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Isoquinoline Coumarin Derivatives as Chemiluminescence Activators in Reactions of Lipid Peroxidation

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Abstract

This study deals with participation of isoquinoline derivatives of coumarin in the peroxidase reaction catalyzed by the cytochrome c–cardiolipin complex. We have studied coumarin derivatives called coumarin-314 (C-314), coumarin-334 (C-334) and coumarin-525 (C-525). These substances are considered as specific physical activators of chemiluminescence, which accompanies the lipid peroxidation reaction. In the course of the scientific research, a spectrophotometric study of the effect of methanol on the structure of cytochrome c was performed, the optical properties of these substances were studied in the medium of a phosphate buffer, and a spectrophotometric study was performed with parallel registration of the chemiluminescence of a mixture in which cytochrome c catalyzed by a complex with cardiolipin lipoperoxidase reaction in the presence of isoquinolysin derivatives of coumarin. The conclusions of this work contain identification of the reversibility of the action of methanol on the structure of cytochrome c, which proves the possibility of using this alcohol in the study of this protein, the positions of absorption maxima and corresponding values of molar absorption coefficients in the medium of 20 mM phosphate buffer (pH = 7.4) for C-314 (λmax = 447.5 nm; ε = 32360.4 L/(mol cm)), C-334 (λmax = 460 nm; ε = 44 012 L/(mol cm)), and C-525 (λmax = 460 nm; ε = 32 703.56 L/(mol cm)). We also demonstrated that the said substances are substrates of cytochrome c/cardiolipin complex-catalyzed peroxidase reaction. Mass flow of these substances during an average statistical experiment in measurement of chemiluminescence (322 s) for C-314, C-334 and C-525 amounted to 31.89, 37.61 and 25.94%, respectively.

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REFERENCES

  1. T. Nishikido, J. Oyama, A. Shiraki, et al., J. Am. Heart Assoc. 5 (4), e002863 (2016). https://doi.org/10.1161/JAHA.115.002863

    Article  Google Scholar 

  2. G. L. Caldeira, I. L. Ferreira, and A. C. Rego, J. Alzheimers Dis. 34, 115 (2013). https://doi.org/10.3233/JAD-121444

    Article  Google Scholar 

  3. H. H. Gaballah, S. S. Zakaria, M. M. Elbatsh, and N. M. Tahoon, Chem. Biol. Interact. 251, 10 (2016). https://doi.org/10.1016/j.cbi.2016.03.023

    Article  Google Scholar 

  4. L. Fan, L. Jiang, and Z. Du, Metab. Brain Dis. 30, 1269 (2015). https://doi.org/10.1007/s11011-015-9703-z

    Article  Google Scholar 

  5. N. Yalcinkaya, H. Haytural, B. Bilgic, et al., Neurosci. Lett. 615, 72 (2016). https://doi.org/10.1016/j.neulet.2016.01.029

    Article  Google Scholar 

  6. E. V. Proskurnina, Yu. A. Vladimirov, and A. M. Polimova, in Neuroscience for Medicine and Psychology: Proc. 11 Int. Interdisc. Conf. (Sudak, 2015), p. 309 [in Russian].

  7. Yu. A. Vladimirov, E. V. Proskurnina, D. Yu. Izmailov, et al., Biochemistry (Moscow) 74 (3), 301 (2009).

    Article  Google Scholar 

  8. Yu. A. Vladimirov, E. V. Proskurnina, D. Yu. Izmailov, et al., Biochemistry (Moscow) 71 (9), 998 (2006).

    Article  Google Scholar 

  9. Yu. A. Vladimirov, E. V. Proskurnina, D. Yu. Izmailov, et al., Biochemistry (Moscow) 91 (8), 1019 (2006).

    Google Scholar 

  10. A. N. Osipov, G. O. Stepanov, Yu. A. Vladimirov, et al., Biochemistry (Moscow) 71 (10), 1218 (2006).

    Article  Google Scholar 

  11. E. M. Demin, E. V. Proskurnina, and Yu. A. Vladimirov, Moscow Univ. Chem. Bull. 63 (5), 297 (2008).

    Article  Google Scholar 

  12. Yu. A. Vladimirov, E. M. Demin, E. V. Proskurnina, A. N. Osipov, Biochemistry (Moscow), Ser. A: Membr. Cell Biol. 3 (4), 467 (2009).

