Radical scavenging capacities of some thiazolylthiazolidine-2,4-dione derivatives

Bozdağ‐Dündar, Oya; Çoban, Tülay; Ceylan–Ünlüsoy, Meltem; Ertan, Rahmiye

doi:10.1007/s00044-007-9081-0

Cited by 16 publications

(10 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Indeed, taking folic acid as an example, the reactivity toward H 2 DCFDA was clearly reduced when using the thiazolidine CP compared with pyruvate alone. This higher efficacy of thiazolidines to inhibit the reactivity of single and combined components is probably linked to a capacity to scavenge other radicals like HO• and O 2 •− as demonstrated for chromonyl‐thiazolidine‐2,4‐dione or for several other thiazolidine derivatives . Since folic acid is sensitive to H 2 O 2 and HO•, the fact that thiazolidines scavenge hydroxyl radicals may explain the stabilization effect on this vitamin.…”

Section: Discussionmentioning

confidence: 98%

“…This higher efficacy of thiazolidines to inhibit the reactivity of single and combined components is probably linked to a capacity to scavenge other radicals like HO• and O 2 •2 as demonstrated for chromonyl-thiazolidine-2,4-dione 41 or for several other thiazolidine derivatives. 32,42,43 Since folic acid is sensitive to H 2 O 2 and HO•, the fact that thiazolidines scavenge hydroxyl radicals may explain the stabilization effect on this vitamin. Furthermore, investigations of several synthesized 2-aryl thiazolidine-4-carboxylic acid revealed that the antioxidant activity of this class of molecules may be attributed to the presence of the oxidizable sulfur in the thiazolidine ring.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Antioxidant effect of thiazolidine molecules in cell culture media improves stability and performance

Kuschelewski

Schnellbaecher

Pering

et al. 2017

Biotechnology Progress

View full text Add to dashboard Cite

The ability of cell culture media components to generate reactive species as well as their sensitivity to oxidative degradation, affects the overall stability of media and the behavior of cells cultured in vitro. This study investigates the influence of thiazolidine molecules, formed from the condensation between cysteine and alpha-ketoacids, on the stability of these complex mixtures and on the performance of cell culture processes aiming to produce therapeutically relevant monoclonal antibodies. Results presented in this study indicate that 2-methyl-1,3-thiazolidine-2,4-dicarboxylic acid and 2-(2-carboxyethyl)-1,3-thiazolidine-2,4-dicarboxylic acid, obtained by condensation of cysteine with pyruvate or alpha-ketoglutarate, respectively, are able to stabilize cell culture media formulations, in particular redox sensitive molecules like folic acid, thiamine, l-methionine (met) and l-tryptophan (trp). The use of thiazolidine containing feeds in Chinese hamster ovary fed-batch processes showed prolonged culture duration and increased productivity. This enhanced performance was correlated with lower reactive species generation, extracellularly and intracellularly. Moreover, an anti-oxidative response was triggered via the induction of superoxide dismutase and an increase in the total glutathione pool, the major intracellular antioxidant. In total, the results confirm that cells in vitro are not cultured in an oxidant-free environment, a concept that has to be considered when studying the influence of reactive species in human diseases. Furthermore, this study indicates that thiazolidines are an interesting class of antioxidant molecules, capable of increasing cell culture media stability and process performance. © 2017 American Institute of Chemical Engineers Biotechnol. Prog., 33:759-770, 2017.

show abstract

Section: Discussionmentioning

confidence: 98%

Section: Discussionmentioning

confidence: 99%

Antioxidant effect of thiazolidine molecules in cell culture media improves stability and performance

Kuschelewski

Schnellbaecher

Pering

et al. 2017

Biotechnology Progress

View full text Add to dashboard Cite

show abstract

“…Antioxidant properties of a series of 2,4dichlorothiazolylthiazolidine-2,4-dione and 4-chloro-2benzylsulfanylthiazolyl-thiazolidine-2,4-dione derivatives 179 (Scheme 86) were reported in two different in vitro assays: superoxide anion radical formation and DPPH radical scavenging activity [408].…”

Section: Anti-and Prooxidant Agentsmentioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

