Abstract
A structure — hemolytic activity relationship in isobornylphenol derivatives was analysed. The morphological transformation of erythrocytes under the influence of some representatives of this class of compounds was demonstrated by scanning electron microscopy. The hemolytic activity of the test compounds can vary within wide limits, depending on the structure and position of substituents determining the nature of the interaction of the compound with the cell membrane.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
J. Takebayashi, J. Chen, A. Tai, in Advanced Protocols in Oxidative Stress II, Methods in Molecular Biology, Ed. D. Armstrong, Humana Press, New York—Dordrecht— Heidelberg—London, 2010, 594,287.
O. G. Shevchenko, L. N. Shishkina, Uspekhi sovremennoy biologii [Advances in Modern Biology], 2014, 134, 133 (in Russian).
O. G. Shevchenko, S. N. Plyusnina, I. Yu. Chukicheva, I. V. Fedorova, A. V. Kutchin, Biochem. Moscow Suppl. Ser. A, 2013, 7,302.
E. V. Buravlev, D. V. Belykh, I. Yu. Chukicheva, I. S. Tarabukina, O. G. Shevchenko, A. V. Kutchin, Russ. J. Bioorg. Chem., 2013, 39,434.
E. V. Buravlev, O. G. Shevchenko, A. V. Kutchin, Bioorg. Med. Chem. Lett., 2015, 25,826.
E. V. Buravlev, I. Yu. Chukicheva, O. G. Shevchenko, Yu. K. Suponitskii, A. V. Kutchin, Russ. Chem. Bull., 2016, 65, 1406.
I. Yu. Chukicheva, M. A. Torlopov, E. V. Buravlev, O. G. Shevchenko, A. V. Kutchin, Russ. J. Bioorg. Chem., 2014, 40,76.
I. Yu. Chukicheva, O. A. Shumova, O. G. Shevchenko, O. V. Sukrusheva, A. V. Kutchin, Russ. Chem. Bull., 2016, 65,721.
S. V. Pestova, E. E. Izmest´ev, O. G. Shevchenko, S. A. Rubtsova, A. V. Kutchin, Russ. Chem. Bull., 2015, 64,723.
E. S. Izmest´ev, D. V. Sudarikov, O. G. Shevchenko, S. A. Rubtsova, A. V. Kutchin, Russ. J. Bioorg. Chem., 2015, 38,77.
A. Danilov, M. Shaposhnikov, O. Shevchenko, N. Zemskaya, A. Zhavoronkov, A. Moskalev, Oncotarget, 2015, 6, 19428.
C. P. Jayalakshmi, J. D. Sharma, Environ. Res., 1986, 41,235.
H. G. Shertzer, G. L. Bannenberg, M. Rundgren, P. Moldéus, Biochem. Pharmacol., 1991, 42, 1587.
E. Yu. Parshina, L. Ya. Gendel, A. B. Rubin, Biophysics, 2009, 54,706.
E. Yu. Parshina, L. Ya. Gendel, A. B. Rubin, Khim. Farm. Zh. [Chem. Pharm. J.], 2012, 46, 17 (in Russian).
E. Yu. Parshina, L. Ya. Gendel, A. B. Rubin. Biol. Bull., 2007, 34,537.
J.-J. Koh, S. Qiu, H. Zou, R. Lakshminarayanan, J. Li, X. Zhou, C. Tang, P. Saraswathi, C. Verma, D. T. H. Tan, A. L. Tan, S. Liu, R. W. Beuerman, Biochim. Biophys. Acta., 2013, 1828,834.
O. I. Kiselev, Khimiopreparaty i khimioterapiya grippa [Chemotherapy Drugs and Chemotherapy of Influenza], St. Petersburg, 2012, 272 pp. (in Russian).
A. S. Sokolova, O. I. Yarovaya, A. V. Shernyukov, Y. V. Gatilov, Y. V. Razumova, V. V. Zarubaev, T. S. Tretiak, A. G. Pokrovsky, O. I. Kiselev, N. F. Salakhutdinov, Eur. J. Med. Chem., 2015, 105,263.
