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Title: The synthesis of galectin-3-targeted cancer imaging agents
Author: Lees, Glenn
Awarding Body: University of Birmingham
Current Institution: University of Birmingham
Date of Award: 2014
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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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry ; RC0254 Neoplasms. Tumors. Oncology (including Cancer)