Abstract
Dimers containing β-cyclodextrin (β-CD) moieties at both ends of dicarboxylic acids were prepared by the reaction of bis(m-nitrophenyl) dicarboxylate with a large excess of β-CD, and were purified by dialysis and gel chromatography. The interaction of the dimers with potassium 2-p-toluidinylnaphthalene-6-sulfonate (TNS) was studied by the fluorescence technique and compared with that of β-CD and poly(acryloyl-β-CD). The dimers were found to bring about a much greater enhancement and blue shift of the TNS fluorescence than β-CD but less than the polymer. The succinate dimer enhanced the TNS fluorescence twofold more than the glutarate dimer. Dissociation constants and stoichiometries were determined by fluorometric titration and continuous variation methods. The dimer complexes showed exclusively 2:1 stoichiometry (CD: TNS), even in the concentration range in which β-CD showed 1:1 stoichiometry. The 2:1 complexes of the dimers were much more stable than the 2:1 complex of β-CD and were comparable to that of the polymer. Thus, two CD units linked by the chain were found to cooperate in binding one TNS molecule.
Similar content being viewed by others
Article PDF
References
J. H. Fendler and E. J. Fendler, “Catalysis in Micellar and Macromolecular Systems,” Academic Press, New York, N.Y., 1975.
M. L. Bender and M. Komiyama “Cyclodextrin Chemistry,” Springer Verlag, Basel, 1978.
A. Harada, M. Furue, and S. Nozakura, Macromolecules, 9, 701 (1976).
A. Harada, M. Furue, and S. Nozakura, Macromolecules, 9, 705 (1976).
A. Harada, M. Furue, and S. Nozakura, Macromolecules, 10, 676 (1977).
L. Stryer, Science, 162, 526 (1968).
L. Brand and J. R. Gohlke, Ann. Rev. Biochem., 41, 843 (1972).
R. L. Van Etten, G. A. Clowes, J. F. Sebastian, and M. L. Bender, J. Am. Chem. Soc., 89, 3253 (1967).
I. M. Klotz and D. L. H. Hunston, Biochemistry, 10, 3065 (1971).
C. J. Selisker and L. Brand, Science, 171, 799 (1971).
E. M. Kosower and H. Dodiuk, Chem. Phys. Lett., 26, 545 (1974).
E. M. Kosower, H. Dodiuk, K. Tanizawa, M. Ottolenghi, and N. Orbach, J. Am. Chem. Soc., 97, 2167 (1975).
G. R. Fleming, G. Porter, R. J. Robbins, and J. A. Synowic, Chem. Phys. Lett., 52, 228 (1977).
W. O. McClure and G. H. Edelman, Biochemistry, 5, 1908 (1966).
A. Ainworth and M. T. Flanagan, Biochim. Biophys. Acta, 194, 213 (1969).
C. J. Selisker and L. Brand, J. Am. Chem. Soc., 93, 5405 (1971).
C. J. Selisker and L. Brand, J. Am. Chem. Soc., 93, 5414 (1971).
K. Harata, Bull. Chem. Soc. Jpn., 49, 1493 (1976).
H. Kondo, H. Nakatani, and K. Hiromi, J. Biochem., 79, 393 (1976).
R. I. Gelb, I. M. Schwartz, C. T. Murray, and D. A. Laufer, J. Am. Chem. Soc., 100, 3553 (1978).
A. Wishnia and S. J. Lappi, J. Mol. Biol., 82, 77 (1974).
D. J. Cram and J. M. Cram, Acc. Chem. Res., 11, 8 (1978).
J. M. Lehn, Acc. Chem. Res., 11, 49 (1978).
M. Bourgoin, K. H. Wong, J. Y. Hui, and J. Smid, J. Am. Chem. Soc., 97, 3462 (1975).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Harada, A., Furue, M. & Nozakura, Si. Cooperative Binding by Cyclodextrin Dimers. Polym J 12, 29–33 (1980). https://doi.org/10.1295/polymj.12.29
Issue Date:
DOI: https://doi.org/10.1295/polymj.12.29
Keywords
This article is cited by
-
Porous β-cyclodextrin nanotubular assemblies enable high-efficiency removal of bisphenol micropollutants from aquatic systems
Nano Research (2020)
-
Cyclodextrin-based hyperbranched polyester: synthesis, characterization, and antimicrobial activity
Journal of Coatings Technology and Research (2018)
-
Rendering cellulose fibers antimicrobial using cationic β-cyclodextrin-based polymers included with antibiotics
Cellulose (2009)
-
Continuous lifetime distributions of ?-cyclodextrin-anilinonaphthalene sulfonic acid inclusion complexes
Journal of Fluorescence (1991)