Radiosynthesis and evaluation of peptide probe containing short-lived positron-emitting radionuclides via a Pictet-Spengler reaction

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A procedure for the synthesis of a carbon-11 labeled oligopeptide containing [1-11C]1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid ([1-11C]Tpi) from the corresponding TrpHCl-containing peptides has been developed involving a Pictet-Spengler reaction with [11C]formaldehyde. The radiolabeling of a TrpHCl-containing RGD peptide using the Pictet-Spengler reaction was successful. Furthermore, the remote-controlled synthesis of a [1-11C]Tpi-containing RGD (1) peptide was attempted using an automatic production system to generate [11C]CH3I. The radiochemical yield of the compound 1 at the end of synthesis was 5.9 % (n=4), for a total synthesis time of about 35 min. The usefulness of our synthesis was demonstrated PET studies using the compound 1 for the mouse bearing MIAPaca-2 and BxPC-3, a small cell pancreatic cancer cell line. The BxPC-3 cell-to-muscle and MIAPaca-2 cell-to-muscle of 1 at 22 min were retained at a low level of 2.8 and 1.3, respectively.