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Complexes of organotin compounds with bis- and trisphosphonate derivatives of 2,6-di-tert-butylphenol having antioxidant activity

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Abstract

Complexes of organotin compounds R2SnCl2 with bisand trisphosphonate derivatives of 2,6-di-tert-butyl-4-methylphenol (ionol) were synthesized. X-ray diffraction studies were carried out for some of them. The redox properties of the synthesized compounds were characterized by cyclic voltammetry. Antioxidant/prooxidant activity of the complexes was studied using a new electrochemical method based on measuring the rate of hydrogen atom transfer to the stable radical 2,2´-diphenyl-1-picrylhydrazyl (DPPH). The data obtained were compared with the results of studying activity of the compounds during lipid peroxidation (LP) in biological samples. A correlation is observed between the results on antioxidant activity obtained by electrochemical DPPH test and using biological samples. Unlike the initial organotin compounds, the synthesized complexes have antioxidant activity, whereas phosphorus-containing phenols exhibit the properties of efficient antioxidants and chelating agents.

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References

  1. W. Droege, Physiol. Rev., 2002, 82, 47.

    Article  Google Scholar 

  2. E. F. Schisterman, in Methods in Molecular Biology, Vol. 196, Oxidants and Antioxidants: Ultrastructure and Molecular Biology Protocols, Ed. D. Armstrong, Humana Press Inc., Totowa, 2002, p. 343.

  3. E. R. Milaeva, V. Yu. Tyurin, Yu. A. Gracheva, E. V. Grigor´ev, V. S. Petrosyan, Yu. T. Pimenov, N. T. Berberova, Appl. Organomet. Chem., 2002, 16, 655.

    Article  Google Scholar 

  4. N. A. Antonova, M. N. Kolyada, V. P. Osipova, Yu. T. Pimenov, N. T. Berberova, V. Yu. Tyurin, Yu. A. Gracheva, E. R. Milaeva, Dokl. Chem. (Engl. Transl.), 2008, 419, 62 [Dokl. Akad. Nauk, 2008, 419, 342].

    CAS  Google Scholar 

  5. S. L. Davydova, Yu. T. Pimenov, E. R. Milaeva, Rtut´, olovo, svinets i ikh organicheskie proizvodnye v okruzhayushchei srede [Mercury, Tin, Lead, and Their Organic Derivatives in the Environment], AGTU, Astrakhan, 2001, 148 pp. (in Russian).

    Google Scholar 

  6. M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, N. Kourkoumelis, E. R. Milaeva, Yu. A. Gracheva, V. Yu. Tyurin, I. Verginadis, S. Karkabounas, M. Baril, I. S. Butler, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 767 [Izv. Akad. Nauk, Ser. Khim., 2007, 737].

    Article  CAS  Google Scholar 

  7. E. B. Burlakova, in Khimicheskaya i biologicheskaya kinetika. Novye gorizonty [Chemical and Biological Kinetics. New Frontiers], Khimiya, Moscow, 2005, Vol. 2, p. 10 (in Russian).

    Google Scholar 

  8. E. T. Denisov, T. G. Denisova, Handbook of Antioxidants: Bond Dissociation Energies, Rate Constants, Activation Energies, and Enthalpies of Reactions, CRC Press, Boca Raton, 1999, p. 174.

    Google Scholar 

  9. E. N. Frankel, Autooxidation in Food and Biological Systems, Eds M. Simic, M. Karel, Plenum, New York, 1980, p. 141.

  10. E. R. Milaeva, O. A. Gerasimova, J. Zhang, D. B. Shpakovsky, S. A. Syrbu, A. S. Semeykin, O. I. Koifman, E. G. Kireeva, E. F. Shevtsova, S. O. Bachurin, N. S. Zefirov, J. Inorg. Biochem., 2008, 102, 1348.

