Rational Design of Mono-Substituted Gd-DOTA as Highly Stable and Efficient MRI Contrast Agents for Hepatobiliary and Inflammation Imaging

J Med Chem. 2024 Sep 12;67(17):15476-15493. doi: 10.1021/acs.jmedchem.4c01084. Epub 2024 Aug 27.

Abstract

Hepatobiliary-specific magnetic resonance imaging contrast agents (MRI CAs) play a crucial role in the early diagnosis of hepatocellular carcinoma (HCC). However, only two acyclic CAs, Gd-BOPTA and Gd-EOB-DTPA, exhibit unfavorable kinetic inertness. Our study focused on the development of superior stable innovative macrocyclic CAs. By introducing a lipophilic benzyloxy group (OBn) into the H4DOTA ring (Gd-L1), we achieved significant enhancement in kinetic inertness. In vivo experiments in mice demonstrated that 40% of the dosage was distributed to the liver at 5 min, providing sustained hepatic enhancement for over 35 min. We also developed an MPO-responsive MRI CA (Gd-L3), which can participate in the "peroxidase cycle" as the substrate, generating oligomers with a 3.8-fold increase in relaxivity, and selectively enhance the lesion in an acute gout mouse model. Overall, our work represents a significant advancement in the field of hepatic and inflammatory MRI, offering promising avenues for early diagnosis and improved imaging outcomes.

MeSH terms

  • Animals
  • Carcinoma, Hepatocellular / diagnostic imaging
  • Contrast Media* / chemical synthesis
  • Contrast Media* / chemistry
  • Drug Design
  • Heterocyclic Compounds
  • Humans
  • Inflammation / diagnostic imaging
  • Liver Neoplasms / diagnostic imaging
  • Liver* / diagnostic imaging
  • Liver* / metabolism
  • Magnetic Resonance Imaging* / methods
  • Male
  • Mice
  • Organometallic Compounds* / chemical synthesis
  • Organometallic Compounds* / chemistry

Substances

  • Contrast Media
  • gadolinium 1,4,7,10-tetraazacyclododecane-N,N',N'',N'''-tetraacetate
  • Organometallic Compounds
  • Heterocyclic Compounds