Bis (β-cyclodextrin)s linked with an aromatic diamine as fluorescent sensor for the molecular recognition of bile salts

Journal of Solution Chemistry

Volumn 38, Issue 4, 2009, Pages 417-428

  Zhao, Yan ^a   Gu, Juan ^a   Chi, Shao Ming ^a   Yang, Yong Cun ^a   Zhu, Hong You ^b   Huang, Rong ^b   Wang, Yu Fei ^a  

^a YUNNAN NORMAL UNIVERSITY   (China)

^b YUNNAN UNIVERSITY   (China)

Author keywords

Bile salts; Bridged bis( cyclodextrin)s; Fluorescence spectroscopy; Inclusion phenomena; Molecular recognition; ROESY

Indexed keywords

EID: 61449158607     PISSN: 00959782     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10953-009-9387-2     Document Type: Article

References (29)

1. J. Szejti 1998 Introduction and general overview of cyclodextrin chemistry Chem. Rev. 98 1743 1753 10.1021/cr970022c
2. L. Omar M.I. El-Barghouthi N.A. Masoud A.A. Abdoh M.M. Al Omari M.B. Zughul A.A. Badwan 2007 Inclusion complexation of loratadine with natural and modified cyclodextrins: phase solubility and thermodynamic studies J. Solution Chem. 36 605 616 10.1007/s10953-007-9136-3
3. T. Stalin N. Rajendiran 2006 A study on the spectroscopy and photophysics of 4-hydroxy-3-methoxybenzoic acid in different solvents, pH and β-cyclodextrin J. Mol. Struct. 794 35 45 10.1016/j.molstruc.2006.01.038
4. H. Nakashima N. Yoshida 2006 Fluorescent detection for cyclic and acyclic alcohol guests by naphthalene-appended amino-β-cyclodextrins Org. Lett. 8 4997 5000 10.1021/ol0616079
5. T. Kuwabara H. Nakajima M. Nanasawa A. Ueno 1999 Color change indicators for molecules using methyl red-modified cyclodextrins Anal. Chem. 71 2844 2849 10.1021/ac9814041
6. Y. Liu J. Shi D.S. Guo 2007 Novel permethylated β-cyclodextrin derivatives appended with chromophores as efficient fluorescent sensors for the molecular recognition of bile salts J. Org. Chem. 72 8227 8234 10.1021/jo071131m
7. A. Ruebner Z. Yang D. Leung R. Breslow 1999 A cyclodextrin dimer with a photocleavable linker as a possible carrier for the photosensitizer in photodynamic tumor therapy Proc. Natl. Acad. Sci. USA 96 14692 14693 10.1073/pnas.96.26.14692
8. M. Narita S. Mima N. Ogawa F. Hamada 2001 Fluorescent molecular sensory system based on bis pyrene modified γ-cyclodextrin dimer for steroids and endocrine disruptors Anal. Sci. Mar. 17 379 385
9. H. Ikeda Y. Lidaka A. Ueno 2003 Remarkably enhanced excimer formation of naphthylacetate in cation-charged γ-cyclodextrin Org. Lett. 5 1625 1627 10.1021/ol0342608
10. Y. Liu H.M. Yu Y. Chen Y.L. Zhao 2006 Synthesis of bridged and metallobridged bis(β-cyclodextrin)s containing fluorescent oxamidobisbenzoyl linkers and their selective binding towards bile salts Chem. Eur. J. 12 3858 3868 10.1002/chem.200501187
11. Y. Liu Y. Song Y. Chen X.Q. Li F. Ding R.Q. Zhong 2004 Biquinolino-modified β-cyclodextrin dimers and their metal complexes as efficient fluorescent sensors for the molecular recognition of steroids Chem. Eur. J. 10 3685 3696 10.1002/chem.200305724
12. J.M. Benito M.G. Garcia C.O. Mellet I. Baussanne J. Defaye J.M.G. Fernandez 2004 Optimizing saccharide-directed molecular delivery to biological receptors: design, synthesis, and biological evaluation of glycodendrimer- cyclodextrin conjugates J. Am. Chem. Soc. 126 10355 10363 10.1021/ja047864v
13. J.J. Michels J. Huskens D.N. Reinhoudt 2002 Noncovalent binding of sensitizers for lanthanide(III) luminescence in an EDTA-bis(β-cyclodextrin) ligand J. Am. Chem. Soc. 124 2056 2064 10.1021/ja017025y
