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Альманах клинической медицины. 2014; 1: 65-69

БИОАНТИОКСИДАНТЫ (ЧАСТЬ 2)

Гудков С. В., Брусков В. И., Куликов А. В., Шарапов М. Г., Куликов Д. А., Молочков А. В.

https://doi.org/10.18786/2072-0505-2014-31-65-69

Аннотация

На основе анализа последних научных данных представлена синтетическая классификация известных биоантиоксидантов, рассмотрены особенности их строения и функционирования. Во второй части описаны серосодержащие соединения,
хелаторы ионов металлов переменной валентности, соединения, содержащие гидроксильную или аминогруппу, а также наночастицы.

Список литературы

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6. Seo M.S., Kang S.W., Kim K., Baines I.C., Lee T.H., Rhee S.G. Identification of a new type of mammalian peroxiredoxin that forms an intramolecular disulfide as a reaction intermediate. J Biol Chem 2000;275(27):20346-54.

7. Wood Z.A., Poole L.B., Karplus P.A. Peroxiredoxin evolution and the regulation of hydrogen peroxide signaling. Science. 2003; 300(5619):650-3.

8. Hanschmann E.M., Godoy J.R., Berndt C., Hudemann C., Lillig C.H. Thioredoxins, glutaredoxins, and peroxiredoxins-molecular mechanisms and health significance: from cofactors to antioxidants to redox signaling. Antioxid Redox Signal 2013;19(13):1539-605.

9. Sharma S., Rais A., Sandhu R., Nel W., Ebadi M. Clinical significance of metallothioneins in cell therapy and nanomedicine. Int J Nanomedicine 2013;8:1477-88.

10. Sokolov A.V., Kostevich V.A., Runova O.L., Gorudko I.V., Vasilyev V.B., Cherenkevich S.N., Panasenko O.M. Proatherogenic modification of LDL by surface-bound myeloperoxidase. Chem Phys Lipids 2014;180:72-80.

11. Sokolov A.V., Solovyov K.V., Kostevich V.A., Chekanov A.V., Pulina M.O., Zakharova E.T., Shavlovski M.M., Panasenko O.M., Vasilyev V.B. Protection of ceruloplasmin by lactoferrin against hydroxyl radicals is pH dependent. Biochem Cell Biol 2012;90(3): 397-404.

12. Giurgea N., Constantinescu M.I., Stanciu R., Suciu S., Muresan A. Ceruloplasmin – acute-phase reactant or endogenous antioxidant? The case of cardiovascular disease. Med Sci Monit 2005;11(2):RA48-51.

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14. Гудков С.В., Штаркман И.Н., Смирнова В.С., Черников А.В., Брусков В.И. Гуанозин и инозин как природные антиоксиданты и радиопротекторы для мышей при действии летальных доз γ-облучения. Доклады Академии наук 2006;407(1):115-8. [Gudkov S.V., Shtarkman I.N., Smirnova V.S., Chernikov A.V., Bruskov V.I. Guanosine and inosine as natural antioxidants and radioprotectors for mice under lethal doses of γ-radiation. Doklady Akademii nauk 2006;407(1):115-8 (in Russian)].

15. Gudkov S.V., Shtarkman I.N., Smirnova V.S., Chernikov A.V., Bruskov V.I. Guanosine and inosine display antioxidant activity, protect DNA in vitro from oxidative damage induced by reactive oxygen species, and serve as radioprotectors in mice. Radiat Res 2006;165(5):538-45.

16. Гудков С.В., Гудкова О.Ю., Штаркман И.Н., Гапеев А.Б. Гуанозин и инозин как природные генопротекторы для клеток крови мышей при воздействии рентгеновского излучения. Радиационная биология. Радиоэкология 2006;46(6):713-8. [Gudkov S.V., Gudkova O.Yu., Shtarkman I.N., Gapeev A.B. Guanosine and inosine as natural genoprotectors for mice blood cells under X-ray radiation. Radiatsionnaya biologiya. Radioekologiya 2006;46(6):713-8 (in Russian)].

