Abstract
This review is focused on literature data and our own research of the nontrivial quinoid pathway for the oxidation of adrenaline. All catecholamines can be oxidized similarly with formation of corresponding aminochromes. This process is simulated in vitro in an alkaline medium and is known as the adrenaline autoxidation chain reaction, whose products are adrenochrome and radical compounds, superoxide anions (\({\text{O}}_{2}^{{ - {\kern 1pt} \centerdot }}\)), and other. This reaction was previously used to determine the activity of superoxide dismutase as a model of superoxide generation. We have proposed various new methodical approaches that allow the determination of the enzyme activity and reveal the anti/prooxidant properties of various compounds and materials. This pathway of conversion of one of the catecholamines (dopamine) is currently described as a “preclinical model of Parkinson’s disease.” In this regard, we have proposed the reaction of adrenaline autoxidation to be used in search for substances that can inhibit the process of quinoid oxidation, that is, to identify potential neuroprotective agents. Experimental and theoretical studies of this reaction expand the understanding of the mechanisms of free radical processes that occur in the body.
Similar content being viewed by others
REFERENCES
V. V. Menshikov and T. D. Bolshakova, in Adrenaline and Noradrenaline (Nauka, Moscow, 1964), p. 284 [in Russian].
S. Baez, J. Segura-Aguilar, M. Widersten, et al., J. Biochem. 324, 25 (1997).
M. P. Rigobello, G. Scutari, R. Boscolo, and A. Bindoli, Nitric Oxide 5, 39 (2001).
Y. Fu, L. Buryanovskyy, and Z. Zhang, J. Biol. Chem. 283, 23829 (2008).
V. S. Fluxa, D. Wahler, and J. L. Reymond, Nat. Protoc. 3, 1270 (2008).
C. Foppoli, R. Coccia., C. Cini, and M. A. Rosei, Biochim. Biophys. Acta 1334, 200 (1997).
A. Bindoli, M. P. Rigobello, and L. Galzigna, Toxicol. Lett. 48, 3 (1989).
F. Marques, R. O. Duarte, J. J. Moura, and M. P. Bicho, Biopl. Signals 5 (5), 275 (1996).
A. Bindoli, M. P. Rigobello, and D. J. Deeble, Free Radic. Biol. Med. 13, 391 (1992).
K. Polewski, Biochim. Biophys. Acta 1523, 56 (2000).
T. V. Sirota, Biochemistry (Moscow) Suppl. Ser. B: Biomed. Chem. 6 (3), 254 (2012).
V. G. Kolpakov, Zh. Nevropatol. Psikhiatrii im. S. S. Korsakova 74, 1254 (1974).
S. Baez and J. Segura-Aguilar, Biochem. Mol. Med., 56, 37 (1995).
A. F. Rump, J. Schierholz, R. Rosen, et al., Arzneimittelforschung 51, 964 (2001).
V. M. Costa, R. Silva, L. M. Ferreira, et al., Chem. Res. Toxicol. 20, 1183 (2007).
J. Smythies, A. De Iuliis, L. Zanatta, and L. Galzigna, Neurotox. Res. 4 (1), 77 (2002).
J. Smythies, Antioxid. Redox. Signal. 2 (3), 575 (2000).
P. Munoz, S. Huenchuguala, I. Paris, and J. Segura-Aguilar, Parkinsons Dis. 2012, 920953 (2012). https://doi.org/10.1155/2012/920953
