Supramolecular systems based on calix[4]resorcine with mono-, di-, and tetracationic surfactants: Synergetic structural and solubilization behavior

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 448, Issue 1, 2014, Pages 67-72

  Pashirova, Tatiana N ^a   Ziganshina, Albina Yu ^a   Sultanova, Elza D ^a   Lukashenko, Svetlana S ^a   Kudryashova, Yuliana R ^a   Zhiltsova, Elena P ^a   Zakharova, Lucia Ya ^a   Konovalov, Alexander I ^a  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

1,4 Diazabicyclo 2.2.2 octane; Amphiphile; Calix 4 resorcine; Cationic surfactant; Critical association concentration; Self assembly

Indexed keywords

AMPHIPHILES; BIOPHYSICS; CATIONIC SURFACTANTS; DYES; SELF ASSEMBLY; SOLUBILITY; SUPRAMOLECULAR CHEMISTRY;

1 ,4-DIAZABICYCLO[2.2.2]OCTANE; CALIX[4]RESORCINE; CRITICAL ASSOCIATION CONCENTRATIONS; DYE SOLUBILIZATION; PHYSICOCHEMICAL METHODS; SOLUBILIZATION BEHAVIOR; SULFONATE GROUPS; SUPRAMOLECULAR SYSTEMS;

AGGREGATES;

1,4 DIAZABICYCLO[2.2.2]OCTANE; CALIX[4]RESORCINE; DYE; DYE SUDAN; IONIC SURFACTANT; RESORCINOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONDUCTOMETRY; HYDROPHOBICITY; LIGHT SCATTERING; MEASUREMENT; MORPHOLOGY; PHYSICOCHEMICAL MODEL; PRIORITY JOURNAL; SOLUBILIZATION; SUPRAMOLECULAR CHEMISTRY; SURFACE TENSION; SURFACE TENSION MEASUREMENT; ZETA POTENTIAL;

EID: 84896794128     PISSN: 09277757     EISSN: 18734359     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2014.02.012     Document Type: Article

References (56)

