Binding of flavanone with β -CD/ctDNA: a spectroscopic investigation
Binding of flavanone with β -CD/ctDNA: a spectroscopic investigation
The inclusion complexation of flavanone with β -cyclodextrin was studied by ultraviolet absorption, steady state fluorescence, time-resolved fluorescence, and 2D ROESY nuclear magnetic resonance spectroscopic techniques. A 1:1 stoichiometric ratio was determined for the inclusion of flavanone with β -cyclodextrin. The Stern Volmer constant for the accessible fraction of the binding of flavanone with β -cyclodextrin, and the binding constant for the flavanone β - cyclodextrin complex are reported. The flavanone β -cyclodextrin inclusion complex was characterized by 2D ROESY NMR spectroscopy. The binding of flavanone with ctDNA and the effect of β -cyclodextrin on the binding of flavanone to ctDNA were studied by absorption and fluorescence techniques. Binding constants are reported for the binding of flavanone with ctDNA and flavanone β -cyclodextrin with ctDNA. The mode of binding of flavanone to DNA and formation of inclusion complex with β -cyclodextrin are proposed, supported by molecular modeling. The studies imply that β -cyclodextrin acts as carrier of flavanone for binding with DNA.
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- Shen, X.; Belletete, M.; Durocher, G. J . Phys. Chem. B. 1997, 101, 82128220.
- Bender, M. L.; Komiyama, M. In Cyclodextrin Chemistry; SpringerVerlag: New York, NY, USA, 1978.
- Saenger, W. Angew. Chem., Int. Ed. Engl. 1980, 19, 344362.
- Szejtli, J. In Cyclodextrins and Their Inclusion Complexes; Akademiai Kiado: Budapest, Hungary, 1982.
- Li, S.; Purdy, W. C. Chem. Rev. 1992, 92, 14571470.
- Szejtli, J. In Cyclodextrin Technology; Kluwer Academic Publishers: Dordrecht, Germany, 1988.
- Yousuf, S.; Enoch I. V. M. V. AAPS Pharm. Sci. Tech. 2013, 14, 770781.
- Brewster, M. E.; Vandecruys, R.; Verreck, G.; Noppe, M.; Peeters, J. J. Incl. Phenom. Macro. Chem. 2002, 44, 3538.
- Enoch, I. V. M. V.; Yousuf, S. J. Solution Chem. 2013, 42, 470484.
- Stefansson, E.; Loftssonn, T. J. Incl. Phenom. Macro. Chem. 2002, 44, 2327.
- Boumendjel, A.; Ronot, X.; Boutonnat, J. Curr. Drug Targets, 2009, 10, 363371.
- Ducki, S. Anticancer Agents Med. Chem. 2009, 9, 336347.
- Kontogiorgis, C.; Mantzanidou, M.; Hadjipavlou-Litina, D. Mini. Rev. Med. Chem. 2008, 8, 12241242.
- Tomar, V.; Bhattacharjee, G.; Kamaluddin, S.; Srivastava, R. K.; Puri, S. K. Eur. J. Med. Chem. 2010, 45, 745751.
- Mojzis, J.; Varinska, L.; Mojzisova, G.; Kostova, I.; Mirossay, L. Pharmacol. Res. 2008, 57, 259265.
- Sivakumar, P. M.; Priya, S.; Doble, M. Chem. Biol. Drug. Des. 2009, 73, 403415.
- Halfon, B.; Ciftci, E.; Topcu, G. Turk. J. Chem. 2013, 37, 464472.
- Pouget, C.; Lauthier F.; Simon, A.; Fagnere, C.; Basly, J. -P.; Delage, C.; Chulia, A. -J. Bio-org. Med. Chem. Lett. 2001, 11, 30953097.
- Qu, X.; Ren, J.; Riccelli, P. V.; Benight, R.; Chaives, J. B. Biochem. 2003, 42, 1196011967.
- Pindur, U.; Jansen, M.; Lemster, T. Curr. Med. Chem. 2005, 12, 28052847.
- Lakowicz, J. R. In Principles of Fluorescence Spectroscopy, 3rd ed., Springer, Singapore, 2000.
- Panda, D.; Khatua, S.; Datta, A. J. Phys. Chem. B 2007, 111, 16481656.
- Ibrahim, M. S.; Shehatta, I. S.; Al-Nayeli, A. A.; J. Pharm. Biomed. Anal. 2002, 28, 217225.
- Frezza, M.; Dou, Q. P.; Xiao, Y.; Samouei, H.; Rashidi, M.; Samari, F.; Hemmateenejad, B. J. Med. Chem. 2011, 54, 61666176.
- Sameena, Y.; Enoch, I. V. M. V. J. Lumin. 2013, 138, 105116.
- Yan, L.; Ke, G.; Lv, J.; Gui S. Z., Qing, F. L. J. Fluoresc. 2011, 21, 409414.
- Bernstein, H. J. RasMol 2.7.5.2. Molecular graphics visualization tool. Based on RasMol 2.6 by Roger Sayle Biomolecular structures group. Stevenage, Hertfordshire, UK: Glaxo Welcome Research & Development, 2011.