(III)-Based MRI Contrast Agents with Highly Rigid Open-Chain Derivatives. In: Chemistry - A European Journal. 2016 ; Vol. 22, No. 3. pp. 896-901.
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