pH-responsive vesicle-like particles based on inclusion complexes between cyclodextrins and methyl orange

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 358, Issue 1-3, 2010, Pages 115-121

  Zhang, Huacheng ^a   Sun, Lizhen ^a   Liu, Zhaona ^a   An, Wei ^a   Hao, Aiyou ^a   Xin, Feifei ^a   Shen, Jian ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Cyclodextrins; Inclusion complexes; Methyl orange; Particles; pH responsive; Vesicle like

Indexed keywords

AGGREGATES; AZO DYES; COMPLEXATION; CYCLODEXTRINS; DATA STORAGE EQUIPMENT; DRUG INTERACTIONS; DYNAMIC LIGHT SCATTERING; FLUORESCENCE; HYSTERESIS MOTORS; LIGHT TRANSMISSION; SILANES; TRANSMISSION ELECTRON MICROSCOPY;

CD COMPLEX; CDS; CONFOCAL SCANNING MICROSCOPY; FLUORESCENCE MEASUREMENTS; FLUORESCENT PROBES; FORMATION MECHANISM; HOST GUEST INTERACTIONS; INCLUSION COMPLEX; METHYL ORANGE; MICROAGGREGATES; PARTICLES; PH-RESPONSIVE; TEM;

AGGLOMERATION;

4 HYDROXYBUTYRIC ACID; BETA CYCLODEXTRIN; CYCLODEXTRIN; METHYL ORANGE; WATER;

ARTICLE; BIOMIMETICS; COATED VESICLE; CONFOCAL LASER MICROSCOPY; DYNAMIC LIGHT SCATTERING; FLUORESCENCE; LASER; LIGHT SCATTERING; MOLECULAR DYNAMICS; MOLECULAR MIMICRY; NUCLEAR MAGNETIC RESONANCE; PARTICLE SIZE; PH; PRIORITY JOURNAL; TRANSMISSION ELECTRON MICROSCOPY;

EID: 77049112953     PISSN: 09277757     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2010.01.026     Document Type: Article

References (58)

