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Composition on the basis of phosphonoacetic acid. Synthesis and antiviral activity

  • Supplement: Rossiiskii Khimicheskii Zhurnal–Zhurnal Rossiiskogo Khimicheskogo Obshchestva im. D.I. Mendeleeva (Russian Chemistry Journal)
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Abstract

A manufacturable technology for the production of an antiviral composition containing phosphonoacetic acid, involing РН-alkylation of dimethyl phosphite with methyl chloroacetate under phase-transfer conditions and subsequent in situ hydrolysis of the intermediate product, was developed. The composition showed expressed antiviral effect against herpesviral infections caused by herpes simplex virus 1 and 2 and cytomegalovirus. The composition in the effective concentration range was found to exhibit no cytotoxic effect on VERO green monkey kidney and М-19 human diploid cell cultures. The resulting data suggest potential uses of the composition as an antiviral agent in practical medicine and as an antiviral additive to synthetic detergents for sanitation in health care and food production facilities.

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References

  1. Gerpesvirusnye infektsii cheloveka: rukovodstvo dlya vrachei (Herpesviral Infections: Manual for Doctors), Isakov, V.A., tEd., St. Petersburg: Spetsial’naya Literatura, 2013.

  2. Bacon, T.N., Levin, M.J., Leary, J.J., Sarisky, R.T., and Sutton, D., Clin. Microbiol. Rev., 2003, vol. 16, no. 1, pp. 114–128.

    Google Scholar 

  3. Kleymann, G., Expert Opinion on Investigational Drugs, 2005, vol. 14, no. 2, p. 135–161.

    Article  CAS  Google Scholar 

  4. Neyts, J., Snoeck, R., Schols, D., Himpens, B., and De Clercq, E., J. Virol. Methods., 1991, vol. 35, pp. 27–38.

    Google Scholar 

  5. Smith, J.S. and Robinson, N.J., J. Infectious Diseases, 2002, Expert Opin. Investig. Drugs, vol. 186, no. 1, pp. S3–S28.

    Article  Google Scholar 

  6. Guimarães, M.A., Tibana, A., Nunes, M.P., and Netto dos Santos, K.R., Braz. J. Microbiol., 2000, vol. 31, pp. 193–199.

    Article  Google Scholar 

  7. Kim, H., Ryu, J.-H., and Beuchat, L.R., Appl. Environ. Microbiol., 2007, vol. 73, no. 4, pp. 1256–1265.

    Article  CAS  Google Scholar 

  8. Kozlov, R.S., Klin. Mikrobiol. Antimikrob. Khimioter., 2000, vol. 2, no. 1, pp. 16–30.

    Google Scholar 

  9. Shipkowitz, N.L., Bower, R.N., Appell, R., Nordeen, C., Overby, L., Roderich, W., Schleicher, J.B., and von Esch, A., Appl. Microbiol., 1973, vol. 26, pp. 264–267.

    CAS  Google Scholar 

  10. Nylen, P., Chem. Ber., 1924, vol. 57, no. 6, pp. 1023–1038.

    Article  Google Scholar 

  11. Overby, L., Robishaw, E.E., Schleicher, J.B., Reuter, A., Shipkowitz, N.L, and Mao, J.C.-H., Antimicrob. Agents Chemother., 1974, vol. 6, pp. 360–365.

    Article  CAS  Google Scholar 

  12. Huang, E.-S., J. Virol., 1975, vol. 16, pp. 1560–1565.

    CAS  Google Scholar 

  13. Herrin, Th.R., Fairgrieve, J.S., Bower, R.R., Shipkowitz, N.L., and Mao, J.C.-H., J. Med. Chem., 1977, vol. 20, no. 5, pp. 660–663.

    Article  CAS  Google Scholar 

  14. Erikson, B., Oberg, B., and Wahren, G., BBA-Gene Struct. Expr., 1982, vol. 696, pp. 115–123.

    Article  Google Scholar 

  15. Mao, J. C.-H., Otis, E.R., von Esch, A.M., Herrin, T.R., and Fairgrieve, J.S., Antimicrob. Agents Chemother., 1985, vol. 27, no. 2, pp. 197–202.

    Article  CAS  Google Scholar 

  16. Lambert, R.W., Martin, J.A., Thomas, G.J., Duncan, I.B., Hall, M.J., and Heimer, E.P., J. Med. Chem., 1989, vol. 32, no. 2, pp. 367–374.

