Stable vesicles assembled by "supramolecular amphiphiles" with double hydrophobic chains

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 414, Issue , 2012, Pages 41-49

  Sun, Tao ^a   Shen, Jian ^b   Yan, Hui ^c   Hao, Jingcheng ^a   Hao, Aiyou ^a  

^a SHANDONG UNIVERSITY   (China)

^b WEIFANG UNIVERSITY   (China)

^c Liaocheng Universtiy   (China)

Author keywords

Cyclodextrin; Double chains; Phthalate ester; Stable; Supramolecular amphiphiles; Vesicles

Indexed keywords

AMPHIPHILES; COMPUTER SIMULATION; CYCLODEXTRINS; DYNAMIC LIGHT SCATTERING; ESTERIFICATION; ESTERS; MOLECULAR DYNAMICS; SCANNING ELECTRON MICROSCOPY; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

DOUBLE CHAIN; PHTHALATE ESTER; STABLE; SUPRAMOLECULAR AMPHIPHILES; VESICLES;

SUPRAMOLECULAR CHEMISTRY;

EID: 84868325938     PISSN: 09277757     EISSN: 18734359     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2012.08.045     Document Type: Article

References (48)

1. Gebers J., Rolland D., Frauenrath H. Coordination-driven self-assembly of PEO-functionalized perylene bisimides supramolecular diversity from a limited set of molecular building blocks. Angew. Chem. Int. Ed. 2009, 48:4480-4483.
2. Wang Y.P., Ma N., Wang Z.Q., Zhang X. Photo-controlled reversible supramolecular assembly of an azobenzene-containing surfactant with α-cyclodextrin. Angew. Chem. Int. Ed. 2007, 49:2823-2826.
3. Park C., Im M.S., Lee S., Lim J., Kim C. Tunable fluorescent dendron-cyclodextrin nanotubes for hybridization with metal nanoparticles and their biosensory function. Angew. Chem. Int. Ed. (Engl.) 2008, 120:10070-10074.
4. Jiang L., Peng Y., Yan Y., Deng M., Wang Y., Huang J. " Annular Ring" microtubes formed by SDS@2β-CD complexes in aqueous solution. Soft Matter 2010, 6:1731-1736.
5. Park C., Lee I., Lee S., Song Y., Rhue M., Kim C. Cyclodextrin-covered organic nanotubes derived from self-assembly of dendrons and their supramolecular transformation. Proc. Natl. Acad. Sci. U.S.A. 2006, 103:1199-1203.
6. Tang Y., Zhou L., Li J., Luo Q., Huang X., Wu P., Wang Y., Xu J., Shen J., Liu J. Giant nanotubes loaded with artificial peroxidase centers: self-assembly of supramolecular amphiphiles as a tool to functionalize nanotubes. Angew. Chem. Int. Ed. (Engl.) 2010, 122:4012-4016.
7. Wang Z., Li Z., Liu Z. Photostimulated reversible attachment of gold nanoparticles on multiwalled carbon nanotubes. J. Phys. Chem. C 2009, 113:3899-3902.
8. Maciollek A., Munteanu M., Ritter H. New generation of polymeric drugs: copolymer from NIPAAM and cyclodextrin methacrylate cntaining supramolecular-attached antitumor derivative. Macromol. Chem. Phys. 2010, 211:245-249.
9. Takashima Y., Nakayama T., Miyauchi M., Kawaguchi Y., Yamaguchi H., Harada A. Complex formation and gelation between copolymers containing pendant azobenzene groups and cyclodextrin polymers. Chem. Lett. 2004, 33:890-891.
10. Li X., Qi Z., Liang K., Bai X., Xu J., Liu J., Shen J. An artificial supramolecular nanozyme based on β-cyclodextrin-modified gold nanoparticles. Catal. Lett. 2008, 124:413-417.
11. Luo C., Zuo F., Zheng Z., Cheng X., Ding X., Peng Y. Tunable smart surface of gold nanoparticles achieved by light-controlled molecular recognition effection. Macromol. Rapid Commun. 2008, 29:149-154.
