Synthesis of diene ligands with H-bonding capabilities for bioimaging applications

Glowacka, Paulina (2015) Synthesis of diene ligands with H-bonding capabilities for bioimaging applications. Doctoral thesis, University of East Anglia.

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Abstract

Investigations of the synthesis of novel bioprobes (Scheme A), potentially useful in bioreactions and sugar sensing, are described. A preliminary study is reported that
aims to validate the feasibility of tricarbonyl iron complexes and their derivatives in applications as a constituent part of IR/fluorescent bioprobes. Infrared spectroscopy has significant potential in studying these carbonylmetal-based bioprobes, as the MCO signals fall in a window in the water background spectrum at about 2000 cm–1
where absorptions of most of organic functional groups are absent. Their narrow vibrational stretching modes provide information about the iron complex and its environment.
Scheme A
In the first project, novel tricarbonyliron complexes were synthesised by N-acylation with various amines. This procedure allowed direct access to novel amide products.
(Scheme B).
Scheme B
Work towards the development of reactions for the preparation of 9- aminomethylanthracene is described. An improved preparation of this fluorophore in good yield from readily available precursors (Scheme C) was developed.
Scheme C
Furthermore, the synthesis of bioprobes suitable for sugar analytes using 9- aminomethylanthracene derivatives containing boronic acids were also investigated.
The synthesis of bioprobes with self-immolative linkers that also contain both fluorophores and tricarbonyliron complexes and a study of their enzymatic cleavage
reactions is also described. The reaction of an electrophilic cyclohexadienyliron(1+) complex with 7-amino-4-methylcoumarin gave a new fluorescent compound, Scheme D. The methodology was then applied to the preparation of a novel series of fluorescent compounds which are valuable precursors in prodrug applications.
Scheme D
Finally, a study was made of the reaction of PABA derivatives with different protecting groups to incorporate the carbonyl group followed by attempted reactions with these new fluorescent compounds to give fully-functional target molecules, but this was unsuccessful (Scheme E).
Scheme E
(Please note that Schemes A-E in the abstract are diagrams which have not copied over)

Item Type: Thesis (Doctoral)
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Jackie Webb
Date Deposited: 26 Jun 2015 10:17
Last Modified: 26 Jun 2015 10:31
URI: https://ueaeprints.uea.ac.uk/id/eprint/53391
DOI:

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