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June 2015, № 6 (181)

Korotkova A.M., Davydova O.K. EFFECTS OF SYNTHETIC ALKYLRESORCINOLS ON DNA TOPOLOGICAL CHANGES, MEDIATED BY REACTIVE OXYGEN SPECIES IN VITRO SYSTEMThe problem of live systems protection against an oxidizing stress by means of various low-molecular organic compounds capable to neutralize reactive oxygen species attracts the growing interest in search, study and prospects of practical use of both naturaland synthetic antioxidants. Alkylresorcinols known by the function of adaptogens at plants and microorganisms can be also included to their number. In turn, a well-documented effect of alkylresorcinols concerning biopolymers and cells is change of their functional activity and resistance to extreme influences. Because the genetic structure is a one of the most vulnerable targets of various destructive factors, including oxidizing stressinductors, the aim of the work is experimental justification of a role of synthetic alkylresorcinols differing in chemical structure in protection of DNA against reactive oxygen species. The effects of destruction of topologically various molecules of pUC19 plasmid DNA associated with formation of single-stranded breaks and which are expressed in change of a ratio of the supercoiled and nicked molecules under the influence of reactive oxygen species are estimated by agarose gel electrophoresis. The system of photochemical induction of superoxide anion by a spontaneous reoxidation of photoreduced flavin with the subsequent formation of multiple active forms of oxygen is used as a model of an oxidizing stress. The significant prevention of DNA deep degradation in the presence of alkylresorcinols, directly dependent both from length of their alkyl and from the used concentration as compared with the oxidized tests is shown. On the basis of data of infrared spectroscopy the question of possible transformations of alkylresorcinols protecting of DNAconformation in the conditions of an oxidizing stress is discussed. The experimental studies of protector effects ofalkylresorcinol from reactive oxygen species concerning to DNA molecules are forming a basis for pharmaceutical preparations development. Key words: alkylresorcinol, methylresorcinol, hexylresorcinol, dodecylresorcinol, antioxidant effect,reactive oxygen species, DNA damage, plasmid DNA pUC19.


1. El-Bahr S.M. Biochemistry of free radicals and oxidative stress // Scien. Intern. — 2013. — Vol. 1. — №5. — P. 111-117.

2. Alfadda A.A., Sallam R.M. Review article. reactive oxygen species in health and disease // J. Biomed. Biotech. — 2012. — Vol. 2012. — 14 p.

3. Jena N.R. DNA damage by reactive species: mechanisms, mutation and repair // J. Biosci. — 2012. — №37(3). — Р. 503–517.

4. Parikka K., Rowland I.R., Welch R.W., Wahala K. In vitro antioxidant activity and antigenotoxicity of 5-n-alkylresorcinols // J. Agric. Food Chem. — 2006. №54. Р. 1646-1650.

5. Stasiuk M., Kozubek A. Biological activity of phenolic lipids // Cell. Mol. Life Sci. 2010. — Vol. 67. — P. 841–860.

6. El-Registan G.I., Mulyukin A.L., NikolaevYu.A., Gal'chenko V.F., Suzina N.E., Duda V.I. Adaptogenic functions of extracellular autoregulators of microorganisms // Microbiology. — 2006. — Т. 75. — №4. — С. 380-389.

7. HladyszowskiJ., Zubik L., Kozubek A. Quantum mechanical and experimental oxidation studies of pentadecylresorcinol, olovetol, orcinol and resorcinol // Free Rad. Res. — 1998. — Vol. 28. — Р. 359–368.

8. Kamnev A.A., Dykman R.L., Kovacs K., Pankratov A.N., Tugarova A.V., Homonnay Z., Kuzmann E. Redox interactions between structurally different alkylresorcinols and iron (III) in aqueous media: frozen-solution Fe Mцssbauer spectroscopic studies, redox kinetics and quantum chemical evaluation of the alkylresorcinolreactivities // Struct. Chem. — 2014. — Vol. 25. — P. 649-657.

9. Kozubek A., Nienartowicz B. Cereal grain resorcinolic lipids inhibit H2O2-induced peroxidation of biological membranes // Act. Bioch. Polon. — 1995. — №42. — Р. 309-316.

10. Struski D.G., Kozubek A., Naturforsch Z. Cereal grain alk(en)ylresorcinols protect lipids against ferrous ions-induced peroxidation // Biosc. — 1992. — Vol. 47. — P. 41-46.

11. StepanenkoI Yu., Nikolaev Yu.A., Mulyukin A.L., Kozlova A.N., El'-Registan G.I., Strakhovskaya M.G., Belenikina N.S., Revina A.A. Protection of saccharomyces cerevisiae against oxidative and radiation-caused damage by alkylhydroxybenzenes // Microbiology. 2004. — Т. 73. — №2. — P. 163-169.

12. Gryazeva I.V., Davydova O.K., Deryabin D.G., Sviridova T.G., Sviridov A.P. Progmosiruemaya experimenalno viyavlyaemaya antioxidantnaya activnost alkyloksibenzolov (alkylresorcinov) // Vopr. Boil. Medic. Farm. Chim. — 2013. — №8. — S. 41-46.

