TY - JOUR
T1 - Anthranilic acid analogs as diamagnetic CEST MRI contrast agents that feature an intramolecular-bond shifted hydrogen
AU - Song, Xiaolei
AU - Yang, Xing
AU - Ray Banerjee, Sangeeta
AU - Pomper, Martin G.
AU - Mcmahon, Michael T.
N1 - Publisher Copyright:
© 2014 John Wiley & Sons, Ltd.
PY - 2015/1/1
Y1 - 2015/1/1
N2 - 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.
AB - 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.
KW - Chemical exchange saturation transfer
KW - Molecular imaging
KW - N-aryl anthranilic acid derivatives
KW - N-sulfonyl anthranilic acid derivatives
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U2 - 10.1002/cmmi.1597
DO - 10.1002/cmmi.1597
M3 - Article
C2 - 24771546
AN - SCOPUS:84923079914
SN - 1555-4309
VL - 10
SP - 74
EP - 80
JO - Contrast Media and Molecular Imaging
JF - Contrast Media and Molecular Imaging
IS - 1
ER -