12. Liu J., Sondjaja R., Tam K.C. Alpha-cyclodextrin induced self-assembly of a double-hydrophilic block copolymer in aqueous solution. Langmuir 2007, 23:5106-5109.
13. Tao W., Liu Y., Jiang B., Yu S., Huang W., Zhou Y., Yan D. A linear-hyperbranched supramolecular amphiphile and its self-assembly into vesicles with great ductility. J. Am. Chem. Soc. 2012, 134:762-764.
14. Zhang H., Shen J., Liu Z., Bai Y., An W., Hao A. Controllable vesicles based on unconventional cyclodextrin inclusion complexes. Carbohydr. Res. 2009, 344:2028-2035.
15. Zhang H., An W., Liu Z., Hao A., Hao J., Shen J., Zhao X., Sun H., Sun L. Redox-responsive vesicles prepared from supramolecular cyclodextrin amphiphiles. Carbohydr. Res. 2009, 345:87-96.
16. Zou J., Guan B., Liao X., Jiang M., Tao F. Dual reversible self-assembly of PNIPAM-based amphiphilies formed by inclusion complexation. Macromolecule 2009, 42:7465-7473.
17. Sun T., Li Y., Zhang H., Li J., Xin F., Kong L., Hao A. PH-reversible vesicles based on the supramolecular amphiphilies formed by cyclodextrin and anthraquinone derivate. Colloids Surf. A 2011, 375:87-96.
18. Sun T., Zhang H., Yan H., Li J., Cheng G., Hao A., Qiao H., Xin F. Sensitive fluorescent vesicles based on the supramolecular inclusion of β-cyclodextrins with N-alkylamino-1-anthraquinone. Supramol. Chem. 2011, 23:351-364.
19. Lehn J.M. Toward self-organization and complex matter. Science 2002, 295:2400-2403.
20. Allen T.M., Cullis P.R. Drug delivery systems: entering the mainstream. Science 2004, 303:1818-1822.
21. Christensen S.M., Stamou D. Surface-based lipid vesicle reactor systems: fabrication and applications. Soft Matter 2007, 3:828-836.
22. Zhang H., Xin F., An W., Hao A., Wang X., Zhao X., Liu Z., Sun L. Oxidizing-responsive vesicles made from tadpole-like supramolecular amphiphiles based on inclusion complexes between driving molecules and beta-cyclodextrin. Colloids Surf. A 2010, 363:78-85.
23. Okahata Y., Soboi Y., Iijima N., Hirabayashi K., Kunitake T., Kajiyama T. Molecular and crystal structure of the lipid-model amphiphile, dioctadecylammonium bromide hydrate. Bull. Chem. Soc. Jpn. 1988, 61:1485-1490.
24. Kajiyama T., Kumano A., Takayanagi M., Okahata Y., Kunitake T. Contemporary Topics in Polymer Science 1984, vol. 4:829. Plenum Press, New York.
25. Sun T., Zhao W., Hao A., Sun L. Effectively promotion of Beirut reaction by β-cyclodextrin in water. Synthetic Commun. 2011, 41:3097-3105.
26. Uekama K., Hirayama F., Irie T. Cyclodextrin drug carrier systems. Chem. Rev. 1998, 98:2045-2076.
27. Nitta K., Miyake J., Watanabe J., Ikeda Y. Gel formation driven by tunable hydrophobic domain: design of acrylamide macromonomer with oligo hydrophobic segment. Biomacromolecules 2012, 13:1002-1009.
28. Wang L., Liu H., Hao J. Stable porphyrin vesicles formed in non-aqueous media and dried to produce hollow shells. Chem. Commun. 2009, 135:1353-1355.
29. Yin H., Lei S., Zhu S., Huang J., Ye J. Micelle to vesicle transition induced by organic additives in the catanionic surfactant system. Chem. Eur. J. 2006, 12:2825-2835.
30. McNicholas S., Rencurosi A., Lay L., Mazzaglia A., Sturiale L., Perez M., Darcy R. Amphiphilic N-glycosyl-thiocarbamoyl cyclodextrins: synthesis, self-assembly, and fluorimetry of recognition by lens culinaris lectin. Biomacromolecules 2007, 8:1851-1857.
