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Journal article

Synthesis of a non-peptidic PET tracer designed for α5β1 integrin receptor

Université de Fribourg

  • Monaco, Alessandra Cyclotron Unit, University Hospital of Geneva, Switzerland - School of Pharmaceutical Sciences, University of Geneva and University of Lausanne, Switzerland
  • Michelin, Olivier Swiss Institute of Bioinformatics, University of Lausanne, Switzerland
  • Prior, John CHUV, Department of Nuclear Medicine, Lausanne, Switzerland
  • Rüegg, Curzio Faculty of Science, Department of Medicine, University of Fribourg, Switzerland
  • Scapozza, Leonardo School of Pharmaceutical Sciences, University of Geneva and University of Lausanne, Switzerland
  • Seimbille, Yann Cyclotron Unit, University Hospital of Geneva, Switzerland - School of Pharmaceutical Sciences, University of Geneva and University of Lausanne, Switzerland
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    01.03.2014
Published in:
  • Journal of labelled compounds & radiopharmaceuticals. - 2014, vol. 57, no. 5, p. 365-370
<em>α</em>₅<em>β</em>₁ integrin receptor
PET, 1-azide-2-[¹⁸F]fluoroethane
click chemistry
peptido-mimetic
English Arginine–glycine–aspartic acid (RGD)-containing peptides have been traditionally used as PET probes to noninvasively image angiogenesis, but recently, small selective molecules for α₅β₁ integrin receptor have been developed with promising results. Sixty-one antagonists were screened, and tert-butyl (S)-3-(2-((3R,5S)-1-(3-(1-(2-fluoroethyl)-1H-1,2,3-triazol-4- yl)propanoyl)-5-((pyridin-2-ylamino)methyl)pyrrolidin-3-yloxy)acetamido)-2-(2,4,6- trimethylbenzamido)propanoate (FPMt) was selected for the development of a PET tracer to image the expression of α₅β₁ integrin receptors. An alkynyl precursor (PMt) was initially synthesized in six steps, and its radiolabeling was performed according to the azide–alkyne copper(II)-catalyzed Huisgen's cycloaddition by using 1-azido-2-[¹⁸F]fluoroethane ([¹⁸F]12). Different reaction conditions between PMt and [¹⁸F]12 were investigated, but all of them afforded [¹⁸F]FPMt in 15 min with similar radiochemical yields (80–83%, decay corrected). Overall, the final radiopharmaceutical ([¹⁸F]FPMt) was obtained after a synthesis time of 60–70 min in 42–44% decay-corrected radiochemical yield.
Faculty
Faculté des sciences et de médecine
Department
Médecine 3ème année
Language
  • English
Classification
Biological sciences
License
License undefined
Identifiers
Persistent URL
https://folia.unifr.ch/global/documents/303628
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