One-step radiosynthesis of 4-nitrophenyl 2-[(18) F]fluoropropionate ([(18) F]NFP); improved preparation of radiolabeled peptides for PET imaging

Mohammad B Haskali; Peter D Roselt; John A Karas; Wayne Noonan; Christian W Wichmann; Andrew Katsifis; Rodney J Hicks; Craig A Hutton

doi:10.1002/jlcr.3111

One-step radiosynthesis of 4-nitrophenyl 2-[(18) F]fluoropropionate ([(18) F]NFP); improved preparation of radiolabeled peptides for PET imaging

J Labelled Comp Radiopharm. 2013 Dec;56(14):726-30. doi: 10.1002/jlcr.3111. Epub 2013 Sep 16.

Authors

Mohammad B Haskali¹, Peter D Roselt, John A Karas, Wayne Noonan, Christian W Wichmann, Andrew Katsifis, Rodney J Hicks, Craig A Hutton

Affiliation

¹ School of Chemistry, The University of Melbourne, Vic., 3010, Australia; Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Vic., 3010, Australia; The Centre for Molecular Imaging and Translational Research Laboratory, The Peter MacCallum Cancer Centre, Melbourne, Vic., Australia.

PMID: 24339012
DOI: 10.1002/jlcr.3111

Abstract

The versatile (18) F-labeled prosthetic group, 4-nitrophenyl 2-[(18) F]fluoropropionate ([(18) F]NFP), was synthesized in a single step in 45 min from 4-nitrophenyl 2-bromopropionate, with a decay corrected radiochemical yield of 26.2% ± 2.2%. Employing this improved synthesis of [(18) F]NFP, [(18) F]GalactoRGD - the current 'gold standard' tracer for imaging the expression of αV β3 integrin - was prepared with high specific activity in 90 min and 20% decay corrected radiochemical yield from [(18) F]fluoride.

Keywords: PET imaging; RGD peptide; [18F]fluoride; fluoropropionate; radiofluorination.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Azides / chemical synthesis*
Fluorine Radioisotopes / chemistry*
Isotope Labeling / methods*
Peptides / chemical synthesis
Positron-Emission Tomography*
Radiopharmaceuticals / chemical synthesis*

Substances

Azides
Fluorine Radioisotopes
Peptides
Radiopharmaceuticals
4-nitrophenyl 2-fluoropropionate