Synthesis of (68)Ga-labeled NOTA-RGD-GE11 heterodimeric peptide for dual integrin and epidermal growth factor receptor-targeted tumor imaging

J Labelled Comp Radiopharm. 2015 Jun 15;58(7):299-303. doi: 10.1002/jlcr.3296. Epub 2015 May 21.

Abstract

Radiolabeled Arg-Gly-Asp (RGD) peptide analogs have been extensively studied for αvβ3 integrin-targeted angiogenesis imaging. According to recently presented evidence, the dodecapeptide GE11 has high affinity to the epidermal growth factor receptor (EGFR), which is overexpressed in many types of cancer. Dual-receptor molecular imaging probes with two different heterodimeric peptides exhibit improved cancer targeting efficacy. In the present study, the design and synthesis of a new RGD-GE11 peptide heterodimer for dual αvβ3 integrin/EGFR-targeted cancer imaging are described. The RGD-GE11 heterodimer was linked with 6-aminohexanoic acid (6-Ahx) and cysteine and conjugated with 1,4,7-triazacyclononane-N,N',N″-triacetic acid (NOTA) to form NOTA-RGD-cys-6-Ahx-GE11. The monomeric peptides, NOTA-cys-6-Ahx-GE11 and c(RGDyK), were formed by a peptide synthesizer. The peptide heterodimer NOTA-RGD-GE11 was obtained by NOTA-cys-6-Ahx-GE11 and maleimidopropyl-c(RGDyK) conjugation with a thioether linkage. The NOTA peptide conjugate was labeled with freshly eluted (68)Ga and purified using reversed-phase high-performance liquid chromatography. The (68)Ga-NOTA-RGD-cys-6-Ahx-GE11 was successfully prepared, in this study, with a radiochemical yield of 85% and a radiochemical purity of >98%. These results warrant further investigation of this heterodimeric peptide's binding affinity to the receptors.

Keywords: GE11; Ga-68; RGD; epidermal growth factor receptor (EGFR); heterodimer peptide; integrin αvβ3; positron emission tomography (PET).

MeSH terms

  • Coordination Complexes / chemical synthesis*
  • Coordination Complexes / chemistry*
  • Coordination Complexes / pharmacology
  • Epidermal Growth Factor / metabolism
  • Integrin alphaVbeta3 / metabolism
  • Oligopeptides / chemistry*
  • Peptides / chemistry*
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / pharmacology
  • Positron-Emission Tomography
  • Radiopharmaceuticals / chemical synthesis*

Substances

  • 68Ga-1,4,7-triazacyclononane-1,4-7-triacetic acid-isothiocyanatobenzyl-c(Arg-Gly-Asp-Tyr-Lys)
  • 68Ga-NOTA-RGD-GE11
  • Coordination Complexes
  • GE11 peptide
  • Integrin alphaVbeta3
  • Oligopeptides
  • Peptides
  • Peptides, Cyclic
  • Radiopharmaceuticals
  • Epidermal Growth Factor