zldmЗаводская лаборатория. Диагностика материаловIndustrial laboratory. Diagnostics of materials1028-68612588-0187ООО «Издательство «ТЕСТ-ЗЛ»10.26896/1028-6861-2019-85-1-I-28-34zldm-869Research ArticleАНАЛИЗ ВЕЩЕСТВАSUBSTANCES ANALYSISВольтамперометрический способ определения глутатиона на золотоуглеродсодержащем электродеVoltammetric method for determination of glutathione on a gold-carbon-containing electrodeГашевскаяА. С.GashevskayaA. S.

Томск

Tomsk

asg30@tpu.ruДорожкоЕ. В.DorozhkoE. V.

Томск

Tomsk

КоротковаЕ. И.KorotkovaE. I.

Томск

Tomsk

ПашковскаяЭ. А.PashkovskayaE. A.

Томск

Tomsk

ВороноваО. А.VoronovaO. A.

Томск

Tomsk

ПлотниковЕ. В.PlotnikovE. V.

Томск

Tomsk

ДёринаК. В.DerinaK. V.

Томск

Tomsk

ЛипскихО. И.LipskikhO. I.

Томск

Tomsk

Национальный исследовательский Томский политехнический университетРоссияNational Research Tomsk Polytechnic UniversityRussian FederationНациональный исследовательский Томский государственный университетРоссияNational Research Tomsk State UniversityRussian Federation201913022019851(I)2834Copyright © Гашевская А.С., Дорожко Е.В., Короткова Е.И., Пашковская Э.А., Воронова О.А., Плотников Е.В., Дёрина К.В., Липских О.И., 20192019Гашевская А.С., Дорожко Е.В., Короткова Е.И., Пашковская Э.А., Воронова О.А., Плотников Е.В., Дёрина К.В., Липских О.И.Gashevskaya A.S., Dorozhko E.V., Korotkova E.I., Pashkovskaya E.A., Voronova O.A., Plotnikov E.V., Derina K.V., Lipskikh O.I.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.zldm.ru/jour/article/view/869

Глутатион (GSH), один из наиболее важных антиоксидантов тиоловой природы, участвующий в разных биохимических процессах в организме человека, в лабораторной практике необходимо определять как в биологических жидкостях (слюна, моча, сыворотка крови), так и фармацевтических препаратах. Для этого широко используют различные инструментальные методы анализа, такие как спектрофотометрия, флуориметрия, высокоэффективная жидкостная хроматография, ЯМР, капиллярный электрофорез и электрохимические методы. Последние характеризуются простотой реализации, невысокой стоимостью и возможностью миниатюризации приборной базы. Исследовано электрохимическое поведение восстановленного (GSH) и окисленного (GSSG) глутатиона на золотоуглеродсодержащем электроде (AuУСЭ) методом катодной вольтамперометрии при разных способах удаления кислорода из электрохимической ячейки: деаэрация азотом и введение раствора сульфита натрия (4 моль/дм3). Установлено, что следы H2O2, которые остаются в приэлектродном слое на AuУСЭ даже после удаления кислорода, влияют на электрохимические свойства GSH при катодной развертке потенциала от 0 до – 1,8 В: GSH окисляется H2O2 до GSSG, наиболее информативным продуктом этой реакции является O2. Предложено косвенное определение GSH по току восстановления кислорода в среде Na2SO3 в диапазоне концентраций от 0,5 · 10–8 до 4,2 · 10–8 моль/дм3 с пределом обнаружения 2,5 · 10–9 моль/дм3. Предложенный вольтамперометрический способ апробирован при определении GSH в некоторых фармацевтических препаратах.

