Literature DB >> 22231017

Novel electrophilic synthesis of 6-[¹⁸F]fluorodopamine and comprehensive biological evaluation.

Olli Eskola1, Tove J Grönroos, Alexandru Naum, Päivi Marjamäki, Sarita Forsback, Jörgen Bergman, Sami Länkimäki, Jan Kiss, Timo Savunen, Juhani Knuuti, Merja Haaparanta, Olof Solin.   

Abstract

PURPOSE: 6-[(18)F]Fluorodopamine (4-(2-aminoethyl)-5-[(18)F]fluorobenzene-1,2-diol, 6-[(18)F]FDA) is a tracer for imaging sympathetically innervated tissues. Previous electrophilic labelling methods produced 6-[(18)F]FDA with low specific radioactivity (SA) which has limited its wider use. Our aim was to employ electrophilic labelling and increase the SA to around 15 GBq/μmol. We also sought to determine an extensive biodistribution pattern for 6-[(18)F]FDA in rats in order to thoroughly identify tissues with dense sympathetic innervation that were specifically labelled with 6-[(18)F]FDA. In addition, to investigate the safety profile of 6-[(18)F]FDA in larger animals, we performed in vivo studies in pigs.
METHODS: 6-[(18)F]FDA was synthesised using high SA electrophilic [(18)F]F(2) as the labelling reagent. Biodistribution and metabolism of 6-[(18)F]FDA was determined ex vivo in rats, and in vivo studies were done in pigs.
RESULTS: 6-[(18)F]FDA was synthesised with 2.6 ± 1.1% radiochemical yield. The total amount of purified 6-[(18)F]FDA was 663 ± 291 MBq at the end of synthesis (EOS). SA, decay corrected to EOS, was 13.2 ± 2.7 GBq/μmol. Radiochemical purity exceeded 99.0%. Specific uptake of 6-[(18)F]FDA was demonstrated in heart, lung, pancreas, adrenal gland, lower large intestine (LLI), eye, thyroid gland, spleen and stomach tissue. 6-[(18)F]FDA in rat plasma declined rapidly, with a half-life of 2 min, indicating fast metabolism. In vivo PET studies in pigs confirmed the tracer could be used safely without pharmacological effects.
CONCLUSION: 6-[(18)F]FDA was synthesised with good radiopharmaceutical quality and yields high enough for several human PET studies. The SA of 6-[(18)F]FDA was improved by 50- to 500-fold compared to previous electrophilic methods. Uptake of 6-[(18)F]FDA was specific in various peripheral organs, indicating that 6-[(18)F]FDA PET can be used to investigate sympathoneural functions beyond cardiac studies when higher specific uptake is achieved.

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Year:  2012        PMID: 22231017     DOI: 10.1007/s00259-011-2032-5

Source DB:  PubMed          Journal:  Eur J Nucl Med Mol Imaging        ISSN: 1619-7070            Impact factor:   9.236


  31 in total

Review 1.  Sympathetic modulation of immunity: relevance to disease.

Authors:  Denise L Bellinger; Brooke A Millar; Sam Perez; Jeff Carter; Carlo Wood; Srinivasan ThyagaRajan; Christine Molinaro; Cheri Lubahn; Dianne Lorton
Journal:  Cell Immunol       Date:  2008-03-04       Impact factor: 4.868

2.  Fluorine-18-labeled fluorine gas for synthesis of tracer molecules.

Authors:  J Bergman; O Solin
Journal:  Nucl Med Biol       Date:  1997-10       Impact factor: 2.408

3.  Photochemistry of diazonium salts. 4. Synthesis of ring-fluorinated tyramines and dopamines.

Authors:  K L Kirk
Journal:  J Org Chem       Date:  1976-07-09       Impact factor: 4.354

4.  Fate of tritiated 6-fluorodopamine in rats: a false neurotransmitter for positron emission tomographic imaging of sympathetic innervation and function.