31. An W., Zhang H., Sun L., Hao A., Hao J., Xin F. Reversible vesicles based on one and two head supramolecular cyclodextrin amphiphile induced by methanol. Carbohydr. Res. 2010, 345:914-921.
32. Zhang H., Li Y., Sun H., Xin F., Liu Z., Hao A., Li J., Shen J., Xu S., An W., Sun L., Sun T., Zhao W., Li Y., Kong L. Fluorescent vesicular particles assembled by inclusion complexes between cyclodextrins and BPB. J. Disp. Sci. Technol. 2011, 32:834-839.
33. Zhong D.Y., Franke J., Blomker T., Erker G., Chi L.F., Fuchs H. Manipulating surface diffusion ability of single molecules by scanning tunneling microscopy. Nano Lett. 2009, 9:132-136.
34. Choisnard L., Gze A., Putaux J.L., Wong Y.S., Wouessidjewe D. Nanoparticles of β-cyclodextrin esters obtained by self-assembling of biotransesterified β-cyclodextrin. Biomacromolecules 2006, 7:515-520.
35. Wang D., Dong R., Long P., Hao J. Photo-induced phase transition from multilamellar vesicles to wormlike micelles. Soft Matter 2011, 7:10713-10719.
36. Liu Y.C., Le Ny A.M., Schmidt J., Talmon Y., Chmelka B.F., JrC.T.Lee Photo-assisted gene delivery using light-responsive catanionic vesicles. Langmuir 2009, 25:5713-5724.
37. Maurice R., Eftink M.L., Bystrom K., Perlmutter H.D., Kristol D.S. Cyclodextrin inclusion compounds: studies of the variation in the size of the acyclic guests. J. Am. Chem. Soc. 1989, 111:6765-6772.
38. Bardelang D., Rockenbauer A., Karoui H., Finet J.P., Tordo P. Inclusion complexes of PBN-type nitrone spin traps and their superoxide spin adducts with cyclodextrin derivatives: parallel determination of the association constants by NMR titrations and 2D-EPR simulations. J. Phys. Chem. B 2005, 109:10521-10530.
39. MacCarthy P. Simplified experimental route for obtaining Job's curves. Anal. Chem. 1978, 50:2165.
40. Denadai ñ.M.L., Teixeira K.I., Santoro M.M., Pimenta A.M.C., Cortés M.E., Sinisterra R.D. Supramolecular self-assembly of β-cyclodextrin: an effective carrier of the antimicrobial agent chlorhexidine. Carbohydr. Res. 2007, 342:2286-2296.
41. Schneider H.J., Hacket F., Rudiger V. NMR studies of cyclodextrins and cyclodextrin complexes. Chem. Rev. 1998, 98:1755-1785.
42. Zhang H., Strutt N.L., Stoll R.S., Li H., Zhu Z., Stoddar J.F. Dynamic clicked surfaces based on functionalised pillar[5] arene. Chem. Commun. 2011, 47:11420-11422.
43. Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 1998, 98:1743-1753.
44. Israelachvili J.N., Mitchell D.J., Nirham B.W. Theory of self-assembly of hydrocarbon amphiphiles into micelles and bilayers. J. Chem. Soc. Faraday Trans. II 1976, 72:1525-1568.
45. Maillet J.B., Lachet V., Coveney P.V. Large scale molecular dynamics simulation of self-assembly processes in short and long chain cationic surfactants. Phys. Chem. Chem. Phys. 1999, 1:5277-5290.
46. Wang Z., Larson R.G. Molecular dynamics simulations of threadlike cetyltrimethylammonium chloride micelles: effects of sodium chloride and sodium salicylate salts. J. Phys. Chem. B 2009, 113:13697-13710.
47. Yakovlev D.S., Boek E.S. Molecular dynamics simulations of mixed cationic/anionic wormlike micelles. Langmuir 2007, 23:6588-6597.
48. Sun H. COMPASS: an ab initio force-field optimized for condensed-phase applications-overview with details on alkane and benzene compounds. J. Phys. Chem. B 1998, 102:7338-7364.