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UBC Theses and Dissertations
Carbohydrate-bearing ligands for biologically active metal ions Green, David
Abstract
Two distinct projects involving carbohydrates in bioinorganic chemistry are discussed in this thesis. In one study, several gallium and indium complexes with pendant carbohydrates were prepared and examined for potential use in radiopharmaceutical applications. Carbohydrate-bearing 3-hydroxy-4-pyridinone ligand precursors and their tris(ligand)gallium(III) and indium(III) complexes were synthesized and characterized by mass spectrometry, elemental analysis, ]H and l 3C NMR spectroscopy, and in the case of one intermediate, by X-ray crystallography. With three equivalents of ligand, neutral complexes formed with the pyridinone moiety (as expected) complexing the gallium(III) and indium(III) metal centers. In the other study, a series of 3-hydroxy-4-pyridinones and their glycoside pro-drugs (pyridinone glycosides) were prepared and studied. The pyridinones have the potential to be used in metal chelation therapy to aid in the treatment of neurodegenerative disorders such as Alzheimer's disease. The pyridinone glycosides were synthesized via a Mitsunobu coupling and characterized by mass spectrometry, elemental analysis, !H and 1 3C NMR spectroscopy, and in one case by X-ray crystallography. The glycoside pro-drugs mask the metal chelation portion of the pyridinones by protecting the 3- hydroxy position. The glycosidic cleavage of the pyridinone glycosides was studied (and kinetic parameters determined for one compound) with Agrobacterium sp. P-glucosidase. This enzyme cleaves the pyridinone glycosides unmasking the pyridinones and making them available for metal chelation. A series of the 3-hydroxy-4-pyridinones also displayed significant antioxidant protection in a radical quenching assay.
Item Metadata
Title |
Carbohydrate-bearing ligands for biologically active metal ions
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Creator | |
Publisher |
University of British Columbia
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Date Issued |
2004
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Description |
Two distinct projects involving carbohydrates in bioinorganic chemistry are discussed
in this thesis. In one study, several gallium and indium complexes with pendant
carbohydrates were prepared and examined for potential use in radiopharmaceutical
applications. Carbohydrate-bearing 3-hydroxy-4-pyridinone ligand precursors and their
tris(ligand)gallium(III) and indium(III) complexes were synthesized and characterized by
mass spectrometry, elemental analysis, ]H and l 3C NMR spectroscopy, and in the case of one
intermediate, by X-ray crystallography. With three equivalents of ligand, neutral complexes
formed with the pyridinone moiety (as expected) complexing the gallium(III) and
indium(III) metal centers. In the other study, a series of 3-hydroxy-4-pyridinones and their
glycoside pro-drugs (pyridinone glycosides) were prepared and studied. The pyridinones
have the potential to be used in metal chelation therapy to aid in the treatment of
neurodegenerative disorders such as Alzheimer's disease. The pyridinone glycosides were
synthesized via a Mitsunobu coupling and characterized by mass spectrometry, elemental
analysis, !H and 1 3C NMR spectroscopy, and in one case by X-ray crystallography. The
glycoside pro-drugs mask the metal chelation portion of the pyridinones by protecting the 3-
hydroxy position. The glycosidic cleavage of the pyridinone glycosides was studied (and
kinetic parameters determined for one compound) with Agrobacterium sp. P-glucosidase.
This enzyme cleaves the pyridinone glycosides unmasking the pyridinones and making them
available for metal chelation. A series of the 3-hydroxy-4-pyridinones also displayed
significant antioxidant protection in a radical quenching assay.
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Extent |
9086324 bytes
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Genre | |
Type | |
File Format |
application/pdf
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Language |
eng
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Date Available |
2009-11-27
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Provider |
Vancouver : University of British Columbia Library
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Rights |
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.
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DOI |
10.14288/1.0061177
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URI | |
Degree | |
Program | |
Affiliation | |
Degree Grantor |
University of British Columbia
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Graduation Date |
2004-11
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Campus | |
Scholarly Level |
Graduate
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Aggregated Source Repository |
DSpace
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Rights
For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use.