Sulfur - fluorine bond in PET radiochemistry

Giancarlo Pascali; Lidia Matesic; Bo Zhang; Andrew T. King; Andrea J. Robinson; Alison T. Ung; Benjamin H. Fraser

doi:10.1186/s41181-017-0028-6

Sulfur - fluorine bond in PET radiochemistry

Giancarlo Pascali^*, Lidia Matesic, Bo Zhang, Andrew T. King, Andrea J. Robinson, Alison T. Ung, Benjamin H. Fraser

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

19 Citations (Scopus)

33 Downloads (Pure)

Abstract

The importance of the sulfur-fluorine bond is starting to increase in modern medicinal chemistry literature. This is due to a better understanding of the stability and reactivity of this moiety depending on the various oxidation states of sulfur. Furthermore, several commercial reagents used for mild and selective fluorination of organic molecules are based on the known reactivity of S-F groups. In this review, we will show how these examples are translating into the ¹⁸F field, both for use as stable tags in finished radiopharmaceuticals and as mildly reactive fluoride-relay intermediates. Finally, we also discuss current opportunities where examples of non-radioactive S-F applications/chemistry may be translated into future ¹⁸F radiochemistry applications.

Original language	English
Article number	9
Pages (from-to)	18
Journal	EJNMMI Radiopharmacy and Chemistry
Volume	2
DOIs	https://doi.org/10.1186/s41181-017-0028-6
Publication status	Published - Jul 2017
Externally published	Yes

Bibliographical note

Copyright the Author(s) 2017. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

Keywords

Sulfur-fluorine bond
Sulfonyl fluoride
18F
PET
Fluoride relay
Fluorosulfate
Deoxyfluorination
Sulfurhexafluoride

Access to Document

10.1186/s41181-017-0028-6

Publisher version (open access)Final published version, 1.21 MBLicence: CC BY

Cite this

@article{f30e70bc25bc4918af3df46d66fbbbd6,

title = "Sulfur - fluorine bond in PET radiochemistry",

abstract = "The importance of the sulfur-fluorine bond is starting to increase in modern medicinal chemistry literature. This is due to a better understanding of the stability and reactivity of this moiety depending on the various oxidation states of sulfur. Furthermore, several commercial reagents used for mild and selective fluorination of organic molecules are based on the known reactivity of S-F groups. In this review, we will show how these examples are translating into the 18F field, both for use as stable tags in finished radiopharmaceuticals and as mildly reactive fluoride-relay intermediates. Finally, we also discuss current opportunities where examples of non-radioactive S-F applications/chemistry may be translated into future 18F radiochemistry applications. ",

keywords = "Sulfur-fluorine bond, Sulfonyl fluoride, 18F, PET, Fluoride relay, Fluorosulfate, Deoxyfluorination, Sulfurhexafluoride",

author = "Giancarlo Pascali and Lidia Matesic and Bo Zhang and King, {Andrew T.} and Robinson, {Andrea J.} and Ung, {Alison T.} and Fraser, {Benjamin H.}",

note = "Copyright the Author(s) 2017. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.",

year = "2017",

month = jul,

doi = "10.1186/s41181-017-0028-6",

language = "English",

volume = "2",

pages = "18",

journal = "EJNMMI Radiopharmacy and Chemistry",

issn = "2365-421X",

publisher = "Springer, Springer Nature",

}

TY - JOUR

T1 - Sulfur - fluorine bond in PET radiochemistry

AU - Pascali, Giancarlo

AU - Matesic, Lidia

AU - Zhang, Bo

AU - King, Andrew T.

AU - Robinson, Andrea J.

AU - Ung, Alison T.

AU - Fraser, Benjamin H.

N1 - Copyright the Author(s) 2017. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.

PY - 2017/7

Y1 - 2017/7

N2 - The importance of the sulfur-fluorine bond is starting to increase in modern medicinal chemistry literature. This is due to a better understanding of the stability and reactivity of this moiety depending on the various oxidation states of sulfur. Furthermore, several commercial reagents used for mild and selective fluorination of organic molecules are based on the known reactivity of S-F groups. In this review, we will show how these examples are translating into the 18F field, both for use as stable tags in finished radiopharmaceuticals and as mildly reactive fluoride-relay intermediates. Finally, we also discuss current opportunities where examples of non-radioactive S-F applications/chemistry may be translated into future 18F radiochemistry applications.

AB - The importance of the sulfur-fluorine bond is starting to increase in modern medicinal chemistry literature. This is due to a better understanding of the stability and reactivity of this moiety depending on the various oxidation states of sulfur. Furthermore, several commercial reagents used for mild and selective fluorination of organic molecules are based on the known reactivity of S-F groups. In this review, we will show how these examples are translating into the 18F field, both for use as stable tags in finished radiopharmaceuticals and as mildly reactive fluoride-relay intermediates. Finally, we also discuss current opportunities where examples of non-radioactive S-F applications/chemistry may be translated into future 18F radiochemistry applications.

KW - Sulfur-fluorine bond

KW - Sulfonyl fluoride

KW - 18F

KW - PET

KW - Fluoride relay

KW - Fluorosulfate

KW - Deoxyfluorination

KW - Sulfurhexafluoride

U2 - 10.1186/s41181-017-0028-6

DO - 10.1186/s41181-017-0028-6

M3 - Article

C2 - 29503850

SN - 2365-421X

VL - 2

SP - 18

JO - EJNMMI Radiopharmacy and Chemistry

JF - EJNMMI Radiopharmacy and Chemistry

M1 - 9

ER -

Sulfur - fluorine bond in PET radiochemistry

Abstract

Bibliographical note

Keywords

Access to Document

Fingerprint

Cite this