Authors:  P C Chang; K Szemeredi; E Grossman; I J Kopin; D S Goldstein
Journal:  J Pharmacol Exp Ther       Date:  1990-11       Impact factor: 4.030

5.  Kinetic model for the fate of 6-[18F]fluorodopamine in the human heart: a novel means to examine cardiac sympathetic neuronal function.

Authors:  David S Goldstein; Meyer Katzper; Oscar Linares; Irwin J Kopin
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  2001-11-09       Impact factor: 3.000

6.  Direct radiofluorination of dopamine: 18F-labeled 6-fluorodopamine for imaging cardiac sympathetic innervation in humans using positron emission tomography.

Authors:  R Chirakal; G Coates; G Firnau; G J Schrobilgen; C Nahmias
Journal:  Nucl Med Biol       Date:  1996-01       Impact factor: 2.408

7.  Neuronal uptake and metabolism of 2- and 6-fluorodopamine: false neurotransmitters for positron emission tomographic imaging of sympathetically innervated tissues.

Authors:  G Eisenhofer; D Hovevey-Sion; I J Kopin; R Miletich; K L Kirk; R Finn; D S Goldstein
Journal:  J Pharmacol Exp Ther       Date:  1989-01       Impact factor: 4.030

8.  6-[18F]fluorodopamine positron emission tomographic scanning in the assessment of cardiac sympathoneural function--studies in normal humans.

Authors:  D S Goldstein; C Holmes; J E Stuhlmuller; J W Lenders; I J Kopin
Journal:  Clin Auton Res       Date:  1997-02       Impact factor: 4.435

9.  Comparison of high specific activity (-) and (+)-6-[18F]fluoronorepinephrine and 6-[18F]fluorodopamine in baboons: heart uptake, metabolism and the effect of desipramine.

Authors:  Y S Ding; J S Fowler; S L Dewey; J Logan; D J Schlyer; S J Gatley; N D Volkow; P T King; A P Wolf
Journal:  J Nucl Med       Date:  1993-04       Impact factor: 10.057

10.  Effects of ring fluorination on the cardiovascular actions of dopamine and norepinephrine in the dog.

Authors:  L I Goldberg; J D Kohli; D Cantacuzene; K L Kirk; C R Creveling
Journal:  J Pharmacol Exp Ther       Date:  1980-06       Impact factor: 4.030

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  4 in total

1.  Efficient automated syntheses of high specific activity 6-[18F]fluorodopamine using a diaryliodonium salt precursor.

Authors:  Kiel D Neumann; Linlin Qin; Amy L Vāvere; Bin Shen; Zheng Miao; Frederick T Chin; Barry L Shulkin; Scott E Snyder; Stephen G DiMagno
Journal:  J Labelled Comp Radiopharm       Date:  2015-12-23       Impact factor: 1.921

2.  6-[18F]fluoro-L-DOPA uptake in the rat pancreas is dependent on the tracer metabolism.

Authors:  Teemu Kalliokoski; Johanna Tuomela; Laura Haavisto; Sarita Forsback; Anniina Snellman; Semi Helin; Tove J Grönroos; Olof Solin; Merja Haaparanta-Solin
Journal:  Mol Imaging Biol       Date:  2013-11-12       Impact factor: 3.488

3.  18F-glutathione conjugate as a PET tracer for imaging tumors that overexpress L-PGDS enzyme.

Authors:  Ho-Lien Huang; Ying-Cheng Huang; Wei-Yuan Lee; Chun-Nan Yeh; Kun-Ju Lin; Chung-Shan Yu
Journal:  PLoS One       Date:  2014-08-11       Impact factor: 3.240

4.  Enzyme inhibition of dopamine metabolism alters 6-[18F]FDOPA uptake in orthotopic pancreatic adenocarcinoma.

Authors:  Johanna Tuomela; Sarita Forsback; Laura Haavisto; Tero Vahlberg; Tove J Grönroos; Olof Solin; Merja Haaparanta-Solin
Journal:  EJNMMI Res       Date:  2013-03-14       Impact factor: 3.138

  4 in total

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