14. Y. Zhao Z.M. Yang H.Y. Zhu J. Gu Y.F. Wang 2007 Molecular recognition of a novel bridged bis(β-cyclodextrin) tethered with aromatic diamine with dyes Acta Phys.-Chim. Sin. 23 394 398 (in Chinese)
15. Y. Liu B.H. Han Y. Chen 2002 Molecular recognition and complexation thermodynamics of dye guest molecules by modified cyclodextrins and calixarenesulfonates J. Phys. Chem. B 106 4678 4687 10.1021/jp015603r
16. R. Breslow Z.W. Yang R. Ching G. Trojandt F. Odobel 1998 Sequence selective binding of peptides by artificial receptors in aqueous solution J. Am. Chem. Soc. 120 3536 3537 10.1021/ja973991y
17. Y. Zhao X.Q. Liu J. Gu L.Q. Wang H.Y. Zhu R. Huang Y.F. Wang Z.M. Yang 2008 Synthesis of novel bis(β-cyclodextrin)s linked with aromatic diamine and their molecular recognition with model substrates J. Phys. Org. Chem. 21 440 448 10.1002/poc.1345
18. Y. Zhao X.Q. Liu H.Y. Zhu Z.M. Yang R. Huang 2006 Synthesis of a novel aromatic diamino-bridged bis(β-cyclodextrin) and its inclusion complexation with dye molecules Chin. Chem. Lett. 17 1543 1546
19. C. Boulanger C.D. Giorgio J. Gaucheron P. Vierling 2004 Transfection with fluorinated lipoplexes based on new fluorinated cationic lipids and in the presence of a bile salt surfactant Bioconjug. Chem. 15 901 908 10.1021/bc049942+
20. Setchell, K.D.R., Street, J.M., Sjovall, J.: The bile acids. In: Setchell, K.D.R., Kritcheveky, D., Nair, P.P. (eds.) The Bile Acids: Chemistry, Physiology, and Metabolism, vol. 4, Chap. 12, p. 543. Plenum Press, New York and London (1988)
21. C. Jullian J. Morales-Montecinos G. Zapata-Torres B. Aguilera J. Rodriguez V. Arán C. Olea-Azar 2008 Characterization, phase-solubility, and molecular modeling of inclusion complex of 5-nitroindazole derivative with cyclodextrins Bioorg. Med. Chem. 16 5078 5084 10.1016/j.bmc.2008.03.026
22. α -dansyl-L-lysine-β-cyclodextrin J. Org. Chem. 64 382 387 10.1021/jo9807870
23. K. Hamasaki H. Ikeda A. Nakamura A. Ueno F. Toda I. Suzuki T. Osa 1993 Fluorescent sensors of molecular recognition. Modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence J. Am. Chem. Soc. 115 5035 5040 10.1021/ja00065a012
24. H. Ikeda M. Nakamura N. Ise N. Oguma A. Nakamura T. Ikeda F. Toda A. Ueno 1996 Fluorescent cyclodextrins for molecule sensing: fluorescent properties, NMR characterization, and inclusion phenomena of N-dansylleucine-modified cyclodextrins J. Am. Chem. Soc. 118 10980 10988 10.1021/ja960183i
25. H.A. Benesi J.H. Hidebrand 1949 A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons J. Am. Chem. Soc. 71 2703 2707 10.1021/ja01176a030
26. Y. Liu Y.W. Yang E.C. Yang X.D. Guan 2004 Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(β-cyclodextrin)s J. Org. Chem. 69 6590 6602 10.1021/jo049143k
27. F. Ollila O.T. Pentikainen S. Forss M.S. Johnson J.P. Slotte 2001 Characterization of bile salt/cyclodextrin interactions using isothermal titration calorimetry Langmuir 17 7107 7111 10.1021/la0109258
28. P.R. Cabrer E. Alvarez-Parrilla F. Meijide J.A. Seijas E.R. Nunez J.V. Tato 1999 Complexation of sodium cholate and sodium deoxycholate by β-cyclodextrin and derivatives Langmuir 15 5489 5495 10.1021/la9817359
29. Z.J. Tan X.X. Zhu G.R. Brown 1994 Formation of inclusion complexes of cyclodextrins with bile salt anions as determined by NMR titration studies Langmuir 10 1034 1039 10.1021/la00016a014