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Free Radical Research Volume 32, 2000 - Issue 6
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Original Article

4-Mercaptoimidazoles derived from the naturally occurring antioxidant ovothiols 2. Computational and experimental approach of the radical scavenging mechanism

Vincent Zoete Laboratoire de Chimie Organique Physique associée à l'Ecole Nationale Supérieure de Chimie de Lille, ESA CNRS 8009, Bâtiment C3, UST Lille I, 59655, Villeneuve d'Ascq, France
,
Herve Vezin Centre de Recherche et d'Etudes en Simulations et Modélisation Moléculaire, Bâtiment C5, UST Lille I, 59655, Villeneuve d'Ascq, France
,
Fabrice Bailly Laboratoire de Chimie Organique Physique associée à l'Ecole Nationale Supérieure de Chimie de Lille, ESA CNRS 8009, Bâtiment C3, UST Lille I, 59655, Villeneuve d'Ascq, France
,
Gerard Vergoten Centre de Recherche et d'Etudes en Simulations et Modélisation Moléculaire, Bâtiment C5, UST Lille I, 59655, Villeneuve d'Ascq, France
,
Jean-Pierre Catteau Laboratoire de Chimie Organique Physique associée à l'Ecole Nationale Supérieure de Chimie de Lille, ESA CNRS 8009, Bâtiment C3, UST Lille I, 59655, Villeneuve d'Ascq, France
&
Jean-Luc Bernier Centre de Recherche et d'Etudes en Simulations et Modélisation Moléculaire, Bâtiment C5, UST Lille I, 59655, Villeneuve d'Ascq, France
Pages 525-533 | Received 05 Jul 1999, Published online: 07 Jul 2009

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Kunal Roy & Indrani Mitra. (2009) Advances in quantitative structure–activity relationship models of antioxidants. Expert Opinion on Drug Discovery 4:11, pages 1157-1175.
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L. Rackova, M. Stefek & M. Majekova. (2002) Structural aspects of antioxidant activity of substituted pyridoindoles. Redox Report 7:4, pages 207-214.
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Articles from other publishers (21)

