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Synthesis of positively charged galactose-bearing surfactants

Abstract

An approach to the synthesis of cationic carbohydrate surfactants with potential antimicrobial and transfecting activities is proposed.

Abbreviations

DDAB:

dioctadecyldimethylammonium bromide

CTAB:

hexadecyltrimethylammonium bromide

DODAC:

dioleoyl dimethylammonium chloride

References

  1. Merianos, J.J., in Disinfection, Sterilization, and Preservation, Block, S.S., Ed., Lea & Febiger, 1922, pp. 225–255.

  2. Cabral, J.P.S., Can. J. Microbiol., 1992, vol. 38, pp. 115–123.

    CAS  Article  PubMed  Google Scholar 

  3. Vieira, D.B. and Carmona-Ribeiro, A.M., J. Antimicrob. Chemother., 2006, vol. 58, pp. 760–767.

    CAS  Article  PubMed  Google Scholar 

  4. Viscardi, G., Quagliotto, P., Barolo, C., Savarino, P., Barni, E., and Fisicaro, E., J. Org. Chem., 2000, vol. 65, pp. 8197–8203.

    CAS  Article  PubMed  Google Scholar 

  5. Bhattacharya, S. and Mandal, S.S., Biochemistry (US), 1998, vol. 37, pp. 7764–7777.

    CAS  Google Scholar 

  6. Li, S. and Thacker, J., Biochem. Biophys. Res. Commun., 1997, vol. 231, pp. 531–534.

    CAS  Article  PubMed  Google Scholar 

  7. Martin, B., Sainlos, M., Aissaoui, A., Oudrhiri, N., Hauchecorne, M., Vigneron, J.-P., Lehn, J.-M., and Lehn, P., Curr. Pharm. Design, 2005, vol. 11, pp. 375–394.

    CAS  Article  Google Scholar 

  8. Pinnaduwage, P., Schmitt, L., and Huang, L., Biochim. Biophys. Acta, 1989, vol. 985, pp. 33–37.

    CAS  Article  PubMed  Google Scholar 

  9. Rose, J.K., Buonocore, L., and Whitt, M.A., BioTechniques, 1991, vol. 10, pp. 520–525.

    CAS  PubMed  Google Scholar 

  10. Ballas, N., Zakai, N., Sela, I., and Loyter, A., Biochim. Biophys. Acta, 1988, vol. 939, pp. 8–18.

    CAS  Article  Google Scholar 

  11. Tabatt, K., Sameti, M., Olbrich, C., Muller, R.H., and Lehr, C.-M., Eur. J. Pharm. Biopharm., 2004, vol. 57, pp. 155–162.

    CAS  Article  PubMed  Google Scholar 

  12. Masotti, A., Mossa, G., Cametti, C., Ortaggi, G., Bianco, A., Del Grosso, N., Malizia, D., and Esposito, C., Colloid. Surface. B, 2009, vol. 68, pp. 136–144.

    CAS  Article  Google Scholar 

  13. Lappalainen, K., Pirila, L., Jaaskelainen, I., Syrjanen, K., and Syrjanen, S., Anticancer Res., 1996, vol. 16, pp. 2485–2489.

    CAS  PubMed  Google Scholar 

  14. Wielbo, D., Shi, N., and Sernia, C., Biochem. Biophys. Res. Commun., 1997, vol. 232, pp. 794–799.

    CAS  Article  PubMed  Google Scholar 

  15. Meyer, O., Kirpotin, D., Hong, K., Sternberg, B., Park, J.W., Woodle, M.C., and Papahadjopoulos, D., J. Biol. Chem., 1998, vol. 273, pp. 15621–15627.

    CAS  Article  PubMed  Google Scholar 

  16. Hu, Q., Shew, C.R., Bally, M.B., and Madden, T.D., Biochim. Biophys. Acta, 2001, vol. 1514, pp. 1–13.

    CAS  Article  PubMed  Google Scholar 

  17. Gaucheron, J., Wong, T., Wong, K.F., Maurer, N., and Cullis, P.R., Bioconjugate Chem., 2002, vol. 13, pp. 671–675.

    CAS  Article  Google Scholar 

  18. Cui, Z. and Mumper, R.J., Bioconjugate Chem., 2002, vol. 13, pp. 1319–1327.

    CAS  Article  Google Scholar 

  19. Shi, N., Zhang, Y., Zhu, C., Boado, R.J., and Pardridge, W.M., Proc. Natl. Acad. Sci. USA, 2001, vol. 98, pp. 12754–12759.

    CAS  Article  PubMed  Google Scholar 

  20. Choosakoonkriang, S., Wiethoff, C.M., Anchordoquy, T.J., Koe, G.S., Smith, J.G., and Middaugh, C.R., J. Biol. Chem., 2001, vol. 276, pp. 8037–8043.