    Article  CAS  Google Scholar 

  11. Z.-Q. Liu, Chem. Rev., 2010, 110, 5675.

    Article  CAS  Google Scholar 

  12. E. Niki, Free Radical Biol. Med., 2010, 49, 503.

    Article  CAS  Google Scholar 

  13. G. Litwinenko, K. U. Ingold, J. Org. Chem., 2003, 68, 3433.

    Article  Google Scholar 

  14. E. Baciocchi, A. Calcagni, O. Lanzalinga, J. Org. Chem., 2008, 73, 4110.

    Article  CAS  Google Scholar 

  15. R. Scherer, H. T. Godoy, Food Chem., 2009, 112, 654.

    Article  CAS  Google Scholar 

  16. A. L. Dawidowicz, D. Wianowska, M. Olszowy, Food Chem., 2012, 131, 1037.

    Article  CAS  Google Scholar 

  17. K. Mishra, H. Ojha, N. K. Chaudhury, Food Chem., 2012, 130, 1036.

    Article  CAS  Google Scholar 

  18. O. P. Sharma, T. K. Bhat, Food Chem., 2009, 113, 1202.

    Article  CAS  Google Scholar 

  19. S. Chevion, M. A. Roberts, M. Chevion, Free Radical Biol. Med., 2000, 28, 860.

    Article  CAS  Google Scholar 

  20. B. H. Kipp, C. Faraj, G. Li, D. Njus, Bioelectrochem., 2004, 64, 7.

    Article  CAS  Google Scholar 

  21. Kh. Brainina, A. Ivanova, E. Sharafutdinova, E. Lozovskaya, E. Shkarina, Talanta, 2007, 71, 13.

    Article  CAS  Google Scholar 

  22. M. Ortiz, L. Nunez-Vergara, J. Squella, J. Electroanal. Chem., 2002, 519, 46.

    Article  CAS  Google Scholar 

  23. R. Salazar, P. Navarrete-Encina, J. Squella, C. Barrientos, V. Pardo-Jimenes, L. Nunez-Vergara, Electrochim. Acta, 2010, 56, 841.

    Article  CAS  Google Scholar 

  24. R. Salazar, P. Navarrete-Encina, J. Squella, L. Nunez-Vergara, J. Electroanal. Chem., 2008, 622, 29.

    Article  CAS  Google Scholar 

  25. V. Yu. Tyurin, Wu Yaohuan, A. V. Dolganov, E. R. Milaeva, Dokl. Chem. (Engl. Transl.), 2011, 436, 31 [Dokl. Akad. Nauk, 2011, 436, 641].

    CAS  Google Scholar 

  26. V. Yu. Tyurin, N. N. Meleshonkova, A. V. Dolganov, A. P. Glukhova, E. R. Milaeva, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 647 [Izv. Akad. Nauk, Ser. Khim., 2011, 633].

    Article  CAS  Google Scholar 

  27. V. Yu. Tyurin, J. Zhang, A. P. Glukhova, E. R. Milaeva, Makrogeterotsikly [Macroheterocycles], 2011, 4, 211 (in Russian).

    Article  CAS  Google Scholar 

  28. V. Yu. Tyurin, J. Zhang, A. A. Moiseeva, E. R. Milaeva, E. R. Belykh, E. V. Buravlev, T. K. Rocheva, I. Yu. Chukicheva, A. V. Kuchin, Dokl. Chem. (Engl. Transl.), 2013, 450, 543 [Dokl. Akad. Nauk, 2013, 450, 543].

    Google Scholar 

  29. T. Rocheva, V. Tyurin, D. Belykh, A. Moiseeva, J. Zhang, E. Buravlev, I. Chukicheva, A. Kutchin, E. Milaeva, Am. J. Anal. Chem. 2014, 5, 1028–1036, http://dx.doi.org/10.4236/ajac.2014.515109.

    Article  CAS  Google Scholar 

  30. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, D. B. Shpakovskii, E. R. Milaeva, Russ. J. Gen. Chem. (Engl. Transl.), 2006, 76, 832 [Zh. Obshch. Khim., 2006, 76, 868].

    Article  CAS  Google Scholar 

  31. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, D. B. Shpakovskii, E. R. Milaeva, Russ. J. Gen. Chem. (Engl. Transl.), 2006, 76, 1753 [Zh. Obshch. Khim., 2006, 76, 1834].

    Article  CAS  Google Scholar 

  32. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, D. B. Shpakovskii, E. R. Milaeva, Russ. J. Gen. Chem. (Engl. Transl.), 2005, 75, 1968 [Zh. Obshch. Khim., 2005, 75, 2058].

    Article  CAS  Google Scholar 

  33. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, E. R. Milaeva, Heteroat. Chem., 2008, 19, 490.

    Article  CAS  Google Scholar 

  34. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, E. R. Milaeva, Heteroat. Chem., 2008, 19, 562.

