Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2010;10(11):1048-59.
doi: 10.2174/156802610791384298.

PET designated flouride-18 production and chemistry

Orit Jacobson  1 , Xiaoyuan Chen
Affiliations
Review

PET designated flouride-18 production and chemistry

Orit Jacobson et al. Curr Top Med Chem. 2010.

Abstract

Positron emission tomography (PET) is a nuclear medicine imaging technology which allows for four-dimensional, quantitative determination of the distribution of labeled biological compounds within the human body. PET is becoming an increasingly important tool for the measurement of physiological, biochemical and pharmacological functions at the molecular level in healthy and pathological conditions. This review will focus on Flouride-18, one of the common isotopes used for PET imaging, which has a half life of 109.8 minutes. This isotope can be produced with an efficient yield in a cyclotron as a nucleophile or as an electrophile. Flouride-18 can be thereafter introduced into small molecules or biomolecules using various chemical synthetic routes, to give the desired imaging agent.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Primary and secondary precursors used in electrophilic fluorination reactions.
Scheme 2
Scheme 2
[18F]-Aliphatic alkylation. a; synthesis of [18F]-fluoroalkyl agents. b; radiosynthesis of [18F]-FCHOLINE. c; synthesis of spiperone derivative via alkylation with [18F]-fluoroalkyl agent.
Scheme 3
Scheme 3
Direct [18F]-aliphatic fluorination on sulfonate esters precursors.
Scheme 4
Scheme 4
Aromatic nucleophilic fluorination. a; attempt to synthesize [18F]-radiolabeled hydroxyflutamide derivative in a direct fluorination on the aromatic nitro group. b; Radiosynthesis of [18F]-radiolabeled hydroxyflutamide derivative with several radiosynthesis steps.
Scheme 5
Scheme 5
Aromatic nucleophilic fluorination on diaryliodonium salts. a; fluorination on dihomoaryliodonium. b; 18F-introduction into electron-rich aryl diaryliodonium salts. c; fluorination on pyridines and quinolines.
Scheme 6
Scheme 6
Examples of 18F-labelled prosthetic groups.
Scheme 7
Scheme 7
Radiosynthesis of [18F]SFB using different precursors for the labeling, for biomolecules conjugation.
Scheme 8
Scheme 8
18F-Labeling “click chemistry” reactions, using 2-[18F]fluoroethylazide and 1-(azidomethyl)-4-[18F]-fluorobenzene.
Scheme 9
Scheme 9
18F-Labeling of silicon based biomolecules. a; direct fluorination on silica-modifies biomolecules. b; labeling of Si-18F-prosthetic groups for further conjugation with biomolecules.
Scheme 10
Scheme 10
Al18F-complexation with NOTA-conjugated biomolecule.
See this image and copyright information in PMC

References

    1. Bonasera TA, Ortu G, Rozen Y, Krais R, Freedman NM, Chisin R, Gazit A, Levitzki A, Mishani E. Potential (18)F-labeled biomarkers for epidermal growth factor receptor tyrosine kinase. Nucl. Med. Biol. 2001;28:359–374. - PubMed
    1. Jhanwar YS, Straus DJ. The role of PET in lymphoma. J. Nucl. Med. 2006;47:1326–1334. - PubMed
    1. Gofrit ON, Mishani E, Orevi M, Klein M, Freedman N, Pode D, Shapiro A, Katz R, Libson E, Chisin R. Contribution of 11C-choline positron emission tomography/computerized tomography to preoperative staging of advanced transitional cell carcinoma. J. Urol. 2006;176:940–944. discussion 944. - PubMed
    1. Niemeyer MG, Kuijper AF, Gerhards LJ, D'Haene EG, van der Wall EE. Nitrogen-13 ammonia perfusion imaging: relation to metabolic imaging. Am. Heart J. 1993;125:848–854. - PubMed
    1. Ter-Pogossian MM, Herscovitch P. Radioactive oxygen-15 in the study of cerebral blood flow, blood volume, and oxygen metabolism. Semin. Nucl. Med. 1985;15:377–394. - PubMed

MeSH terms

Substances