M. L. Genova, N. M. Abd-Elsalam, S. M. el-Mahdy, et al., Arch. Biochem. Biophys. 447 (2), 167 (2006).
S. O. Tapbergenov, Vopr. Med. Khim. 28, 52 (1982).
I. S. Severina, N. V. Pyatakova, A. Yu. Shchegolev, and T. A. Sidorova, Biomed. Khim. 54, 679 (2008).
A. M. Utevskiy and S. O. Tapbergenov, Ukr. Biokhim. Zh. 54, 307 (1982
K. Jomova and M. Valko, Toxicology 283 (2–3), 65 (2011).
C. Beauchamp and I. Fridovich, Anal. Biochem. 44 (1), 276 (1971).
M. Nishikimi, N. A. Rao, and K. Yagi, Biochem. Biophys. Res. Commun. 46 (2), 849 (1972).
H. P. Misra and I. Fridovich, J. Biol. Chem., 247, 3170 (1972).
T. V. Sirota, Vopr. Med. Khim. 45, 263 (1999).
T. V. Sirota, RF Patent No. 2 144 674 (2000).
T. V. Sirota, N. V. Lange, N. I. Kosjakova, et al., Curr. Topics Biophys. 24, 185 (2000).
S. Green, A. Mazur, and E. Shorr, J. Biol. Chem., 220, 237 (1956).
T. V. Sirota, A. I. Miroshnikov, and K. N. Novikov, Biophysics (Moscow) 55 (6), 911 (2010).
A. B. Shcherbakov, V. K. Ivanov, T. V. Sirota, and Yu. D. Tretyakov, Dokl. Akad. Nauk 437 (2), 197 (2011).
T. V. Sirota, M. V. Zakharchenko, and M. N. Kondrashova, Biochemistry (Moscow) Suppl. Ser. B: Biomed. Chem. 7 (1), 79 (2013). 60 (1), 63 (2014).
K. O. Semen, G. J. M. den Hartog, D. V. Kaminsky, et al., Nat. Products Chem. Res. 2, 122 (2013). https://doi.org/10.4172/2329-6836.1000122
O. P. Yelisyeyeva, K. O. Semen, G. V. Ostrovska, et al., Food Chem. 147, 152 (2014).
T. V. Sirota, Bull. Exp. Biol. Med. 149 (4), 412 (2010).
T. V. Sirota, N. E. Lyamina, and L. I. Weisfeld, Biophysics (Moscow) 62 (5), 691 (2017).
T. V. Sirota, Biochemistry (Moscow) Suppl. Ser. B: Biomed. Chem. 8 (4), 323 (2014).
T. V. Sirota, Biomed. Khim. 62 (6), 650 (2016).
T. V. Sirota, Biomed. Khim. 61 (1), 115 (2015).
http://www.dpva.info/Guide/GuidePhysics/Solvability/SolvabilityOfSomeGases.
42. http://www.o8ode.ru/article/learn/ugaz.htm.
http://www.o8ode.ru/article/answer/voda_bez_vozduha_gazov.htm.
C. Karunakaran, H. Zhang, J. Joseph, et al., Chem. Res. Toxicol. 18 (3), 494 (2005).
D. C. Ramirez, S. E. Gomez Mejiba, and R. P. Mason, Free Radic. Biol. Med. 38, 201 (2005).
S. P. Goss, R. J. Singh, and B. Kalyanaraman, Biol. Chem. 274, 28233 (1999).
D. B. Medinas, G. Cerchiaro, D. F. Trindade, and O. Augusto, IUBMB Life 59, 255 (2007).
M. G. Bonini, S. A. Gabel, K. Ranguelova, et al., J. Biol. Chem. 284, 14618 (2009).
D. B. Medinas, J. C. Toledo, Jr., G. Cerchiaro, et al., Chem. Res. Toxicol. 22 (4), 639 (2009).
V. L. Voeikov, N. D. Vilenskaya, Do Mihn Ha, et al., Zh. Fiz. Khim. 86, 1 (2012).
E. E. Dubinina, in Products of Oxygen Metabolism in the Functional Activity of Cells (St. Petersburg, 2006), p. 111 [in Russian].
