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Synthesis of 2’-bromo-2’-fluoro-2’-deoxycytidine derivatives towards [18F]gemcitabine

Stark, Roderick Thomas 2020. Synthesis of 2’-bromo-2’-fluoro-2’-deoxycytidine derivatives towards [18F]gemcitabine. PhD Thesis, Cardiff University.
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Abstract

Gemcitabine is a frequently used chemotherapeutic agent against a range of cancers – pancreatic cancer in particular. One of its disadvantages is its poor specificity, needing to overcome many deactivation pathways in order to impart its anticancer properties. As such, a fluorine-18 labelled gemcitabine would provide in vivo pharmacokinetic information specific for each patient in a step towards personalised treatment. Herein described is a synthetic route towards compounds that may be screened as a fluorine-18 radiolabelling precursors for the synthesis of [18F]gemcitabine. The developed strategy centres on the synthesis of key 2-bromo-2-fluororibonolactone, which was produced in a diastereoselective fashion. The synthesised lactone was then reacted with cytosine derivatives to deliver the radiofluorination substrates. Fluorination with fluorine-19 demonstrated the suitability of the substrates towards substitution, with initial [18F]fluorination studies also conducted. Tissue culture studies were also carried out, in order to evaluate the bioactivity of the synthesised compounds, relative to gemcitabine.

Item Type: Thesis (PhD)
Date Type: Completion
Status: Unpublished
Schools: Chemistry
Date of First Compliant Deposit: 23 September 2020
Last Modified: 23 Sep 2021 01:30
URI: http://orca.cardiff.ac.uk/id/eprint/135062

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