    Article  CAS  Google Scholar 

  35. A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, E. R. Milaeva, Heteroat. Chem., 2008, 19, 733.

    Article  CAS  Google Scholar 

  36. V. Yu. Tyurin, Yu. A. Gracheva, E. R. Milaeva, A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, A. V. Maryashkin, M. P. Bubnov, K. A. Kozhanov, V. K. Cherkasov, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 774 [Izv. Akad. Nauk, Ser. Khim., 2007, 744].

    Article  CAS  Google Scholar 

  37. N. A. Antonova, V. P. Osipova, M. N. Kolyada, I. V. Smolyaninov, N. T. Berberova, V. Yu. Tyurin, Wu Yaohuan, E. R. Milaeva, Dokl. Chem. (Engl. Transl.), 2010, 432, 165 [Dokl. Akad. Nauk, 2010, 432, 629].

    CAS  Google Scholar 

  38. A. J. Gordon, R. A. Ford, The Chemist´s Companion, Jonh Wiley and Sons, Inc., New York, 1973, 560 pp.

    Google Scholar 

  39. X-AREA, X-RED32; Stoe and Cie GmbH, Darmstadt, Germany.

  40. L. J. Farrugia, J. Appl. Crystallogr., 2012, 45, 849.

    Article  CAS  Google Scholar 

  41. G. M. Sheldrick, Acta Crystallogr., Sect A: Found. Crystallogr., 2008, 64, 112.

    Article  CAS  Google Scholar 

  42. C. F. Macrae, P. R. Edington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, J. van de Streek, J. Appl. Crystallogr., 2006, 39, 453.

    Article  CAS  Google Scholar 

  43. E. N. Stroev, V. G. Makarova, Praktikum po biologicheskoi khimii [Practical Works on Biological Chemistry], Vysshaya Shkola, 1986, 279 pp. (in Russian).

    Google Scholar 

  44. E. V. Grigoriev, N. S. Yashina, V. S. Petrosyan, L. Pellerito, A. Gianguzza, A. Pellerito, E. V. Avtomonov, J. Lorberth, A. A. Prischenko, M. V. Livantsov, J. Org. Chem., 1999, 577, 113.

    Article  CAS  Google Scholar 

  45. V. D. Pokhodenko, A. A. Beloded, V. G. Koshechko, Okislitel´no-vosstanovitel´nye reaktsii svobodnykh radikalov [Redox Reactions of Free Radicals], Naukova Dumka, Kiev, 1977, 276 pp. (in Russian).

    Google Scholar 

  46. E. Solon, A. J. Bard, J. Am. Chem. Soc., 1964, 86, 1926.

    Article  CAS  Google Scholar 

  47. E. Solon, A. J. Bard, J. Phys. Chem., 1964, 68, 1144.

    Article  CAS  Google Scholar 

  48. D. A. Hall, P. J. Elvino, Electrochim. Acta, 1967, 12, 1363.

    Article  CAS  Google Scholar 

  49. Z. Galus, Fundamentals of Electrochemical Analysis, Ellis Horwood, Chichester, 1976.

    Google Scholar 

  50. W. Brand-Williams, M. Cuvelier, C. Berset, Food Sci. Technol., 1995, 28, 25.

    CAS  Google Scholar 

  51. V. Bondet, W. Brand-Williams, C. Berset, Lebensm.-Wiss. Technol., 1997, 30, 609.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    V. Yu. Tyurin, Wu Yaohuan, A. A. Prishchenko, D. B. Shpakovsky, Yu. A. Gracheva, T. A. Antonenko, V. A. Tafeenko, D. V. Al´bov, L. A. Aslanov & E. R. Milaeva

  2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi proezd, 142432, Chernogolovka, Moscow Region, Russian Federation

    E. R. Milaeva

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  1. V. Yu. Tyurin
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  2. Wu Yaohuan
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  3. A. A. Prishchenko
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  4. D. B. Shpakovsky
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  8. D. V. Al´bov
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Correspondence to V. Yu. Tyurin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1419–1429, June, 2015.

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Tyurin, V.Y., Yaohuan, W., Prishchenko, A.A. et al. Complexes of organotin compounds with bis- and trisphosphonate derivatives of 2,6-di-tert-butylphenol having antioxidant activity. Russ Chem Bull 64, 1419–1429 (2015). https://doi.org/10.1007/s11172-015-1026-z

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