Amide conjugates of the DO3A-N-(alpha-amino)propionate ligand: leads for stable, high relaxivity Contrast Agents for MRI? - Archive ouverte HAL Access content directly
Journal Articles Contrast Media and Molecular Imaging Year : 2013

Amide conjugates of the DO3A-N-(alpha-amino)propionate ligand: leads for stable, high relaxivity Contrast Agents for MRI?

M.F. Ferreira
  • Function : Author
A.F. Martins
  • Function : Author
C.I.O. Martins
  • Function : Author
É. Tóth
T.B. Rodrigues
  • Function : Author
D. Calle
  • Function : Author
S. Cerdan
  • Function : Author
P. López-Larrubia
  • Function : Author
J.A. Martins
  • Function : Author
C.F.G.C. Geraldes
  • Function : Author

Abstract

A novel synthetic methodology for preparing amide conjugates of the DO3A-N-(α-amino)propionate chelator is described, using the synthesis of the DO3A-N-(α-benzoylamido)propionate chelator as an illustrative example. The model Gd[DO3A-N-(α-benzoylamido)propionate] chelate displays accelerated water exchange, stability in a wide pH range and inertness towards transmetallation by Zn(2+) . The Gd[DO3A-N-(α-benzoylamido)propionate] complex is mainly excreted via the kidneys, producing a significant increase in the kidney medulla/cortex enhancement ratio in MR images of Wistar rats, reflecting probably its higher lipophilicity compared with Gd(DTPA). The results presented suggest that Gd[DO3A-N-(α-amido)propionate] chelates can be valuable leads for preparing potentially safe high relaxivity MRI contrast agents.

Dates and versions

hal-00748283 , version 1 (05-11-2012)

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M.F. Ferreira, A.F. Martins, C.I.O. Martins, É. Tóth, T.B. Rodrigues, et al.. Amide conjugates of the DO3A-N-(alpha-amino)propionate ligand: leads for stable, high relaxivity Contrast Agents for MRI?. Contrast Media and Molecular Imaging, 2013, 8 (1), pp.40-49. ⟨10.1002/cmmi.1492⟩. ⟨hal-00748283⟩
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