17. Асадуллина Н.Р., Гудков С.В., Брусков В.И. Антиоксидантные свойства ксантозина при воздействии рентгеновского излучения. Фундаментальные исследования 2011;(10):22-5. [Asadullina N.R., Gudkov S.V., Bruskov V.I. Antioxidant properties of Xantosine under X-ray radiation. Fundamentalnye issledovaniya 2011;(10):22-5 (in Russian)].

18. Asadullina N.R., Usacheva A.M., Gudkov S.V. Protection of mice against X-ray injuries by the post-irradiation administration of inosine-5’-monophosphate. J Radiat Res 2012;53(2):211-6.

19. Попова Н.Р., Гудков С.В., Брусков В.И. Природные пуриновые соединения как радиозащитные средства. Радиационная биология. Радиоэкология 2014;54(1):38-49. [Popova N.R., Gudkov S.V., Bruskov V.I. Natural purine compounds as radioprotective agents. Radiatsionnaya biologiya. Radio-ekologiya 2014;54(1):38-49 (in Russian)].

20. Tan D.-X., Chen L.D., Poeggeler B., Manchester L.C., Reiter R.J. Melatonin: a potent endogenous hydroxyl radical scavenger. Endocr J 1993;1:57-60.

21. Salucci S., Burattini S., Battistelli M., Baldassarri V., Curzi D., Valmori A., Falcieri E. Melatonin prevents chemical-induced haemopoietic cell death. Int J Mol Sci 2014;15(4):6625-40.

22. Jucker W. Carotenoids. Chimia (Aarau) 2011;65(1-2):109-10.

23. Bolhassani A., Khavari A., Bathaie S.Z. Saffron and natural carotenoids: Biochemical activities and anti-tumor effects. Biochim Biophys Acta 2014;1845(1):20-30.

24. Halliwell B., Gutteridge J.M. The antioxidants of human extracellular fluids. Arch Biochem Biophys 1990;280(1):1-8.

25. Chambial S., Dwivedi S., Shukla K.K., John P.J., Sharma P. Vitamin C in disease prevention and cure: An overview. Indian J Clin Biochem 2013;28(4):314-28.

26. Padayatty S.J., Katz A., Wang Y., Eck P., Kwon O., Lee J.H., Chen S., Corpe C., Dutta A., Dutta S.K., Levine M. Vitamin C as an antioxidant: evaluation of its role in disease prevention. J Am Coll Nutr 2003;22(1):18-35.

27. Пиотровский Л.Б., Киселев О.И. Фуллерены в биологии. СПб.: Росток; 2006. [Piotrovskiy L.B., Kiselev O.I. Fullerenes in Biology. Saint Petersburg: Rostok; 2006 (in Russian)].

28. Krusic P.J., Wasserman E., Keizer P.N., Morton J.R., Preston K.F. Radical reactions of c60. Science 1991;254(5035):1183-5.

29. Andrievsky G.V., Bruskov V.I., Tykhomyrov A.A., Gudkov S.V. Peculiarities of the antioxidant and radioprotective effects of hydrated C60 fullerene nanostructures in vitro and in vivo. Free Radic Biol Med 2009;47(6):786-93.

30. Bensasson R.V., Brettreich M., Frederiksen J., Göttinger H., Hirsch A., Land E.J., Leach S., McGarvey D.J., Schönberger H. Reactions of e(-)(aq), CO(2)(*)(-), HO(*), O(2)(*)(-) and O(2)((1) delta(g)) with a dendro[60]fullerene and C(60)[C(COOH)(2)](n) (n = 2-6). Free Radic Biol Med 2000;29(1):26-33.

31. Wolff D.J., Barbieri C.M., Richardson C.F., Schuster D.I., Wilson S.R. Trisamine C(60)-fullerene adducts inhibit neuronal nitric oxide synthase by acting as highly potent calmodulin antagonists. Arch Biochem Biophys 2002;399(2):130-41.

32. Engel P.S., Billups W.E., Abmayr D.W. Jr., Tsvaygboym K., Wang R. Reaction of single-walled carbon nanotubes with organic peroxides. J Phys Chem C 2008;112(3):695-700.

33. Lucente-Schultz R.M., Moore V.C., Leonard A.D., Price B.K., Kosynkin D.V., Lu M., Partha R., Conyers J.L., Tour J.M. Antioxidant single-walled carbon nanotubes. J Am Chem Soc 2009; 131(11):3934-41.

