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Towards Highly-Reactive Pyri(mi)dinol-Based Fluorescent Antioxidant Indicators And Cyclopropane Lipids: Autoxidizability and Potential as Inhibitors of Lipoxygenases

Chapter 2
In solution, py(mi)ridinols 1.33, 1.34 and 1.35 are 2-, 5- and 28-fold more reactive antioxidants, respectively, than α-TOH (the most potent lipid-soluble antioxidant in nature). In order to develop a highly-reactive fluorescent indicator of lipid peroxidation in cells, we sought to couple these antioxidants with boron-dipyrro- methene (BODIPY) dyes, such that the resulting conjugates will display a significant fluorecence enhancement upon oxidation. This chapter details efforts towards the synthesis of these compounds.

Chapter 3
Lipoxygenases are a family of important enzymes that catalyze the dioxygenation of arachidonic acid to yield a variety of potent lipid mediators that have been implicated in the pathogenesis of numerous degenerative conditions. We have undertaken a preliminary study of the effect of replacing the unsaturation in the related polyunsaturated lipid linoleic acid with cyclopropane rings on both the oxidizability of the lipid, as well as lipoxygenase’s ability to utilize it as a substrate. We anticipate that these analogs will be useful in co-crystallization studies with the enzyme that will provide unique insight into substrate acquisition, binding and the necessary conformation for catalysis. / Thesis (Master, Chemistry) -- Queen's University, 2011-11-10 16:15:05.643

Identiferoai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:OKQ.1974/6868
Date11 November 2011
CreatorsYANG, JIANXING
ContributorsQueen's University (Kingston, Ont.). Theses (Queen's University (Kingston, Ont.))
Source SetsLibrary and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada
LanguageEnglish, English
Detected LanguageEnglish
TypeThesis
RightsThis publication is made available by the authority of the copyright owner solely for the purpose of private study and research and may not be copied or reproduced except as permitted by the copyright laws without written authority from the copyright owner.
RelationCanadian theses

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