Novel electrophilic synthesis of 6-[18F]fluorodopamine and comprehensive biological evaluation View Full Text


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Article Info

DATE

2012-01-10

AUTHORS

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

ABSTRACT

Purpose6-[18F]Fluorodopamine (4-(2-aminoethyl)-5-[18F]fluorobenzene-1,2-diol, 6-[18F]FDA) is a tracer for imaging sympathetically innervated tissues. Previous electrophilic labelling methods produced 6-[18F]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-[18F]FDA in rats in order to thoroughly identify tissues with dense sympathetic innervation that were specifically labelled with 6-[18F]FDA. In addition, to investigate the safety profile of 6-[18F]FDA in larger animals, we performed in vivo studies in pigs.Methods6-[18F]FDA was synthesised using high SA electrophilic [18F]F2 as the labelling reagent. Biodistribution and metabolism of 6-[18F]FDA was determined ex vivo in rats, and in vivo studies were done in pigs.Results6-[18F]FDA was synthesised with 2.6 ± 1.1% radiochemical yield. The total amount of purified 6-[18F]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-[18F]FDA was demonstrated in heart, lung, pancreas, adrenal gland, lower large intestine (LLI), eye, thyroid gland, spleen and stomach tissue. 6-[18F]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.Conclusion6-[18F]FDA was synthesised with good radiopharmaceutical quality and yields high enough for several human PET studies. The SA of 6-[18F]FDA was improved by 50- to 500-fold compared to previous electrophilic methods. Uptake of 6-[18F]FDA was specific in various peripheral organs, indicating that 6-[18F]FDA PET can be used to investigate sympathoneural functions beyond cardiac studies when higher specific uptake is achieved. More... »

PAGES

800-810

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s00259-011-2032-5

DOI

http://dx.doi.org/10.1007/s00259-011-2032-5

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1016372264

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/22231017


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21 schema:description Purpose6-[18F]Fluorodopamine (4-(2-aminoethyl)-5-[18F]fluorobenzene-1,2-diol, 6-[18F]FDA) is a tracer for imaging sympathetically innervated tissues. Previous electrophilic labelling methods produced 6-[18F]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-[18F]FDA in rats in order to thoroughly identify tissues with dense sympathetic innervation that were specifically labelled with 6-[18F]FDA. In addition, to investigate the safety profile of 6-[18F]FDA in larger animals, we performed in vivo studies in pigs.Methods6-[18F]FDA was synthesised using high SA electrophilic [18F]F2 as the labelling reagent. Biodistribution and metabolism of 6-[18F]FDA was determined ex vivo in rats, and in vivo studies were done in pigs.Results6-[18F]FDA was synthesised with 2.6 ± 1.1% radiochemical yield. The total amount of purified 6-[18F]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-[18F]FDA was demonstrated in heart, lung, pancreas, adrenal gland, lower large intestine (LLI), eye, thyroid gland, spleen and stomach tissue. 6-[18F]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.Conclusion6-[18F]FDA was synthesised with good radiopharmaceutical quality and yields high enough for several human PET studies. The SA of 6-[18F]FDA was improved by 50- to 500-fold compared to previous electrophilic methods. Uptake of 6-[18F]FDA was specific in various peripheral organs, indicating that 6-[18F]FDA PET can be used to investigate sympathoneural functions beyond cardiac studies when higher specific uptake is achieved.
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27 schema:keywords Conclusion6
28 GBq/
29 MBq
30 PET
31 PET studies
32 Purpose6
33 Results6
34 addition
35 adrenal gland
36 aim
37 amount
38 animals
39 biodistribution
40 biodistribution pattern
41 biological evaluation
42 cardiac studies
43 comprehensive biological evaluation
44 decay
45 dense sympathetic innervation
46 effect
47 electrophilic
48 electrophilic labelling
49 electrophilic method
50 electrophilic synthesis
51 end
52 end of synthesis
53 evaluation
54 ex vivo
55 eyes
56 fast metabolism
57 function
58 gland
59 heart
60 high specific uptake
61 human PET studies
62 innervation
63 intestine
64 labeling
65 labeling method
66 labeling reagent
67 large animals
68 large intestine
69 low specific radioactivity
70 lung
71 metabolism
72 method
73 min
74 order
75 organs
76 pancreas
77 patterns
78 peripheral organs
79 pharmacological effects
80 pigs
81 plasma
82 profile
83 purity
84 quality
85 radioactivity
86 radiochemical purity
87 radiochemical yield
88 radiopharmaceutical quality
89 rat plasma
90 rats
91 reagents
92 safety profile
93 specific radioactivity
94 specific uptake
95 spleen
96 stomach tissue
97 study
98 sympathetic innervation
99 synthesis
100 thyroid gland
101 tissue
102 total amount
103 tracer
104 uptake
105 use
106 vivo
107 vivo PET studies
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109 wide use
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