34. Fenoglio I., Tomatis M., Lison D., Muller J., Fonseca A., Nagy J.B., Fubini B. Reactivity of carbon nanotubes: free radical generation or scavenging activity? Free Radic Biol Med 2006;40(7):1227-33.

35. Cirillo G., Hampel S., Klingeler R., Puoci F., Iemma F., Curcio M., Parisi O.I., Spizzirri U.G., Picci N., Leonhardt A., Ritschel M., Büchner B. Antioxidant multi-walled carbon nanotubes by free radical grafting of gallic acid: new materials for biomedical applications. J Pharm Pharmacol 2011;63(2):179-88.

36. Galano A. Carbon nanotubes: promising agents against free radicals. Nanoscale 2010;2(3):373-80.

37. Hsieh S.F., Bello D., Schmidt D.F., Pal A.K., Rogers E.J. Biological oxidative damage by carbon nanotubes: fingerprint or footprint? Nanotoxicology 2012;6(1):61-76.

Almanac of Clinical Medicine. 2014; 1: 65-69

THE BIOANTIOXIDANTS (PART 2)

Gudkov S. V., Bruskov V. I., Kulikov A. V., Sharapov M. G., Kulikov D. A., Molochkov A. V.

https://doi.org/10.18786/2072-0505-2014-31-65-69

Abstract

Based on the analysis of the latest scientific data, the paper suggests a synthetic classification of the known bioantioxidants, peculiarities of their structure and functioning. The second part of the review describes the sulfur-containing compounds, chelators
of the metal ions of variable valency, compounds containing hydroxyl or amino group, and nanoparticles.

References

1. Men'shchikova E.B., Lankin V.Z., Zenkov N.K., Bondar' I.A., Krugovykh N.F., Trufakin V.A. Okislitel'nyi stress. Prooksidanty i antioksidanty. M.: Slovo; 2006. [Men'shchikova E.B., Lankin V.Z., Zenkov N.K., Bondar’ I.A., Krugovykh N.F., Trufakin V.A. Oxidative stress. Pro-oxidants and antioxidants. Moscow: Slovo; 2006 (in Russian)].

2. Kolesnichenko L.S., Kulinskii V.I. Glutationtransferazy. Uspekhi sovremennoi biologii 1989;107(2):179-94. [Kolesnichenko L.S., Kulinskiy V.I. Glutathionoxidase. Uspekhi sovremennoy biologii 1989;107(2):179-94 (in Russian)].

3. Gudkov S.V. Mekhanizmy obrazovaniya aktivnykh form kisloroda pod vliyaniem fizicheskikh faktorov i ikh genotoksicheskoe deistvie [dissertatsiya]. Pushchino: ITEB RAN; 2012. [Gudkov S.V. The mechanisms of the reactive oxygen species production under the influence of physical factors and their genotoxic acti vity [dissertation]. Pushchino: ITEB RAS; 2012 (in Russian)].

4. Gudkov S.V., Bruskov V.I. Guanozin i inozin (riboksin). Antioksidantnye i radiozashchitnye svoistva. Saarbrücken: Lambert Academic Publishing; 2011. [Gudkov S.V., Bruskov V.I. Guanosine and inosine (riboxin). Antioxidant and radioprotective properties. Saarbrücken: Lambert Academic Publishing; 2011 (in Russian)].

5. Collet J.F., Messens J. Structure, function, and mechanism of thioredoxin proteins. Antioxid Redox Signal 2010;13(8):1205-16.

6. Seo M.S., Kang S.W., Kim K., Baines I.C., Lee T.H., Rhee S.G. Identification of a new type of mammalian peroxiredoxin that forms an intramolecular disulfide as a reaction intermediate. J Biol Chem 2000;275(27):20346-54.

7. Wood Z.A., Poole L.B., Karplus P.A. Peroxiredoxin evolution and the regulation of hydrogen peroxide signaling. Science. 2003; 300(5619):650-3.

8. Hanschmann E.M., Godoy J.R., Berndt C., Hudemann C., Lillig C.H. Thioredoxins, glutaredoxins, and peroxiredoxins-molecular mechanisms and health significance: from cofactors to antioxidants to redox signaling. Antioxid Redox Signal 2013;19(13):1539-605.

