Abstract
Carbon-11 (β+ emitter, t 1/2 = 20.4 min) radiolabeled l-glutamine is a potentially useful molecular imaging agent that can be utilized with positron emission tomography for both human oncological diagnosis and plant imaging research. Based upon a previously reported [11C]cyanide end-capping labeling method, a systematic investigation of nucleophilic cyanation reactions and acidic hydrolysis reaction parameters, including base, metal ion source, phase transfer catalyst, solvent, reaction temperature and reaction time, was conducted. The result was a milder, more reliable, two-step method which provides l-[5-11C]-glutamine with a radiochemical yield of 63.8 ± 8.7 % (range from 51 to 74 %, n = 10) with >90 % radiochemical purity and >90 % enantiomeric purity. The total synthesis time was 40–50 min from the end of bombardment. In addition, an Fmoc derivatization method was developed to measure the specific activity of this radiotracer.
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This manuscript has been co-authored by employees of Brookhaven Science Associates, LLC under Contract No. DE-AC02-98CH10886 with the U.S. Department of Energy, Office of Biological and Environmental Research within the Office of Science. Additional support was provided by the German Academic Exchange Service (Deutscher Akademischer Austauschdienst, DAAD), Bonn, which supported Tassilo Gleede, Barbara Riehl, Lena Kersting, and Aylin Sibel Cankaya. The US Government retains and the publisher, by accepting the article for publication, acknowledges that the USA retains a non-exclusive, paid-up irrevocable, world-wide license to publish or reproduce the published form of this manuscript, or allow others to do so, for US Government purpose.
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Gleede, T., Riehl, B., Shea, C. et al. Investigation of SN2 [11C]cyanation for base-sensitive substrates: an improved radiosynthesis of l-[5-11C]-glutamine. Amino Acids 47, 525–533 (2015). https://doi.org/10.1007/s00726-014-1883-z
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DOI: https://doi.org/10.1007/s00726-014-1883-z