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Volumn 118, Issue , 2013, Pages 33-41

Contrasting binding of fisetin and daidzein in γ-cyclodextrin nanocavity

Author keywords

Excited state intramolecular proton transfer; Fluorescence anisotropy; Induced circular dichroism; Molecular docking; Steady state and Time resolved fluorescence spectroscopy

Indexed keywords

DAIDZEIN; FISETIN; GAMMA CYCLODEXTRIN;

EID: 84871923952     PISSN: 10111344     EISSN: 18732682     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2012.10.010     Document Type: Article
Times cited : (28)

References (46)
  • 1
    • 0001868668 scopus 로고
    • Vitamin P: Flavonols as vitamins
    • St. Rusznyák, and A. Szent-Györgyi Vitamin P: flavonols as vitamins Nature 138 1936 27
    • (1936) Nature , vol.138 , pp. 27
    • Rusznyák, St.1    Szent-Györgyi, A.2
  • 3
    • 11144308272 scopus 로고    scopus 로고
    • Intake of specific flavonoid classes and coronary heart disease-A case-control study in Greece
    • P. Lagiou, E. Samoli, and A. Lagiou Intake of specific flavonoid classes and coronary heart disease-a case-control study in Greece European J. Clin. Nutr. 58 2004 1643 1648
    • (2004) European J. Clin. Nutr. , vol.58 , pp. 1643-1648
    • Lagiou, P.1    Samoli, E.2    Lagiou, A.3
  • 4
    • 78650744461 scopus 로고    scopus 로고
    • Multiple prototropism of fisetin in sodium cholate and related bile salt media
    • T. Selvam, and A.K. Mishra Multiple prototropism of fisetin in sodium cholate and related bile salt media Photochem. Photobiol. Sci. 10 2011 66 75
    • (2011) Photochem. Photobiol. Sci. , vol.10 , pp. 66-75
    • Selvam, T.1    Mishra, A.K.2
  • 5
    • 0036849077 scopus 로고    scopus 로고
    • The biochemistry and medical significance of the flavonoids
    • B.H. Havsteen The biochemistry and medical significance of the flavonoids Pharmacol. Therapeut. 96 2002 67 202
    • (2002) Pharmacol. Therapeut. , vol.96 , pp. 67-202
    • Havsteen, B.H.1
  • 6
    • 0033637140 scopus 로고    scopus 로고
    • The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer
    • E. Middleton Jr., C. Kandaswami, and T.C. Theoharides The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer Pharmacol. Rev. 52 2000 673 751
    • (2000) Pharmacol. Rev. , vol.52 , pp. 673-751
    • Middleton, Jr.E.1    Kandaswami, C.2    Theoharides, T.C.3
  • 7
    • 3142540615 scopus 로고    scopus 로고
    • Investigations on the binding and antioxidant properties of the plant flavonoid fisetin in model biomembranes
    • B. Sengupta, A. Banerjee, and P.K. Sengupta Investigations on the binding and antioxidant properties of the plant flavonoid fisetin in model biomembranes FEBS Lett. 570 2004 77 81
    • (2004) FEBS Lett. , vol.570 , pp. 77-81
    • Sengupta, B.1    Banerjee, A.2    Sengupta, P.K.3
  • 8
    • 84860389318 scopus 로고    scopus 로고
    • Photophysical behavior of fisetin in dimyristoylphosphatidylcholine liposome membrane
    • M. Mohapatra, and A.K. Mishra Photophysical behavior of fisetin in dimyristoylphosphatidylcholine liposome membrane J. Phys. Chem. B 115 2011 9962 9970
    • (2011) J. Phys. Chem. B , vol.115 , pp. 9962-9970
    • Mohapatra, M.1    Mishra, A.K.2
  • 9
    • 0033850592 scopus 로고    scopus 로고
    • Dietary intakes of flavonols, flavones and isoflavones by Japanese women and the inverse correlation between quercetin intake and plasma LDL cholesterol concentration
    • Y. Arai, S. Watanabe, M. Kimira, K. Shimoi, R. Mochizuki, and N. Kinae Dietary intakes of flavonols, flavones and isoflavones by Japanese women and the inverse correlation between quercetin intake and plasma LDL cholesterol concentration J. Nutr. 130 2000 2243 2250
    • (2000) J. Nutr. , vol.130 , pp. 2243-2250
    • Arai, Y.1    Watanabe, S.2    Kimira, M.3    Shimoi, K.4    Mochizuki, R.5    Kinae, N.6
