Synthesis of [F-18]RGD-K5 by catalyzed [3+2] cycloaddition for imaging integrin alpha(v)beta(3) expression in vivo

Leila Mirfeizi*, Joe Walsh, Hartmuth Kolb, Lachlan Campbell-Verduyn, Rudi A. Dierckx, Ben L. Feringa, Philip H. Elsinga, Tjibbe de Groot, Ivan Sannen, Guy Bormans, Sofie Celen

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

In the last few years click chemistry reactions, and in particular copper-catalyzed cycloadditions have been used extensively for the preparation of new bioconjugated molecules such as F-18-radiolabeled radiopharmaceuticals for positron emission tomography (PET). This study is focused on the synthesis of the Siemens imaging biomarker [F-18]RGD-K5. This cyclic peptide contains an amino acid sequence which is a well known binding motif for integrin alpha(v)beta(3) involved in cellular-adhesion to the extracellular matrix. We developed an improved "click" chemistry method using Cu(I)-Monophos as catalyst to conjugate [F-18]fluoropentyne to the RGD-azide precursor yielding [F-18]RGD-K5. A comparison is made with the registered Siemens method with respect to synthesis, purification and quality control. [F-18]RGD-K5 was obtained after 75 min overall synthesis time with an overall radiochemical yield of 35% (EOB). The radiochemical purity was >98% and the specific radioactivity was 100-200 GBq/mu mol at the EOS. (C) 2013 Elsevier Inc. All rights reserved.

Original languageEnglish
Pages (from-to)710-716
Number of pages7
JournalNuclear Medicine and Biology
Volume40
Issue number5
DOIs
Publication statusPublished - Jul-2013

Keywords

  • POSITRON-EMISSION-TOMOGRAPHY
  • CYCLIC RGD PEPTIDES
  • CLICK CHEMISTRY
  • RADIATION-DOSIMETRY
  • TERMINAL ALKYNES
  • CELL-ADHESION
  • ANGIOGENESIS
  • BIODISTRIBUTION
  • F-18-AH111585
  • RADIOTRACERS

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