Abstract
The study of the host–guest association of Morin hydrate (MO) with β-cyclodextrin (β-CD) and C-hexylpyrogllol[4]arene (C-HPA) is reported in this paper. The iInclusion complexation of MO is studied by ultraviolet-visible, steady-state fluorescence, time-resolved fluorescence, 1H nuclear magnetic resonance (NMR), and two dimentional rotating-frame nuclear overhauser effect correlation (2D ROESY) spectroscopic techniques. The stoichiometry and the binding constant for the MO–β-CD complex are derived from the linearity of the Benesi–Hildebrand equation. The binding constant for the MO–C-HPA complex is calculated from the nonlinear curve fitting of fluorescence intensities. The effects of the acid strength on the absorption and fluorescence spectra of MO are studied in the absence and the presence of β-CD/C-HPA host molecules. The pK a values of the ground and the excited states are reported.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
V. Sivaramakrishnan, P. N. M. Shilpa, V. R. P. Kumar, et al., Chem.-Biol. Interact., 171, 79–88 (2008).
R. R. Zhang, A. K. Kang, M. J. Piao, et. al., Chem.-Biol. Interact., 177, 21–27 (2009).
V. Sivaramakrishnan and S. N. Devaraj, Chem.-Biol. Interact., 183, 284–292 (2010).
S. Subash and P. Subramanian, Asian Pac. J. Trop. Dis., 103–106 (2012).
T. W. Wu, L. H. Zeng, J. Wu, et al., Biochem. Pharmacol., 47, 1099–1103 (1994).
L. D. Kok, Y. P. Wong, T. W. Wu, et al., Life Sci., 67, 91–99 (2000).
R. Zhang, K. A. Kang, M. J. Piao, et al., Chem.-Biol. Interact., 177, 21–27 (2009).
G. Ibarretxe, M. V. Sanchez-Gomez, M. R. Campos-Esparza, et al., Glia, 53, 201–211 (2006).
T. Yugarani, B. K. Tan, M. Teh, et al., Lipids, 27, 181–186 (1992).
D. J. Cram, Nature, 356, 29–36 (1992).
M. M. Conn and J. Rebek Jr., Chem. Rev., 97, 1647–1668 (1997).
B. C. Hamann, K. D. Shimizu, and J. Rebek Jr., Angew. Chem., Int. Ed. Engl., 35, 1326–1329 (1996).
A. Shivanyuk, J. C. Friese, S. Doring, et al., J. Org. Chem., 68, 6489–6496 (2003).
J. Rebek Jr., Chem. Commun., 637–643 (2000).
L. J. Prins, J. J. Verhage, F. de Jong, et al., Chem.–Eur. J., 8, 2302–2313 (2002).
H. Ito, T. Kusukawa, and M. Fujita, Chem. Lett., 598/599 (2000).
J. Szejtli, Cyclodextrin and Their Inclusion Complexes, Akademiai Kiado, Budapest (1982).
S. Li and W. C. Purdy, Chem. Rev., 92, 1457 (1992).
J. Szejtli, in: Cyclodextrin Technology, Kluwer Academic Publishers, Dordrecht (1988).
G. Wenz, Angew. Chem., Int. Ed. Engl., 33, 803 (1994).
M. Jorgenson and D. R. Hartter, J. Am. Chem. Soc., 85, 878 (1963).
G. W. V. Cave, J. Antesberger, L. J. Barbour, et al., Angew. Chem., Int. Ed., 43, 5263–5266 (2004).
A. Douhal, Cyclodextrin Materials Photochemistry, Photophysics and Photobiology, vol. 1, Elsevier, Amsterdam (2006). pp. 9–11.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © 2015 S. Chandrasekaran, I. V. Muthu, V. Enoch.
The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 56, No. 7, pp. 1389-1397, November-December, 2015.
Rights and permissions
About this article
Cite this article
Chandrasekaran, S., Muthu, I.V. & Enoch, V. Host–guest association of Morin with β-CD and C-hexylpyrogallol[4]arene: Structure of the complexes and the effect of pH. J Struct Chem 56, 1325–1333 (2015). https://doi.org/10.1134/S0022476615070136
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476615070136