Radiolabeling of RGD peptide and preliminary biological evaluation in mice bearing U87MG tumors

Bioorganic & Medicinal Chemistry
Jianbo LiLan Zhang

Abstract

2-[(18)F]Fluoroethyl azide ([(18)F]FEA) and terminal alkynyl modified propioloyl RGDfK were selected in this study. [(18)F]FEA was prepared by nucleophilic radiofluorination of 2-azidoethyl 4-toluenesulfonate with radiochemical yield of 71 ± 4% (n = 5, decay-corrected). We assessed the various conditions of the CuAAC reaction between [(18)F]FEA and propioloyl RGDfK, which included peptide concentration, reaction time, temperature and catalyst dosage. The (18)F-labeled-RGD peptide ([(18)F]F-RGDfK) could be obtained in 60 min by a two-step radiochemical synthesis route, with total radiochemical yield of 60 ± 2% (n = 3, decay-corrected) through click chemistry. [(18)F]F-RGDfK showed high stability in phosphate buffered saline and new-born calf serum. Micro-PET imaging at 1 h post injection of [(18)F]F-RGDfK showed medium concentration of radioactivity in tumors while much decreased concentration in tumors in the blocking group. These results showed that [(18)F]F-RGDfK obtained by click chemistry maintained the affinity and specificity of the RGDfK peptide to integrin α(v)β(3). This study provided useful information for peptide radiofluorination by using click chemistry.

Citations

Nov 29, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Abdullah A H Ahmad FuaadIstvan Toth
Jul 25, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marc PretzeConstantin Mamat
Jul 9, 2014·BioMed Research International·Kathrin KettenbachTobias L Ross
Jul 14, 2017·Chemistry : a European Journal·Hema S KrishnanSteven H Liang
Jun 11, 2017·Journal of Labelled Compounds & Radiopharmaceuticals·B LugatoP Ferraboschi

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