Investigations into Porphyrin- and Naphthalenediimide-Based Materials for the Molecular Imaging of Prostate Cancer

Abstract

This project aimed to investigate porphyrins and naphthalenediimide-based materials for the molecular imaging of prostate cancer.

Chapter 2 begins the development of a porphyrin-based imaging probe, suitable for radiolabelling, and targeted towards prostate cancer. It details the synthesis of a range of functionalised porphyrins, as well as the investigation into their UV-vis and fluorescence properties. Some preliminary radiolabelling studies were also completed.

Chapter 3 addresses the linking strategies developed to bind the porphyrin with a targeting biomolecule. It first presents a Pictet-Spengler type approach published by Bertozzi et al,1 highlighting some of the problems in reproducing the published result, then focuses on the development of novel unsymmetrical naphthalenediimides as potential bifunctional linkers for multimodal imaging and prostate cancer targeting. The synthesis and characterisation of these molecules is detailed, along with the coupling attempts to the porphyrin molecules synthesised in Chapter 2. Due to the difficulty of this process, a number of adaptations had to be made, to both the molecules and the procedures used, all of which are presented.

Chapter 4 presents the naphthalenediimides as bifunctional, dual purpose linkers and imaging agents for prostate cancer. Bespoke naphthalenediimides were designed and synthesised for this process and employed as co-initiators in the ring opening polymerisation of lactide, leading to a terminally functionalised fluorescent polymer. This material was further functionalised with bombesin [7-13] using copper catalysed click-chemistry. The structure and fluorescence properties of the resulting materials was studied using confocal microscopy.

Date of Award	22 Jul 2020
Original language	English
Awarding Institution	University of Bath
Supervisor	Sofia Pascu (Supervisor) & Ian Eggleston (Supervisor)