Amide conjugates of the DO3A‐N‐(α‐amino)propionate ligand: leads for stable, high relaxivity contrast agents for MRI?. (29th October 2012)

• Record Type: Journal Article
• Authors: Ferreira, Miguel F.; Martins, André F.; Martins, Catarina I. O.; Ferreira, Paula M.; Tóth, Éva; Rodrigues, Tiago B.; Calle, Daniel; Cerdan, Sebastian; López‐Larrubia, Pilar; Martins, José A.; Geraldes, Carlos F. G. C.
• Is Part Of: Contrast media & molecular imaging. Volume 8:Number 1(2013:Jan./Feb.)
• Page Start: 40
• Page End: 49
• Publication Date: 2012-10-29
• Subjects: Diagnostic imaging -- Periodicals; Magnetic resonance imaging -- Periodicals; Contrast media (Diagnostic imaging) -- Periodicals; Contrast Media -- Periodicals; Diagnostic Imaging -- Periodicals; Substances de contraste -- Périodiques; Diagnostics moléculaires -- Périodiques; Imagerie médicale; Substance de contraste; Périodique électronique (Descripteur de forme); Ressource Internet (Descripteur de forme); 616.0754
• DOI: 10.1002/cmmi.1492
• Languages: English
• ISSNs: 1555-4309

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>A novel synthetic methodology for preparing amide conjugates of the DO3A‐<italic>N</italic>‐(<italic>α</italic>‐amino)propionate chelator is described, using the synthesis of the DO3A‐<italic>N</italic>‐(<italic>α</italic>‐benzoylamido)propionate chelator as an illustrative example. The model Gd[DO3A‐<italic>N</italic>‐(<italic>α</italic>‐benzoylamido)propionate] chelate displays accelerated water exchange, stability in a wide pH range and inertness towards transmetallation by Zn²⁺. The Gd[DO3A‐<italic>N</italic>‐(<italic>α</italic>‐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‐<italic>N</italic>‐(<italic>α</italic>‐amido)propionate] chelates can be valuable leads for preparing potentially safe high relaxivity MRI contrast agents. Copyright © 2012 John Wiley &amp; Sons, Ltd.</p> </abstract>