Back to Search
Start Over
F-18 peptide labelling: Neurotensin derivatives
- Source :
- Synthesis and Application of Isotopically Labelled Compounds, Vol. 7, U. Pleiss, R. Voges (eds.), John Wiley & Sons, Ltd., 2001, 380-383
- Publication Year :
- 2001
-
Abstract
- The tridecapeptide Neurotensin (NT) exhibits a high specific affinity to receptors located on various tumours like small cell lung carcinoma or human colon carcinoma. The purpose of this study was to evaluate the potential of using succinimidyl-4-[18F]fluorobenzoate ([18F]SFB) for the specific radiolabelling of a non-lysine containing oligopeptide. This was demonstrated using the C-terminal bioactive hexapeptide NT(8-13) as well as its partially reduced stabilised congeners [Arg8ps(CH2NH)Arg9]NT(8-13), [Arg8ps(CH2NH)Arg9, Tle12]NT(8-13). The radiosynthesis of [18F]SFB started from ethyl trimethylammonium benzoate via a standard three-step procedure. Finally O-(N-succinimidyl) N,N,N',N'-tetramethyluronium tetrafluoroborate was used as activating agent to give [18F]SFB in 40 % overall radiochemical yield related to [18F]F- within 100 min (Wester et al. Nucl. Med. Biol. 1996, 23, 365). Our labelling experiments revealed that [18F]SFB reacts with selected N-terminal Arg-peptides with moderate to good chemoselectivities in aqueous buffered solutions (phosphate-borate buffer; pH 7.1 - 8.3). To shorten the period of time necessary for a complete consumption of [18F]SFB we found it advisable to heat the mixture to 40 - 50 °C for 20 min. The desired products were obtained after HPLC purification in radiochemical yields of 10 to 43 % (80 - 120 min) related to [18F]SFB. The conditions mentioned above allow the active ester to react specifically with the a-amino group of the N-terminal arginine unit. The radioactive product was identified by chromatographic comparison with a reference compound. The reactions carried out with nonradioactive SFB were shown to give the corresponding 4-FB peptides of which their structural identity was confirmed by proton NMR and MS studies. The labelled peptides display in v
Details
- Database :
- OAIster
- Journal :
- Synthesis and Application of Isotopically Labelled Compounds, Vol. 7, U. Pleiss, R. Voges (eds.), John Wiley & Sons, Ltd., 2001, 380-383
- Notes :
- English
- Publication Type :
- Electronic Resource
- Accession number :
- edsoai.on1415594510
- Document Type :
- Electronic Resource