1. Sun T., Shen J., Yan H., Hao J., Hao A. Stable vesicles assembled by "supramolecular amphiphiles" with double hydrophobic chains. Colloid. Surf. A 2012, 414:41-49.
2. Zhu L., Han Y., Tian M., Wang Y. Complex formation and aggregate transitions of sodium dodecyl sulfate with an oligomeric connecting molecule in aqueous solution. Langmuir 2013, 29:12084-12092.
3. Kharlamov S.V., Kashapov R.R., Pashirova T.N., Zhiltsova E.P., Lukashenko S.S., Ziganshina A.Yu., Gubaidullin A.T., Zakharova L.Ya., Gruner M., Habicher W.D., Konovalov A.I. Supramolecular amphiphile based on calix[4]resorcinarene and cationic surfactant for controlled self-assembly. J. Phys. Chem. s 2013, 117:20280-20288.
4. Zhang X., Wang C. Supramolecular amphiphiles. Chem. Soc. Rev. 2011, 40:94-101.
5. α-side chains in Tris buffer (pH 9.3). Colloid. Surf. A 2013, 420:10-21.
6. Li J., Jiang H., Hu W., Zou G., Zhang Q. Morphology modulation in an azobenzene based supramolecular amphiphiles system. J. Photochem. Photobiol. A 2012, 245:28-32.
7. Wang C., Yin S., Chen S., Xu H., Wang Z., Zhang X. Controlled self-assembly manipulated by charge-transfer interactions: from tubes to vesicles. Angew. Chem. Int. Ed. 2008, 47:9049-9052.
8. Wang K., Guo D., Liu Y. Temperature-controlled supramolecular vesicles modulated by p-sulfonatocalix[5]arene with pyrene. Chem. Eur. J. 2010, 16:8006-8011.
9. Li Q., Chen X., Yue X., Huang D., Wang X. Construction and transformation of stimuli-responsive vesicles from the ferrocene derivative supramolecular amphiphiles. Colloid. Surf. A 2012, 409:98-104.
10. Wang Y., Ma N., Wang Z., Zhang X. Photocontrolled reversible supramolecular assemblies of an azobenzene-containing surfactant with alpha-cyclodextrin. Angew. Chem. Int. Ed. 2007, 46:2823-2826.
11. Xing Y., Wang C., Han P., Wang Z., Zhang X. Acetylcholinesterase responsive polymeric supra-amphiphiles for controlled self-assembly and disassembly. Langmuir 2012, 28:6032-6036.
12. Sun T., Ma M., Yan H., Shen J., Su J., Hao A. Vesicular particles directly assembled from the cyclodextrin/UR-144 supramolecular amphiphiles. Colloid. Surf. A 2013, 424:105-112.
13. Zhang J., Ma P.X. Cyclodextrin-based supramolecular systems for drug delivery. Adv. Drug Deliver. Rev. 2013, 65:1215-1233.
14. Sharma R., Mahajan S., Mahajan R.K. Physicochemical studies of morpholinium based ionic liquid crystals and their interaction with cyclodextrins. Fluid Phase Equilib. 2014, 361:104-115.
15. Uzunova V.D., Cullinane C., Brix K., Nau W.M., Day A.I. Toxicity of cucurbit[7]uril and cucurbit[8]uril: an exploratory in vitro and in vivo study. Org. Biomol. Chem. 2010, 8:2037-2042.
16. Ko Y.H., Kim E., Hwang I., Kim K. Supramolecular assemblies built with host-stabilized charge-transfer interactions. Chem. Commun. 2007, 1305-1315.
17. Wang K., Guo D., Wang X., Liu Y. Multistimuli responsive supramolecular vesicles based on the recognition of p-sulfonatocalixarene and its controllable release of doxorubicin. ASC Nano 2011, 5:2880-2894.
18. Bize C., Garrigues J., Blanzat M., Rico-Lattes I., Bistri O., Colasson B., Reinaud O. Spontaneous vesicles formation of a catanionic association involving a head and tail functionalized amino-calix[6]arene. Chem. Commun. 2010, 46:586-588.
19. Oshima T., Oishi K., Ohto K., Inoue K. Extraction of catecholamines by calixarene carboxylic acid derivatives. J. Inclusion Phenom. Macrocyclic Chem. 2006, 55:79-85.
20. Uhlenheuer D.A., Petkau K., Brunsveld L. Combining supramolecular chemistry with biology. Chem. Soc. Rev. 2010, 39:2817-2826.
21. Arantes L.M., Scarelli C., Marsaioli A.J., Paula E., Fernandes S.A. Proparacaine complexation with β-cyclodextrin and p-sulfonic acid calix[6]arene, as evaluated by varied 1 H-NMR approaches. Magn. Reson. Chem. 2009, 47:757-763.