I. Yu. Chukicheva, I. V. Timusheva, L. V. Spirikhin, A. V. Kutchin, Chem. Nat. Compd., 2007, 43,245.
A. V. Kutchin, I. Yu. Chukicheva, I. V. Fedorova, O. A. Shumova, Dokl. Chem., 2011, 437,127.
I. Yu. Chukicheva, O. A. Shumova, A. V. Kuchin, Chem. Nat. Compd., 2012, 48,43.
S. V. Logvinov, M. B. Plotnikov, A. A. Zhdankina, G. A. Chernysheva, V. I. Smol´yakova, I. S. Ivanov, A. V. Kuchin, I. Yu. Chukicheva, E. Yu. Varakuta, Neurosci. Behav. Physiol., 2012, 42, 1019.
T. M. Plotnikova, G. A. Chernysheva, V. I. Smolyakova, P. P. Shchetinin, A. V. Kuchin, I. Y. Chukicheva, M. B. Plotnikov, Bull. Exp. Biol. and Med., 2014, 157,211.
T. Plotnikova, M. Plotnikov, G. Chernysheva, V. Smol´yakova, P. Shchetinin, A. Kuchin, I. Chukicheva, Key Eng. Mater., 2016, 683,469.
I. Yu. Chukicheva, A. V. Kutchin, Ros. Khim. Zh. [Russ. Chem. J.], 2004, 48, No. 3, 21 (in Russian).
I. Yu. Chukicheva, I. V. Fedorova, O. A. Shumova, A. V. Kutchin, Russ. J. Bioorg. Chem., 2011, 38,855.
E. V. Buravlev, I. Yu. Chukicheva, D. V. Belykh, A. V. Kuchin, Chem. Nat. Compd., 2007, 43,678.
E. V. Buravlev, I. Yu. Chukicheva, K. Yu. Suponitskii, A. V. Kuchin, Russ. J. Gen. Chem., 2008, 78, 1411.
E. V. Buravlev, I. Yu. Chukicheva, A. V. Kuchin, Chem. Nat. Compd., 2010, 46,33.
E. V. Buravlev, I. Yu. Chukicheva, I. A. Dvornikova, A. V. Churakov, A. V. Kutchin, Russ. J. Org. Chem., 2012, 48, 938.aaa
L. N. Shishkina, L. I. Mazaletskaya, K. M. Marakulina, Yu. K. Lukanina, I. G. Plashchina, N. I. Sheludchenko, E. V. Buravlev, I. V. Fedorova, I. Yu. Chukicheva, A. V. Kutchin, Russ. Chem. Bull., 2014, 63, 2007.
E. V. Buravlev, I. Yu. Chukicheva, O. V. Sukrusheva, O. G. Shevchenko, A. V. Kutchin, Russ. Chem. Bull., 2015, 64, 1406.
I. Yu. Chukicheva, O. V. Sukrusheva, A. V. Kutchin, Russ. J. Gen. Chem., 2015, 85, 1397.
I. Yu. Chukicheva, O. V. Sukrusheva, L. I. Mazaletskaya, A. V. Kutchin, Russ. J. Org. Chem., 2016, 52,813.
I. Yu. Chukicheva, O. V. Sukrusheva, L. I. Mazaletskaya, A. V. Kuchin, Russ. J. Gen. Chem., 2016, 86, 2325.
E. V. Buravlev, I. Yu. Chukicheva, O. G. Shevchenko, K. Yu. Suponitsky, A. V. Kutchin, Russ. Chem. Bull., 2017, 66,91.
E. V. Buravlev, I. Yu. Chukicheva, O. G. Shevchenko, A. V. Kutchin, Russ. Chem. Bull., 2017, 66,297.
M. R. Clemens, H. D. Waller, Chem. Phys. Lipid, 1987, 45,251.
J. M. Berg, J. A. F. Kamp, B. H. Lubin, B. Roelofsen, F. A. Kuypers, Free Radic. Biol. Med., 1992, 12,487.
E. V. Buravlev, I. Yu. Chukicheva, O. G. Shevchenko, K. Yu. Suponitsky, A. V. Kutchin, Russ. J. Bioorg. Chem., 2011, 37,614.
