Synthesis and In Vivo PET Imaging of Hyaluronan Conjugates of Oligonucleotides

Bioconjug Chem. 2016 Feb 17;27(2):391-403. doi: 10.1021/acs.bioconjchem.5b00477. Epub 2015 Nov 12.

Abstract

Synthesis for (68)Ga-labeled 1,4,7-triazacyclononane-1,4,7-triacetic acid (NOTA)-chelated oligonucleotide hyaluronan (HA) tetra- and hexasaccharide conjugates is described. A solid-supported technique is used to introduce NOTA-chelator into the 3'-terminus of oligonucleotides and a copper-free strain promoted azide alkyne cycloaddition (SPAAC) to HA/oligonucleotide conjugation. Protecting group manipulation, required for the HA-moieties, is carried out after the SPAAC-conjugation. Positron emission tomography (PET) is used (1) in the whole-body distribution kinetic studies of the conjugates in healthy rats and (2) to show the potential of hyaluronan-induced targeting of oligonucleotides into the infarcted area of rats with myocardial infarction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chelating Agents / chemical synthesis
  • Chelating Agents / chemistry
  • Chelating Agents / pharmacokinetics
  • Gallium Radioisotopes / chemistry*
  • Gallium Radioisotopes / pharmacokinetics
  • Heterocyclic Compounds / chemical synthesis
  • Heterocyclic Compounds / chemistry*
  • Heterocyclic Compounds / pharmacokinetics
  • Heterocyclic Compounds, 1-Ring
  • Hyaluronic Acid / chemical synthesis
  • Hyaluronic Acid / chemistry*
  • Hyaluronic Acid / pharmacokinetics
  • Kinetics
  • Male
  • Myocardial Infarction / diagnosis
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry*
  • Oligonucleotides / pharmacokinetics
  • Positron-Emission Tomography / methods*
  • Rats
  • Rats, Sprague-Dawley
  • Tissue Distribution

Substances

  • Chelating Agents
  • Gallium Radioisotopes
  • Heterocyclic Compounds
  • Heterocyclic Compounds, 1-Ring
  • Oligonucleotides
  • 1,4,7-triazacyclononane-N,N',N''-triacetic acid
  • Hyaluronic Acid