  • 10
    • 0035865819 scopus 로고    scopus 로고
    • Flavonoids protect neuronal cells from oxidative stress by three distinct mechanisms
    • K. Ishige, D. Schubert, and Y. Sagara Flavonoids protect neuronal cells from oxidative stress by three distinct mechanisms Free Radic. Biol. & Med. 30 2001 433 446
    • (2001) Free Radic. Biol. & Med. , vol.30 , pp. 433-446
    • Ishige, K.1    Schubert, D.2    Sagara, Y.3
  • 11
    • 4444360215 scopus 로고    scopus 로고
    • Induction of PC12 cell differentiation by flavonoids is dependent upon extracellular signal-regulated kinase activation
    • Y. Sagara, J. Vanhnasy, and P. Maher Induction of PC12 cell differentiation by flavonoids is dependent upon extracellular signal-regulated kinase activation J. Neurochem. 90 2004 1144 1155
    • (2004) J. Neurochem. , vol.90 , pp. 1144-1155
    • Sagara, Y.1    Vanhnasy, J.2    Maher, P.3
  • 14
    • 79960904702 scopus 로고    scopus 로고
    • Improved antiangiogenic and antitumour activity of the combination of the natural flavonoid fisetin and cyclophosphamide in Lewis lung carcinoma-bearing mice
    • Y.S. Touil, J. Seguin, D. Scherman, and G.G. Chabot Improved antiangiogenic and antitumour activity of the combination of the natural flavonoid fisetin and cyclophosphamide in Lewis lung carcinoma-bearing mice Cancer Chemoth. Pharm. 68 2011 445 455
    • (2011) Cancer Chemoth. Pharm. , vol.68 , pp. 445-455
    • Touil, Y.S.1    Seguin, J.2    Scherman, D.3    Chabot, G.G.4
  • 15
    • 54249097888 scopus 로고    scopus 로고
    • A novel dietary flavonoid fisetin inhibits androgen receptor signaling and tumor growth in athymic nude mice
    • N. Khan, M. Asim, F. Afaq, Z.M. Abu, and H. Mukhtar A novel dietary flavonoid fisetin inhibits androgen receptor signaling and tumor growth in athymic nude mice Cancer Res. 68 2008 8555 8563
    • (2008) Cancer Res. , vol.68 , pp. 8555-8563
    • Khan, N.1    Asim, M.2    Afaq, F.3    Abu, Z.M.4    Mukhtar, H.5
  • 16
    • 79951814995 scopus 로고    scopus 로고
    • Anticancer activity of a combination of cisplatin and fisetin in embryonal carcinoma cells and xenograft tumors
    • R. Tripathi, T. Samadder, S. Gupta, A. Surolia, and C. Shaha Anticancer activity of a combination of cisplatin and fisetin in embryonal carcinoma cells and xenograft tumors Mol. Cancer Ther. 10 2011 255 268
    • (2011) Mol. Cancer Ther. , vol.10 , pp. 255-268
    • Tripathi, R.1    Samadder, T.2    Gupta, S.3    Surolia, A.4    Shaha, C.5
  • 18
    • 0033011895 scopus 로고    scopus 로고
    • Dietary isoflavones: Biological effects and relevance to human health
    • K.D.R. Setchell, and A. Cassidy Dietary isoflavones: biological effects and relevance to human health J. Nutr. 129 1999 758 767
    • (1999) J. Nutr. , vol.129 , pp. 758-767
    • Setchell, K.D.R.1    Cassidy, A.2
  • 19
    • 0032427961 scopus 로고    scopus 로고
    • Does high soy milk intake reduce prostate cancer incidence? the adventist health study (United States)
    • B.K. Jacobsen, S.F. Knutsen, and G.E. Fraser Does high soy milk intake reduce prostate cancer incidence? The adventist health study (United States) Cancer Causes Control 9 1998 553 557
    • (1998) Cancer Causes Control , vol.9 , pp. 553-557
    • Jacobsen, B.K.1    Knutsen, S.F.2    Fraser, G.E.3
  • 20
    • 79960035234 scopus 로고    scopus 로고
    • Anthocyanin-rich blackberry extract suppresses the DNA-damaging properties of topoisomerase i and II poisons in colon carcinoma cells
    • M. Esselen, U. Boettler, N. Teller, S. Bachler, M. Hutter, C.E. Rufer, S. Skrbek, and D. Marko Anthocyanin-rich blackberry extract suppresses the DNA-damaging properties of topoisomerase I and II poisons in colon carcinoma cells J. Agric. Food Chem. 59 2011 6966 6973
    • (2011) J. Agric. Food Chem. , vol.59 , pp. 6966-6973
