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Exploring transition metal fluoride chelates – synthesis, properties and prospects towards potential PET probes

Exploring transition metal fluoride chelates – synthesis, properties and prospects towards potential PET probes
Exploring transition metal fluoride chelates – synthesis, properties and prospects towards potential PET probes
The coordination chemistry of the first row transition metal trifluorides with terpy (2,2’:6’,2’’-terpyridine) and Me3-tacn (1,4,7-trimethyl-1,4,7-triazacyclononane) was explored to identify potential systems for 18F radiolabelling. The complexes [MF3(L)] (M = Cr, Mn, Fe, Co; L = Me3-tacn, terpy) were synthesised and fully characterised by UV-vis and IR spectroscopy, microanalysis, and, for the diamagnetic [CoF3(L)], using 1H, 19F{1H} and 59Co NMR spectroscopy. Single crystal X-ray analyses are reported for [MF3(Me3-tacn)] (M = Mn, Co), [FeF3(terpy)] and [FeF3(BnMe2-tacn)]. Stability tests on [MF3(Me3-tacn)] (M = Cr, Mn, Fe) and [M’F3(terpy)] (M’ = Cr, Fe) were performed and Cl/19F halide exchange reactions on [CrCl3(Me3-tacn)] using [Me4N]F in anhydrous MeCN solution, and [FeCl3(Me3-tacn)] using [Me4N]F in anhydrous MeCN or KF in aqueous MeCN solution were also carried out. Halide exchange reactions proved to be successful in forming [FeF3(Me3-tacn)] in aqueous MeCN solution within 30 minutes. Based upon the clean Cl/F exchange and the good stability observed for [FeF3(Me3-tacn)] in a range of competitive media, this was identified as a possible candidate for radiolabelling. 18F/19F isotopic exchange was achieved by addition of [18F]F- in the cyclotron target water to a MeCN solution of the benzyl-substituted analogue, [FeF3(BnMe2-tacn)], at a range of concentrations down to 24 nM with heating to 80 C for 10 mins.; the resulting [Fe18F19F2(BnMe2-tacn)] shows radiochemical purity (RCP)  90% after 2 h in a range of formulations, including 10% EtOH/phosphate buffered saline (PBS) and 10% EtOH/human serum albumin (HSA). This is the first reported complex with a transition metal directly bonded to [18F]F.
0300-9246
6767-6776
Blower, Philip J.
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Levason, William
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Luthra, Sajinder K.
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McRobbie, Graeme
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Monzittu, Francesco
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Mules, Thomas O.
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Reid, Gillian
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Subhan, M. Nadeem
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Blower, Philip J.
bab2bda7-a8cb-481c-b9e8-9ebcb2a8d3b4
Levason, William
e7f6d7c7-643c-49f5-8b57-0ebbe1bb52cd
Luthra, Sajinder K.
fcb54474-75fa-4b01-8df7-f55c03468430
McRobbie, Graeme
b12f273f-dd78-4ff8-a423-b0b5158091c7
Monzittu, Francesco
7c94332d-ed34-4ee6-b8b3-c17c14b11849
Mules, Thomas O.
793a3c22-73e3-4bd5-8cc4-907eef71af80
Reid, Gillian
37d35b11-40ce-48c5-a68e-f6ce04cd4037
Subhan, M. Nadeem
cbb61d0d-1072-45b8-83b7-17b3e29a71a9

Blower, Philip J., Levason, William, Luthra, Sajinder K., McRobbie, Graeme, Monzittu, Francesco, Mules, Thomas O., Reid, Gillian and Subhan, M. Nadeem (2019) Exploring transition metal fluoride chelates – synthesis, properties and prospects towards potential PET probes. Dalton Transactions, 48 (20), 6767-6776. (doi:10.1039/C8DT03696A).

Record type: Article

Abstract

The coordination chemistry of the first row transition metal trifluorides with terpy (2,2’:6’,2’’-terpyridine) and Me3-tacn (1,4,7-trimethyl-1,4,7-triazacyclononane) was explored to identify potential systems for 18F radiolabelling. The complexes [MF3(L)] (M = Cr, Mn, Fe, Co; L = Me3-tacn, terpy) were synthesised and fully characterised by UV-vis and IR spectroscopy, microanalysis, and, for the diamagnetic [CoF3(L)], using 1H, 19F{1H} and 59Co NMR spectroscopy. Single crystal X-ray analyses are reported for [MF3(Me3-tacn)] (M = Mn, Co), [FeF3(terpy)] and [FeF3(BnMe2-tacn)]. Stability tests on [MF3(Me3-tacn)] (M = Cr, Mn, Fe) and [M’F3(terpy)] (M’ = Cr, Fe) were performed and Cl/19F halide exchange reactions on [CrCl3(Me3-tacn)] using [Me4N]F in anhydrous MeCN solution, and [FeCl3(Me3-tacn)] using [Me4N]F in anhydrous MeCN or KF in aqueous MeCN solution were also carried out. Halide exchange reactions proved to be successful in forming [FeF3(Me3-tacn)] in aqueous MeCN solution within 30 minutes. Based upon the clean Cl/F exchange and the good stability observed for [FeF3(Me3-tacn)] in a range of competitive media, this was identified as a possible candidate for radiolabelling. 18F/19F isotopic exchange was achieved by addition of [18F]F- in the cyclotron target water to a MeCN solution of the benzyl-substituted analogue, [FeF3(BnMe2-tacn)], at a range of concentrations down to 24 nM with heating to 80 C for 10 mins.; the resulting [Fe18F19F2(BnMe2-tacn)] shows radiochemical purity (RCP)  90% after 2 h in a range of formulations, including 10% EtOH/phosphate buffered saline (PBS) and 10% EtOH/human serum albumin (HSA). This is the first reported complex with a transition metal directly bonded to [18F]F.

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TM_fluorides_paper_R2 final 23_02_2019 - Accepted Manuscript
Restricted to Repository staff only until 24 April 2020.
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ESI_transition_metals_R2 final 23_02_2019
Restricted to Repository staff only until 18 March 2020.
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More information

Accepted/In Press date: 18 March 2019
e-pub ahead of print date: 24 April 2019

Identifiers

Local EPrints ID: 429570
URI: https://eprints.soton.ac.uk/id/eprint/429570
ISSN: 0300-9246
PURE UUID: 1d289bdf-27a0-4137-ae9a-f2eeaea06076
ORCID for William Levason: ORCID iD orcid.org/0000-0003-3540-0971
ORCID for Gillian Reid: ORCID iD orcid.org/0000-0001-5349-3468

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Date deposited: 29 Mar 2019 17:30
Last modified: 05 Jun 2019 00:38

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Contributors

Author: Philip J. Blower
Author: William Levason ORCID iD
Author: Sajinder K. Luthra
Author: Graeme McRobbie
Author: Francesco Monzittu
Author: Thomas O. Mules
Author: Gillian Reid ORCID iD
Author: M. Nadeem Subhan

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