Structure-activity relationships of 111In- and 99mTc-labeled quinolin-4-one peptidomimetics as ligands for the vitronectin receptor: potential tumor imaging agents

Bioconjug Chem. 2006 Sep-Oct;17(5):1294-313. doi: 10.1021/bc060063s.

Abstract

The integrin receptor alpha(v)beta(3) is overexpressed on the endothelial cells of growing tumors and on some tumor cells themselves. Radiolabeled alpha(v)beta(3) antagonists have demonstrated potential application as tumor imaging agents and as radiotherapeutic agents. This report describes the total synthesis of eight new HYNIC and DOTA conjugates of receptor alpha(v)beta(3) antagonists belonging to the quinolin-4-one class of peptidomimetics, and their radiolabeling with (99m)Tc (for HYNIC) and (111)In (for DOTA). Tethering of the radionuclide-chelator complexes was achieved at two different sites on the quinolin-4-one molecule. All such derivatives maintained high affinity for receptor alpha(v)beta(3) and high selectivity versus receptors alpha(IIb)beta(3), alpha(v)beta(5), alpha(5)beta(1). Biodistribution of the radiolabeled compounds was evaluated in the c-neu Oncomouse mammary adenocarcinoma model. DOTA conjugate (111)In-TA138 presented the best biodistribution profile. Tumor uptake at 2 h postinjection was 9.39% of injected dose/g of tissue (%ID/g). Activity levels in selected organs was as follows: blood, 0.54% ID/g; liver, 1.94% ID/g; kidney, 2.33% ID/g; lung, 2.74% ID/g; bone, 1.56% ID/g. A complete biodistribution analysis of (111)In-TA138 and the other radiolabeled compounds of this study are presented and discussed. A scintigraphic imaging study with (111)In-TA138 showed a clear delineation of the tumors and rapid clearance of activity from nontarget tissues.

MeSH terms

  • Adenocarcinoma / metabolism
  • Adenocarcinoma / pathology
  • Animals
  • Breast Neoplasms* / metabolism
  • Breast Neoplasms* / pathology
  • Chelating Agents / chemistry
  • Diagnostic Imaging
  • Heterocyclic Compounds, 1-Ring / chemistry
  • Humans
  • Indium Radioisotopes / chemistry
  • Indium Radioisotopes / metabolism
  • Integrin alphaVbeta3 / metabolism*
  • Ligands
  • Mice
  • Molecular Probes* / chemical synthesis
  • Molecular Probes* / chemistry
  • Molecular Probes* / metabolism
  • Molecular Structure
  • Quinolines / chemistry*
  • Structure-Activity Relationship
  • Technetium* / chemistry
  • Technetium* / metabolism

Substances

  • Chelating Agents
  • Heterocyclic Compounds, 1-Ring
  • Indium Radioisotopes
  • Integrin alphaVbeta3
  • Ligands
  • Molecular Probes
  • Quinolines
  • Technetium
  • quinoline