    • Esselen, M.1    Boettler, U.2    Teller, N.3    Bachler, S.4    Hutter, M.5    Rufer, C.E.6    Skrbek, S.7    Marko, D.8
  • 21
    • 0037383299 scopus 로고    scopus 로고
    • Bioavailability, disposition, and dose-response effects of soy isoflavones when consumed by healthy women at physiologically typical dietary intakes
    • K.D.R. Setchell, N.M. Brown, P.B. Desai, L. Zimmer-Nechimias, B. Wolfe, A.S. Jakate, V. Creutzinger, and J.E. Heubi Bioavailability, disposition, and dose-response effects of soy isoflavones when consumed by healthy women at physiologically typical dietary intakes J. Nutr. 133 2003 1027 1035
    • (2003) J. Nutr. , vol.133 , pp. 1027-1035
    • Setchell, K.D.R.1    Brown, N.M.2    Desai, P.B.3    Zimmer-Nechimias, L.4    Wolfe, B.5    Jakate, A.S.6    Creutzinger, V.7    Heubi, J.E.8
  • 22
    • 79955473013 scopus 로고    scopus 로고
    • Antioxidant and prooxidant properties of flavonoids
    • D. Prochazkova, I. Bousova, and N. Wilhelmova Antioxidant and prooxidant properties of flavonoids Fitoterapia 82 2011 513 523
    • (2011) Fitoterapia , vol.82 , pp. 513-523
    • Prochazkova, D.1    Bousova, I.2    Wilhelmova, N.3
  • 23
    • 14744287885 scopus 로고    scopus 로고
    • Polyphenols and prevention of cardiovascular diseases
    • C. Manach, A. Mazur, and A. Scalbert Polyphenols and prevention of cardiovascular diseases Curr. Opin. Lipidol. 16 2005 77 84
    • (2005) Curr. Opin. Lipidol. , vol.16 , pp. 77-84
    • Manach, C.1    Mazur, A.2    Scalbert, A.3
  • 24
    • 0000579491 scopus 로고
    • Excited state proton-transfer spectroscopy of 3-hydroxyflavone and quercetin
    • P.K. Sengupta, and M. Kasha Excited state proton-transfer spectroscopy of 3-hydroxyflavone and quercetin Chem. Phy. Lett. 68 1979 382 385
    • (1979) Chem. Phy. Lett. , vol.68 , pp. 382-385
    • Sengupta, P.K.1    Kasha, M.2
  • 25
    • 22144446738 scopus 로고    scopus 로고
    • Interactions of the plant flavonoid fisetin with macromolecular targets: Insights from fluorescence spectroscopic studies
    • B. Sengupta, A. Banerjee, and B. Sengupta Interactions of the plant flavonoid fisetin with macromolecular targets: Insights from fluorescence spectroscopic studies Photochem. Photobiol. B: Biol. 80 2005 79 86
    • (2005) Photochem. Photobiol. B: Biol. , vol.80 , pp. 79-86
    • Sengupta, B.1    Banerjee, A.2    Sengupta, B.3
  • 26
    • 0036712277 scopus 로고    scopus 로고
    • Excited-state proton transfer reaction in a new benzofuryl 3-hydroxychromone derivative: The influence of low polar solvents
    • A.P. Demchenko, S. Ercelen, A.D. Roshal, and A.S. Klymchenko Excited-state proton transfer reaction in a new benzofuryl 3-hydroxychromone derivative: the influence of low polar solvents Polish J. Chem. 76 2002 1287 1299
    • (2002) Polish J. Chem. , vol.76 , pp. 1287-1299
    • Demchenko, A.P.1    Ercelen, S.2    Roshal, A.D.3    Klymchenko, A.S.4
  • 28
    • 33745097261 scopus 로고    scopus 로고
    • Encapsulation of 3-hydroxyflavone and fisetin in b-cyclodextrins: Excited state proton transfer fluorescence and molecular mechanics studies
    • references cited therein
    • A. Banerjee, and P.K. Sengupta Encapsulation of 3-hydroxyflavone and fisetin in b-cyclodextrins: excited state proton transfer fluorescence and molecular mechanics studies Chem. Phys. Lett. 424 2006 379 386 and references cited therein
    • (2006) Chem. Phys. Lett. , vol.424 , pp. 379-386
    • Banerjee, A.1    Sengupta, P.K.2
  • 30
    • 77249122561 scopus 로고    scopus 로고
    • Design and development of nanovehicle-based delivery systems for preventive or therapeutic supplementation with flavonoids
    • G. Leonarduzzi, G. Testa, B. Sottero, P. Gamba, and G. Poli Design and development of nanovehicle-based delivery systems for preventive or therapeutic supplementation with flavonoids Curr. Med. Chem. 17 2010 74 95