Quan V. Vo, Nguyen Thi Hoa & Adam Mechler. (2023) Study of the Mechanism and Kinetics of the Radical Scavenging Activity of 2-Mercaptoimidazole. The Journal of Physical Chemistry A 127:23, pages 4934-4939.
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Quan V. Vo, Do Thi Ngoc Hang, Nguyen Thi Hoa, Pham Cam Nam, Tuan Quang Duong & Adam Mechler. (2023) The radical scavenging activity of 4-mercaptoimidazole: theoretical insights into the mechanism, kinetics and solvent effects. New Journal of Chemistry 47:21, pages 10381-10390.
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Hongkun Xue, Pengcheng Li, Jiayue Bian, Yuchao Gao, Yumei Sang & Jiaqi Tan. (2022) Extraction, purification, structure, modification, and biological activity of traditional Chinese medicine polysaccharides: A review. Frontiers in Nutrition 9.
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Yanshole, Yanshole, Zelentsova & Tsentalovich. (2019) Ovothiol A is the Main Antioxidant in Fish Lens. Metabolites 9:5, pages 95.
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Jacqueline Wiebe, Vasyl Zaliskyy & Eric A. C. Bushnell. (2019) A Computational Investigation of the Binding of the Selenium Analogues of Ergothioneine and Ovothiol to Cu(I) and Cu(II) and the Effect of Binding on the Redox Potential of the Cu(II)/Cu(I) Redox Couple. Journal of Chemistry 2019, pages 1-7.
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Heng-Yue Xue, Jing-Ru Li, Yan-Geng Liu, Qi Gao, Xiao-Wen Wang, Jun-Wei Zhang, Masaru Tanokura & You-Lin Xue. (2019) Optimization of the ultrafiltration-assisted extraction of Chinese yam polysaccharide using response surface methodology and its biological activity. International Journal of Biological Macromolecules 121, pages 1186-1193.
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Rui Fausto, Gulce O. Ildiz, Elisa M. Brás & Bernardo A. Nogueira. 2019. Molecular Spectroscopy—Experiment and Theory. Molecular Spectroscopy—Experiment and Theory 199 222 .
Stéphane La Barre & Stephen S. BatesAnna Palumbo, Immacolata Castellano & Alessandra Napolitano. 2018. Blue Biotechnology. Blue Biotechnology 583 610 .
Le-Le Shao, Jie Xu, Mei-Jia Shi, Xiao-Ling Wang, Yin-Ting Li, Li-Min Kong, Robert C Hider & Tao Zhou. (2017) Preparation, antioxidant and antimicrobial evaluation of hydroxamated degraded polysaccharides from Enteromorpha prolifera. Food Chemistry 237, pages 481-487.
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Jiajie Yan, Jia-fei Poon, Vijay P. Singh, Paul Gates & Lars Engman. (2015) Regenerable Thiophenolic Radical-Trapping Antioxidants. Organic Letters 17:24, pages 6162-6165.
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Arash Mirzahosseini, Gábor Orgován, Gergő Tóth, Sándor Hosztafi & Béla Noszál. (2015) The complete microspeciation of ovothiol A disulfide: A hexabasic symmetric biomolecule. Journal of Pharmaceutical and Biomedical Analysis 107, pages 209-216.
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Gian Russo, Maria Russo, Immacolata Castellano, Alessandra Napolitano & Anna Palumbo. (2014) Ovothiol Isolated from Sea Urchin Oocytes Induces Autophagy in the Hep-G2 Cell Line. Marine Drugs 12:7, pages 4069-4085.
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Arash Mirzahosseini, Gábor Orgován, Sándor Hosztafi & Béla Noszál. (2014) The complete microspeciation of ovothiol A, the smallest octafarious antioxidant biomolecule. Analytical and Bioanalytical Chemistry 406:9-10, pages 2377-2387.
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Phil De Luna, Eric A. C. Bushnell & James W. Gauld. (2013) A Density Functional Theory Investigation into the Binding of the Antioxidants Ergothioneine and Ovothiol to Copper.. The Journal of Physical Chemistry A 117:19, pages 4057-4065.
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Eric A. C. Bushnell, Grant B. Fortowsky & James W. Gauld. (2012) Model Iron–Oxo Species and the Oxidation of Imidazole: Insights into the Mechanism of OvoA and EgtB?. Inorganic Chemistry 51:24, pages 13351-13356.
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Ho Young Jung, In Young Bae, Suyong Lee & Hyeon Gyu Lee. (2011) Effect of the degree of sulfation on the physicochemical and biological properties of Pleurotus eryngii polysaccharides. Food Hydrocolloids 25:5, pages 1291-1295.
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Vania Urias-Orona, Joselina Huerta-Oros, Elizabeth Carvajal-Millán, Jaime Lizardi-Mendoza, Agustin Rascón-Chu & Alfonso A. Gardea. (2010) Component Analysis and Free Radicals Scavenging Activity of Cicer arietinum L. Husk Pectin. Molecules 15:10, pages 6948-6955.
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Christine E. Hand, Nicholas J. Taylor & John F. Honek. (2005) Ab initio studies of the properties of intracellular thiols ergothioneine and ovothiol. Bioorganic & Medicinal Chemistry Letters 15:5, pages 1357-1360.
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Lucia Račková, Magdaléna Májeková, Daniela Košt’álová & Milan Štefek. (2004) Antiradical and antioxidant activities of alkaloids isolated from Mahonia aquifolium. Structural aspects. Bioorganic & Medicinal Chemistry 12:17, pages 4709-4715.
Crossref
Fabrice Bailly, Nathalie Azaroual & Jean-Luc Bernier. (2003) Design, synthesis and glutathione peroxidase-Like properties of ovothiol-Derived diselenides. Bioorganic & Medicinal Chemistry 11:21, pages 4623-4630.
Crossref
Fabrice Bailly, Vincent Zoete, Joseph Vamecq, Jean-Pierre Catteau & Jean-Luc Bernier. (2000) Antioxidant actions of ovothiol-derived 4-mercaptoimidazoles: glutathione peroxidase activity and protection against peroxynitrite-induced damage. FEBS Letters 486:1, pages 19-22.
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