    Google Scholar 

  13. E. M. Demin, D. Yu. Izmailov, E. V. Proskurnina, and Yu. A. Vladimirov, Regulation of the Radical-dependent Stage of Apoptosis by Antioxidants (MAKS-Press, Moscow, 2012) [in Russian].

    Google Scholar 

  14. Yu. A. Vladimirov, in Medical and Biological Applications of Lasers: Proc. 40th Int. Sci.-Pract. Conf. (Yalta, 2013), p. 174 [in Russian].

  15. Yu. A. Vladimirov, E. V. Proskurnina, and A. V. Alekseev, Biochemistry (Moscow) 78 (10), 1086 (2013).

    Article  Google Scholar 

  16. E. M. Demin, E. V. Proskurnina, Yu. A. Vladimirov, in Proc. 2nd Russian Congress of Analysts (Moscow, 2013), p. 275 [in Russian].

  17. A. S. Vikulina, A. V. Alekseev, E. V. Proskurnina, and Yu. A. Vladimirov, Biochemistry (Moscow) 80 (10), 1298 (2015).

    Article  Google Scholar 

  18. V. E. Kagan, V. A. Tyurin, J. Jiang, et al., Nature Chem. Biol. 1, 223 (2005).

    Article  Google Scholar 

  19. N. A. Belikova, Y. A. Vladimirov, A. N. Osipov, et al., Biochemistry 45, 4998 (2006).

    Article  Google Scholar 

  20. L. Milazzo, L. Tognaccini, B. D. Howes, et al., Biochemistry 56, 1887 (2017). https://doi.org/10.1021/acs.biochem.6b01281

    Article  Google Scholar 

  21. Y. A. Vladimirov, C. Sarisozen, G. K. Vladimirov, et al., Pharm. Res. 34, 1264 (2017). https://doi.org/10.1007/s11095-017-2143-1

    Article  Google Scholar 

  22. D. A. Capdevila, S. Oviedo Rouco, F. Tomasina, et al., Biochemistry 54, 7491 (2015). https://doi.org/10.1021/acs.biochem.5b00922

    Article  Google Scholar 

  23. H. Kobayashi, S. Nagao, and S. Hirota, Angew Chem. Int. Ed. Engl. 55, 14019 (2016). https://doi.org/10.1002/anie.201607419

    Article  Google Scholar 

  24. A. Bhujade, G. Gupta, S. Talmale, et al., Food Funct. 4, 338 (2013). https://doi.org/10.1039/c2fo30167a

    Article  Google Scholar 

  25. D. A. Vasina, D. D. Zhdanov, E. V. Orlova, et al., Biochemistry (Moscow) 82, 24 (2017). https://doi.org/10.1134/S0006297917010035

    Article  Google Scholar 

  26. S. Li, T. Wang, L. Zhai, et al., J. Mol. Neurosci. 64, 144 (2018). https://doi.org/10.1007/s12031-017-1012-z

    Article  Google Scholar 

  27. P. Bemani, M. Mohammadi, and A. Hakakian, Asian Pac. J. Cancer Prev. 19, 97 (2018). https://doi.org/10.22034/APJCP.2018.19.1.97

