Chemical Reviews, volume 116, issue 2, pages 719-766

18F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography

Sean Preshlock ¹

Matthew Tredwell ¹

Véronique Gouverneur ¹

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Chemistry Research Laboratory, University of Oxford, Oxford OX1 3TA, United Kingdom |

Publication type: Journal Article

Publication date: 2016-01-11

American Chemical Society (ACS)

Journal: Chemical Reviews

Quartile SCImago

Quartile WOS

Impact factor: 62.1

ISSN: 00092665, 15206890

DOI: 10.1021/acs.chemrev.5b00493

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General Chemistry

Abstract

Diverse radiochemistry is an essential component of nuclear medicine; this includes imaging techniques such as positron emission tomography (PET). As such, PET can track diseases at an early stage of development, help patient care planning through personalized medicine and support drug discovery programs. Fluorine-18 is the most frequently used radioisotope in PET radiopharmaceuticals for both clinical and preclinical research. Its physical and nuclear characteristics (97% β(+) decay, 109.8 min half-life, 635 keV positron energy) and high specific activity make it an attractive nuclide for labeling and molecular imaging. Arenes and heteroarenes are privileged candidates for (18)F-incorporation as they are metabolically robust and therefore widely used by medicinal chemists and radiochemists alike. For many years, the range of (hetero)arenes amenable to (18)F-fluorination was limited by the lack of chemically diverse precursors, and of radiochemical methods allowing (18)F-incorporation in high selectivity and efficiency (radiochemical yield and purity, specific activity, and radio-scalability). The appearance of late-stage fluorination reactions catalyzed by transition metal or small organic molecules (organocatalysis) has encouraged much research on the use of these activation manifolds for (18)F-fluorination. In this piece, we review all of the reactions known to date to install the (18)F substituent and other key (18)F-motifs (e.g., CF3, CHF2, OCF3, SCF3, OCHF2) of medicinal relevance onto (hetero)arenes. The field has changed significantly in the past five years, and the current trend suggests that the radiochemical space available for PET applications will expand rapidly in the near future.

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Public Library of Science (PLoS)	Public Library of Science (PLoS), 2, 0.35% Public Library of Science (PLoS) 2 publications, 0.35%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 2, 0.35% American Association for the Advancement of Science (AAAS) 2 publications, 0.35%
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Scientific Research Publishing	Scientific Research Publishing, 1, 0.18% Scientific Research Publishing 1 publication, 0.18%
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Preshlock S., Tredwell M., Gouverneur V. 18F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography // Chemical Reviews. 2016. Vol. 116. No. 2. pp. 719-766.

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Preshlock S., Tredwell M., Gouverneur V. 18F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography // Chemical Reviews. 2016. Vol. 116. No. 2. pp. 719-766.

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TY - JOUR

DO - 10.1021/acs.chemrev.5b00493

UR - https://doi.org/10.1021/acs.chemrev.5b00493

TI - 18F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography

T2 - Chemical Reviews

AU - Preshlock, Sean

AU - Tredwell, Matthew

AU - Gouverneur, Véronique

PY - 2016

DA - 2016/01/11 00:00:00

PB - American Chemical Society (ACS)

SP - 719-766

IS - 2

VL - 116

SN - 0009-2665

SN - 1520-6890

ER -

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BibTex Copy

@article{2016_Preshlock,

author = {Sean Preshlock and Matthew Tredwell and Véronique Gouverneur},

title = {18F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography},

journal = {Chemical Reviews},

year = {2016},

volume = {116},

publisher = {American Chemical Society (ACS)},

month = {jan},

url = {https://doi.org/10.1021/acs.chemrev.5b00493},

number = {2},

pages = {719--766},

doi = {10.1021/acs.chemrev.5b00493}

}

MLA

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MLA Copy

Preshlock, Sean, et al. “18F-Labeling of Arenes and Heteroarenes for Applications in Positron Emission Tomography.” Chemical Reviews, vol. 116, no. 2, Jan. 2016, pp. 719-766. https://doi.org/10.1021/acs.chemrev.5b00493.

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Publisher

American Chemical Society (ACS)

Journal

Chemical Reviews

Quartile SCImago

Quartile WOS

Impact factor

62.1

ISSN

00092665 (Print)
15206890 (Electronic)