13. Golod N.A., Loiko N.G., Galchenko V.F., Nikolaev Y.A., El'-Registan G.I., Lobanov K.V., Mironov A.S., Voieikova T.A. Involvement of alkylhydroxybenzenes, microbial autoregulators, in controlling the expression of stress regulons // Microbiology. — 2009. — Т. 78. — №6. — P. 678-688.

14. Gryzeva I.V., Davydova O.K., Deryabin D.G. Evaluation of the potential of alkylresorcinols as superoxide anion scavengers and sox-regulon modulators using nitroluetetrazolium and bioluminescent cell-based assays // Cell. Mol. Biology Let. — 2015. — Vol. 20. — №1. — Р. 24-37.

15. Davydova O.K., Deryabin D.G., Nikiyan A.N., El'-Registan G.I. Mechanisms of interaction between DNA and chemical analogues of microbial anabiosisautoinducers // Microbiology. — 2005. — Т. 74. — №5. — P. 533-541.

16. Davydova O.K., Deryabin D.G., El'-Registan G.I. IR spectroscopic research on the impact of chemical analogues of autoregulatory d1 factors of microorganisms on structural changes in DNA // Microbiology. — 2007. — Т. 76. — №3. — P. 266-272.

17. Mulyukin A.L., Kozlova A.N., El'-Registan G.I., Vakhrushev M.A., Strazhevskaya N.B., Shmyrina A.S., Zhdanov R.I., Suzina N.E., Duda V.I. Effect of alkylhydroxybenzenes, microbial anabiosis inducers, on the structural organization of pseudomonas aurantiaca DNA and on the induction of phenotypic dissociation // Microbiology. — 2005. — Т. 74. — №2. — P. 128-135.

18. Massey V. Activation of molecular oxygen by flavins and flavoproteins // J. Biol. Chem. — 1994. — Vol. 269. — №36. — Р. 459-462.

19. Grivennikova V.G., Vinogradov A.D. Generaciya activnyh form kisloroda mitochondriyami // Usp. Boil. chim. — 2013. — T. 53. — S. 245-296.

20. Brudastov Y.A, Bachurskaya N.S., Petrova E.V., Brudastov A.N. Bactericidnye effecti activnyh metabolitov kisloroda // Vestnik OGU. — 2006. — №12. — S. 27-31.

21. Davydova O.K., Deryabin D.G., El'-Registan G.I. Long-term preservation of dna in aqueous solutions in the presence of the chemical analogues of microbial autoregulators // Microbiology. — 2006. — Т. 75. — №5. — P. 654-661.

22. Perron N., Garcia C., Pinzon J., Chaur M., Brumaghim J. Antioxidant and prooxidant effects of polyphenol compounds on copper-mediated DNA damage // J. Inorg. Biochem. — 2011. — Vol. 105. — P. 745-753.

23. Prech E. Opredelenie stroeniya organichekih soedinenii. Tablici spectralnyh dannih. — M.: Binom. Laboratoriya znanii, 2012. — 438s.

24. Perez-Gonzalez A., Rebollar-Zepeda A.M., Leon-Carmona J.R., Galano A. Reactivity indexes and O-H bond dissociation energies of a large series of polyphenols: implications for their free radical scavenging activity // J. Mex. Chem. Soc. — 2012. — №56(3). — Р. 241-249.

25. Foti M.C., Amorati R., Pedulli G.F., Daquino C., Pratt D.A. Ingold K.U. Influence of "remote" intramolecular hydrogen bonds on the stabilities of phenoxyl radicals and benzyl cations // J. Org. Chem. — 2010. — №75(13). — Р. 34–40.

26. Perez-Gonzalez A., Rebollar-Zepeda A.M., Leon-Carmona J.R., Galano A. Reactivity indexes and O-H bond dissociation energies of a large series of polyphenols: implications for their free radical scavenging activity // J. Mex. Chem. Soc. — 2012. — №56(3). — Р. 241-249.

27. Foti M.C., Amorati R., Pedulli G.F., Daquino C., Pratt D.A. Ingold K.U. Influence of "remote" intramolecular hydrogen bonds on the stabilities of phenoxyl radicals and benzyl cations // J. Org. Chem. — 2010. — №75(13). — Р. 34–40.

28. Dykman R.L. Physicheskie I chimichesie zakonomernosti okislitelno-vosstanovitelnih processov s uchastiem alkylresorcinov i zheleza (III) / Aftoref. diss.soisk.cand.chimic.nauk. — Saratov. — 2014. — 24s.

29. Dayan F.E., Watson S.B., Nanayakkara N.P. Biosynthesis of lipid resorcinols and benzoquinones in isolated secretory plant root hairs // J. Exper. Bot. -2007. — Vol. 58. — №12. — Р. 1–10.

30. Shadyro O.I. Quinones as free-radical fragmentation inhibitors in biologically important molecules / O.I. Shadyro, G.K. Glushonok, T.G. Glushonok, I.P. Edimecheva, A.G. Moroz, A.A. Sosnovskaya, I.L. Yurkova, G.I. Polozov // Free Rad. Res. — 2002. — Vol. 36. — №8. — P. 859-867.

About this article

Authors: Korotkova A.M., Davydova O.K.

Year: 2015

Sergey Aleksandrovich

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