    Article  Google Scholar 

  28. S. A. Susin, E. Daugas, L. Ravagnan, et al., J. Exp. Med. 192, 571 (2000).

    Article  Google Scholar 

  29. Yu. A. Vladimirov and A. I. Archakov, Lipid Peroxidation in Biological Membranes (Nauka, Moscow, 1972) [in Russian].

    Google Scholar 

  30. Yu. A. Vladimirov and E. V. Proskurnina, Usp. Biol. Khim. 49, 341 (2009).

    Google Scholar 

  31. W. Lepeschkin, Science 76, 409 (1932). https://doi.org/10.1126/science.76.1975.409

    Article  ADS  Google Scholar 

  32. W. W. Lepeschkin, Science 76, 168 (1932). https://doi.org/10.1126/science.76.1964.168

    Article  ADS  Google Scholar 

  33. A. G. Gurvich, Mitogenetic Radiation (Gosmedizdat, Moscow, 1934) [in Russian].

    Google Scholar 

  34. Yu. A. Vladimirov, O. A. Azizova, A. I. Deev, et al., Itogi Nauki Tekh., Ser.: Biofiz. 29 (VINITI, Moscow, 1991).

    Google Scholar 

  35. Yu. A. Vladimirov, E. V. Proskurnina, and D. Yu. Izmailov, Bull. Exp. Biol. Med. 144 (3) 390 (2007).

    Article  Google Scholar 

  36. A. I. Zhuravlev and S. M. Zubkova, Antioxidants: Free Radical Pathology, Aging, 2nd ed. (Belye Al’vy, Moscow, 2014) [in Russian].

    Google Scholar 

  37. A. M. Polimovam M. M. Sozarukova, E. V. Proskurnina, and Yu. A. Vladimirov, in Proc. 2nd Russian Congress of Analysts (Moscow, 2013), p. 276 [in Russian].

  38. Yu. A. Vladimirov and F. F. Litvin, Biofizika 4, 601 (1959).

    Google Scholar 

  39. B. N. Tarusov, A. I. Polivoda, and A. I. Zhuravlev, Biofizika 6, 490 (1961).

    Google Scholar 

  40. L. A. Romodin, Yu. A. Vladimirov, N. P. Lysenko, and E. N. Zarudnaya, Izv. Mezhd. Akad. Agrarn. Obraz., No. 42-1, 112 (2018).

  41. P. O. Volkova, A. V. Alekseev, A. A. Dzhatdoeva, et al., Moscow. Univ. Chem. Bull. 71 (1), 87 (2016).

    Article  Google Scholar 

  42. G. K. Vladimirov, M. M. Sozarukova, and D. Yu. Izmailov, in Science and Practice: New Discoveries, Proc. Int. Conf., Ed. by I. M. Shvets, L. A. Ismagilova, V. A. Gur’eva, and V. A. Sedenko (Kirov, 2015), pp. 717–726.

  43. Yu. A. Vladimirov and A. Ya Potapenko, Physicochemical Basis of Photobiological Processes: A Manual for Students in Medicine and Biology (Vysshaya Shkola, Moscow, 1989) [in Russian].

  44. V. S. Sharov, E. S. Dremina, and Yu. A. Vladimirov, Biofizika 40, 428 (1995).

    Google Scholar 

  45. Yu. A. Vladimirov, M. P. Sherstnev, and T. K. Azimbaev, Biofizika 40, 323 (1995).

    Google Scholar 

  46. Yu. A. Vladimirov, V. S. Sharov, E. S. Driomina, et al., Free Radic. Biol. Med. 18, 739 (1995).

    Article  Google Scholar 

  47. PubChem Database. https://pubchem.ncbi.nlm.nih.gov.

  48. J. Jiang, A. Bakan, A. A. Kapralov, et al., Free Radic. Biol. Med. 71, 221 (2014). https://doi.org/10.1016/j.freeradbiomed.2014.02.029

    Article  Google Scholar 

  49. A. S. Vikulina, A. A. Dzhatdoeva, E. N. Lobichenko, et al., Zh. Anal. Khim. 72, 639 (1987).

    Google Scholar 

  50. Isolation and Analysis of Natural Biologically Active Substances (Tomsk State Univ., Tomsk, 2017) [in Russian].

  51. V. S. Sharov, K. Briviba, and H. Sies, Free Radic. Biol. Med. 21, 833 (1996).

    Article  Google Scholar 

  52. Yu. A. Vladimirov and E. V. Proskurnina, Lectures in Medical Biophysics (Akademkniga, Moscow, 2007) [in Russian].

    Google Scholar 

  53. O. V. Vasiljeva, O. B. Lyubitsky, G. I. Klebanov, and Yu. A. Vladimirov, Membr. Cell Biol. 12, 223 (1998).

    Google Scholar 

  54. A. Mandal, C. L. Hoop, M. DeLucia, et al., Biophys. J. 109, 1873 (2015). https://doi.org/10.1016/j.bpj.2015.09.016

    Article  ADS  Google Scholar 

  55. V. E. Kagan, A. Bayir, H. Bayir, et al., Mol. Nutr. Food Res. 53, 104 (2009). https://doi.org/10.1002/mnfr.200700402

    Article  Google Scholar 

  56. V. E. Kagan, G. G. Borisenko, Y. Y. Tyurina, et al., Free Radic. Biol. Med. 37, 1963 (2004). https://doi.org/10.1016/j.freeradbiomed.2004.08.016

