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Selenium Centered Radicals: How Do They Differ from Sulfur Centered Radicals?

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Abstract

Selenium centered radical cations generated by the reaction of hydroxyl radicals with three different types of selenium compounds belonging to the classes of selenoamino acids, diselenides and selenoethers were studied by pulse radiolysis coupled with transient absorption detection. Nature, absorption spectrum, lifetime and reactivity of these selenium radicals were compared with the radical cations from sulfur analogues. The observed distinct differences in these two types of radicals have been highlighted.

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References

  1. Stadtman TC (1996) Selenocysteine. Annu Rev Biochem 65:83–100

    Article  Google Scholar 

  2. Priyadarsini KI, Singh BG, Kunwar A (2013) Current developments on synthesis, redox reactions and biochemical studies of selenium antioxidants. Curr Chem Biol 7:37–46

    Article  Google Scholar 

  3. Rotruck JT, Pope AL, Ganther HE, Swanson AB, Hafeman DG, Hoekstra WG (1973) Selenium: biochemical role as a component of glutathione peroxidase. Science 179:588–590

    Article  ADS  Google Scholar 

  4. Wessjohann LA, Schneider A, Abbas M, Brandt W (2007) Selenium in chemistry and biochemistry in comparison to sulfur. Biol Chem 388:997–1006

    Article  Google Scholar 

  5. Kuntić VS, Stanković MB, Vujić ZB, Brborić JS, Uskoković-Marković SM (2013) Radioprotectors—the evergreen topic. Chem Biodivers 10:1791–1803

    Article  Google Scholar 

  6. Andreassen CN, Grau C, Lindegaard JC (2003) Chemical radioprotection: a critical review of amifostine as a cytoprotector in radiotherapy. Sem Radiat Oncol 13:62–72

    Article  Google Scholar 

  7. Douki T, Cadet J (2008) Radiation-induced damage to DNA: from model compounds to cell. In: Spotheim-Maurizot M, Mostafavi M, Douki T, Belloni J (eds) Radiation chemistry—From basics to applications in material and life sciences, chap. 12. EDP Sciences, Les Ulis, p 177

    Google Scholar 

  8. Zheng S, Newton GL, Gonick G, Fahey RC, Ward JF (1988) Radioprotection of DNA by thiols: relationship between the net charge on a thiol and its ability to protect DNA. Radiat Res 114:11–27

    Article  Google Scholar 

  9. Asmus KD, Bonifacic M (1999) Sulfur centered reactive intermediates as studied by radiation chemical and complementary techniques. In: Alfassi ZB (ed) S-centered radicals, chap. 6. Wiley, Hoboken, p 141

    Google Scholar 

  10. Lanzalunga O, Lapi A (2012) Recent photo-and radiation chemical studies of sulfur radical cations. J Sulfur Chem 33:101–129

    Article  Google Scholar 

  11. Asmus KD (1979) Stabilization of oxidized sulfur centers in organic sulfides. Radical cations and odd-electron sulfur-sulfur bonds. Acc Chem Res 12:436–442

    Article  Google Scholar 

  12. Asmus KD, Bahnemann D, Fischer Ch-H, Veltwisch D (1979) Structure and stability of radical cations from cyclic and open-chain dithia compounds in aqueous solutions. J Am Chem Soc 101:5322–5329

    Article  Google Scholar 

  13. Mukherjee AJ, Zade SS, Singh HB, Sunoj RB (2010) Organoselenium chemistry: role of intramolecular interactions. Chem Rev 110:4357–4416

    Article  Google Scholar 

  14. Mishra B, Priyadarsini KI, Mohan H (2006) Effect of pH on the one-electron oxidation of organoselenium compounds in aqueous solutions. J Phys Chem A 110:1894–1900

    Article  Google Scholar 

  15. Mishra B, Kumbhare LB, Jain VK, Priyadarsini KI (2008) Pulse radiolysis studies on reactions of oxidizing radicals with selenocystine derivatives. J Phys Chem B 112:4441–4446

    Article  Google Scholar 

  16. Mishra B, Sharma A, Naumov S, Priyadarsini KI (2009) Novel reactions of one-electron oxidized radicals of selenomethionine in comparison with methionine. J Phys Chem B 113:7709–7715

    Article  Google Scholar 

  17. Singh BG, Thomas E, Kumakura F, Iwaoka M, Priyadarsini KI (2010) One-electron redox processes in a cyclic selenide and selenoxide: a pulse radiolysis study. J Phys Chem A 114:8271–8277

