68Ga-Labeled bismacrocyclic methylene phosphonate as potential bone seeking PET radiopharmaceutical

Bioorg Chem. 2020 Nov:104:104185. doi: 10.1016/j.bioorg.2020.104185. Epub 2020 Aug 26.

Abstract

Phosphonates-based agents are well-known bone-seeking radiopharmaceuticals with application in detection and therapy. With higher sensitivity and resolution offered by Positron Emission Tomography (PET), tracers based on this technique are gaining huge attention. 68Ga-based generator and radiotracers render independence from the on-site cyclotron. We report the development of 68Ga-labeled DOTA-based bismacrocyclic phosphonate derivative, for bone PET imaging. The synthesis and characterization of 68Ga- DO3P-AME-DO3P was carried out in > 95% purity. The radiotracer displayed high stability and low binding affinity (<3%) to blood serum. High in vitro binding affinity were observed for synthetic hydroxyapatite, SAOS-2, osteoclast and osteoblast cells. In vivo pharmacokinetics revealed fast washout with biphasic release pattern. The deposition of radiotracer in osseous tissues was high (Bone/Muscle ratio:18), as studied from the biodistribution studies. In vivo PET/CT and biodistribution analyses revealed the ability of 68Ga-DO3P-AME-DO3P to target and accumulate in bone, thus displaying its potential as a PET bone imaging agent.

Keywords: Bone imaging; DOTA; Gallium-68; PET/CT; Phosphonates; Skeletal metastases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides / blood
  • Acetamides / chemistry*
  • Acetamides / pharmacokinetics
  • Bone and Bones / diagnostic imaging*
  • Gallium Radioisotopes
  • Humans
  • Macrocyclic Compounds / blood
  • Macrocyclic Compounds / chemistry*
  • Macrocyclic Compounds / pharmacokinetics
  • Molecular Structure
  • Organophosphorus Compounds / blood
  • Organophosphorus Compounds / chemistry*
  • Organophosphorus Compounds / pharmacokinetics
  • Positron-Emission Tomography*
  • Radiopharmaceuticals / blood
  • Radiopharmaceuticals / chemistry*
  • Radiopharmaceuticals / pharmacokinetics
  • Tissue Distribution

Substances

  • 10'-bis(acetamido)-ethane-bis(1,4,7-tri(methylene phosphonic acid)-1,4,7,10-tetraazacyclododecane)
  • Acetamides
  • Gallium Radioisotopes
  • Macrocyclic Compounds
  • Organophosphorus Compounds
  • Radiopharmaceuticals