9. Sharma S., Rais A., Sandhu R., Nel W., Ebadi M. Clinical significance of metallothioneins in cell therapy and nanomedicine. Int J Nanomedicine 2013;8:1477-88.

10. Sokolov A.V., Kostevich V.A., Runova O.L., Gorudko I.V., Vasilyev V.B., Cherenkevich S.N., Panasenko O.M. Proatherogenic modification of LDL by surface-bound myeloperoxidase. Chem Phys Lipids 2014;180:72-80.

11. Sokolov A.V., Solovyov K.V., Kostevich V.A., Chekanov A.V., Pulina M.O., Zakharova E.T., Shavlovski M.M., Panasenko O.M., Vasilyev V.B. Protection of ceruloplasmin by lactoferrin against hydroxyl radicals is pH dependent. Biochem Cell Biol 2012;90(3): 397-404.

12. Giurgea N., Constantinescu M.I., Stanciu R., Suciu S., Muresan A. Ceruloplasmin – acute-phase reactant or endogenous antioxidant? The case of cardiovascular disease. Med Sci Monit 2005;11(2):RA48-51.

13. Boldyrev A.A. Karnozin. Biologicheskoe znachenie i vozmozhnosti primeneniya v meditsine. M.: Izdatel'stvo MGU; 1998 [Boldyrev A.A. Carnosin. Biological significance and possibilities of medical application. Moscow: Izdatel’stvo MGU; 1998 (in Russian)].

14. Gudkov S.V., Shtarkman I.N., Smirnova V.S., Chernikov A.V., Bruskov V.I. Guanozin i inozin kak prirodnye antioksidanty i radioprotektory dlya myshei pri deistvii letal'nykh doz γ-oblucheniya. Doklady Akademii nauk 2006;407(1):115-8. [Gudkov S.V., Shtarkman I.N., Smirnova V.S., Chernikov A.V., Bruskov V.I. Guanosine and inosine as natural antioxidants and radioprotectors for mice under lethal doses of γ-radiation. Doklady Akademii nauk 2006;407(1):115-8 (in Russian)].

15. Gudkov S.V., Shtarkman I.N., Smirnova V.S., Chernikov A.V., Bruskov V.I. Guanosine and inosine display antioxidant activity, protect DNA in vitro from oxidative damage induced by reactive oxygen species, and serve as radioprotectors in mice. Radiat Res 2006;165(5):538-45.

16. Gudkov S.V., Gudkova O.Yu., Shtarkman I.N., Gapeev A.B. Guanozin i inozin kak prirodnye genoprotektory dlya kletok krovi myshei pri vozdeistvii rentgenovskogo izlucheniya. Radiatsionnaya biologiya. Radioekologiya 2006;46(6):713-8. [Gudkov S.V., Gudkova O.Yu., Shtarkman I.N., Gapeev A.B. Guanosine and inosine as natural genoprotectors for mice blood cells under X-ray radiation. Radiatsionnaya biologiya. Radioekologiya 2006;46(6):713-8 (in Russian)].

17. Asadullina N.R., Gudkov S.V., Bruskov V.I. Antioksidantnye svoistva ksantozina pri vozdeistvii rentgenovskogo izlucheniya. Fundamental'nye issledovaniya 2011;(10):22-5. [Asadullina N.R., Gudkov S.V., Bruskov V.I. Antioxidant properties of Xantosine under X-ray radiation. Fundamentalnye issledovaniya 2011;(10):22-5 (in Russian)].

18. Asadullina N.R., Usacheva A.M., Gudkov S.V. Protection of mice against X-ray injuries by the post-irradiation administration of inosine-5’-monophosphate. J Radiat Res 2012;53(2):211-6.

19. Popova N.R., Gudkov S.V., Bruskov V.I. Prirodnye purinovye soedineniya kak radiozashchitnye sredstva. Radiatsionnaya biologiya. Radioekologiya 2014;54(1):38-49. [Popova N.R., Gudkov S.V., Bruskov V.I. Natural purine compounds as radioprotective agents. Radiatsionnaya biologiya. Radio-ekologiya 2014;54(1):38-49 (in Russian)].

20. Tan D.-X., Chen L.D., Poeggeler B., Manchester L.C., Reiter R.J. Melatonin: a potent endogenous hydroxyl radical scavenger. Endocr J 1993;1:57-60.

