Synthesis of p-tert-butylthiacalix[4]arenes functionalized with tris(2-aminoethyl)amine fragments at the lower rim and their interaction with model lipid membranes

Joshua B. Puplampu,^a Luidmila S. Yakimova,^a Alena A. Vavilova,^a Dzhigangir A. Fayzullin,^b Yuriy F. Zuev,^b and Ivan I. Stoikov^a,b@

^aKazan Federal University, A.M. Butlerov Chemical Institute, 420008 Kazan, Russian Federation

^bKazan Institute of Biochemistry and Biophysics, Russian Academy of Sciences, 420111 Kazan, Russian Federation

^@Corresponding author E-mail: ivan.stoikov@mail.ru

DOI: 10.6060/mhc140489s

Macroheterocycles 2014 7(4) 337-344

New tetrasubstituted derivatives of thiacalix[4]arene functionalized with tris(2-aminoethyl)amine fragments at the lower rim in the cone, partial cone and 1,3-alternate conformations have been synthesized. It has been shown that during the interaction of interaction tris(2-aminoethyl)amine with thiacalix[4]arenes in cone and partial cone conformation, cyclic fragments are formed. The structure with acyclic fragments is obtained in case of the thiacalix[4]arenes in 1,3-alternate conformation. The interaction of these compounds with a biomembrane model system was studied. It has been shown that the interaction of these compounds with model lipid membranes depends not only on the presence of hydrophilic-hydrophobic groups but also on the spatial orientation of these groups.

Keywords: Thiacalix[4]arenes, liposomes, membranes, molecular recognition.

References:

Click here to expand or collapse this section

1. Zhang L., Lee H-K., Pruess T.H., White H.S., Bulaj G.J. Med. Chem. 2009, 52, 1514-1517.
http://dx.doi.org/10.1021/jm801481y

2. Walrant A., Bechara C., Alves I.D., Sagan S. Nanomedicine 2012, 7, 133-143.
http://dx.doi.org/10.2217/nnm.11.165

3. Vive`s E., Brodin P., Lebleu B.A. J. Biol. Chem. 1997, 272, 16010-16017.
http://dx.doi.org/10.1074/jbc.272.25.16010

4. Torchilin V.P., Rammohan R., Weissig V., Levchenko T.S. Proc. Natl Acad. Sci. USA 2001, 98, 8786-8791.
http://dx.doi.org/10.1073/pnas.151247498

5. Pantos A., Tsogas I., Paleos C.M. Biochim. Biophys. Acta, Biomembr. 2008, 1778, 811–823.
http://dx.doi.org/10.1016/j.bbamem.2007.12.003

6. Boon J.M., Lambert T.N., Smith B.D., Beatty A.M., Ugrinova V., Brown S.N. J. Org. Chem. 2002, 67, 2168-2174
http://dx.doi.org/10.1021/jo016416s

7. Albelda M.T. García-Espana E., Jimenez H.R., Llinares J.M., Soriano C., Sornosa-Ten A., Verdejo B. Dalton Trans. 2006, 4474-4481.
http://dx.doi.org/10.1039/b605639c

8. Nakai C., Glinsmann W. Biochemistry 1977, 16, 5636-5641.
http://dx.doi.org/10.1021/bi00644a039

9. Galukhin A.V., Stoikov I.I. Mendeleev Commun. 2014, 24, 82-84.
http://dx.doi.org/10.1016/j.mencom.2014.03.005

10. Andreyko E.A., Padnya P.L., Daminova R.R., Stoikov I.I. RSC Advanced 2014, 4, 3556-3565.
http://dx.doi.org/10.1039/c3ra44052d

11. Galukhin A.V., Shabalin K.V., Antipin I.S., Konovalov A.I., Stoikov I.I. Mendeleev Commun. 2013, 23, 41-43.
http://dx.doi.org/10.1016/j.mencom.2013.01.015

12. Galukhin A.V., Zaikov E.N., Antipin I.S., Konovalov A.I., Stoikov I.I. Macroheterocycles 2012, 5, 266-274.
http://dx.doi.org/10.6060/mhc2012.120781s

13. Mostovaya O.A., Agafonova M.N., Galukhin A.V., Khayrutdinov B.I., Islamov D., Kataeva O.N., Antipin I.S., Konovalov A.I., Stoikov I.I. J. Phys. Org. Chem. 2014, 27, 57-65.
http://dx.doi.org/10.1002/poc.3236

14. Bagnacani V., Sansone F., Donofrio G., Baldini L., Casnati A., Ungaro R. Org. Lett. 2008, 10, 18, 3953-3956.
http://dx.doi.org/10.1021/ol801326d

15. Goun E.A., Pillow T.H., Jones L.R., Rothbard J.B., Wender P.A. ChemBioChem 2006, 7, 1497-1515.
http://dx.doi.org/10.1002/cbic.200600171

16. Nishihara M., Perret F., Takeuchi T. Futaki S., Lazar A.N., Coleman A.W., Sakai N., Matile S. Org. Biomol. Chem. 2005, 3, 1659-1669.
http://dx.doi.org/10.1039/b501472g

17. Asfari Z., Böhmer V., Harrowfield J., Vicens J. Calixarenes 2001. Dordrecht: Kluwer Academic Publishers, 2001. 700 p.