C. C. Santos, F. M. Araujo, R. S. Ferreira, et al., Toxicol. in Vitro 42, 54 (2017). https://doi.org/10.1016/j.tiv.2017.04.004
J. Segura-Aguilarand and S. Huenchuguala, Front Neurosci. 12, 106 (2018). https://doi.org/10.3389/fnins.2018.00106
J. Segura-Aguilar, I. Paris, P. Munoz, et al., Neurochem, 129 (6), 898 (2014). https://doi.org/10.1111/jnc.12686
A. Herrera-Soto, G. Diaz-Veliz, S. Mora, et al., Neurotox. Res. 32 (1), 134 (2017). https://doi.org/10.1007/s12640-017-9719-8
S. Huenchuguala, P. Munoz, R. Graumann, et al., Neurotoxicology 55, 10 (2016). https://doi.org/10.1016/j.neuro.2016.04.014
T. V. Sirota, Biomed. Khim. 65 (4), 316 (2019).
T. V. Sirota, Biophysics (Moscow) 61 (1), 17 (2016).
A. V. Lebedev, M. V. Ivanova, A. A. Timoshin, and E. K. Ruuge, Biomed. Khim. 54 (6), 687 (2008).
J. Smythies, Neurotox. Res. 4 (2), 147 (2002).
G. S. Behonick, M. J. Novak, E. W. Nealley, and S. L. Baskin, J. Appl. Toxicol. 21 (1) 15 (2001).
T. V. Sirota, V. I. Novoselov, V. G. Safronova, et al., IEEE Trans. Plasma Sci. 34 (4), 1351 (2006).
A. I. Gritsuk, T. V. Sirota, L. V. Dravitsa, and E. A. Craddock, Biomed. Khim. 52 (6), 601 (2006).
T. V. Sirota, V. G. Safronova, A. G. Amelina, et al., Biophysics (Moscow) 53 (5), 457 (2008).
V. I. Kulinsky and L. S. Kolesnichenko, Usp. Biol. Khim. 31, 157 (1990).
N. K. Zenkov, V. Z. Lankin, and E. B. Menshchikova, in Oxidative Stress (Nauka/Interperiodica, Moscow, 2001), p. 154 [in Russian].
E. B. Menshchikova, V. Z. Lankin, and N. K. Zenkov, in Oxidative Stress: Prooxidants and Antioxidants (Slovo, Moscow, 2006), p. 394 [in Russian].
G. F. Rushworth and I. L. Megson, Pharmacol. Ther. 141 (2), 150 (2014). https://doi.org/10.1016/j.pharmthera.2013.09.006
M. A. Martinez-Banaclocha, Med. Hypotheses 79 (1), 8 (2012).
D. S. Goldstein, Y. Jinsmaa, P. Sullivan, and Y. Sharabi, Neurochem. Res. 42 (11), 3289 (2017). https://doi.org/10.1007/s11064-017-2371-0
L. D. Coles, P. J. Tuite, G. Oz, and U. R. Mishra, J. Clin. Pharmacol. 58 (2), 158 (2018). https://doi.org/10.1002/jcph.1008
https://natureweight.ru/glutation.
Y. Izumi, Yakugaku Zasshi 133 (9), 983 (2013).
N. K. Zenkov, E. B. Menshchikova, and V. O. Tkachev, Biochemistry (Moscow) 78 (1), 19 (2013).
J. A. Lee, H. J. Son, J. W. Choi, et al., Neurochem. Int. 112, 96 (2018). .https://doi.org/10.1016/j.neuint.2017.11.006
F. I. Tarazi, Z. T. Sahli, M. Wolny, and S. A. Mousa, Pharmacol. Ther. 144 (2), 123 (2014). https://doi.org/10.1016/j.pharmthera.2014.05.010
ACKNOWLEDGMENTS
The author thanks the chief specialist N.E. Lyamina for technical assistance in conducting experiments and preparing publications.
Funding
This work was mainly carried out within the framework of budget financing of ITEB RAS on topic 04 of the direction 63.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
CONFLICT OF INTEREST
The authors declare that there is no conflict of interest.
COMPLIANCE WITH ETHICAL STANDARDS
This paper does not describe any research using humans and animals as objects.
Additional information
Translated by E. Puchkov
Abbreviations: ROS, reactive oxygen species; PD, Parkinson’s disease; SOD, superoxide dismutase.
Rights and permissions
About this article
Cite this article
Sirota, T.V. A Chain Reaction of Adrenaline Autoxidation is a Model of Quinoid Oxidation of Catecholamines. BIOPHYSICS 65, 548–556 (2020). https://doi.org/10.1134/S0006350920040223
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0006350920040223