Production and transport of gaseous 18F-synthons: 18F-acyl fluorides

Huailei Jiang, Stephen G. DiMagno, Timothy R DeGrado

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Fluorine-18 (18F, T1/2 = 109.7 min) is a positron-emitting isotope that has found extensive application as a radiolabel for positron emission tomography (PET). Although gaseous 11C-CO2 and 11C-CH4 are practically transported from cyclotron to radiochemistry processes, 18F-fluoride is routinely transported in aqueous solution because it is commonly produced by proton irradiation of 18O-enriched water. In most cases, subsequent dry-down steps are necessary to prepare reactive 18F-fluoride for radiofluorination. In this work, a simple module was designed to generate gaseous 18F-acyl fluorides from aqueous 18F-fluoride solution by solid phase 18F-radiofluorination of acyl anhydride. The gaseous 18F-acyl fluorides were purified through a column containing Porapak Q/Na2SO4, resulting in high yields (>86%), purities (>99%) and specific activities (>1200 GBq/μmol). Prototypic 18F-acetyl fluoride (18F-AcF) was readily transported through 15 m of 0.8 mm ID polypropylene tubing with low (0.64 ± 0.12%) adsorption to the tubing. Following dissolution of 18F-AcF in solvent containing base, highly reactive 18F-flouride was generated immediately and used directly for 18F-labeling reactions. These data indicate that 18F-acyl fluorides represent a new paradigm for preparation and transport of anhydrous, reactive 18F-fluoride for radiofluorinations.

Original languageEnglish (US)
Pages (from-to)181-185
Number of pages5
JournalJournal of Fluorine Chemistry
Volume180
DOIs
StatePublished - Dec 1 2015

Fingerprint

Fluorides
fluoride
fluorides
Tubing
positrons
Radiochemistry
radiochemistry
Cyclotrons
Proton irradiation
Positron emission tomography
proton irradiation
Fluorine
Anhydrides
Polypropylenes
Positrons
fluorine
anhydrides
polypropylene
Isotopes
Positron-Emission Tomography

Keywords

  • F-fluorination
  • Acyl fluoride
  • Fluorine-18
  • Positron emission tomography
  • Radiochemistry
  • Radiofluorination

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Environmental Chemistry

Cite this

Production and transport of gaseous 18F-synthons : 18F-acyl fluorides. / Jiang, Huailei; DiMagno, Stephen G.; DeGrado, Timothy R.

In: Journal of Fluorine Chemistry, Vol. 180, 01.12.2015, p. 181-185.

Research output: Contribution to journalArticle

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abstract = "Fluorine-18 (18F, T1/2 = 109.7 min) is a positron-emitting isotope that has found extensive application as a radiolabel for positron emission tomography (PET). Although gaseous 11C-CO2 and 11C-CH4 are practically transported from cyclotron to radiochemistry processes, 18F-fluoride is routinely transported in aqueous solution because it is commonly produced by proton irradiation of 18O-enriched water. In most cases, subsequent dry-down steps are necessary to prepare reactive 18F-fluoride for radiofluorination. In this work, a simple module was designed to generate gaseous 18F-acyl fluorides from aqueous 18F-fluoride solution by solid phase 18F-radiofluorination of acyl anhydride. The gaseous 18F-acyl fluorides were purified through a column containing Porapak Q/Na2SO4, resulting in high yields (>86{\%}), purities (>99{\%}) and specific activities (>1200 GBq/μmol). Prototypic 18F-acetyl fluoride (18F-AcF) was readily transported through 15 m of 0.8 mm ID polypropylene tubing with low (0.64 ± 0.12{\%}) adsorption to the tubing. Following dissolution of 18F-AcF in solvent containing base, highly reactive 18F-flouride was generated immediately and used directly for 18F-labeling reactions. These data indicate that 18F-acyl fluorides represent a new paradigm for preparation and transport of anhydrous, reactive 18F-fluoride for radiofluorinations.",
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N2 - Fluorine-18 (18F, T1/2 = 109.7 min) is a positron-emitting isotope that has found extensive application as a radiolabel for positron emission tomography (PET). Although gaseous 11C-CO2 and 11C-CH4 are practically transported from cyclotron to radiochemistry processes, 18F-fluoride is routinely transported in aqueous solution because it is commonly produced by proton irradiation of 18O-enriched water. In most cases, subsequent dry-down steps are necessary to prepare reactive 18F-fluoride for radiofluorination. In this work, a simple module was designed to generate gaseous 18F-acyl fluorides from aqueous 18F-fluoride solution by solid phase 18F-radiofluorination of acyl anhydride. The gaseous 18F-acyl fluorides were purified through a column containing Porapak Q/Na2SO4, resulting in high yields (>86%), purities (>99%) and specific activities (>1200 GBq/μmol). Prototypic 18F-acetyl fluoride (18F-AcF) was readily transported through 15 m of 0.8 mm ID polypropylene tubing with low (0.64 ± 0.12%) adsorption to the tubing. Following dissolution of 18F-AcF in solvent containing base, highly reactive 18F-flouride was generated immediately and used directly for 18F-labeling reactions. These data indicate that 18F-acyl fluorides represent a new paradigm for preparation and transport of anhydrous, reactive 18F-fluoride for radiofluorinations.

AB - Fluorine-18 (18F, T1/2 = 109.7 min) is a positron-emitting isotope that has found extensive application as a radiolabel for positron emission tomography (PET). Although gaseous 11C-CO2 and 11C-CH4 are practically transported from cyclotron to radiochemistry processes, 18F-fluoride is routinely transported in aqueous solution because it is commonly produced by proton irradiation of 18O-enriched water. In most cases, subsequent dry-down steps are necessary to prepare reactive 18F-fluoride for radiofluorination. In this work, a simple module was designed to generate gaseous 18F-acyl fluorides from aqueous 18F-fluoride solution by solid phase 18F-radiofluorination of acyl anhydride. The gaseous 18F-acyl fluorides were purified through a column containing Porapak Q/Na2SO4, resulting in high yields (>86%), purities (>99%) and specific activities (>1200 GBq/μmol). Prototypic 18F-acetyl fluoride (18F-AcF) was readily transported through 15 m of 0.8 mm ID polypropylene tubing with low (0.64 ± 0.12%) adsorption to the tubing. Following dissolution of 18F-AcF in solvent containing base, highly reactive 18F-flouride was generated immediately and used directly for 18F-labeling reactions. These data indicate that 18F-acyl fluorides represent a new paradigm for preparation and transport of anhydrous, reactive 18F-fluoride for radiofluorinations.

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