18. Gutsche C.D. Calixarenes. - An Introduction. 2nd Edition. Cambridge: RSC, 2008. 280 p.

19. Iki N., Miyano S. J. Inclusion Phenom. Macrocycl. Chem. 2001, 41, 99-105.
http://dx.doi.org/10.1023/A:1014406709512

20. Lhotak P. Eur. J. Org. Chem. 2004, 71, 1675-1692.
http://dx.doi.org/10.1002/ejoc.200300492

21. Morohashi N., Narumi F., Iki N., Hattori T., Miyano S. Chem. Rev. 2006, 106, 5291-5316.
http://dx.doi.org/10.1021/cr050565j

22. Steed J.W., Atwood J.L. Supramolecular Chemistry. 2nd Edition. Weinheim: John Wiley Hoboken, 2009. 998 p.
http://dx.doi.org/10.1002/9780470740880

23. Atwood J.L., Steed J.W. Organic Nanostructures. Wiley-VCH, Weinheim, 2008. 233 p.
http://dx.doi.org/10.1002/9783527622504

24. Vicens J., Harrowfield J. Calixarenes in the Nanoworld. London: Springer, 2007. 395 p.
http://dx.doi.org/10.1007/978-1-4020-5022-4

25. Gutsche C.D. Calixarenes Revisited. In Monographs in Supramolecular Chemistry. London: RSC, 1998. 233 p.

26. Faizullin D.A., Vylegzhanina N.N., Gnezdilov O.I., Salnikov V.V., Galukhin A.V., Stoikov I.I., Antipin I.S., Zuev Y.F. Appl. Magn. Reson. 2011, 40, 231-243.
http://dx.doi.org/10.1007/s00723-011-0202-z

27. Iki N., Narumi F., Fujimoto T., Morohashi N., Miyano S. J. Chem. Soc., Perkin Trans. 2 1998, 2745-2750.
http://dx.doi.org/10.1039/a803734e

28. Galukhin A.V., Andreyko E.A., Rizvanov I.H., Stoikov I.I. Mendeleev Commun. 2013, 23, 196-198.
http://dx.doi.org/10.1016/j.mencom.2013.07.005

29. Stoikov I.I., Yushkova E.A., Bukharaev A.A., Biziaev D.A., Selivanovskaya S.Yu., Chursina M.A., Antipin I.S., Konovalov A.I., Zharov I. J. Phys. Org. Chem. 2012, 25, 1177-1185.
http://dx.doi.org/10.1002/poc.2981

30. Stoikov I.I., Vavilova A.A., Badaeva R.D., Gorbachuk V.V., Evtugyn V.G., Sitdikov R.R., Yakimova L.S., Zharov I. J. Nanopart. Res. 2013, 15, 1617-1631
http://dx.doi.org/10.1007/s11051-013-1617-2

31. Vavilova A.A., Nosov R.V., Yakimova L.S., Antipin I.S., Stoikov I.I. Macroheterocycles 2013, 6, 219-226.
http://dx.doi.org/10.6060/mhc130748s

32. Vavilova A.A., Nosov R.V., Yagarmina A.N., Mostovaya O.A., Antipin I.S., Konovalov A.I., Stoikov I.I. Macroheterocycles 2012, 5, 396-403.
http://dx.doi.org/10.6060/mhc2012.121105s

33. Chakrabarti A., Chawla H.M., Pant N., Singh S.P., Upreti S. Tetrahedron 2006, 62, 8974-8981.
http://dx.doi.org/10.1016/j.tet.2006.07.016

34. Gaub H., Buschl R., Ringsdorf H., Sackmann E. Chem. Phys.Lipids 1985, 37, 19-43.
http://dx.doi.org/10.1016/0009-3084(85)90072-6

35. Barry J.A., Gawrisch K. Biochemistry 1994, 33, 8082-8088.
http://dx.doi.org/10.1021/bi00192a013

36. Feller S.E., Brown C.A., Gawrisch K. Biophys. J. 2002, 82, 1396-1404.
http://dx.doi.org/10.1016/S0006-3495(02)75494-5

37. Holte L.L., Gawrisch K. Biochemistry 1997, 36, 4669-4674.
http://dx.doi.org/10.1021/bi9626416

38. Rottenberg H. Biochemistry 1992, 31, 9473-9481.
http://dx.doi.org/10.1021/bi00154a021

39. Chiou J.-S., Krishna P.R., Kamaya H., Ueda I. Biochim. Biophys. Acta 1992, 1110, 225-233.
http://dx.doi.org/10.1016/0005-2736(92)90363-Q

40. Schrader T. Nat. Chem. 2012, 4, 519-520.
http://dx.doi.org/10.1038/nchem.1386

41. Zadmard R., Arendt M., Schrader T. J. Am. Chem. Soc. 2004, 126, 7752-7753.
http://dx.doi.org/10.1021/ja049191m

42. Zadmard R., Schrader T. J. Am. Chem. Soc. 2005, 127, 904-915.
http://dx.doi.org/10.1021/ja045785d

43. Costa P.J., Marques I., Félix V. Biochim. Biophys. Acta 2014, 1838, 890-901.

Attachment	Size
mhc140489s.pdf	813.15 KB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Synthesis of p-tert-butylthiacalix[4]arenes functionalized with tris(2-aminoethyl)amine fragments at the lower rim and their interaction with model lipid membranes

References: