Tuning phenols with Intra-Molecular bond Shifted HYdrogens (IM-SHY) as diaCEST MRI contrast agents

Xing Yang, Nirbhay N. Yadav, Xiaolei Song, Sangeeta Ray, Hannah Edelman, Il Minn, Peter C Van Zijl, Martin Gilbert Pomper, Michael T Mcmahon

Research output: Contribution to journalArticle

Abstract

The optimal exchange properties for chemical exchange saturation transfer (CEST) contrast agents on 3 T clinical scanners were characterized using continuous wave saturation transfer, and it was demonstrated that the exchangeable protons in phenols can be tuned to reach these criteria through proper ring substitution. Systematic modification allows the chemical shift of the exchangeable protons to be positioned between 4.8 to 12 ppm from water and enables adjustment of the proton exchange rate to maximize CEST contrast at these shifts. In particular, 44 hydrogen-bonded phenols are investigated for their potential as CEST MRI contrast agents and the stereoelectronic effects on their CEST properties are summarized. Furthermore, a pair of compounds, 2,5-dihydroxyterephthalic acid and 4,6-dihydroxyisophthalic acid, were identified which produce the highest sensitivity through incorporating two exchangeable protons per ring.

Original languageEnglish (US)
Pages (from-to)15824-15832
Number of pages9
JournalChemistry - A European Journal
Volume20
Issue number48
DOIs
StatePublished - Nov 24 2014

Keywords

  • chemical exchange saturation transfer
  • imaging agents
  • magnetic resonance imaging
  • medicinal chemistry
  • molecular imaging

ASJC Scopus subject areas

  • Medicine(all)

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