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New chemical and radiochemical routes to [18F]Rho6G-DEG-F, a delocalized lipophilic cation for myocardial perfusion imaging with PET

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Abstract

New chemical and radiochemical syntheses are described for the preparation of [18F]Rho6G-DEG-F, an 18F-labeled analogue of the fluorescent dye rhodamine 6G, which has shown promise as myocardidal perfusion imaging agent. Tosylated precursors of [18F]Rho6G-DEG-F amenable to 18F-labeling were obtained either through a two-step synthesis from rhodamine 6G lactone (33% yield), or in one step from rhodamine 575 (64% yield), then purified by preparative C18 chromatography. Manual synthesis of [18F]Rho6G-DEG-F was achieved in a single radiochemical step from either the tosylate salt or the tosylate/formate double salt in DMSO under standard nucleophillic aliphatic 18F-fluorination conditions (K[18F]F/K2CO3/Kryptofix 2.2.2.). Incorporation of the [18F]F was found to be satisfactory (≥34% by TLC), despite the protic character of the precursor molecules. [18F]Rho6G-DEG-F was manually synthesized in final decay-corrected radiochemical yields of 11–26% (tosylate salt) and 9–21% (tosylate/formate double salt). The protocol was transferred to an automated synthesis unit, where the product was obtained in 3–9% radiochemical yield (n = 3) decay corrected to start-of-synthesis, >99% radiochemical purity, and a molar activity of 122–267 GBq μmol−1 (3.3–7.2 Ci μmol−1).

Graphical abstract: New chemical and radiochemical routes to [18F]Rho6G-DEG-F, a delocalized lipophilic cation for myocardial perfusion imaging with PET

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Publication details

The article was received on 27 Jun 2017, accepted on 24 Aug 2017 and first published on 25 Aug 2017


Article type: Research Article
DOI: 10.1039/C7MD00326A
Citation: Med. Chem. Commun., 2017, Advance Article
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    New chemical and radiochemical routes to [18F]Rho6G-DEG-F, a delocalized lipophilic cation for myocardial perfusion imaging with PET

    J. A. H. Inkster, S. Zhang, V. Akurathi, A. Belanger, S. Dubey, S. T. Treves and A. B. Packard, Med. Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7MD00326A

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