title: The cysteine releasing pattern of some antioxidant thiazolidine-4-carboxylic acids.
abstract: Oxidative stress that corresponds to a significant increase in free radical concentration in cells can cause considerable damage to crucial biological macromolecules if not prevented by cellular defense mechanisms. The low-molecular-weight thiol glutathione (GSH) constitutes one of the main intracellular antioxidants. It is synthesized via cysteine, an amino acid found only in limited amounts in cells because of its neurotoxicity. Thus, to ensure an efficient GSH synthesis in case of an oxidative stress, cysteine should be provided extracellularly. Yet, given its nucleophilic properties and its rapid conversion into cystine, its corresponding disulfide, cysteine presents some toxicity and therefore is usually supplemented in a prodrug approach. Here, some thiazolidine-4-carboxylic acids were synthesized and evaluated for their antioxidant properties via the DDPH and CUPRAC assays. Then, the cysteine releasing capacity of the obtained compounds was investigated in aqueous and organic medium in order to correlate the relevant antioxidant properties of the molecules with their cysteine releasing pattern. As a result, the structures' antioxidative properties were not only attributed to cysteine release but also to the thiazolidine cycle itself.
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yeditepe University, Istanbul, Turkey. Electronic address: filizesraonen@gmail.com.
authors.forename: F Esra
authors.initials: FE
authors.lastname: Önen Bayram
authors.affiliation: Department of Toxicology, Faculty of Pharmacy, Yeditepe University, Istanbul, Turkey.
authors.forename: Hande
authors.initials: H
authors.lastname: Sipahi
authors.affiliation: Department of Analytical Chemistry, Faculty of Pharmacy, Yeditepe University, Istanbul, Turkey.
authors.forename: Ebru Türköz
authors.initials: ET
authors.lastname: Acar
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yeditepe University, Istanbul, Turkey.
authors.forename: Reyhan
authors.initials: R
authors.lastname: Kahveci Ulugöl
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yeditepe University, Istanbul, Turkey.
authors.forename: Kerem
authors.initials: K
authors.lastname: Buran
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Yeditepe University, Istanbul, Turkey.
authors.forename: Hülya
authors.initials: H
authors.lastname: Akgün
mesh_terms: D000975:Antioxidants / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry*; D015394:Molecular Structure; D053778:Thiazolidines / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D053778:Thiazolidines; C003438:thiazolidine-4-carboxylic acid; D003545:Cysteine
keywords: Cysteine; Heterocycle cleavage; Oxidative stress; Prodrug; Thiazolidine