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

By 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 and Sofie Celen

Abstract

<p>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.</p>

Topics: POSITRON-EMISSION-TOMOGRAPHY, CYCLIC RGD PEPTIDES; CLICK CHEMISTRY; RADIATION-DOSIMETRY; TERMINAL ALKYNES; CELL-ADHESION; ANGIOGENESIS; BIODISTRIBUTION; F-18-AH111585; RADIOTRACERS
Year: 2013
DOI identifier: 10.1016/j.nucmedbio.2013.04.003
OAI identifier: oai:pure.rug.nl:publications/68c3e991-85d6-40f9-afa8-df7afdceb968
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