The antimicrobial and antiviral activity of calixarenes

Authors

  • R. V. Rodik Institute of Organic Chemistry of the NAS of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.15.830

Keywords:

calixarene, bactericidal activity, antiviral activity, fungicidal activity, antituberculosis activity

Abstract

Calixarenes is a promising class of macrocyclic compounds, which are widely used in the design of biologically active substances. Among calixarenes there are anion channel blockers and modulators of cationic pumps, selective enzyme inhibitors and compounds simulating their action, substances with the antithrombotic and antitumour effect. The antimicrobial and antiviral activities of modified calixarenes have been intensively studied in recent years. The results on bactericidal, fungicidal, antituberculosis, as well as antiviral activity of calixarenes have been systematized and analyzed in this review. The data about the mechanisms of action of different types of calixarenes on biological objects are presented. It has been found that the basis of the antimicrobial action of many calixarenes is the interaction with the components of the outer membrane or cell wall. Moreover, functionalization of the calixarene platform with pharmacophoric groups possessing the antimicrobial activity does not always lead to increase in the expected activity. Polycationic calixarenes show the highest antibacterial action, while polyanionic macrocycles inhibit the activity of viruses. Calixarenes modified with cyclopeptide fragments are selective binders and blockers of important bacterial cell glycoproteins. They are mimetics of vancomycin by their mechanism of action and the level of the bactericidal activity. The water soluble calixarene with polyethylene glycol groups has a unique mechanism of the antituberculosis action. It inhibits the growth of M. tuberculosis inside human macrophage cells. The chemotherapeutic indexes of the compounds studied are more than ten units, indicating their low cytotoxicity.

