Since the discovery of Lipoic acid in the early 1950s, there have been several studies to further investigate properties and applications of this interesting, naturally occurring compound. In 1956, the dynamic nature of disulfide bonds in Lipoic acid was reported, which can exist through conversions of monomeric disulfide, polymeric disulfide, and reduced form (dithiol) from one to another under proper conditions. This dynamic nature and reducibility of disulfide bonds via thiol-disulfide exchange, opened doors to the use of Lipoic acid in drug delivery systems, especially for delivery to cancer cells that suffer from overexpression of glutathione – a thiol-bearing tripeptide – that can trigger biodegradation of disulfide bonds and a consequent release. This work comprises studies on polymerization of the ethyl ester derivative of Lipoic acid (LpOEt). Kinetics and thermodynamics of radical ring-opening polymerization of LpOEt and living characteristics of anionic ring-opening polymerization of LpOEt were studied. Copolymerization of LpOEt with a Lipoic acid-derived crosslinker in miniemulsion resulted in formation of biodegradable nanoparticles. Polymerization of sodium salt of Lipoic acid (LpONa) under UV irradiation was studied, and the polymer was used to form shell-crosslinked capsules.
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Raeisi, Mojdeh, "Lipoates as Building Blocks of Macromolecules" (2021). Chemistry Theses and Dissertations. 19.
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