TY - JOUR
T1 - Tuning phenols with Intra-Molecular bond Shifted HYdrogens (IM-SHY) as diaCEST MRI contrast agents
AU - Yang, Xing
AU - Yadav, Nirbhay N.
AU - Song, Xiaolei
AU - Ray Banerjee, Sangeeta
AU - Edelman, Hannah
AU - Minn, Il
AU - van Zijl, Peter C.M.
AU - Pomper, Martin G.
AU - McMahon, Michael T.
N1 - Publisher Copyright:
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2014/11/24
Y1 - 2014/11/24
N2 - 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.
AB - 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.
KW - chemical exchange saturation transfer
KW - imaging agents
KW - magnetic resonance imaging
KW - medicinal chemistry
KW - molecular imaging
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U2 - 10.1002/chem.201403943
DO - 10.1002/chem.201403943
M3 - Article
C2 - 25302635
AN - SCOPUS:84964698872
SN - 0947-6539
VL - 20
SP - 15824
EP - 15832
JO - Chemistry (Weinheim an der Bergstrasse, Germany)
JF - Chemistry (Weinheim an der Bergstrasse, Germany)
IS - 48
ER -