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References

  1. http://www.who.int/drugresistance/documents/surveillancereport/en/
  2. Leeds J. A., Schmitt E. K., Krastel P. Expert Opin. Investig. Drugs, 2006, Vol. 15, pp.211-226.
  3. Parisien A., Allain B., Zhang J., Mandeville R., Lan C. Q. J. Appl. Microbiol., 2007, Vol. 104, pp.1-13.
  4. Zhou M., Luo H., Li Z., Wu F., Huang C., Ding Z., Li R. Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, pp.306-315.
  5. Blondelle S. E., Houghten R. A. Tibtech.1996, Vol. 14, pp.60-65.
  6. Draggers E. M., Hale S. P., Lee J., Terrett N. Nature, 2008, Vol. 7, pp.608-624.
  7. Gutsche D. Calixarenes: Synthesis and Historical Perspectives in: Encyclopedia of Supramolecular Chemistry. M. Dekker, 2004, pp.153-160.
  8. Böhmer V. Angew. Chem. Int. Ed. Engl., 1995, Vol. 34, pp.713-745.
  9. Calixarenes for Separations. Lumetta G. J., Rogers R. D., Gopalan A. S. et al. American Chemical Society, Washington 2000, 366 p.
  10. Balasahe S., Nimsea T. Kim Chem. Soc. Rev., 2013, Vol. 42, pp.366-386.
  11. Rodik R. V., Boyko V. I., Kalchenko V. I. Curr. Med. Chem., 2009, Vol. 16, pp.1630-1643.
  12. de Fatima A., Fernandes S. A., Sabino A. A. Curr. Drug Disc. Tech., 2009, Vol. 6, pp.151-170.
  13. Helttunen K., Moridi N., Shahgaldian P. Nissinen M. Org. Biomol. Chem., 2012, Vol. 10, pp.2019-2025.
  14. Casnati A., Fabbi M., Pelizzi N., Pochini A., Francgesco S., Ungaro R., di Modugno E., Tarzia G. Bioorg. Med. Chem. Lett., 1996, Vol. 6, pp.2699-2704.
  15. Casnati A., Sansone F., Ungaro R. Acc. Chem. Res. 2003, Vol. 36, pp.246-254.
  16. Frish L., Sanson F., Casnati A., Ungaro R., Cohen Y. J. Org. Chem., 2000, Vol. 65, pp.5026-5030.
  17. Sansone F., Baldini L., Casnati A., Lazzarotto M., Ugozzoli F., Ungaro R. PNAS, 2002, Vol. 49, pp.4842-4847.
  18. Dibama H. M., Clarot I., Fontanay S., Salem A. B., Mourer M., Finance C., Duval R. E., Regnouf-de-Vains J.-B. Bioorg. Med. Chem. Lett., 2009, Vol. 19, pp.2679-2682.
  19. Ben Salem A., Regnouf-de-Vains J.-B. Tetrahedron Lett., 2001, Vol. 42, pp.7033-7036.
  20. Ben Salem A., Regnouf-de-Vains J.-B. Tetrahedron Lett., 2003, Vol. 44, pp.6769-6771.
  21. Korchowiec B., Ben Salem A., Corvis Y., Regnouf de Vains J.-B., Korchowiec J., Rogalska E. J. Phys. Chem. B, 2007, Vol. 111, pp.13231-13242.
  22. Ben Salem A., Sautrey G., Fontanay S., Duval R. E., Regnouf-de-Vains J.-B. Bioorg. Med. Chem. 2011, Vol. 19, pp.7534-7540.
  23. Mourer M., Fontanay S., Duval R. E., Regnouf-de-Vains J.-B. Helv. Chim. Acta 2012, Vol. 95, pp.1373-1386.
  24. Grare M., Mourer M., Fontanay S., Regnouf-de-Vains J.-B., Finance C., Duval R. E. J. Antimicrob. Chemother., 2007, Vol. 60, pp.575-581.
  25. Grare M., Mourer M., Regnouf de Vains J.-B., Finance C., Duval R.-E. Pat. Biol., 2006, Vol. 54, pp.470-476.
  26. Sautrey G., Orlof M., Korchowiec B., Regnouf-de-Vains J.-B., Rogalska E. J. Phys. Chem. B., 2011, Vol. 115, pp.15002-15012.
  27. Formosa C., Grare M., Jauvert E., Coutable A., Regnouf-de-Vains J.-B., Mourer M., Duval R., Dague E. Sci. Rep., 2012, Vol. 2, p.575.
  28. Grare M., Massimba H., Dibama H. M., Lafosse S., Ribon A., Mourer M., Finance C., Regnouf-de-Vains J.-B., Duval R. E. Clin. Microbiol. Infect., 2010, Vol. 16, pp.432-438.
  29. Mourer M., Dibama H. M., Fontanay S., Grare M., Duval R. E., Finance C., Regnouf-de-Vains J.-B. Bioorg. Med. Chem., 2009, Vol. 17, pp.5496-5509.
  30. de Namor A. F. D., Cleverley R. M., Zapata-Ormachea M. L. Chem. Rev. 1998, Vol. 98, pp.2495-2525.
  31. Soomro A. M., Oad R. K., Memon S., Qureshi I. Pak. J. Anal. Environ. Chem., 2012, Vol. 13, No.1, pp.36-39.
  32. Melezhyk I. O., Rodik R. V., Iavorska N. V., Klymchenko A. S., Mely Y., Shepelevych V. V., Skivka L. M., Kalchenko V. I. Anti-Infective Agents, 2014, in press.
  33. Birnie C. R., Malamud D., Schnaare R. L. Antimicrob. Agents Chemother., 2000, Vol. 44, pp. 2514-2517.
  34. Mecca Т., Cunsolo F. Tetrahedron 2007, Vol. 63, pp.10764-10767.
  35. Jain M. K., Jahagirdar D. V. Biochem. J. (Great Britain), 1985, Vol. 227, pp.789-794.
  36. Hart P. D., Armstrong J. A., Brodaty E. Infect. and Immun., 1996, Vol. 64, pp.1491-1493.
  37. Hart P. D. Science, 1968, Vol. 162, pp.686-689.
  38. Colston M. J., Hailes H. C., Stavropoulos E., Herve A. C., Herve G., Goodworth K. J., Hill A. M., Jenner P., Hart P. D., Tascon R. E. Infect. and Immun., 2004, Vol. 72, pp.6318-6323.
  39. Mourer M., Dibama H. M., Constant P., Daffé M., Regnouf-de-Vains J.-B. Bioorg. Med. Chem., 2012, Vol. 20, pp.2035-2041.
  40. Psychogio N., Regnouf-de-Vains J.-B. Tetrahedron Lett., 2002, Vol. 43, pp.7691-7693.
  41. Lamartine R., Tsukada M., Wilson D., Shirata A. C. R. Chimie, 2002, Vol. 5, pp.163-169.
  42. Saberov V. S., Marichev K. O., Korotkikh M. I., Shvaika O. P., Rodik R. V., Drapailo А. B., Pekhtereva T. M., Komarovska-Porokhnyavets O. Z., Lubenets V. I., Novikov V. P. J. of Organic and Pharmaceutical Chemistry, 2014, Vol. 12, No.2, pp.36-43.
  43. Paquet V., Zumbuehl A., Carreira E. M. Bioconjugate Chem., 2006, Vol. 17, pp.1460-1463.
  44. Hwang K. M., Qi Y. M., Liu S.-Y. U. S. Patent US5312837, 1994.
  45. Hwang K. M., Qi Y. M., Liu S.-Y. U. S. Patent US5196452 1993.
  46. Hwang K. M., Qi Y. M., Liu S. Y., Choy W., Chen J. WO Patent 9403164, 1994.
  47. Takeshi Y., Kazuhiro F., Makiko O. Patent of Japan JP10203906A2, 1998.
  48. Coveney D., Costello B. U. S. Patent 2005113454, 2005, EU Patent EP1367044, 2003.
  49. Harris S. J. WO Patent 0244121, 2002.
  50. Harris S. J. WO9519974A2, 1995.
  51. Tsou L. K., Dutschman G. E. Gullen E. A., Telpoukhovskai M., Cheng Y. C., Hamilton A. D. Bioorg. Med. Chem. Lett., 2010, Vol. 20, pp.2137-2139.
  52. Motornaya A. E., Alimbarova L. M., Shokova E. A., Kovalev V. V. Pharmaceutical Chemistry Journal (Russian), 2006. Vol. 40, pp.68-72.
  53. Mourer M., Psychogios N., Laumond G., Aubertin A.-M., Regnouf-de-Vains J.-B. Bioorg. Med. Chem., 2010, Vol. 18, pp.36-45.
  54. Kral V., Cigler P., Konvalinka J., Kozisek M., Prejdova J., Gruener B., Plesek J., Lepsik M., Pokorna J., Kraeusslich H.-G. Bodem J. WO Patent 2005073240, 2005.

Published

2015-03-12

How to Cite

(1)
Rodik, R. V. The Antimicrobial and Antiviral Activity of Calixarenes. J. Org. Pharm. Chem. 2015, 13, 67-78.

Issue

Section

Original Researches