Development of organofluorine (radio)chemistry

Bugert, Anna 2025. Development of organofluorine (radio)chemistry. PhD Thesis, Cardiff University. Item availability restricted.

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Abstract

PET is a molecular imaging technique that visualises the biological distribu7on of a positron-emi;ng radiotracer in vivo. Applica7ons of PET are numerous and include the diagnosis and treatment of oncological and neurological disorders and the development of novel therapeu7cs. The development of radiotracers is hindered by the extensive criteria that dictate, among other factors, the lipophilicity, non-specific binding and metabolic stability of candidate radiotracers. This thesis describes the development of a novel method for the 18F-and 19F-fluorina7on of cubanes, that enables the synthesis of cubyl-containing 18F-radiotracers for applica7ons in Positron Emission Tomography (PET) Imaging. This work encompasses three parts. In the first part (Chapter 2), the synthesis of cubyl-containing substrates, required to test our 18F- and 19F-fluorina7on condi7ons, is described. Ten iodocubyl substrates bearing ester, alcohol, ketone and amide func7onal groups were synthesised for fluorina7on substrate scope studies. Finally, the op7misa7on of an eight-step synthesis of a cubyl alanine analogue was described, to provide a basis for future work. In the second part (Chapter 3), the first synthesis of a fluorocubane using nucleophilic fluoride sources is described. The op7misa7on of a fluorodeiodina7on reac7on is discussed in detail, which provided a star7ng point for the development of the corresponding 18F-reac7on. Eleven fluorocubanes could be synthesised in up to 63 % yield, which were used as authen7c 19F-references for assessing 18F-fluorina7on outcomes. Finally, the third part (Chapter 4) describes the first synthesis of an 18F-fluorinated cubane. The op7misa7on of the 18F-fluorodeiodina7on reac7on is discussed. Eight [18F]fluorocubanes could be synthesised in up to 34 % radiochemical yield.

Item Type:	Thesis (PhD)
Date Type:	Completion
Status:	Unpublished
Schools:	Schools > Chemistry
Date of First Compliant Deposit:	26 November 2025
Last Modified:	26 Nov 2025 11:50
URI:	https://orca.cardiff.ac.uk/id/eprint/182653

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