A comparative study of trans- and cis-isomers of a bone-seeking agent, DO2A2P

Bioorg Med Chem Lett. 2015 Feb 1;25(3):571-4. doi: 10.1016/j.bmcl.2014.12.016. Epub 2014 Dec 13.

Abstract

The macrocyclic bone-seeking agent, DO2A2P, bears a cyclen core and two pairs of peripheral phosphonate and carboxylate groups. The geometric disposition of the peripheral functionalities gives arise to a pair of geometric isomers: cis-DO2A2P and trans-DO2A2P. In order to compare the biological behavior of the isomer pair, cis-DO2A2P was synthesized. Both isomers were successfully radiolabeled with (177)Lu, which might potentiate their applications in both radiotherapy and imaging of bone diseases. Through a set of biological assays including the hydroxyapatite binding, in vitro stability, and in vivo distribution, we demonstrated that the geometric pair of DO2A2P had virtually identical biological properties.

Keywords: Bisphosphonate; Bone-seeking agent; Geometric isomer; Lutetium-177; Macrocyclics.

Publication types

  • Comparative Study
  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Contrast Media / chemistry
  • Heterocyclic Compounds, 1-Ring / chemistry*
  • Isomerism
  • Isotope Labeling
  • Lutetium / chemistry
  • Mice
  • Organophosphonates / chemistry*
  • Radioisotopes
  • Tomography, Emission-Computed, Single-Photon
  • Whole Body Imaging

Substances

  • Contrast Media
  • Heterocyclic Compounds, 1-Ring
  • Organophosphonates
  • Radioisotopes
  • cis-DO2A2P
  • trans-DO2A2P
  • Lutetium