21. Salucci S., Burattini S., Battistelli M., Baldassarri V., Curzi D., Valmori A., Falcieri E. Melatonin prevents chemical-induced haemopoietic cell death. Int J Mol Sci 2014;15(4):6625-40.

22. Jucker W. Carotenoids. Chimia (Aarau) 2011;65(1-2):109-10.

23. Bolhassani A., Khavari A., Bathaie S.Z. Saffron and natural carotenoids: Biochemical activities and anti-tumor effects. Biochim Biophys Acta 2014;1845(1):20-30.

24. Halliwell B., Gutteridge J.M. The antioxidants of human extracellular fluids. Arch Biochem Biophys 1990;280(1):1-8.

25. Chambial S., Dwivedi S., Shukla K.K., John P.J., Sharma P. Vitamin C in disease prevention and cure: An overview. Indian J Clin Biochem 2013;28(4):314-28.

26. Padayatty S.J., Katz A., Wang Y., Eck P., Kwon O., Lee J.H., Chen S., Corpe C., Dutta A., Dutta S.K., Levine M. Vitamin C as an antioxidant: evaluation of its role in disease prevention. J Am Coll Nutr 2003;22(1):18-35.

27. Piotrovskii L.B., Kiselev O.I. Fullereny v biologii. SPb.: Rostok; 2006. [Piotrovskiy L.B., Kiselev O.I. Fullerenes in Biology. Saint Petersburg: Rostok; 2006 (in Russian)].

28. Krusic P.J., Wasserman E., Keizer P.N., Morton J.R., Preston K.F. Radical reactions of c60. Science 1991;254(5035):1183-5.

29. Andrievsky G.V., Bruskov V.I., Tykhomyrov A.A., Gudkov S.V. Peculiarities of the antioxidant and radioprotective effects of hydrated C60 fullerene nanostructures in vitro and in vivo. Free Radic Biol Med 2009;47(6):786-93.

30. Bensasson R.V., Brettreich M., Frederiksen J., Göttinger H., Hirsch A., Land E.J., Leach S., McGarvey D.J., Schönberger H. Reactions of e(-)(aq), CO(2)(*)(-), HO(*), O(2)(*)(-) and O(2)((1) delta(g)) with a dendro[60]fullerene and C(60)[C(COOH)(2)](n) (n = 2-6). Free Radic Biol Med 2000;29(1):26-33.

31. Wolff D.J., Barbieri C.M., Richardson C.F., Schuster D.I., Wilson S.R. Trisamine C(60)-fullerene adducts inhibit neuronal nitric oxide synthase by acting as highly potent calmodulin antagonists. Arch Biochem Biophys 2002;399(2):130-41.

32. Engel P.S., Billups W.E., Abmayr D.W. Jr., Tsvaygboym K., Wang R. Reaction of single-walled carbon nanotubes with organic peroxides. J Phys Chem C 2008;112(3):695-700.

33. Lucente-Schultz R.M., Moore V.C., Leonard A.D., Price B.K., Kosynkin D.V., Lu M., Partha R., Conyers J.L., Tour J.M. Antioxidant single-walled carbon nanotubes. J Am Chem Soc 2009; 131(11):3934-41.

34. Fenoglio I., Tomatis M., Lison D., Muller J., Fonseca A., Nagy J.B., Fubini B. Reactivity of carbon nanotubes: free radical generation or scavenging activity? Free Radic Biol Med 2006;40(7):1227-33.

35. Cirillo G., Hampel S., Klingeler R., Puoci F., Iemma F., Curcio M., Parisi O.I., Spizzirri U.G., Picci N., Leonhardt A., Ritschel M., Büchner B. Antioxidant multi-walled carbon nanotubes by free radical grafting of gallic acid: new materials for biomedical applications. J Pharm Pharmacol 2011;63(2):179-88.

36. Galano A. Carbon nanotubes: promising agents against free radicals. Nanoscale 2010;2(3):373-80.

37. Hsieh S.F., Bello D., Schmidt D.F., Pal A.K., Rogers E.J. Biological oxidative damage by carbon nanotubes: fingerprint or footprint? Nanotoxicology 2012;6(1):61-76.