Anthranilic acid analogs as diamagnetic CEST MRI contrast agents that feature an intramolecular-bond shifted hydrogen

Research output: Contribution to journalArticle

Abstract

Diamagnetic chemical exchange saturation transfer (diaCEST) agents are a new class of imaging agents, which have unique magnetic resonance (MR) properties similar to agents used for optical imaging. Here we present a series of anthranilic acid analogs as examples of diaCEST agents that feature an exchangeable proton shifted downfield, namely, an intramolecular-bond shifted hydrogen (IM-SHY), which produces significant and tunable contrast at frequencies of 4.8-9.3 ppm from water. Five analogs of N-sulfonyl anthranilic acids are all highly soluble and produced similar CEST contrast at ~6-8 ppm. We also discovered that flufenamic acid, a commercial nonsteroidal anti-inflammatory drug, displayed CEST contrast at 4.8 ppm. For these N-H IM-SHY agents, the contrast produced was insensitive to pH, making them complementary to existing diaCEST probes. This initial IM-SHY library includes the largest reported shifts for N-H protons on small organic diaCEST agents, and should find use as multifrequency MR agents for in vivo applications.

Original languageEnglish (US)
Pages (from-to)74-80
Number of pages7
JournalContrast Media and Molecular Imaging
Volume10
Issue number1
DOIs
StatePublished - Jan 1 2015

Keywords

  • Chemical exchange saturation transfer
  • Molecular imaging
  • N-aryl anthranilic acid derivatives
  • N-sulfonyl anthranilic acid derivatives

ASJC Scopus subject areas

  • Radiology Nuclear Medicine and imaging

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