Glutathione (GSH) is one of the most important thiol-containing antioxidants involved into various biochemical processes in the human body. Glutathione determination in biological fluids (saliva, urine, serum) and pharmaceutical preparations is rather important for clinical practice. Various analytical methods — spectrophotometry, fluorimetry, high-performance liquid chromatography, NMR spectroscopy, capillary electrophoresis and electrochemical methods — are widely used for this purpose. Electrochemical methods are characterized by easy implementation, low cost and possibility of miniaturization. The electrochemical behavior of reduced (GSH) and oxidized (GSSG) glutathione on a gold-carbon-containing electrode (AuCE) was studied using cathodic voltammetry with different methods of removing oxygen from an electrochemical cell: nitrogen sparging and addition of sodium sulfite (4 mol/dm3). It has been shown that traces of H2O2 that remain in the near-electrode layer on the AuCE even after oxygen removal influence the electrochemical properties of GSH at a cathode sweep of the potential from 0 to –1.8 V: GSH is oxidized by H2O2 to GSSG, the most important product of this reaction is O2. An indirect determination of GSH by the current of oxygen reduction in the Na2SO3 medium in the concentration range from 0.5 × 10–8 to 4.2 × 10–8 mol/dm3 with a detection limit of 2.5 × 10–9 mol/dm3 is proposed. The developed voltammetric method is approved for the determination of GSH in certain pharmaceutical preparations.