    Article  CAS  Google Scholar 

  17. Manfredini, S., Solaroli, N., Angusti, A., Nalin, F., and Durini, E., Antivir. Chem. Chemother., 2003, vol. 14, no. 4, pp. 183–194.

    Article  CAS  Google Scholar 

  18. Bondarenko, N.A., Kharlamov, A.V., and Artyushin, O.I., Innovats. Tekhnol., 2013, vol. 14, no. 3, pp. 11–15.

    Google Scholar 

  19. Malevannaya, R.A., Tsvetkov, E.N., and Kabachnik, M.I., Zh. Obshch. Khim., 1971, vol. 41, no. 7, pp. 1426–1434.

    CAS  Google Scholar 

  20. Chen, R. and Breuer, E., Heteroatom Chem., 2003, vol. 14, no. 1, pp. 67–71.

    Article  CAS  Google Scholar 

  21. Rukovodstvo po eksperimental’nomu (doklinicheskomu) izucheniyu novykh farmakologicheskikh veshchestv [Guidelines on Experimental (Preclinical) Testing of New Pharmacolog ical Substances], Khabriev, R.Yu., Ed., Moscow: Meditsina, 2005, 2 ed., pp. 547-549.

  22. Cotarelo, M., Catalan, P., Sanchez-Carrillo, C., Menasalvas, A., and Cercenado, E., J. Antimicrob. Chemother., 1999, vol. 44, pp. 705–708.

    Article  CAS  Google Scholar 

  23. De Clerg, E., Descamhs, J., Verhelst, G., Walker, R.T., Jones, A.S., Torrence, P.F., and Shugar, D., J Inf. Dis., 1980, vol. 141, no. 5, pp. 563–574.

    Article  Google Scholar 

  24. Kruppenbacher, J.P., Klass, R., and Eggers, H.J., Antiviral Res., 1994, vol. 23, pp. 11–22.

    Google Scholar 

  25. Tsvetkov, E.N. and Kharitonov, A.N., Zh. Obshch. Khim., 1985, vol. 55, no. 11, pp. 2481–2483.

    CAS  Google Scholar 

  26. Bondarenko, N.A., Rudomino, M.V., and Tsvetkov, E.N., Russ. Chem. Bull., 1990, vol. 39, no. 9, p. 1989.

    Article  Google Scholar 

  27. Bondarenko, N.A., Kharlamov, A.V., and Vendilo A.G., Russ. Chem. Bull., 2009, vol. 58, no. 9, pp. 1872–1885.

    Article  Google Scholar 

  28. Hutchinson, D.W., Cload, P.A., and Haugh, M.C., Phosph. Sulfur, Silicon Relat. Elem., 1983, vol. 14, no. 3, pp. 285–294.

    Article  CAS  Google Scholar 

  29. Noren, J.O., Helgstrand, E., Johansson, G., Misiorny, A., and Stening, G., J. Med. Chem., 1983, vol. 26, no. 2, pp. 264–270.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Ivanovskii Research Institute of Virology, ul. Gamalei 16, Moscow, 123098, Russia

    L. M. Alimbarova & I. F. Barinskii

  2. State Research Institute of Chemical Reagents and Special Purity Chemical Substances (IREA), ul. Bogorodskii val 3, Moscow, 107076, Russia

    A. V. Kharlamov & N. A. Bondarenko

Authors
  1. L. M. Alimbarova
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  2. A. V. Kharlamov
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  3. N. A. Bondarenko
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  4. I. F. Barinskii
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Correspondence to A. V. Kharlamov.

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Original Russian Text © L.M. Alimbarova, A.V. Kharlamov, N.A. Bondarenko, I.F. Barinskii, 2014, published in Rossiiskii Khimicheskii Zhurnal, 2014, Vol. 58, No. 1, pp. 23–30.

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Alimbarova, L.M., Kharlamov, A.V., Bondarenko, N.A. et al. Composition on the basis of phosphonoacetic acid. Synthesis and antiviral activity. Russ J Gen Chem 85, 2441–2448 (2015). https://doi.org/10.1134/S1070363215100394

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  • DOI: https://doi.org/10.1134/S1070363215100394

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