1. Lehn J.-M., Atwood J.L., Davies J.E.D., MacNicol D.D., and Vogtle F. Comprehensive Supramolecular Chemistry (1996), Pergamon, Oxford
2. Houseman B.T., Mrksich M., Rojo J., Morales J.C., Penades S., Haseley S.R., Kamerling J.P., Vliegenthart J.F.G., Tromas C., Garcia R., Li G., Gouzy M.F., Fuhrhop J.H., James T.D., Shinkai S., and Lindhorst T.K. Host-Guest Chemistry: Mimetic Approaches to Study Carbohydrate Recognition (2002), Springer, Berlin and Heidelberg
3. Ueno A. Review: fluorescent cyclodextrins for molecule sensing. Supramol. Sci. 3 (1996) 31-36
4. Yamamura H., Yamada S., Kohno K., Okuda N., Araki S., Kobayashi K., Katakai R., Kano K., and Kawai M. Preparation and guest binding of novel β-cyclodextrin dimmers linked with various sulfur-containing linker moieties. J. Chem. Soc., Perkin Trans. 1 (1999) 2943-2948
5. Sasaki K., Nasahiko M., and Kuroda Y. New cyclodextrin dimer and trimer: formation of biphenyl excimer and their molecular recognition. Chem. Commun. (2001) 2630-2631
6. Liu Y., Yang Y.W., Li L., and Chen Y. Cooperative molecular recognition of dyes by dyad and triad cyclodextrin-crown ether conjugates. Org. Biomol. Chem. 2 (2004) 1542-1548
7. Balzani V., Credi A., Raymo F.M., and Stoddart J.F. Artificial molecular machines. Angew. Chem. Int. Ed. 39 (2000) 3348-3391
8. Sakai N., Mareda J., and Matile S. Ion channels and pores made from scratch. Mol. BioSyst. 3 (2007) 658-666
9. Whitesides G.M., and Grzybowski B. Self-assembly at all scales. Science 295 (2002) 2418
10. Voskuhl J., and Ravoo B.J. Molecular recognition of bilayer vesicles. Chem. Soc. Rev. 38 (2009) 495-505
11. Breslow R. Artificial Enzymes (2005), Wiley-VCH Verlag, Weinheim
12. Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98 (1998) 1743-1753
13. Khan A.R., Forgo P., Stine K.J., and D'Souza V.T. Methods for selective modifications of cyclodextrins. Chem. Rev. 98 (1998) 1977-1996
14. Rekharsky M.V., and Inoue Y. Complexation thermodynamics of cyclodextrins. Chem. Rev. 98 (1998) 1875-1917
15. Zhang H., Hao A., Li G., and Sun H. Synthesis and application of cyclodextrin vesicles. Chin. J. Org. Chem. 29 (2009) 166-173
16. Hapiot F., Tilloy S., and Monflier E. Cyclodextrins as supramolecular hosts for organometallic complexes. Chem. Rev. 106 (2006) 767-781
17. Uekama K., Hirayama F., and Irie T. Cyclodextrin drug carrier system. Chem. Rev. 98 (1998) 2045-2076
18. Breslow R., and Dong S.D. Biomimetic reactions catalyzed by cyclodextrins and their derivatives. Chem. Rev. 98 (1998) 1997-2011
19. Villalonga R., Cao R., and Fragoso A. Supramolecular chemistry of cyclodextrins in enzyme technology. Chem. Rev. 107 (2007) 3088-3116
20. Kaifer A.E. Interplay between molecular recognition and redox chemistry. Acc. Chem. Res. 32 (1999) 62-71
21. Harada A. Cyclodextrin-based molecular machines. Acc. Chem. Res. 34 (2001) 456-464
22. Ma X., Wang Q., and Tian H. Photo-driven molecular shuttles. Prog. Chem. 21 (2009) 106-115
23. Zhang H., Shen J., Liu Z., Bai Y., An W., and Hao A. Controllable vesicles based on unconventional cyclodextrin inclusion complexes. Carbohyd. Res. 344 (2009) 2028-2035
24. Liu Y., Li B., You C., Wada T., and Inoue Y. Molecular recognition of dyes by organoselenium-bridged bis(β-cyclodextrin)s. J. Org. Chem. 66 (2001) 225-232
25. Kodaka M. A general rule for circular dichroism induced by a chiral macrocycle. J. Am. Chem. Soc. 115 (1993) 3702-3705
26. Kuwabara T., Nakamura A., Ueno A., and Toda F. Inclusion complexes and guest-induced color changes of pH-indicator-modified β-cyclodextrins. J. Phys. Chem. 98 (1994) 6297-6303
27. Zou J., Tao F., and Jiang M. Optical switching of self-assembly and disassembly of noncovalently connected amphiphiles. Langmuir 23 (2007) 12791-12794
28. Park C., Lim J., Yun M., and Kim C. Photoinduced release of guest molecules by supramolecular transformation of self-assembled aggregates derived from dendrons. Angew. Chem. Int. Ed. 47 (2008) 2959-2963
29. Wang Y., Ma N., Wang Z., and Zhang X. Photocontrolled reversible supramolecular assemblies of an azobenzene-containing surfactant with α-cyclodextrin. Angew. Chem. Int. Ed. 46 (2007) 2823-2826
30. Wang N., Zhang Q., Zhang Y., and Chen H. Inclusion of neurotransmitters in β-cyclodextrin and their structures. Acta Chim. Sin. 61 (2003) 597-602
31. Tian W., Fan X., Liu T., Yang Y., Sun L., Jiang M., and Huang Y. Molecular inclusion complexation and recognition behavior of amphiphilic hyperbranched polymer carrying β-cyclodextrin as pendant groups on shell layer. Chem. J. Chin. Univ. 30 (2009) 632-637
32. Shi J., Guo D.S., Ding F., and Liu Y. Unique regioselective binding of permethylated β-cyclodextrin with azobenzene derivatives. Eur. J. Org. Chem. (2009) 923-931
33. +. J. Phys. Chem. B 101 (1997) 6855-6860
