N. Vasdev, R. Chirakal, Rezwan Ashique
May 1, 2003
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0
Influential Citations
6
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Journal
Journal of Fluorine Chemistry
Abstract
Abstract The detection of 3-nitro- l -tyrosine has been used as a biomarker of “reactive nitrogen species” in biological matrices and has been an ongoing challenge in analytical chemistry. In this work, fluorine-18 labelled 5-fluoro-3-nitro- l -tyrosine (FNT) was synthesized as a potential radiotracer to probe the biological fate of 3-nitro- l -tyrosine. The synthesis of [ 18 F ]FNT was carried out by reaction of [ 18 F ]3-fluoro- l -tyrosine with NaNO3 in TFA solvent for 5 min at 4 °C. The radiochemical yield (RCY) of [ 18 F ]FNT was 96±2% and [ 18 F ]3-fluoro- l -tyrosine, was 29±1%, relative to [ 18 F ]3-fluoro- l -tyrosine and [ 18 F ]F2, respectively. The syntheses of [ 18 F ]FNT were also accomplished by direct fluorination of 3-nitro- l -tyrosine with [ 18 F ]F2 and by nitration of l -tyrosine with NaNO3, followed by fluorination, in TFA (4 °C) or anhydrous HF (−65 °C) solvent. The latter two synthetic routes produced [ 18 F ]FNT in 13.5±1.5% RCY, within 1 h. Products were characterized by use of 1 H , 13 C and 19 F NMR spectroscopy and mass spectrometry.