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New Acylate and Thioacylate Effectors of Mammalian Cholinesterases Based on Cyclic Ammonium Alcohols Containing Elements of the Anabasine Structure

  • N. E. Basova
  • B. N. Kormilitsyn
  • A. Yu. Perchenok
  • E. V. Rozengart
  • V. S. Saakov
  • A. A. Suvorov
Comparative and Ontogenic Biochemistry
  • 8 Downloads

Abstract

We report a pioneering analysis of the interaction between mammalian cholinesterases and 36 acylates and thioacylates of ammonium alcohols with different structure of an alkyl chain between ammonium and etheric atoms and with different structure of a cyclic ammonium group. Among these ethers, which were both substrates and reversible inhibitors of erythrocyte cholinesterase and serum butyrylcholinesterase, specific effectors of both enzymes were identified.

Keywords

cholinesterases substrates reversible inhibitors acylates and thioacylates 

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References

  1. 1.
    Cholinesterases and anticholinesterase agents, Handbuch der Experim. Pharmakologie, Koelle, G.B., Ed., 1963, vol. 15, Berlin, Goettingen, Heidelberg.Google Scholar
  2. 2.
    Golikov, S.N. and Rozengart, V.I., Kholinesterazy i antikholinesteraznye veshchestva (Cholinesterases and Anticholinesterase Substances), Leningrad, 1964.Google Scholar
  3. 3.
    Silver, A., The Biology of Cholinesterases, Amsterdam, 1974.Google Scholar
  4. 4.
    Sadykov, A.S., Rozengart, E.V., Abduvakhabov, A.A., and Aslanov, Kh.A., Kholinesterazy. Aktivnyi tsentr i mekhanizm deistviya (Cholinesterases. Active Center and Mechanism of Action), Tashkent, 1976.Google Scholar
  5. 5.
    Brestkin, A.P., Kuznetsova, L.P., Moralev, S.N., Rozengart, E.V., and Epshtein, L.M., Kholinesterazy nazemnykh zhivotnykh i gidrobiontov (Cholinesterase of Terrestrial Animals and Hydrobionts), Vladivostok, 1997.Google Scholar
  6. 6.
    Moralev, S.N. and Rozengart, E.V., Comparative Enzymology of Cholinesterases, La Jolla, 2007.Google Scholar
  7. 7.
    Rozengart, E.V. and Basova, N.E., Thiosubstrates of cholinesterases of different origin, Zh. Evol. Biokhim. Fiziol., 2008, vol. 44, pp. 12–21.PubMedGoogle Scholar
  8. 8.
    11th International Meeting on Cholinesterases, June 4–9 2012, Kazan, Russia, Chemico-Biological Interaction, Special issue, Lushchekina, S., Masson, P., Lockridge, O., Rosenberry, T.L., and Var folomeev, S.D., Eds., 2013, vol. 203, pp. 1–376.Google Scholar
  9. 9.
    Ellman, G.H., Courtney, K.D., Andres, V., and Featherstone, R.M., A new and rapid colorimetric determination of acetylcholinesterase activity, Biochem. Pharmacol., 1961, vol.7, pp. 88–95.CrossRefPubMedGoogle Scholar
  10. 10.
    Rozengart, E.V. and Basova, N.E., Thioacylates of cyclic ammonium acetylcholine derivatives as substrates and inhibitors of mammalian cholinesterases, Dokl. Ross. Akad. Nauk, 2007, vol. 415, pp. 551–555.Google Scholar
  11. 11.
    Rozengart, E.V. and Basova, N.E., New substrates and reversible inhibitors of cholinesterases based on ethers and thioethers of cyclic ammonium alcohols with noncholine structure, Dokl. Ross. Akad. Nauk, 2008, vol. 418, pp.114–120.Google Scholar
  12. 12.
    Brestkin, A.P., Rozengart, E.V., Abduvakhabov, A.A., and Irgasheva, G.A., Substrate specificity of cholinesterases, Struktura i funktsii khimii prirodnykh i fiziologicheski aktivnykh soedinenii (Structure and Functions of Chemistry of Natural and Physiologically Active Compounds), Nukus, 1990, pp. 3–57.Google Scholar
  13. 13.
    Shestakova, N.N. and Rozengart, E.V., Conformational differences at sorption of choline ligands in the active center of cholinesterase, Bioorg. Khim., 1995, vol. 21, pp. 323–329.PubMedGoogle Scholar
