Highly selective binding behavior of (diethylamino)coumarin-modified β-cyclodextrin with bile acids
- 37 Downloads
A (diethylamino)coumarin-modified β-cyclodextrin (1) increased its fluorescence intensity upon guest binding in an aqueous media, and this phenomenon was used to detect organic compounds, specifically bile acids. The modified β-cyclodextrin chemosensor in this study exhibited remarkable molecular recognition, and particularly high selectivity toward certain bile acids, including lithcholic, chenodeoxycholic, and ursodeoxycholic acid.
KeywordsChemosensor Cyclodextrin Molecular recognition Bile acids Fluorescence
We are grateful to Nihon Shokuhin Kako Co., Ltd. for the generous gift of β-CD. The authors would like to thank Hideki Kurokawa for measuring the elemental analysis, and to Masayo Katsumata from the University of Yamanashi and Yoshihisa Sei from the Tokyou institute of Technology for supporting the NMR measurements. This article is dedicated to the 15th anniversary of the passing of Professor Akihiko Ueno from the Tokyo Institute of Technology, who passed away on March 23, 2003. One of the authors, T. K., hopes that Professor Ueno will enjoy reading this paper in heaven.
- 1.Czarnik, W. (ed.): Fluorescent Chemosensors for Ion and Molecule Recognition. American Chemical Society, Washington DC (1993)Google Scholar
- 3.Szeijtli, J.: Cyclodextrin and Inclusion Compounds. Academic Kiado, Budapest (1982)Google Scholar
- 4.Szejtli, J., Osa, T. (eds.): Comprehensive Supramolecular Chemistry, vol. 3. Pergamon, Oxford (1996)Google Scholar
- 6.Ueno, A., Ikeda, H., Ramamurthy, V. and R, K., Schanze (eds.), Molecular and Supramolecular Photochemistry, vol. 8. Marcel Dekker, New York (2001) pp. 461–503Google Scholar
- 10.Ikeda, H., Nakamura, M., Ise, N., Oguma, N., Nakamura, A., Ikeda, T., Toda, F., Ueno, A.: Fluorescent cyclodextrins for molecule sensing: fluorescent properties, NMR characterization, and inclusion phenomena of N-dansylleucine-modified cyclodextrins. J. Am. Chem. Soc. 118, 10980–10988 (1996)CrossRefGoogle Scholar
- 12.Hamasaki, K., Ikeda, H., Nakamura, A., Ueno, A., Toda, F., Suzuki, I., Osa, T.: Fluorescent sensors of molecular recognition. Modified cyclodextrins capable of exhibiting guest-responsive twisted intramolecular charge transfer fluorescence. J. Am. Chem. Soc. 115, 5035–5040 (1993)CrossRefGoogle Scholar