глутатионвольтамперометриязолотоуглеродсодержащий электродсульфит натриятиоловые соединенияglutathionevoltammetrygold-carbon-containing electrodesodium sulfitethiol compoundsReferencesGalli F., Rossi R., Floridi A., Canestrari F. Protein thiols and glutathione influence the nitric oxide-dependent regulation of the red blood cell metabolism / Nitric Oxide Biol. Chem. 2002. Vol. 6. P. 186 – 199.Galli F., Rossi R., Floridi A., Canestrari F. Protein thiols and glutathione influence the nitric oxide-dependent regulation of the red blood cell metabolism / Nitric Oxide Biol. Chem. 2002. Vol. 6. P. 186 – 199.Dickinson D. A., Forman H. J. Cellular glutathione and thiols metabolism / Biochem. Pharmacol. 2002. Vol. 64. P. 1019 – 1026.Dickinson D. A., Forman H. J. Cellular glutathione and thiols metabolism / Biochem. Pharmacol. 2002. Vol. 64. P. 1019 – 1026.Hassan M. Q., Hadi R. A., Al-Rawi Z. S., et al. The glutathione defense system in the pathogenesis of rheumatoid arthritis / J. Appl. Toxicol. 2001. Vol. 21. N 1. P. 69 – 73.Hassan M. Q., Hadi R. A., Al-Rawi Z. S., et al. The glutathione defense system in the pathogenesis of rheumatoid arthritis / J. Appl. Toxicol. 2001. Vol. 21. N 1. P. 69 – 73.Watanabe K., Guengerich F. P. Limited Reactivity of Formyl Chloride with Glutathione and Relevance to Metabolism and Toxicity of Dichloromethane / Chem. Res. Toxicol. 2016. Vol. 19. P. 1091 – 1096.Watanabe K., Guengerich F. P. Limited Reactivity of Formyl Chloride with Glutathione and Relevance to Metabolism and Toxicity of Dichloromethane / Chem. Res. Toxicol. 2016. Vol. 19. P. 1091 – 1096.Samiec P., Botsch C. D., Flagg E. W., Kurtz J. C. Glutathione in human plasma: decline in association with aging, age related macular degeneration, and diabetes / Free Radical Biol. Med. 1998. Vol. 24. P. 699 – 704.Samiec P., Botsch C. D., Flagg E. W., Kurtz J. C. Glutathione in human plasma: decline in association with aging, age related macular degeneration, and diabetes / Free Radical Biol. Med. 1998. Vol. 24. P. 699 – 704.Weber G. F. Final common pathways in neurodegenerative diseases: regulatory role of the glutathione cycle / Neurosci. Biobehav. Rev. 1999. Vol. 23. P. 1079 – 1086.Weber G. F. Final common pathways in neurodegenerative diseases: regulatory role of the glutathione cycle / Neurosci. Biobehav. Rev. 1999. Vol. 23. P. 1079 – 1086.Gu F., Chauhan V., Chauhan A. Glutathione redox imbalance in brain disorders / Curr. Opin. Clin. Nutr. 2015. Vol. 18. P. 89 – 95.Gu F., Chauhan V., Chauhan A. Glutathione redox imbalance in brain disorders / Curr. Opin. Clin. Nutr. 2015. Vol. 18. P. 89 – 95.Plotnikov E., Korotkova E., Voronova O., et al. Comparative investigation of antioxidant activity of human serum blood by amperometric, voltammetric and chemiluminescent methods / Arch. Med. Sci. 2016. Vol. 12. N 5. P. 1071 – 1076.Plotnikov E., Korotkova E., Voronova O., et al. Comparative investigation of antioxidant activity of human serum blood by amperometric, voltammetric and chemiluminescent methods / Arch. Med. Sci. 2016. Vol. 12. N 5. P. 1071 – 1076.Korotkova E., Bashkim Misini, Dorozhko E., et al. Study of OH· Radicals in Human Serum Blood of Healthy Individuals and Those with Pathological Schizophrenia / Int. J. Mol. Sci. 2011. Vol. 12. N 1. P. 401 – 409.Korotkova E., Bashkim Misini, Dorozhko E., et al. Study of OH· Radicals in Human Serum Blood of Healthy Individuals and Those with Pathological Schizophrenia / Int. J. Mol. Sci. 2011. Vol. 12. N 1. P. 401 – 409.Hormozi-Nezhad M. R., Seyedhosseini E., Robatjazi H. Spectrophotometric determination of glutathione and cysteine based on aggregation of colloidal gold nanoparticles / Scientia Iranica. 