Novel Dyes for use as Boron Carriers in Boron Neutron Capture Therapy of Glioblastoma Multiforme

  • Ashton Robert Peat

Student thesis: Doctoral Thesis

Abstract

This project concerns the synthesis of boron-containing dyes as boron carriers for the medical procedure known as boron neutron capture therapy. A review of current and past research in this field is followed by description and justification of the main classes of dyes investigated (triarylmethanes, xanthenes and quinolines). This is followed by an investigation into the applicability of photochemistry using ultraviolet light for substituting boron onto halogenated aromatic molecules. Successful synthesis of boronated triarylmethanes and quinolines via this route is described. The integration of icosahedral carboranes is then explored, and the successful synthesis of an analogue of the xanthene dye fluorescein containing an integrated covalently-bound icosahedral carborane is detailed. Proposed routes for the carborane-containing analogues of triarylmethanes and quinolines are suggested. Finally, a number of other molecules of interest with potential as boron carriers are discussed (gliolan, florbetapir, procarbazine and cetirizine hydrochloride) and multiple proposed synthetic routes are explained. The attempted synthesis of a boron-containing analogue of cetirizine hydrochloride is also detailed.
To the best of the authors knowledge, none of the molecules described in the abstract as synthesised during this project have previously been described in the literature. The quinoline boronic acid pinacol esters do exist having been generated by more traditional synthetic methods, but not photochemical ones. The carborane-containing fluorescein analogue has not been described by any other publication. A number of proposed syntheses in this project – not attempted due to a lack of the necessary materials – have also not been theorised or reported by any other publication.
Word Count: 38,599 (Body), 51,343 (Total, incl. Appendices).

Date of Award11 Dec 2023
Original languageEnglish
Awarding Institution
  • University of Portsmouth
SupervisorJames Smith (Supervisor) & Pitt Cheryll (Supervisor)

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