    Article  Google Scholar 

  18. Prabhu P, Bag PP, Singh BG, Jain VK, Iwaoka M, Priyadarsini KI (2011) Functional group dependent antioxidant activities of aliphatic selenoethers. Free Radic Res 45:461–468

    Article  Google Scholar 

  19. Singh BG, Thomas E, Sawant S, Takahashi K, Dedachi K, Iwaoka M, Priyadarsini KI (2013) Radical cations of aromatic selenium compounds: role of Se···X non-bonding interactions. J Phys Chem A 117:9259–9265

    Article  Google Scholar 

  20. Upadhyay J, Sharma ML, Navathe CP, Toley MA, Shinde SJ, Nadkarni SA, Sarkar SK (2012) Development of high-voltage pulse-slicer unit with variable pulse duration for pulse radiolysis system. Rev Sci Instrum 83:024709. doi:10.1063/1.3685245

    Article  ADS  Google Scholar 

  21. Arnold AP, Tan KS, Rabenstein DL (1986) Nuclear magnetic resonance studies of the solution chemistry of metal complexes. 23. Complexation of methylmercury by selenohydryl-containing amino acids and related molecules. Inorg Chem 25:2433–2437

    Article  Google Scholar 

  22. Chopade SM, Phadnis PP, Wadawale A, Hodage AS, Jain VK (2012) Synthesis and characterization of (ethylenediamine)/(diammine)platinum(II) coordinated to seleno ligands containing carboxylic acid functionality. Inorg Chim Acta 385:185–189

    Article  Google Scholar 

  23. Hiller K-O, Masloch B, Gobl M, Amus K-D (1981) Mechanism of the OH-radical induced oxidation of methionine in aqueous solution. J Am Chem Soc 103:2734–2743

    Article  Google Scholar 

  24. Hiller K-O, Amus K-D (1983) Formation and reduction reactions of a-amino radicals derived from methionine and its derivatives in aqueous solutions. J Phys Chem 87:3682–3688

    Article  Google Scholar 

  25. Haung ML, Rauk A (2004) Reactions of one-electron-oxidized methionine with oxygen: an ab initio study. J Phys Chem A 108:6222–6230

    Article  Google Scholar 

  26. Metanis N, Keinan E, Dawson PE (2006) Synthetic seleno-glutaredoxin 3 analogues are highly reducing oxidoreductases with enhanced catalytic efficiency. J Am Chem Soc 128:16684–16691

    Article  Google Scholar 

  27. Elliot AJ, McEachern RJ, Armstrong DA (1981) Oxidation of amino-containing disulfides by Br 2- and OH radicals. A pulse radiolysis study. J Phys Chem 85:68–75

    Article  Google Scholar 

  28. Bobrowski K, Pogocki D, Schoneich C (1998) Oxidation of (carboxyalkyl) thiopropionic acid derivativesby hydroxyl radicals. Mechanism and kinetics. J Phys Chem A 102:10512–10521

    Article  Google Scholar 

  29. Bobrowski K, Pogocki D, Schoneich C (1993) Mechanism of the OH radical-induced decarboxylation of 2-(alkylthio)ethanoicacid derivatives. J Phys Chem 97:13677–13684

    Article  Google Scholar 

  30. Singh BG, Nadkarni S, Jain VK, Priyadarsini KI (2015) Effect of alkyl chain length on the one-electron oxidation of selenocarboxylic acids: implication of their antioxidant ability. RSC Adv 5:66621–66627

    Article  Google Scholar 

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Acknowledgments

The authors are thankful to Dr. V. K. Jain and his group members for synthesizing the selenium compounds.

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Authors and Affiliations

  1. Radiation and Photochemistry Division, Bhabha Atomic Research Centre, Trombay, Mumbai, 400085, India

    K. I. Priyadarsini & B. G. Singh

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  1. K. I. Priyadarsini
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  2. B. G. Singh
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Correspondence to K. I. Priyadarsini.

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Priyadarsini, K.I., Singh, B.G. Selenium Centered Radicals: How Do They Differ from Sulfur Centered Radicals?. Proc. Natl. Acad. Sci., India, Sect. A Phys. Sci. 86, 459–464 (2016). https://doi.org/10.1007/s40010-016-0308-7

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  • DOI: https://doi.org/10.1007/s40010-016-0308-7

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