2014. Vol. 19. N 3. P. 958 – 963.Hormozi-Nezhad M. R., Seyedhosseini E., Robatjazi H. Spectrophotometric determination of glutathione and cysteine based on aggregation of colloidal gold nanoparticles / Scientia Iranica. 2014. Vol. 19. N 3. P. 958 – 963.Hepel M., Stobiecka M. Comparative kinetic model of fluorescence enhancement in selective binding of monochlorobimane to glutathione / J. Photochem. Photobiol. A: Chemistry. 2011. Vol. 225. N 1. P. 72 – 80.Hepel M., Stobiecka M. Comparative kinetic model of fluorescence enhancement in selective binding of monochlorobimane to glutathione / J. Photochem. Photobiol. A: Chemistry. 2011. Vol. 225. N 1. P. 72 – 80.Markina M., Lebedeva E., Neudachina L., et al. Determination of Antioxidants in Human Skin by Capillary Zone Electrophoresis and Potentiometry / Anal. Lett. 2016. Vol. 49. N 12. P. 1804 – 1815.Markina M., Lebedeva E., Neudachina L., et al. Determination of Antioxidants in Human Skin by Capillary Zone Electrophoresis and Potentiometry / Anal. Lett. 2016. Vol. 49. N 12. P. 1804 – 1815.Pastore A., Massoud R., Motti G., et al. Fully automated assay for total homocysteine, cysteine, cysteinylglycine, glutathione, cysteamine, and 2-mercaptopropionylglycine in plasma and urine / Clinical Chem. 1998. Vol. 44. N 4. P. 825 – 832.Pastore A., Massoud R., Motti G., et al. Fully automated assay for total homocysteine, cysteine, cysteinylglycine, glutathione, cysteamine, and 2-mercaptopropionylglycine in plasma and urine / Clinical Chem. 1998. Vol. 44. N 4. P. 825 – 832.Tsikas D., Brunner G. High-performance liquid chromatography of glutathione conjugates / Anal. Bioanal. Chem. 1992. Vol. 343. N 3. P. 330 – 334.Tsikas D., Brunner G. High-performance liquid chromatography of glutathione conjugates / Anal. Bioanal. Chem. 1992. Vol. 343. N 3. P. 330 – 334.Salazar J. F., Schorr H., Herrmann W., et al. Measurement of thiols in human plasma using liquid chromatography with precolumn derivatization and fluorescence detection / J. Chromatogr. Sci. 1999. Vol. 37. N 12. P. 469 – 476.Salazar J. F., Schorr H., Herrmann W., et al. Measurement of thiols in human plasma using liquid chromatography with precolumn derivatization and fluorescence detection / J. Chromatogr. Sci. 1999. Vol. 37. N 12. P. 469 – 476.Rae C. D., Williams S. R. Glutathione in the human brain: Review of its roles and measurement by magnetic resonance spectroscopy / Anal. Biochem. 2017. Vol. 529. P. 127 – 143.Rae C. D., Williams S. R. Glutathione in the human brain: Review of its roles and measurement by magnetic resonance spectroscopy / Anal. Biochem. 2017. Vol. 529. P. 127 – 143.Lee P. T., Goncalves L. M., Compton R. G. Electrochemical determination of free and total glutathione in human saliva samples / Sens. Actuat. 2015. Vol. 221. P. 962 – 968.Lee P. T., Goncalves L. M., Compton R. G. Electrochemical determination of free and total glutathione in human saliva samples / Sens. Actuat. 2015. Vol. 221. P. 962 – 968.Harfield J. C., Batchelor-McAuley C., Compton R. G. Electrochemical determination of glutathione: a review / Analyst. 2012. Vol. 137. P. 2285 – 2296.Harfield J. C., Batchelor-McAuley C., Compton R. G. Electrochemical determination of glutathione: a review / Analyst. 