Synthesis of Tc-99m labeled glucosamino-Asp-cyclic(Arg-Gly-Asp-d-Phe-Lys) as a potential angiogenesis imaging agent

Bioorg Med Chem. 2007 Dec 15;15(24):7755-64. doi: 10.1016/j.bmc.2007.08.054. Epub 2007 Sep 1.

Abstract

Angiogenesis imaging agents for single photon emission computed tomography (SPECT) play a role in diagnosing tumor-induced angiogenesis as well as tumor metastasis. We synthesized and evaluated radiolabeled RGD glycopeptides by incorporation of the [(99m)Tc(CO)(3)(H(2)O)(3)](+). (99m)Tc labeled glucosamino-D-c(RGDfK) ([(99m)Tc]2) was prepared in 90-93% radiochemical yields (decay corrected). In vitro cell binding assays demonstrated selective binding [(99m)Tc]2 to human umbilical vein endothelial (HUVE) cells, with inhibition of binding to 37.3% of control levels by 10 microM of cold authentic compounds. In addition, [(99m)Tc]2 was shown to have high binding affinity to purified alpha(v)beta(3) integrin (IC(50)=1.5 nM). These results suggest that these radiolabeled RGD glycopeptides may have value for non-invasive assessment of angiogenesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding, Competitive / drug effects
  • Cells, Cultured
  • Contrast Media / chemical synthesis*
  • Contrast Media / chemistry
  • Contrast Media / pharmacokinetics
  • Endothelial Cells / cytology
  • Endothelial Cells / drug effects
  • Endothelial Cells / metabolism*
  • Glucosamine*
  • Humans
  • Inhibitory Concentration 50
  • Integrin alphaVbeta3 / metabolism
  • Molecular Structure
  • Neovascularization, Pathologic / diagnosis*
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / metabolism
  • Protein Binding
  • Technetium*

Substances

  • Contrast Media
  • Integrin alphaVbeta3
  • Peptides, Cyclic
  • cyclic (arginyl-glycyl-aspartyl-phenylalanyl-lysyl)
  • Technetium
  • Glucosamine