22. Tsou L.K., Dutschman G.E., Gullen E.A., Telpoukhovskaia M., Cheng Y., Hamilton A.D. Discovery of a synthetic dual inhibitor of HIV and HCV infection based on a tetrabutoxy-calix[4]arene scaffold. Bioorg. Med. Chem. Lett. 2010, 20:2137-2139.
23. Mourer M., Psychogios N., Laumond G., Aubertin A., Regnouf-de-Vains J. Synthesis and anti-HIV evaluation of water-soluble calixarene-based bithiazolyl podands. Bioorg. Med. Chem. 2010, 18:36-45.
24. Perret F., Lazar A.N., Coleman A.W. Biochemistry of anionic calix[n]arenes. Chem. Commun. 2011, 47:7303-7319.
25. Beshara C.S., Jones C.E., Daze K.D., Lilgert B.J., Hof F. A simple calixarene recognizes post-translationally methylated lysine. Chembiochem 2010, 11:63-66.
26. Specht A., Loudwig S., Peng L., Goeldner M. Complexing photolabile cholinergic ligands with synthetic and biological receptors: a dynamic survey. J. Inclusion Phenom. Macrocyclic Chem. 2009, 65:157-163.
27. Wang K., Guo D., Zhang H., Li D., Zheng X., Liu Y. Highly effective binding of viologens by p-sulfonatocalixarenes for the treatment of viologen poisoning. J. Med. Chem. 2009, 52:6402-6412.
28. Megyesi M., Biczok L. Considerable change of fluorescence properties upon multiple binding of coralyne to 4-sulfonatocalixarenes. J. Phys. Chem. B 2010, 114:2814-2819.
29. Arena G., Casnati A., Contino A., Magri A., Sansone F., Sciotto D., Ungaro R. Inclusion of naturally occurring amino acids in water soluble calix[4]arenes: a microcalorimetric and 1H NMR investigation supported by molecular modeling. Org. Biomol. Chem. 2006, 4:243-249.
30. Lu Q., Gu J., Yu H., Liu C., Wang L., Zhou Y. Study on the inclusion interaction of p-sulfonated calix[n]arenes with vitamin K3 using methylene blue as a spectral probe. Spectrochim. Acta A 2007, 68:15-20.
31. Wang G., Zhang H., Ding F., Liu Y. Preparation and characterization of inclusion complexes of topotecan with sulfonatocalixarene. J. Inclusion Phenom. Macrocyclic Chem. 2011, 69:85-89.
32. Bakirci H., Koner A.L., Dickman M.H., Kortz U., Nau W.M. Dynamically self-assembling metalloenzyme models based on calixarenes. Angew. Chem. Int. Ed. 2006, 45:7400-7404.
33. Paclet M., Rousseau C.F., Yannick C., Morel F., Coleman A.W. An absence of non-specific immune response towards para-sulphonato-calix[n]arenes. J. Inclusion Phenom. Macrocyclic Chem. 2006, 55:353-357.
34. Shinkai S., Arimura T., Araki K., Kawabata H. Syntheses and aggregation properties of new water-soluble calixarenes. J. Chem. Soc. Perk. T. 1 1989, 2039-2045.
35. Basilio N., Francisco V., Garcia-Rio L. Aggregation of p-sulfonatocalixarene-based amphiphiles and supra-amphiphiles. Int. J. Mol. Sci. 2013, 14:3140-3157.
36. Francisco V., Basilio N., Garcia-Rio L., Leis J.R., Maques E.F., Vazquez-Vazquez C. Novel catanionic vesicles from calixarene and single-chain surfactant. Chem. Commun. 2010, 46:6551-6553.
37. Gattuso G., Notti A., Pappalardo A., Pappalardo S., Parisi M.F., Puntoriero F. A supramolecular amphiphile from a new water-soluble calix[5]arene and n-dodecylammonium chloride. Tetrahedron Lett. 2013, 54:188-191.
38. Zhao H., Guo D., Liu Y. Binding behaviors of p-sulfonatocalix[4]arene with gemini guests. J. Phys. Chem. B 2013, 117:1978-1987.
39. Kashapov R.R., Pashirova T.N., Kharlamov S.V., Ziganshina A.Yu., Ziltsova E.P., Lukashenko S.S., Zakharova L.Ya., Habicher W.D., Latypov Sh.K., Konovalov A.I. Novel self-assembling system based on resorcinarene and cationic surfactant. Phys. Chem. Chem. Phys. 2011, 13:15891-15898.
40. Wintgens V., Coeur C.L., Amiel C., Guigner J., Harangozó J.G., Zsombor M., Biczók L. 4-Sulfonatocalix[6]arene-induced aggregation of ionic liquids. Langmuir 2013, 29:7682-7688.