2012. Vol. 137. P. 2285 – 2296.Hassanvand Z., Jalali F. Electrocatalytic Determination of Glutathione Using Transition Metal Hexacyanoferrates (MHCFs) of Copper and Cobalt Electrode Posited on Graphene Oxide Nanosheets / Anal. Bioanal. Chem. Res. 2018. Vol. 5. N 1. P. 115 – 129.Hassanvand Z., Jalali F. Electrocatalytic Determination of Glutathione Using Transition Metal Hexacyanoferrates (MHCFs) of Copper and Cobalt Electrode Posited on Graphene Oxide Nanosheets / Anal. Bioanal. Chem. Res. 2018. Vol. 5. N 1. P. 115 – 129.Hassan Karimi-Maleh, Mohsen Keyvanfard, Kadijeh Alizad, et al. Electrovatalitc Detetmination of Glutathione Using Multiwall Carbon Nanotubes Paste Electrode as a Sensor and Isoprenaline as a Mediator / Int. J. Electrochem. Sci. 2012. Vol. 7. P. 6816 – 6830.Hassan Karimi-Maleh, Mohsen Keyvanfard, Kadijeh Alizad, et al. Electrovatalitc Detetmination of Glutathione Using Multiwall Carbon Nanotubes Paste Electrode as a Sensor and Isoprenaline as a Mediator / Int. J. Electrochem. Sci. 2012. Vol. 7. P. 6816 – 6830.Masoumeh Taei, Xasan Hadadzadeh, Foroozan Hasanpour. A Voltammetric Sensor Based on Multiwalled Carbon Nanotubes and a New Azoferrocene Derivative for Determination of Glutathione / Sensors J. 2015. Vol. 15. N 8. P. 4472 – 4479.Masoumeh Taei, Xasan Hadadzadeh, Foroozan Hasanpour. A Voltammetric Sensor Based on Multiwalled Carbon Nanotubes and a New Azoferrocene Derivative for Determination of Glutathione / Sensors J. 2015. Vol. 15. N 8. P. 4472 – 4479.Hassan Karimi-Maleh, Fahimeh Tahernejad-Javazmi, Vinod Kumar Gupta, et al. A novel biosensor for liquid phase determination of glutathione and amoxicillin in biological and pharmaceutical samples using a ZnO/CNTs nanocomposite/catechol derivative modified electrode / J. of Mol. Liquids. 2014. Vol. 196. P. 258 – 263.Hassan Karimi-Maleh, Fahimeh Tahernejad-Javazmi, Vinod Kumar Gupta, et al. A novel biosensor for liquid phase determination of glutathione and amoxicillin in biological and pharmaceutical samples using a ZnO/CNTs nanocomposite/catechol derivative modified electrode / J. of Mol. Liquids. 2014. Vol. 196. P. 258 – 263.Hadi Beitollahi, Abbas Gholami, Mohammad Reza Ganjali. Preparation, characterization and electrochemical application of Ag-ZnO nanoplates for voltammetric determination of glutathione and tryptophan using modified carbon paste electrode / Mater. Sci. Eng. C. 2015. Vol. 57. P. 107 – 112.Hadi Beitollahi, Abbas Gholami, Mohammad Reza Ganjali. Preparation, characterization and electrochemical application of Ag-ZnO nanoplates for voltammetric determination of glutathione and tryptophan using modified carbon paste electrode / Mater. Sci. Eng. C. 2015. Vol. 57. P. 107 – 112.Hassan Karimi-Maleh, Fahimeh Tahernejad-Javazmi, Ali A. Ensafi, et al. A high sensitive biosensor based on FePt/CNTs nanocomposite /N-(4-hydroxyphenyl)-3,5-dinitrobenzamide modified carbon paste electrode for simultaneous determination of glutathione and piroxicam / Biosens. Bioelectron. 2014. Vol. 60. P. 1 – 7.Hassan Karimi-Maleh, Fahimeh Tahernejad-Javazmi, Ali A. Ensafi, et al. A high sensitive biosensor based on FePt/CNTs nanocomposite /N-(4-hydroxyphenyl)-3,5-dinitrobenzamide modified carbon paste electrode for simultaneous determination of glutathione and piroxicam / Biosens. Bioelectron. 2014. Vol. 60. P. 1 – 7.Hossein Soltani, Hadi Beitollahi, A.-H. Hatefi-Mehrjardi, Masoud Torkzadeh-Mahani. Voltammetric Determination of Glutathione Using a Modified Single Walled Carbon Nanotubes Paste Electrode / Anal. Bioanal. Electrochem. 2014. Vol. 6. N 1. P. 67 – 79.Hossein Soltani, Hadi Beitollahi, A.-H. Hatefi-Mehrjardi, Masoud Torkzadeh-Mahani. Voltammetric Determination of Glutathione Using a Modified Single Walled Carbon Nanotubes Paste Electrode / Anal. Bioanal. Electrochem. 