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Tuning Phenols with Intra‐Molecular Bond Shifted HYdrogens (IM‐SHY) as diaCEST MRI Contrast Agents
Author(s) -
Yang Xing,
Yadav Nirbhay N.,
Song Xiaolei,
Ray Banerjee Sangeeta,
Edelman Hannah,
Minn Il,
van Zijl Peter C. M.,
Pomper Martin G.,
McMahon Michael T.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403943
Subject(s) - chemistry , phenols , proton , hydrogen bond , contrast (vision) , saturation (graph theory) , ring (chemistry) , nuclear magnetic resonance , molecule , organic chemistry , optics , physics , mathematics , quantum mechanics , combinatorics
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.