    Article  Google Scholar 

  57. L. A. Romodin, E. N. Zarudnaya, and Yu. A. Vladimirov, The Cytochrome c–Cardiolipin Complex: Biological Role and Inhibition by Antioxidants (Pero, Moscow, 2017) [in Russian].

    Google Scholar 

  58. A. Deshpande, S. Nimsadkar, and S. C. Mande, Acta Crystallogr. D. Biol. Crystallogr. 61, 1005 (2005). https://doi.org/10.1107/S0907444905009364

    Article  Google Scholar 

  59. J. N. Rodriguez-Lopez, D. J. Lowe, J. Hernandez-Ruiz, et al., J. Am. Chem. Soc. 123, 11838 (2001).

    Article  Google Scholar 

  60. P. G. Furtmuller, W. Jantschko, M. Zederbauer, et al., Jpn. J. Infect. Dis. 57, S30 (2004).

    Google Scholar 

  61. F. Ito, Y. Sono, and T. Ito, Antioxidants (Basel) 8 (3), 72 (2019). https://doi.org/10.3390/antiox8030072

    Article  Google Scholar 

  62. L. A. Romodin, S. V. Shangin, Yu. A. Vladimirov, et al., Izv. Mezhd. Akad. Agrarn. Obraz., No. 42-1, 118 (2018).

  63. M. J. Cormier and P. M. Prichard, J. Biol. Chem. 243, 4706 (1968).

    Google Scholar 

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Funding

This work was supported by the Russian Foundation for Basic Research, grant no. 18-015-00491 “Study of the mechanism of the reactions of formation of free radicals in cell membranes and mitochondria catalyzed by the complex of cytochrome c with anionic lipids (Cyt−AL)”.

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Authors and Affiliations

  1. Skryabin Moscow State Academy of Veterinary Medicine and Biotechnology, Moscow, Russia

    L. A. Romodin, S. V. Shangin & N. P. Lysenko

  2. Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University), 119991, Moscow, Russia

    Yu. A. Vladimirov & G. K. Vladimirov

  3. Moscow State University, 119991, Moscow, Russia

    Yu. A. Vladimirov

  4. Pirogov Russian National Research Medical University of the Ministry of Health of the Russian Federation, 117997, Moscow, Russia

    Yu. A. Vladimirov

  5. Shubnikov Institute of Crystallography, Federal Research Center “Crystallography and Photonics” of the Russian Academy of Sciences, 119333, Moscow, Russia

    Yu. A. Vladimirov & G. K. Vladimirov

  6. Lebedev Physical Institute of the Russian Academy of Sciences, GSP-1, 119991, Moscow, Russia

    E. I. Demikhov

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  1. L. A. Romodin
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Correspondence to L. A. Romodin.

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Abbreviations: CytC-CL—complex of cytochrome c with cardiolipin; CytC-TOCL—complex of cytochrome c with tetraoleylcardiolipin; EES—excited electronic states; EPR—method of electron paramagnetic resonance; C-314—isoquinolysine derivative of coumarin, coumarin-314; C-334—isoquinolysine derivative of coumarin, coumarin-334; C-525—isoquinolysine derivative of coumarin, coumarin-525; ε—molar absorption coefficient.

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Romodin, L.A., Vladimirov, Y.A., Shangin, S.V. et al. Isoquinoline Coumarin Derivatives as Chemiluminescence Activators in Reactions of Lipid Peroxidation. BIOPHYSICS 65, 577–586 (2020). https://doi.org/10.1134/S0006350920040181

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