Products Cited in Publications Worldwide Lipid Coupled Dibenzothiophene S-Oxide Derivative as a Site Directed and Unquenchable Source of O(3P)

Lipid Coupled Dibenzothiophene S-Oxide Derivative as a Site Directed and Unquenchable Source of O(3P)

Grant W. Cone, B.S.

Abstract

Reactive oxygen species (ROS) and the understanding of how they influence cells provides insights onto how biological organisms react during oxidative stress caused by disease that plague humans and animals alike. In durations of high oxidative stress mediated by ROS, cells ultimately perish and can cause lasting effects on an organism. With such knowledge and the use of medicine, drugs are produced to aid therapies devised to combat the damage done by release of ROS in cells. While ROS have previously been extensively studied, more recent studies elucidated the existence and production of atomic oxygen, the smallest diradical yet known. Atomic oxygen or triplet oxygen with the term symbol 3P [O (3 P)], an extremely short lived and reactive species, produces a unique profile of products comparatively to other ROS and the usage of producing O (3 P) in cells is largely unknown and the benefits of doing so unrealized. The lack of knowledge comparative to other ROS is due to O (3 P) being a rare, if not unlikely, species produced in or by an organism. Currently, species with a Dibenzothiophene S-Oxide (DBTO) moiety are the predominate producers of O (3 P) utilizing photochemical processes. Previously, the production of O (3 P) in cells provided a “shotgun” approach where when incorporated into cells and DBTO’s subsequently photolyzed provided unique oxidation products, however, the usefulness of the technique provided to lack control necessary to provide breakthroughs in useful technology. Synthesizing a novel DBTO, one coupled to a lipid (phosphatidylcholine or PC), L-α-Phosphtidyl-N, N-dimethylethanolamine-N-2-methyldibenzothiophene S-oxide (PC-N-DBTO), provides a means to control the placement of O (3 P) production by predominately incorporating into membranes. Investigations into the usefulness of the novel technique of DBTO incorporation, completed by O (3 P) production in low density lipoprotein (LDL), shown that the unique oxidative product profile stayed intact. Furthermore, the investigation shown that compared to other techniques of incorporation, when the process utilizes PC-N-DBTO photolysis in LDL, that the process is nearly unquenchable using known O (3 P) quenching agent allylsufonate. Additionally, the examination provided evidence that isolation of DBTO to a specific site provides sufficient sequestering for studying the effects of O (3 P) production as a site directed approach.

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Sodium Allylsulfonate

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