Synthesis and characterisation of a selection of phthalocyanines covalently bonded to water-soluble polymers and a ferrocenyl fragment

Abstract

English: This thesis is concerned with the synthesis of phthalocyanine derivatives and their anchoring onto water-soluble polyaspartamides to produce compounds that may have biomedical applications, especially in the photodynamic therapy of cancer. The anchoring of a ferrocenyl fragment, which itself is an anti-neoplastic entity, onto both the polymer and a phthalocyanine entity was also accomplished utilizing biodegradable amide bonds. The electrochemical behaviour of selected phthalocyanines and polymer-anchored phthalocyanines is reported. Phthalocyanines containing both amine and carboxylic acid functional groups were prepared using established methods. The active amine side chains of the polymers derived from aspartic acid and/or lysine were utilized to couple both ferrocenyl and phthalocyanine entities. In addition ferrocenylethylamine was anchored onto a phthalocyanine containing carboxylic acid groups. The phthalocyanine-anchored polymers showed a marked decrease in water-solubility especially when these had additional ferrocenyl fragments anchored onto either the polymeric backbone or onto a polymer-bound phthalocyanine. The attachment of a ferrocenylethylamine onto a polymer-bound phthalocyanine containing three free carboxylic acid groups appears to be a sterically hindered process as only one of the carboxylic acid groups undergoes ami dation even in the presence of excess amine.

Afrikaans: Hierdie tesis behels die sintese van ftalosianien derivate en hulle koppeling aan wateroplosbare poliaspartamiedes om verbindings te vorm wat moontlike biomediese toepassings mag vind, vera! in die fotodinamiese behandeling van kanker. Die koppeling van 'n ferroseniel fragment, wat self 'n neoplastiese fragment is, aan beide die polimeer en 'n ftalosianien entiteit is ook bereik deur van biodegredeerbare amied bindings gebruik te maak. Die elektrochemiese gedrag van geselekteerde ftalosianiene is ook vermeld. Ftalosianiene wat beide am1en en karboksielsuur funksionele groepe bevat is ook berei deur bekende metodes. Die aktiewe amien sykettings van die polimere wat gesintetiseer is vanaf aspartaamsuur en/of lisien is gebruik om beide ferroseniel en ftalosianien entiteite te koppel. Daarby is ferrosenieletielamien gekoppel aan ftalosianienbevattende karboksielsuur groepe. Die ftalosianien gekoppelde polimere het 'n noemenswaardige afname in wateroplosbaarheid getoon, veral wanneer addisionele ferroseniel fragmente gekoppel is aan die polimeriese rugraat of aan 'n polimeergebonde ftalosianien. Die koppeling van ferrosenieletielamien aan 'n polimeergebonde ftalosianien wat oor drie vrye karboksielsuurgroepe beskik, bleik 'n steries verhinderde proses te wees omdat slegs een van die karboksielsure amiedvorming ondergaan in die teenwoordigheid van oormaat ami en.