The synthesis of galectin-3-targeted cancer imaging agents

Lees, Glenn (2014). The synthesis of galectin-3-targeted cancer imaging agents. University of Birmingham. Ph.D.

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Galectin-3 is an animal lectin that recognises and binds to β-galactosides in glycoconjugates and is frequently over-expressed in cancerous states, potentially allowing inhibitors to serve as vector tags for targeted image contrast agents to give enhanced MRI and flourescence images. Derivatives of lactosamine with 3'-arylamides have been shown to be excellent inhibitors of galectin-3: 3'-naphthamide derivatives of lactosamine have previously been shown to bind to galectin-3 with k\(_d\)<1 μM, and form the basis of the target imaging agent, which will also incorporate a spacer unit and a probe molecule.

Problems with the reduction/acylation of an azide in a key disaccharide intermediate could not be resolved by alterations in the reaction conditions; incorporation of the required amide earlier in the synthesis failed to lead to disaccharide products.

Employing a phthalimide as nitrogen protecting group has successfully produced a glycosyl donor precursor that will only require ring opening rather than the troublesome reduction/acylation.

Using a propargyl group to protect the anomeric position in the glysosyl acceptor has allowed for the attachment of the linker via a click reaction and subsequent deprotection reactions and FITC installation has produced one of the compounds required for comparison studies.

Type of Work: Thesis (Doctorates > Ph.D.)
Award Type: Doctorates > Ph.D.
College/Faculty: Colleges (2008 onwards) > College of Engineering & Physical Sciences
School or Department: School of Chemistry
Funders: None/not applicable
Subjects: Q Science > QD Chemistry
R Medicine > RC Internal medicine > RC0254 Neoplasms. Tumors. Oncology (including Cancer)


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