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Influence of Nature of Functional Groups on Interaction of Tetrasubstituted at Lower Rim p-tert-Butyl Thiacalix[4]arenes in 1,3-Alternate Configuration with Model Lipid Membranes

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Abstract

The influence of p-tert-butyl thiacalix[4]arenes (1,3-alternate) functionalized by N-propyl morpholine, N,N-dipropyliden-amine and aminodiacetate fragments on dynamic structure of liposomal membranes prepared from dipalmitoyl phosphatidylcholine was investigated by means of electron spin resonance spin-probe technique and Fourier transform infrared spectroscopy. Nuclear magnetic resonance and transmission electron microscopy techniques were applied to characterize the interacting systems. The obtained results have shown that all studied calixarenes interact with polar domains of bilayer. Depending on functional groups and hydrophobic/hydrophilic properties of calixarenes they can dip into bilayer, locate close to the surface of bilayer or form bridges between positively charged groups of adjacent lipid molecules, thus assisting to disordering or putting in order the lipid molecules.

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References

  1. A. Casnati, F. Sansone, R. Ungaro, Acc. Chem. Res. 36, 246 (2003)

    Article  Google Scholar 

  2. J.M. Boon, D.D. Smith, Curr. Opin. Chem Biol. 6, 749 (2002)

    Article  Google Scholar 

  3. L.H. Hartwell, P. Szankasi, C.J. Robert, A.W. Murray, S.H. Friend, Science 278, 1064 (1997)

    Article  ADS  Google Scholar 

  4. M.A. Mintzer, E.E. Simanek, Chem. Rev. 109, 259 (2009)

    Article  Google Scholar 

  5. C.D. Gutsche, Calixarene Revisited: Monographs in Supramolecular Chemistry (Royal Society of Chemistry, Cambridge, 1998)

  6. L. Mandolini, R. Ungaro, Calixarenes in Action (Imperial College Press, London, 2000)

  7. D. Diamond, K. Nolan, Anal. Chem. 73, 22A (2001)

    Article  Google Scholar 

  8. B. Korchowiec, A. Ben Salem, Y. Corvis, J.-B. Regnouf de Vains, J. Korchowiec, E. Rogalska, J. Phys. Chem. B 111, 13231 (2007)

    Article  Google Scholar 

  9. N. Iki, S. Miyano, J. Incl. Phenom. Macromol. Chem. 41, 99 (2001)

    Article  Google Scholar 

  10. E.A. Shokova, V.V. Kovalev, Russ. J. Org. Chem. 39, 1 (2003)

    Article  Google Scholar 

  11. P. Lhotak, Eur. J. Org. Chem. 2004, 1675 (2004)

    Article  Google Scholar 

  12. N. Morohashi, F. Narumi, N. Iki, T. Hattori, S. Miyano, Chem. Rev. 106, 5291 (2006)

    Article  Google Scholar 

  13. T. Sone, Y. Ohba, K. Moriya, H. Kumada, K. Ito, Tetrahedron 53, 10689 (1997)

    Article  Google Scholar 

  14. H. Kumagai, M. Hagesawa, S. Miyanari, Y. Sugawa, Y. Sato, T. Hori, S. Ueda, H. Kamiyama, S. Miyano, Tetrahedron Lett. 38, 3971 (1997)

    Article  Google Scholar 

  15. N. Kon, N. Iki, S. Miyano, Tetrahedron Lett. 43, 2231 (2002)

    Article  Google Scholar 

  16. N. Kon, N. Iki, Y. Yamane, S. Shirasaki, S. Miyano, Tetrahedron Lett. 45, 207 (2004)

    Article  Google Scholar 

  17. N. Iki, C. Kabuto, T. Fukushima, H. Kumagai, H. Takeya, S. Miyanari, T. Miyashi, S. Miyano, Tetrahedron 56, 1437 (2000)

    Article  Google Scholar 

  18. S. Shokova, V. Tafeenko, V. Kovalev, Tetrahedron Lett. 43, 5153 (2002)

    Article  Google Scholar 

  19. P. Lhotak, T. Smejkal, I. Stibor, J. Havlicek, M. Tkadlecova, H. Petrıckova, Tetrahedron Lett. 44, 8093 (2003)

    Article  Google Scholar 

  20. I.I. Stoikov, A.V. Galukhin, E.N. Zaikov, I.S. Antipin, Mendeleev Commun. 19, 193 (2009)

    Article  Google Scholar 

  21. M.A. Bahri, A. Seret, P. Hans, J. Piette, G. Deby-Dupont, M. Hoebeke, Biophys. Chem. 129, 82 (2007)

    Google Scholar 

  22. M.A. Hayat, S.E. Miller, Negative Staining (McGraw-Hill Publishing, New York, 1990)

    Google Scholar 

  23. V.D. Fedotov, N.N. Vylegzhanina, A.E. Altshuler, V.I. Shlenkin, Yu.F. Zuev, N. Garti, Appl. Magn. Reson. 14, 497 (1998)

    Article  Google Scholar 

  24. Yu.F. Zuev, N.N. Vylegzhanina, N.L. Zakhartchenko, Appl. Magn. Reson. 25, 29 (2003)

    Article  Google Scholar 

  25. W.L. Hubbell, H.M. McConnell, J. Am. Chem. Soc. 93, 314 (1971)

    Article  Google Scholar 

  26. A.M. Vasserman, Uspekhi Khimii 63, 391 (1994)

    Google Scholar 

  27. J.H. Freed, in Spin Labeling. Theory and Application, ed. by L.J. Berliner, chapt. 3 (Academic Press, New York, 1976)

  28. H.M. McConnell, in Spin Labeling. Theory and Application, ed. by L.J. Berliner, chapt. 13 (Academic Press, New York, 1976)

  29. A.M. Vasserman, Yu.A. Zakharova, M.V. Otdel’nova, I.I. Aliev, M.V. Motyakin, Colloid. J. 68, 679 (2006)

    Article  Google Scholar 

  30. R.N.A.H. Lewis, R.N. McElhaney, in Methods in Membrane Lipids, ed. by A. Dopico, chapt. 12 (Springer, Berlin 2007)

  31. R. Koynova, M. Caffrey, Biochim. Biophys. Acta 1376, 91 (1998)

    Google Scholar 

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Acknowledgments

The financial support from the Federal Program “Research and Pedagogical Cadre for Innovative Russia” in years 2009–2013 (nr. p1107 on 26 August 2009), program of the Russian Foundation for Basic Research (grant nr. 09-03-00426-a), program of the Russian Federation President grants for the state support of young Russian scientists - doctor of sciences (grant nr. MD-2747.2010.3) is gratefully acknowledged.

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Correspondence to Yu. F. Zuev.

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Fayzullin, D.A., Vylegzhanina, N.N., Gnezdilov, O.I. et al. Influence of Nature of Functional Groups on Interaction of Tetrasubstituted at Lower Rim p-tert-Butyl Thiacalix[4]arenes in 1,3-Alternate Configuration with Model Lipid Membranes. Appl Magn Reson 40, 231–243 (2011). https://doi.org/10.1007/s00723-011-0202-z

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  • DOI: https://doi.org/10.1007/s00723-011-0202-z

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