The photochemical oxidation of A2E results in the formation of a 5,8,5',8'-bis-furanoid oxide

Experimental Eye Research
J DillonE R Gaillard

Abstract

With age and certain diseases, the retinal pigment epithelium (RPE) accumulates a complex mixture of fluorophores generally called lipofuscin. This mixture has been implicated in those diseases via several possible mechanisms including photochemically mediated damage and detergent effects. Recently, a component of that mixture has been identified, a bis-retinoid pyridinium compound called A2E. Furthermore, the photolysis of this compound has been shown to lead to a series of photooxidation products each differing by 16 amu; with the addition of up to a total of nine oxygen atoms to A2E. It has been suggested that these products consist of a series of epoxides forming along the acyclic side chains. The present study reinvestigates this hypothesis and demonstrates that the bis-oxygenated product is in fact a relatively stable 5-8 5'-8'-bis-furanoid oxide. This is in agreement with the oxidation products observed for a homologue of A2E, beta-carotene. In addition, it was found that the bis-oxygenated photoproduct of A2E contained a mixture of symmetrical and unsymmetrical oxidized products where the second oxygen was present in the cyclohexenyl ring structure in the unsymmetrical product. Most importantly, both of these oxidation ...Continue Reading

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