145

133

View full text Add to dashboard Cite

The presented review is an attempt to summarize a huge volume of data on 5-ene-4-thiazolidinones being a widely studied class of small molecules used in modern organic and medicinal chemistry. The manuscript covers approaches to the synthesis of 5-ene-4-thiazolidinone derivatives: modification of the C5 position of the basic core; synthesis of the target compounds in the one-pot or multistage reactions or transformation of other related heterocycles. The most prominent pharmacological profiles of 5-ene derivatives of different 4-thiazolidinone subtypes belonging to hit-, lead-compounds, drug-candidates and drugs as well as the most studied targets have been discussed. Currently target compounds (especially 5-en-rhodanines) are assigned as frequent hitters or pan-assay interference compounds (PAINS) within high-throughput screening campaigns. Nevertheless, the crucial impact of the presence/nature of C5 substituent (namely 5-ene) on the pharmacological effects of 5-ene-4-thiazolidinones was confirmed by the numerous listed findings from the original articles. The main directions for active 5-ene-4-thiazolidinones optimization have been shown: i) complication of the fragment in the C5 position; ii) introduction of the substituents in the N3 position (especially fragments with carboxylic group or its derivatives); iii) annealing in complex heterocyclic systems; iv) combination with other pharmacologically attractive fragments within hybrid pharmacophore approach. Moreover, the utilization of 5-ene-4-thiazolidinones in the synthesis of complex compounds with potent pharmacological application is described. The chemical transformations cover mainly the reactions which involve the exocyclic double bond in C5 position of the main core and correspond to the abovementioned direction of the 5-ene-4-thiazolidinone modification.

show abstract

“…Thiazolidine-2,4-dione derivatives have been studied extensively and found to have diverse chemical reactivity (Jain et al, 2013;Faiyazalam et al, 2013). Thiazolidine derivatives displayed a broad spectrum of biological activities including antimicrobial (Gouveia et al, 2009;Tuncbilek and Altanlar, 2006), antidiabetic (Murugan et al, 2009;Pattan et al, 2005), antiobesity (Bhattarai et al, 2009), anti-inflammatory (Youssef et al, 2010), antioxidant (Bozdag-Dundar et al, 2009), antiproliferative (Patil et al, 2010), and antitumor (Shimazaki et al, 2008). They inhibit corrosion of mild steels in acidic solution (Donnelly et al, 1974).…”

Section: Introductionmentioning

confidence: 97%

A theoretical study on the structure of thiazolidine-2,4-dione and its 5-substituted derivatives in the gas phase. Implications for the thiazolidine-2,4-dione -water complex

Safi

2016

Arabian Journal of Chemistry

View full text Add to dashboard Cite

The results of a detailed DFT (B3LYP) investigation on five tautomers of thiazolidine-2,4-dione and their 5-substituted derivatives (ACH 3 , ANH 2 , ACl, AF, ACN-and NO 2 ) are presented here. The energy, geometrical parameters, topological parameters of all species in the gas phase have been calculated at B3LYP6-311++G(3df,2p)//B3LYP/311 + G(d,p) level of theory. The proton affinities (Pas), molecular electrostatic potential (MEP), natural valence atomic orbital energies (NNAO) of the basic center exist in the title compound in the gas phase have been calculated at the same level of theory. The specific hydration of the title compound by one water molecule has been also investigated at the same level of theory. Among the thiazolidine-2,4-dione tautomers and its derivatives, the most stable tautomer corresponds to the diketo forms (A), regardless of the substituent type. Results reveal that the oxygen atom of the carbonyl group at position 2 is more basic than the one at position 4. The existence of different hydrogen bond donor and acceptor centers in these molecules led to different kinds of intermolecular hydrogen bonds (CHAEAEAEO, NAHAEAEAEO and C‚OAEAEAEH) and different kinds of complexes. The stability of the cyclic complexes has been investigated using the analysis of Natural Bond Orbital (NBO), Atoms In Molecules topology, and the thermodynamic data. Results suggest that the water molecule prefers to bind with the oxygen atom, which has low intrinsic character. ª 2015 The Author. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

show abstract

Radical scavenging capacities of some thiazolylthiazolidine-2,4-dione derivatives

Cited by 16 publications

References 12 publications

Antioxidant effect of thiazolidine molecules in cell culture media improves stability and performance

Antioxidant effect of thiazolidine molecules in cell culture media improves stability and performance

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

A theoretical study on the structure of thiazolidine-2,4-dione and its 5-substituted derivatives in the gas phase. Implications for the thiazolidine-2,4-dione -water complex

Contact Info

Product

Resources

About