Synthesis of 18F-labeled streptozotocin derivatives and an in-vivo kinetics study using positron emission tomography

Kenji Arimitsu, Yusuke Yagi, Kazuhiro Koshino, Yukina Nishito, Takahiro Higuchi, Hiroyuki Yasui, Hiroyuki Kimura

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1 Citation (Scopus)


Glucose transporter 2 (GLUT2) is involved in glucose uptake by hepatocytes, pancreatic beta cells, and absorptive cells in the intestine and proximal tubules in the kidney. Pancreatic GLUT2 also plays an important role in the mechanism of glucose-stimulated insulin secretion. In this study, novel Fluorine-18-labeled streptozotocin (STZ) derivatives were synthesized to serve as glycoside analogs for in-vivo GLUT2 imaging. Fluorine was introduced to hexyl groups at the 3′-positions of the compounds, and we aimed to synthesize compounds that were more stable than STZ. The nitroso derivatives exhibited relatively good stability during purification and purity analysis after radiosynthesis. We then evaluated the compounds in PET imaging and ex-vivo biodistribution studies. We observed high levels of radioactivity in the liver and kidney, which indicated accumulation in these organs within 5 min of administration. In contrast, the denitroso derivatives accumulated only in the kidney and bladder shortly after administration. Compounds with nitroso groups are thus expected to accumulate in GLUT2-expressing organs, and the presence of a nitroso group is essential for in-vivo GLUT2 imaging.

Original languageEnglish
Article number127400
JournalBioorganic and Medicinal Chemistry Letters
Issue number17
Publication statusPublished - Sept 1 2020


  • Fluorine-18 labeling
  • Glucose transporter 2
  • Metabolic syndrome
  • Positron emission tomography
  • Streptozotocin
  • Type-2 diabetes

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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