34. Banerjee I.A., Yu L., and Matsui H. Application of host-guest chemistry in nanotube-based device fabrication: photochemically controlled immobilization of azobenzene nanotubes on patterned α-CD monolayer/Au substrates via molecular recognition. J. Am. Chem. Soc. 125 (2003) 9542-9543
35. Matsui Y., and Mochida K. Binding forces contributing to the association of cyclodextrin with alcohol in an aqueous solution. Bull. Chem. Soc. Jpn. 52 (1979) 2808-2814
36. Sawunyama P., Jackson M., and Bailey G.W. Interactions of methyl orange with cyclodextrin/sodium-montmorillonite systems probed by UV-visible spectroscopy. J. Colloid Interface Sci. 237 (2001) 153-157
37. Liu Y., Qi A., Han B., Li Y., Zhang Y., and Chen R. Investigation of molecular recognition in supramolecular system. Chin. Sci. Bull. 42 (1997) 1516-1519
38. Zheng Y., Weng J., Zhou L., and Chen S. The synthesis and characterization of the compound of β-cyclodextrin with DMSO. J. Fujian Norm Univ. (Nat. Sci.) 11 (1995) 52-55
39. Chen P. Study on the thermal decomposition kinetics of inclusion complex of β-cyclodextrin and methyl orange. J. Fujian Norm Univ. (Nat. Sci.) 14 (1998) 47-50
40. Kodaka M. Sign of circular dichroism induced by β-cyclodextrin. J. Phys. Chem. 95 (1991) 2110-2112
41. Sun H.Y., Bai Y., Zhao M.G., Hao A.Y., Xu G.Y., Shen J., Li J.Y., Sun T., and Zhang H. New cyclodextrin derivative 6-O-(2-hydroxybutyl)-β-cyclodextrin: preparation and its application in molecular binding and recognition. Carbohyd. Res. 344 (2009) 1999-2004
42. Cramer F., Saenger W., and Spatz H.C. Inclusion compounds XIX the formation of inclusion compounds of α-cyclodextrin in aqueous solutions thermodynamics and kinetics. J. Am. Chem. Soc. 89 (1967) 14-20
43. Namor A.F.D., Traboulssi R., and Lewis D.F.V. Complexation of cyclodextrins with anion constituents of antigenic determinants in water (axial complexes) and in N,N-dimethylformamide (equatorial complexes) a thermodynamic study. J. Chem. Soc., Chem. Commun. (1990) 751-753
44. Lu P., Liu S., Wu F., and Deng N. Formation of the inclusion complex of β-cyclodextrin with methyl orange and its photocatalytic decolorization. Chin. J. Appl. Chem. 20 (2003) 108-111
45. Harada A., Osaki M., Takashima Y., and Yamaguchi H. Ring-opening polymerization of cyclic esters by cyclodextrins. Acc. Chem. Res. 41 (2008) 1143-1152
46. Osaki M., Takashima Y., Yamaguchi H., and Harada A. An artificial molecular chaperone: poly-pseudo-rotaxane with an extensible axle. J. Am. Chem. Soc. 129 (2007) 14452-14457
47. Osaki M., Takashima Y., Yamaguchi H., and Harada A. Polymerization of lactones initiated by cyclodextrins: effects of cyclodextrins on the initiation and propagation reactions. Macromolecules 40 (2007) 3154-3158
48. He Y., Fu P., Shen X., and Gao H. Cyclodextrin-based aggregates and characterization by microscopy. Micron 39 (2008) 495-516
49. Wang L., Liu H., and Hao J. Stable porphyrin vesicles formed in non-aqueous media and dried to produce hollow shells. Chem. Commun. (2009) 1353-1355
50. Perro A., Meunier F., Schmitt V., and Ravaine S. Production of large quantities of "Janus" nanoparticles using wax-in-water emulsions. Colloid Surf. A 332 (2009) 57-62
51. Volodkin D., Arntz Y., Schaaf P., Moehwald H., Voegel J.C., and Ball V. Composite multilayered biocompatible polyelectrolyte films with intact liposomes: stability and temperature triggered dye release. Soft Matter 4 (2008) 122-130
52. Jing B., Chen X., Zhao Y., Wang X., Ma F., and Yue X. Ionic self-assembled solid-like vesicles and their temperature-induced transformation. J. Mater. Chem. 19 (2009) 2037-2042
53. Hamasaki K., Ikeda H., Nakamura A., Ueno A., Toda F., Suzuki I., and Osa T. Fluorescent sensors of molecular recognition modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence. J. Am. Chem. Soc. 115 (1993) 5035-5040
54. Corradini R., Dossena A., Galaverna G., Marchelli R., Panagia A., and Sartor G. Fluorescent chemosensor for organic guests and copper(II) ion based on dansyldiethylenetriamine-modified β-cyclodextrin. J. Org. Chem. 62 (1997) 6283-6289
55. Jong M.R., Engbersen J.F.J., Husken J., and Reinhoudt D.N. Cyclodextrin dimers as receptor molecules for steroid sensors. Chem. Eur. J. 6 (2000) 4034-4040
56. Denadai A.M.L., Teixeira K.I., Santoro M.M., Pimenta A.M.C., Cortes M.E., and Sinisterra R.D. Supramolecular self-assembly of β-cyclodextrin: an effective carrier of the antimicrobial agent chlorhexidine. Carbohyd. Res. 342 (2007) 2286-2296
57. Schneider H.J., Hacket F., Rudiger V., and Ikeda H. NMR studies of cyclodextrins and cyclodextrin complexes. Chem. Rev. 98 (1998) 1755-1785
58. Song A., Dong S., Hao J., and Wang H. Investigations of NMR technologies on self-assembly of amphiphiles. Chin. J. Chem. Phys. 18 (2005) 289-294