    CAS  Article  PubMed  Google Scholar 

  21. Lobo, B.A., Davis, A., Koe, G., Smith, J.G., and Middaugh, C.R., Arch. Biochem. Biophys., 2001, vol. 386, pp. 95–105.

    CAS  Article  PubMed  Google Scholar 

  22. Kikuchi, I.S. and Carmona-Ribeiro, A.M., J. Phys. Chem. B, 2000, vol. 104, pp. 2829–2835.

    CAS  Article  Google Scholar 

  23. Banerjee, R., Das P.K., Srilakshmi G.V., Chaudhuri A., Rao N.M, J. Med. Chem., 1999, vol. 42, pp. 4292–4299.

    CAS  Article  PubMed  Google Scholar 

  24. Banerjee, R., Mahidhar, Y.V., Chaudhuri, A., Gopal, V., and Rao, N.M., J. Med. Chem., 2001, vol. 44, pp. 4176–4185.

    CAS  Article  PubMed  Google Scholar 

  25. Zhang, H., Ma, Y., and Sun, X.-L., Med. Res. Rev. [Online early access] DOI: 10.1002/med.20171. Published Online: July 22, 2009.

  26. Murao, A., Nishikawa, M., Managit, C., Wong, J., Kawakami, S., Yamashita, F., and Hashida, M., Pharm. Res., 2002, vol. 19, pp. 1808–1814.

    CAS  Article  PubMed  Google Scholar 

  27. Mukthavaram, R., Marepally, S., Venkata, M.Y., Vegi, G.N., Sistla, R., and Chaudhuri, A., Biomaterials, 2009, vol. 30, pp. 2369–2384.

    CAS  Article  PubMed  Google Scholar 

  28. Alshoaibi, Z.Ya., Morozova, N.G., and Serebrennikova, G.A., Bioorg. Khim., 2000, vol. 26, pp. 703–706 [Russ. J. Bioorg. Chem. (Eng. Transl.), 2000, vol. 26, pp. 633–636].

    Google Scholar 

  29. Alshoaibi, Z.Ya., Andryushina, T.Yu., Morozova, N.G., and Serebrennikova, G.A., Bioorg. Khim., 2003, vol. 29, pp. 323–325 [Russ. J. Bioorg. Chem. (Eng. Transl.), 2003, vol. 29, pp. 293–295].

    Google Scholar 

  30. Quagliotto, P., Viscardi, G., Barolo, C., D’Angelo, D., Barni, E., Compari, C., Duce, E., and Fisicaro, E., J. Org. Chem., 2005, vol. 70, pp. 9857–9866.

    CAS  Article  PubMed  Google Scholar 

  31. Fukuyama, T., Jow, C.-K., and Cheung, M., Tetrahedron Lett., 1995, vol. 36, pp. 6373–6374.

    CAS  Article  Google Scholar 

  32. Fukuyama, T., Cheung, M., Jow, C.-K., Hidai, Y., and Kan, T., Tetrahedron Lett., 1997, vol. 38, pp. 5831–5834.

    CAS  Article  Google Scholar 

  33. Tolkach, A.M., Polonik, S.G., and Uvarova, N.I., USSR Inventor’s Certificate no. 1428755, Byull. Izobret., 1988, no. 37.

  34. Morozova, N.G., Peredkova, E.V., and Serebrennikova, G.A., Bioorg. Khim., 1996, vol. 22, pp. 799–803 [Russ. J. Bioorg. Chem. (Eng. Transl.), 1996, vol. 22, pp. 675–678].

    CAS  PubMed  Google Scholar 

  35. Kritchevsky, D. and Kirk, M.R., Arch. Biochem. Biophys., 1952, vol. 35, pp. 346–351.

    CAS  Article  Google Scholar 

  36. Dawson, R., Elliott, D., Elliott, W., and Jones, K., Data for Biochemical Research, Oxford: Clarendon, 1986.

    Google Scholar 

  37. Dahmen, J., Frejd, T., Magnusson, G., and Noori, G., Carbohyd. Res., 1982, vol. 111, pp. C1–C4.

    CAS  Article  Google Scholar 

  38. Hudson, C.S. and Johnson, J.M., J. Am. Chem. Soc., 1915, vol. 37, pp. 1270–1275.

    CAS  Article  Google Scholar 

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Correspondence to N. G. Morozova.

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Original Russian Text © N.G. Morozova, M.A. Maslov, V.V. Myagchenkov, G.A. Serebrennikova, 2010, published in Bioorganicheskaya Khimiya, 2010, Vol. 36, No. 5, pp. 714–720.

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Morozova, N.G., Maslov, M.A., Myagchenkov, V.V. et al. Synthesis of positively charged galactose-bearing surfactants. Russ J Bioorg Chem 36, 657–662 (2010). https://doi.org/10.1134/S1068162010050146

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  • DOI: https://doi.org/10.1134/S1068162010050146

Key words

  • antimicrobial activity
  • cationic surfactants
  • galactose
  • Fukuyama reaction
  • transfection