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

Bioorg Med Chem Lett. 2020 Sep 1;30(17):127400. doi: 10.1016/j.bmcl.2020.127400. Epub 2020 Jul 9.

Abstract

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.

Keywords: Fluorine-18 labeling; Glucose transporter 2; Metabolic syndrome; Positron emission tomography; Streptozotocin; Type-2 diabetes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Fluorine Radioisotopes / chemistry
  • Glucose Transporter Type 2 / metabolism
  • Kinetics
  • Mice
  • Positron-Emission Tomography*
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / metabolism
  • Streptozocin / chemical synthesis
  • Streptozocin / chemistry*
  • Streptozocin / metabolism
  • Tissue Distribution

Substances

  • Fluorine Radioisotopes
  • Glucose Transporter Type 2
  • Radiopharmaceuticals
  • Streptozocin
  • Fluorine-18