L. Ya. Gendel´, L. I. Likhacheva, B. N. Bogonatov, O. M. Panasenko, K. E. Kruglyakova, Dokl. Akad. Nauk SSSR, 1984, 277, 493 [Dokl. Chem. (Engl. Transl.), 1984].
L. Ya. Gendel´, L. V. Kim, O. G. Luneva, V. A. Fedin, K. E. Kruglyakova, Izv. Akad.Nauk, Ser. Biol. [Russ. Biol. Bull.], 1996, 508 (in Russian).
V. V. Novitsky, N. V. Ryazantseva, E. A. Stepovaya, Fiziologiya i patofiziologiya eritrotsita [Physiology and Pathophysiology of Erythrocyte], Tomsk Univ. Publ., Tomsk, 2004, 202 pp. (in Russian).
M. P. Sheetz, S. J. Singer, Proc. Natl. Acad. Sci. USA, 1974, 71, 4457.
D. V. Belykh, E. V. Buravlev, I. Yu. Chukicheva, I. S. Tarabukina, O. G. Shevchenko, S. N. Plyusnina, A. V. Kutchin, Russ. J. Bioorg. Chem., 2012, 38,558.
M. Suwalsky, P. Vargas, M. Avello, F. Villena, C. P. Sotomayor, Int. J. Pharm., 2008, 363,85.
M. Suwalsky, J. Belmar, F. Villena, M. J. Gallardo, M. Jemiola-Rzeminska, K. Strzalka, Arch. Biochem. Biophys., 2013, 539,9.
M. Suwalsky, M. Manrique, F. Villena, C. P. Sotomayor, Biophys. Chem., 2009, 141,34.
M. Manrique-Moreno, M. Suwalsky, F. Villena, P. Garidel, Biophys. Chem., 2010, 147,53.
M. Manrique-Moreno, F. Villena, C. P. Sotomayor, A. M. Edwards, M. A. Mucoz, P. Garidel, M. Suwalskya, Biochim Biophys Acta, 2011, 1808, 2656.
O. G. Luneva, L. Ya. Gendel´, Yu. V. Kuznetsov, L. D. Smirnov, Biofizika [Biophysics], 2005, 50, 310 (in Russian).
A. Lypez-Revuelta, J. I. Sánchez-Gallego, A. Hernández-Hernández, J. Sánchez-Yagüe, M. Llanillo, Chem. Biol. Interact., 2006, 161,79.
M. Blasa, M. Candiracci, A. Accorsi, M. P. Piacentini, E. Piatti, Food. Chem., 104, 1635.
S. Chaudhuri, A. Banerjee, K. Basu, B. Sengupta, P. K. Sengupta, Int. J. Biol. Macromol., 2007, 41,42.
Y. Chen, P. Deuster, Chem. Biol. Interact., 2009, 182,7.
Y.-J. Shang, X.-L. Jin, X.-L. Shang, J.-J. Tang, G.-Y. Liu, F. Dai, Y.-P. Qian, G.-J. Fan, Q. Liu, B. Zhou, Food. Chem., 2010, 119, 1435.
P. Filipe, A. M. S. Silva, R. S. G. R. Seixas, D. C. G. A. Pinto, A. Santos, L. K. Patterson, J. N. Silva, J. A. S. Cavaleiro, J. P. Freitas, J.-C. Mazière, R. Santus, P. Morlière, Biochem. Pharm., 2009, 77,957.
P. M. Rodi, V. M. Trucco, A. M. Gennaro, Biophys. Chem., 2008, 135,14.
G. I. Kozinets, Yu. A. Simovart, Poverkhnostnaya arkhitektonika kletok perifericheskoy krovi v norme i pri zabolevaniyakh sistemy krovi [Superficial Architectonics of Peripheral Blood Cells in Norm and in Diseases of the Blood System], Valgus, Tallin, 1984, 115 pp. (in Russian).
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1881—1890, October, 2017.
Rights and permissions
About this article
Cite this article
Shevchenko, O.G., Plyusnina, S.N., Buravlev, E.V. et al. Structure—hemolytic activity relationship in isobornylphenol derivatives. Russ Chem Bull 66, 1881–1890 (2017). https://doi.org/10.1007/s11172-017-1962-x
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-017-1962-x