2014. Vol. 6. N 1. P. 67 – 79.Behzad Rezaei, Hossein Khosropour, Ali Asghar Ensafi, et al. A Differential Pulse Voltammetric Sensor for Determination of Glutathione in Real Samples Using a Trichloro(terpyridine)ruthenium (III)/Multiwall Carbon Nanotubes Modified Paste Electrode / Sensors J. 2015. Vol. 15. N 1. P. 483 – 490.Behzad Rezaei, Hossein Khosropour, Ali Asghar Ensafi, et al. A Differential Pulse Voltammetric Sensor for Determination of Glutathione in Real Samples Using a Trichloro(terpyridine)ruthenium (III)/Multiwall Carbon Nanotubes Modified Paste Electrode / Sensors J. 2015. Vol. 15. N 1. P. 483 – 490.Mohsen Keyvanfard, Khadijeh Alizad. A Sensitive Voltammetric Sensor for Determination of Glutathione Based on Multiwall Carbon Nanotubes Paste Electrode Incorporating Pyrogallol Red / Orientl Journl Chem. 2014. Vol. 30. N 2. P. 593 – 599.Mohsen Keyvanfard, Khadijeh Alizad. A Sensitive Voltammetric Sensor for Determination of Glutathione Based on Multiwall Carbon Nanotubes Paste Electrode Incorporating Pyrogallol Red / Orientl Journl Chem. 2014. Vol. 30. N 2. P. 593 – 599.Liu B., Ma C., Li Y., et al. Voltammetric determination of reduced glutathione using poly(thionine) as a mediator in the presence of Fenton-type reaction / Talanta. 2017. Vol. 170. P. 399 – 405.Liu B., Ma C., Li Y., et al. Voltammetric determination of reduced glutathione using poly(thionine) as a mediator in the presence of Fenton-type reaction / Talanta. 2017. Vol. 170. P. 399 – 405.Ying Huang, Huijie Yan, Yuejin Tong. Electrocatalytic determination of Reduced Glutathione using rutin as a mediator at acetylene black spiked carbon paste electrode / J. Electroanal. Chem. 2015. Vol. 743. P. 25 – 30.Ying Huang, Huijie Yan, Yuejin Tong. Electrocatalytic determination of Reduced Glutathione using rutin as a mediator at acetylene black spiked carbon paste electrode / J. Electroanal. Chem. 2015. Vol. 743. P. 25 – 30.Noskova G. N., Zakharova E. A., Chernov V. I., et al. Properties and application of gold-carbon composite electrodes in electrochemical analysis methods / Izv. Tomsk. Politekh. Univ. Inzh. Georesurs. 2012. Vol. 320. N 3. P. 109 – 115 [in Russian].Noskova G. N., Zakharova E. A., Chernov V. I., et al. Properties and application of gold-carbon composite electrodes in electrochemical analysis methods / Izv. Tomsk. Politekh. Univ. Inzh. Georesurs. 2012. Vol. 320. N 3. P. 109 – 115 [in Russian].Zakharova E. A., Noskova G. N., Elesova E. E., Antonova S. G. Determination of arsenic (V) in waters by the method of inversion voltammetry against the background of sodium sulfite in the presence of manganese (II) ions / Zavod. Lab. Diagn. Mater. 2012. Vol. 79. N 5. P. 17 – 23 [in Russian].Zakharova E. A., Noskova G. N., Elesova E. E., Antonova S. G. Determination of arsenic (V) in waters by the method of inversion voltammetry against the background of sodium sulfite in the presence of manganese (II) ions / Zavod. Lab. Diagn. Mater. 2012. Vol. 79. N 5. P. 17 – 23 [in Russian].Zakharova E. A., Antonova S. G., Noskova G. N., Skvortsova L. N., Te A. V. Methods of the determination of inorganic arsenic species by stripping voltammetry in weakly alkaline media / J. Anal. Chem. 2016. Vol. 71. N 8. P. 823 – 833.Zakharova E. A., Antonova S. G., Noskova G. N., Skvortsova L. N., Te A. V. Methods of the determination of inorganic arsenic species by stripping voltammetry in weakly alkaline media / J. Anal. Chem. 2016. Vol. 71. N 8. P. 823 – 833.Abedinzadeh Z., Gardes-Albert M., Ferradini C. Kinetic study of the oxidation mechanism of glutathione by hydrogen peroxide in