41. Pashirova T.N., Zhiltsova E.P., Kashapov R.R., Lukashenko S.S., Litvinov A.I., Kadirov M.K., Zakharova L.A., Konovalov A.I. Supramolecular systems based on 1-alkyl-4-aza-1-azoniabicyclo[2.2.2]octane bromides. Russ. Chem. Bull. 2010, 59:1745-1752.
42. Gaisin N.K., Gnezdilov O.I., Pashirova T.N., Zhiltsova E.P., Lukashenko S.S., Zakharova L.Ya., Osipova V.V., Dzhabarov V.I. Kolloid. Zh. 2010, 6:755-761.
43. Zhiltsova E.P., Pashirova T.N., Kashapov R.R., Gaisin N.K., Gnezdilov O.I., Lukashenko S.S., Voloshina A.D., Kulik N.V., Zobov V.V., Zakharova L.Ya., Konovalov A.I. Alkylated 1,4-diazabicyclo[2.2.2]octanes: Self-association, catalytic properties, and biological activity. Russ. Chem. Bull. 2012, 61:113-120.
44. Fedorova A.A., Goncharova E.P., Kovpak M.P., Vlassov V.V., Zenkova M.A. Influenza virus inactivated by artificial ribonucleases as a prospective killed virus vaccine. Vaccine 2012, 30:2973-2980.
45. Kazakova E.Kh., Makarova N.A., Ziganshina A.Y., Muslinkina L.A., Muslinkin A.A., Habicher W.D. Novel water-soluble tetrasulfonatomethylcalix[4]resorcinarenes. Tetrahedron Lett. 2000, 41:10111-10115.
46. Zakharova L., Valeeva F., Zakharov A., Ibragimova A., Kudryavtseva L., Harlampidi H. Micellization and catalytic activity of the cetyltrimethylammonium bromide-Brij 97-water mixed micellar system. J. Colloid. Interf. Sci. 2003, 263:597-605.
47. Tehrani-Bagha A.R., Singh R.G., Holmberg K. Solubilization of two organic dyes by anionic, cationic and nonionic surfactants. Colloid. Surf. A 2013, 417:133-139.
48. Tehrani-Bagha A.R., Singh R.G., Holmberg K. Solubilization of two organic dyes by cationic ester-containing gemini surfactants. J. Colloid. Interf. Sci. 2012, 376:112-118.
49. Holmberg K., Jonsson B., Kronberg B., Lindman B. Surfactants and Polymers in Aqueous Solution 2002, 562 pp. J. Wiley and Sons, Ltd, Chichester.
50. Zakharova L.Ya., Kudryashova Yu.R., Selivanova N.M., Voronin M.A., Ibragimova A.I., Solovieva S.E., Gubaidullin A.T., Litvinov A.I., Nizameev I.R., Kadirov M.K., Galyametdinov Yu.G., Antipin I.S., Konovalov A.I. Novel membrane mimetic systems based on amphiphilic oxyethylated calix[4]arene: Aggregative and liquid crystalline behavior. J. Membrane Sci. 2010, 364:90-101.
51. Zakharova L.Ya., Syakaev V.V., Voronin M.A., Valeeva F.V., Ibragimova A.R., Ablakova Y.R., Kazakova E.Kh., Latypov Sh.K., Konovalov A.I. NMR and spectrophotometry study of the supramolecular catalytic system based on polyethyleneimine and amphiphilic sulfonatomethylated calix[4]resorcinarene. J. Phys. Chem. C 2009, 113:6182-6190.
52. Syakaev V.V., Mustafina A.R., Elistratova Ju.G., Latypov Sh.K., Konovalov A.I. Head-to-tail aggregates of sulfonatomethylated calix[4]resorcinarene in aqueous solutions. Supramol. Chem. 2008, 20:453-460.
53. Pashirova T.N., Zhiltsova E.P., Lukashenko S.S., Zakharova L.Ya., Konovalov A.I. Micelle formation and catalytic activity hydrophobic mono- and dicationic derivatives of 1,4-diazabicyclo[2.2.2]octane. Liq. Cryst. Appl. 2009, 1:51-61.
54. Yu J., Sun D., Ai H., Wang X., Zhai L. Novel mechanism for nanotube formation from vesicle: A transition induced by the rearrangement of molecular pairs. Colloid. Surf. A 2013, 422:148-154.
55. Ghosh S., Ghatak C., Banerjee C., Mandal S., Kuchlyan J., Sarkar N. Spontaneous transition of micelle-vesicle-micelle in a mixture of cationic surfactant and anionic surfactant-like ionic liquid: a pure nonlipid small unilamellar vesicular template used for solvent and rotational relaxation study. Langmuir 2013, 29:10066-10076.
56. Chen J., Hao J. Molecular dynamics simulation of cetyltrimethylammonium bromide and sodium octyl sulfate mixtures: aggregate shape and local surfactant distribution. Phys. Chem. Chem. Phys. 2013, 15:5563-5571.