Synthesis, Characterization, and Biodistribution of a Dinuclear Gadolinium Complex with Improved Properties as a Blood Pool MRI Agent

ChemMedChem. 2018 Apr 23;13(8):824-834. doi: 10.1002/cmdc.201800052. Epub 2018 Mar 6.

Abstract

A dinuclear gadolinium(III) chelate containing two moieties of diethylenetriaminepentaacetic acid (DTPA), covalently conjugated to an analogue of deoxycholic acid, was synthesized and thoroughly characterized. A full relaxometric analysis was carried out, consisting of 1) the acquisition of nuclear magnetic resonance dispersion (NMRD) profiles in various media; 2) the study of binding affinity to serum albumin; 3) the measurement of 17 O transverse relaxation rate versus temperature, and 4) a transmetallation assay. In vivo biodistribution MRI studies at 1 T and blood pharmacokinetics assays were carried out in comparison with Gd-DTPA (Magnevist) and gadocoletic acid trisodium salt (B22956/1), two well-known Gd complexes that share the same chelating cage and the same deoxycholic acid residue of the Gd complex investigated herein ((GdDTPA)2 -Chol). High affinity for plasma protein and, in particular, the availability of more than one binding site, allows the complex to reach a fairly high relaxivity value in plasma (∼20 mm-1 s-1 , 20 MHz, 310 K) as well as to show unexpectedly enhanced properties of blood pooling, with an elimination half-life in rats approximately seven times longer than that of B22956/1.

Keywords: GBCAs; blood pool; dinuclear; gadolinium; magnetic resonance imaging.

MeSH terms

  • Animals
  • Contrast Media / chemical synthesis
  • Contrast Media / chemistry*
  • Contrast Media / metabolism
  • Contrast Media / pharmacokinetics*
  • Deoxycholic Acid / analogs & derivatives*
  • Deoxycholic Acid / chemical synthesis
  • Deoxycholic Acid / metabolism
  • Deoxycholic Acid / pharmacokinetics*
  • Female
  • Gadolinium DTPA / analogs & derivatives*
  • Gadolinium DTPA / chemical synthesis
  • Gadolinium DTPA / metabolism
  • Gadolinium DTPA / pharmacokinetics*
  • Magnetic Resonance Imaging
  • Male
  • Rats
  • Rats, Wistar
  • Serum Albumin / metabolism
  • Tissue Distribution

Substances

  • Contrast Media
  • Serum Albumin
  • Deoxycholic Acid
  • Gadolinium DTPA