neutral aqueous medium / Can. J. Chem. 1989. Vol. 67. N 7. P. 1247 – 1255.Abedinzadeh Z., Gardes-Albert M., Ferradini C. Kinetic study of the oxidation mechanism of glutathione by hydrogen peroxide in neutral aqueous medium / Can. J. Chem. 1989. Vol. 67. N 7. P. 1247 – 1255.Shinichi Enami, Hoffmann M. R., Colussi A. J. OH-Radical Specific Addition to Glutathione S-Atom at the Air-Water Interface: Relevance to the Redox Balance of the Lung Epithelial Lining Fluid / J. Phys. Chem. Lett. 2015. Vol. 6. N 19. P. 3935 – 3943.Shinichi Enami, Hoffmann M. R., Colussi A. J. OH-Radical Specific Addition to Glutathione S-Atom at the Air-Water Interface: Relevance to the Redox Balance of the Lung Epithelial Lining Fluid / J. Phys. Chem. Lett. 2015. Vol. 6. N 19. P. 3935 – 3943.Flohe L. The fairytale of the GSSG/GSH redox potential / Biochim. Biophys. Acta. 2013. Vol. 1830. N 5. P. 3139 – 3142.Flohe L. The fairytale of the GSSG/GSH redox potential / Biochim. Biophys. Acta. 2013. Vol. 1830. N 5. P. 3139 – 3142.Pisoschi A. M. Electroanalytical Techniques for the Determination of Sulphite Preservative: An Editorial / Biochem. Anal. Biochem. 2014. Vol. 3. P. 32 – 34.Pisoschi A. M. Electroanalytical Techniques for the Determination of Sulphite Preservative: An Editorial / Biochem. Anal. Biochem. 2014. Vol. 3. P. 32 – 34.Mohamed S. El-Deab, Takeo Ohsaka. Quasi-reversible two-electron reduction of oxygen at gold electrodes modified with a self-assembled submonolayer of cysteine / Electrochem. Comm. 2013. Vol. 5. N 3. P. 214 – 219.Mohamed S. El-Deab, Takeo Ohsaka. Quasi-reversible two-electron reduction of oxygen at gold electrodes modified with a self-assembled submonolayer of cysteine / Electrochem. Comm. 2013. Vol. 5. N 3. P. 214 – 219.Erling Skavas, Tor Hemmingsen. Kinetics and mechanism of sulphite oxidation on a rotating platinum disc electrode in an alkaline solution / Electrochim. Acta. 2007. Vol. 52. P. 3510 – 3517.Erling Skavas, Tor Hemmingsen. Kinetics and mechanism of sulphite oxidation on a rotating platinum disc electrode in an alkaline solution / Electrochim. Acta. 2007. Vol. 52. P. 3510 – 3517.Senning A., ed. Sulfur in organic and inorganic chemistry. Vol. 1 – 3. — NY: M. Dekker, 1972.Senning A., ed. Sulfur in organic and inorganic chemistry. Vol. 1 – 3. — NY: M. Dekker, 1972.Hayon E., Treinin A., Wilf J. Electronic spectra, photochemistry, and autoxidation mechanism of the sulfite-bisulfite-pyrosulfite systems. SO2–, SO3–, SO4–, and SO5– — radicals / J. Am. Chem. Soc. 1972. Vol. 94. P. 47 – 57.Hayon E., Treinin A., Wilf J. Electronic spectra, photochemistry, and autoxidation mechanism of the sulfite-bisulfite-pyrosulfite systems. SO2–, SO3–, SO4–, and SO5– — radicals / J. Am. Chem. Soc. 1972. Vol. 94. P. 47 – 57.Shi X. Generation of and OH radicals in reactions with in organic environmental pollutants and its implications to toxicity / J. Inorg. Biochem. 1994. Vol. 56. P. 155 – 165.Shi X. Generation of and OH radicals in reactions with in organic environmental pollutants and its implications to toxicity / J. Inorg. Biochem. 1994. Vol. 56. P. 155 – 165.Yasemin Oztekin, Almira Ramanaviciene, Arunas Ramanavicius. Electrochemical Glutathione Sensor Based on Electrochemically Deposited Poly-m-aminophenol / Electroanalysis. 2011. Vol. 23. N 3. P. 701 – 709.Yasemin Oztekin, Almira Ramanaviciene, Arunas Ramanavicius. Electrochemical Glutathione Sensor Based on Electrochemically Deposited Poly-m-aminophenol / Electroanalysis. 2011. Vol. 23. N 3. P. 701 – 709.

The authors declare that there are no conflicts of interest present.