  14. 14.
    Shestakova, N.N. and Rozengart, E.V., Conformational aspects of stereospecificity of acetylcholinesterase-catalyzed hydrolysis of β-methylcholine substrates, Dokl. Ross. Akad. Nauk, 1998, vol. 359, no. 5, pp. 695–697.Google Scholar
  15. 15.
    Rozengart, E.V., Basova, N.E., and Suvorov, A.A., Action specificity of piperidylcholine derivatives as substrates of cholinesterases of different origin, Zh. Evol. Biokhim. Fiziol., 2009, vol. 45, no. 1, pp. 25–33.PubMedGoogle Scholar
  16. 16.
    Abduvakhabov, A.A., Sadykov, A.A., Dalimov, D.N., and Aslanov, Kh.A., Alkaloidy i ikh proizvodnye kak instrument dlya izucheniya kholinergicheskoi sistemy (Alkaloids and Their Derivatives as a Tool for Studying the Cholinergic System), Tashkent, 1984.Google Scholar
  17. 17.
    Lukomskaya, N.Ya., Rozengart, E.V., Khovanskikh, A.E., Abduvakhabov, A.A., Zuparova, K.M., Khakimov, Yu.R., and Israilov, D.I., Cholinergic efficacy of anabasine derivatives, Khim.-Farm. Zh., 1990, no.7, pp. 48–50.Google Scholar
  18. 18.
    Rozengart, E.V., Bisalkaloid derivatives of dicarbonic acida based on lupinine, anabasine and cytisine as reversible inhibitors of cholinesterases, Dokl. RAN, 2003, vol. 388, no. 3, pp. 409–412.Google Scholar
  19. 19.
    Rozengart, E.V. and Basova, N.E., Application of bisalkaloid derivatives of dicarbonic acids based on lupinine, anabasine and cytisine as reversible inhibitors of cholinesterase of different origin, Zh. Evol. Biokhim. Fiziol., 2004, vol. 40, pp. 305–310.PubMedGoogle Scholar
  20. 20.
    Kasymov, A.K. and Rozengart, E.V., Cholinesterase hydrolysis of methyl-substituted derivatives of piperidine, Trudy mol. uch.-med. Uzbek. (Proceedings of Young Medical Students of Uzbekistan), 1977, iss. 7, pp. 51–54.Google Scholar
  21. 21.
    Abduvakhabov, A.A., Azlyarova, M.A., Brestkin, A.P., Maizel, E.B., Rozengart, E.V., Sadykov, A.A., and Sadykov, A.S., Iodomethylates of β-(N-morpholine and N-pipecoline)-ethylthioethers of carbonic acids as substrates of cholinesterases, Izv. Akad. Nauk SSSR, Ser. Khim., 1983, no. 11, pp. 2478–2482.Google Scholar
  22. 22.
    Azlyarova, M.A., Abduvakhabov, A.A., and Rozengart, E.V., Synthesis of thioethers of morpholine and pipecoline derivatives and a study of their interaction with cholinesterases, Uzb. Khim. Zh., 1983, no. 2, pp. 56–63.Google Scholar
  23. 23.
    Abduvakhabov, A.A., Kasymov, Sh.K., Aslanov, Kh.A., and Rozengart, E.V., Decahydroquinoline-based substrates of cholinesterases, Uzb. Khim. Zh., 1975, no. 3, pp. 38–41.Google Scholar
  24. 24.
    Zhorov, B.S., Rozengart, E.V., Govyrin, V.A., Khromov-Borisov, N.V., and Brovtsina, N.B., Theoretical conformational analysis of some cholinesterase substrates with cyclic structure of the ammonium grouping, Molek. Biol., 1975, vol. 9, pp. 820–827.Google Scholar
  25. 25.
    Kasymov, Sh.K., Rozengart, E.V., Abduvakhabov, A.A., Aslanov, Kh.A., and Sadykov, A.S., N-(2-acetoxyethyl)morpholine iodomethylate as a specific substrate of cholinesterase, Certificate of Authorship no. 518496 of 27.02.1976, Otkr. Izobr., 1976, no. 23, pp. 496–518.Google Scholar
  26. 26.
    Zuparova, K.M., Khakimov, Yu.R., Israilov, D.I, and Rozengart, E.V., Reversible inhibition of cholinesterases by bisonic derivatives of anabasine and lupinin, Dokl. Akad. Nauk Uzb., 1989, no. 9, pp. 43–45.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • N. E. Basova
    • 1
  • B. N. Kormilitsyn
    • 1
  • A. Yu. Perchenok
    • 1
  • E. V. Rozengart
    • 1
  • V. S. Saakov
    • 1
  • A. A. Suvorov
    • 1
  1. 1.Sechenov Institute of Evolutionary Physiology and BiochemistryRussian Academy of SciencesSt. PetersburgRussia

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