Solid-phase synthesis and fluorine-18 radiolabeling of cycloRGDyK

Ryan A Davis; Kevin Lau; Sven H Hausner; Julie L Sutcliffe

doi:10.1039/c6ob01636g

Solid-phase synthesis and fluorine-18 radiolabeling of cycloRGDyK

Org Biomol Chem. 2016 Sep 21;14(37):8659-8663. doi: 10.1039/c6ob01636g.

Authors

Ryan A Davis¹, Kevin Lau², Sven H Hausner¹, Julie L Sutcliffe³

Affiliations

¹ Radiochemistry Research and Training Facility, USA. jlsutcliffe@ucdavis.edu and Department of Biomedical Engineering, USA and Department of Internal Medicine, Division of Hematology and Oncology, USA.
² Radiochemistry Research and Training Facility, USA. jlsutcliffe@ucdavis.edu and Department of Biomedical Engineering, USA.
³ Radiochemistry Research and Training Facility, USA. jlsutcliffe@ucdavis.edu and Department of Biomedical Engineering, USA and Department of Internal Medicine, Division of Hematology and Oncology, USA and Center for Molecular and Genomic Imaging, University of California, Davis, 2921 Stockton Blvd., Sacramento, CA 95817, USA.

Abstract

Solid-phase peptide synthesis, head-to-tail cyclization, and subsequent radiolabeling provided a reproducible, simple, rapid synthetic method to generate the cyclic peptide radiotracer cRGDyK([¹⁸F]FBA). Herein is reported the first on-resin cyclization and ¹⁸F-radiolabeling of a cyclic peptide (cRGDyK) in an overall peptide synthesis yield of 88% (cRGDyK(NH₂)) and subsequent radiolabeling yield of 14 ± 2% (decay corrected, n = 4). This approach is generally applicable to the development of an automated process for the synthesis of cyclic radiolabeled peptides for positron emission tomography (PET).

MeSH terms

Fluorine Radioisotopes / chemistry*
Isotope Labeling / methods
Peptides, Cyclic / chemical synthesis
Peptides, Cyclic / chemistry*
Positron-Emission Tomography / methods
Solid-Phase Synthesis Techniques / methods

Substances

Fluorine Radioisotopes
Peptides, Cyclic
cyclo(Arg-Gly-Asp-Tyr-Lys)
Fluorine-18

Grants and funding

R01 CA199725/CA/NCI NIH HHS/United States