Study of the complexation of fisetin with cyclodextrins

Journal of Physical Chemistry A

Volumn 110, Issue 36, 2006, Pages 10545-10551

  Guzzo, Mariana R ^a   Uemi, Miriam ^a   Donate, Paulo M ^a   Nikolaou, Sofia ^a   Machado, Antonio Eduardo H ^b   Okano, Laura T ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODEXTRINS; FISETIN; MOLECULAR MODELING; PROTON TRANSFER;

ABSORPTION; COMPLEXATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBABILITY DENSITY FUNCTION; QUANTUM THEORY; ULTRAVIOLET RADIATION;

OLIGOMERS;

CYCLODEXTRIN; FISETIN; FLAVONOID;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SENSITIVITY AND SPECIFICITY; SOLUBILITY; THERMODYNAMICS;

CYCLODEXTRINS; FLAVONOIDS; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; SENSITIVITY AND SPECIFICITY; SOLUBILITY; THERMODYNAMICS;

EID: 33749607744     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0613337     Document Type: Article

References (28)

1. Sytnik, A.; Gormin, D.; Kasha, M. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11968.
2. Guharay, J.; Dennison, S. M.; Sengupta, P. K. Spectrochim. Acta, Part A 1999, 55, 1091.
3. Falkovskaia, E.; Sengupta, P. K.; Kasha, M. Chem. Phys. Lett. 1998, 297, 109.
4. Sengupta, B.; Banerjee, A.; Sengupta, P. K. FEBS Lett. 2004, 570, 777.
5. Sengupta, B.; Banerjee, A.; Sengupta, P. K. J. Photochem. Photobiol, B 2005, 80, 79.
6. Wolfbeis, O. S.; Knierzinger, A.; Schipfer, R. J. Photochem. 1983, 21, 67.
7. Szejtli, J. Chemistry, Physical and Biological Properties of Cyclodextrins. In Cyclodextrins; Szejtli, J., Osa, T., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 3; p 5.
8. Szejtli, J. Inclusion of Guest Molecules, Selectivity and Molecular Recognition by Cyclodextrins. In Cyclodextrins; Szejtli, J., Osa, T., Eds.; Eisevier Science Ltd.: New York, 1996; Vol. 3; p 189.
9. Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703.
10. Higuchi, T.; Connors, K. A. Phase-Solubility Techniques. In Advances in Analytical Chemistry and Instrumentation; Interscience Publishers: New York, 1965; Vol. 4; p 117.
11. Details of the theoretical calculations are provided in the Supporting Information.
12. Details of the results of the theoretical calculations for the intramolecular excited state proton transfer are provided in the Supporting Information.
13. Barra, M.; Bohne, C.; Scaiano, J. C. J. Am. Chem. Soc. 1990, 112, 8075.
14. Jovanovic, S. V.; Steenken, S.; Tosic, M.; Marjanovic, B.; Simic, M. G. J. Am. Chem. Soc. 1994, 116, 4846.
15. Okano, L. T.; Barros, T. C.; Chou, D. T. H.; Bennet, A. T.; Bohne, C. J. Phys. Chem. B 2001, 105, 2122.
16. Detailed results from the quantum-mechanics calculations for the Fis-β-CD complex at different pH values are provided in the Supporting Information.
17. Murphy, R. S.; Barros, T. C.; Barnes, J.; Mayer, B.; Marconi, G.; Bohne, C. J. Phys. Chem. A 1999, 103, 137.
18. Christoff, M.; Okano, L. T.; Bohne, C. J. Photochem. Photobiol., A: Chem. 2000, 134, 169.
19. Haiyun, D.; Jianbin, C.; Guomei, Z.; Shaomin, S.; Jinhao, P. Spectrochim. Acta, Part A 2003, 59, 3421.
20. (a) Szejtli, J. Inclusion of Guest Molecules, Selectivity and Molecular Recognition by Cyclodextrins. In Cyclodextrins; Szejtli, J., Osa, T., Eds.; Elsevier Science Ltd.: New York, 1996; Vol. 3; p 200.
21. (b) Suzuki,M.; Kajtár, M.; Szejtli, J.; Vikmon, M.; Fenyvesi, E. Carbohydr. Res. 1992, 223, 71.
22. 1H NMR spectra in different media are available in the Supporting Information.
23. Rasku, S.; Wähälä, K. Tetrahedron 2000, 56, 913.
24. Awad, H. M.; Boersma, M. G.; Boeren, S.; van Bladeren, P. J.; Vervoort, J.; Rietjens, I. M. C. M. Chem. Res. Toxicol. 2001, 14, 398.
25. Lee, J.-C.; Lee, K.-Y.; Kim, J.; Na, C.-S.; Jung, N.-C.; Chung, G.H.; Jang, Y.-S. Food Chem. Toxicol. 2004, 42, 1383.
26. Awad, H. M.; Boersma, M. G.; Boeren, S.; van Bladeren, P. J.; Vervoort, J.; Rietjens, I. M. C. M. Chem. Res. Toxicol. 2002, 15, 343.
27. Toma, S. H.; Uemi, M.; Nikolaou, S.; Tomazela, D. M.; Eberlin, M. N.; Toma, H. E. Inorg. Chem. 2004, 43, 3521.
28. Schneider, H.-J.; Hacket, F.; Rüdiger, V. Chem. Rev. 1998, 98, 1755.