    • (2010) Curr. Med. Chem. , vol.17 , pp. 74-95
    • Leonarduzzi, G.1    Testa, G.2    Sottero, B.3    Gamba, P.4    Poli, G.5
  • 31
    • 22244468039 scopus 로고    scopus 로고
    • Cyclodextrins: Application in different routes of drug administration
    • S. Shimpi, B. Chauhan, and P. Shimpi Cyclodextrins: application in different routes of drug administration Acta Pharm. 55 2005 139 156
    • (2005) Acta Pharm. , vol.55 , pp. 139-156
    • Shimpi, S.1    Chauhan, B.2    Shimpi, P.3
  • 32
    • 7644236294 scopus 로고    scopus 로고
    • Past, present, and future of cyclodextrin research
    • references cited therein
    • J. Szejtli Past, present, and future of cyclodextrin research Pure Appl. Chem. 76 2004 1825 1845 and references cited therein
    • (2004) Pure Appl. Chem. , vol.76 , pp. 1825-1845
    • Szejtli, J.1
  • 35
    • 0030203710 scopus 로고    scopus 로고
    • Distributed automated docking of flexible ligands to proteins: Parallel applications of AutoDock 2.4
    • G.M. Morris, D.S.R. Goodsell Huey, and A.J. Olson Distributed automated docking of flexible ligands to proteins: parallel applications of AutoDock 2.4 J. Comput.-Aided Mol. Des. 10 1996 293 304
    • (1996) J. Comput.-Aided Mol. Des. , vol.10 , pp. 293-304
    • Morris, G.M.1    Goodsell Huey, D.S.R.2    Olson, A.J.3
  • 36
    • 84871918594 scopus 로고    scopus 로고
    • Hyperchem, Hypercube Inc., USA, 2002
    • Hyperchem, Hypercube Inc., USA, 2002.
  • 37
    • 82755162475 scopus 로고    scopus 로고
    • Encapsulation of 3-hydroxyflavone in γ-cyclodextrin nanocavities: Excited state proton transfer fluorescence and molecular docking studies
    • B. Pahari, S. Chakraborty, and P.K. Sengupta Encapsulation of 3-hydroxyflavone in γ-cyclodextrin nanocavities: excited state proton transfer fluorescence and molecular docking studies J. Mol. Struct. 1006 2011 483 488
    • (2011) J. Mol. Struct. , vol.1006 , pp. 483-488
    • Pahari, B.1    Chakraborty, S.2    Sengupta, P.K.3
  • 38
    • 77955579939 scopus 로고    scopus 로고
    • Inclusion of chrysin in β-cyclodextrin nanocavity and its effect on antioxidant potential of chrysin: A spectroscopic and molecular modeling approach
    • S. Chakraborty, S. Basu, A. Lahiri, and S. Basak Inclusion of chrysin in β-cyclodextrin nanocavity and its effect on antioxidant potential of chrysin: a spectroscopic and molecular modeling approach J. Mole. Struct 977 2010 180 188
    • (2010) J. Mole. Struct , vol.977 , pp. 180-188
    • Chakraborty, S.1    Basu, S.2    Lahiri, A.3    Basak, S.4
  • 39
    • 77953688353 scopus 로고    scopus 로고
    • Encapsulation of serotonin in b-cyclodextrin nano-cavities: Fluorescence spectroscopic and molecular modeling studies
    • S. Chaudhuri, S. Chakraborty, and P.K. Sengupta Encapsulation of serotonin in b-cyclodextrin nano-cavities: Fluorescence spectroscopic and molecular modeling studies J. Mol. Struct. 975 2010 160 165
    • (2010) J. Mol. Struct. , vol.975 , pp. 160-165
    • Chaudhuri, S.1    Chakraborty, S.2    Sengupta, P.K.3
  • 40
    • 0001401520 scopus 로고    scopus 로고
    • Influence of different environments on the excited-state proton transfer and dual fluorescence of fisetin
    • references cited therein
    • J. Guharay, S.M. Dennison, and P.K. Sengupta Influence of different environments on the excited-state proton transfer and dual fluorescence of fisetin Spectrochim. Acta A 55 1999 1091 1099 and references cited therein
    • (1999) Spectrochim. Acta A , vol.55 , pp. 1091-1099
    • Guharay, J.1    Dennison, S.M.2    Sengupta, P.K.3
  • 41
    • 33947347089 scopus 로고
    • The dielectric constant of mixtures of ethyl alcohol and water from -5 to 40
    • J. Wyman The dielectric constant of mixtures of ethyl alcohol and water from -5 to 40 J. Am. Chem. Soc. 53 1931 3292 3301
    • (1931) J. Am. Chem. Soc. , vol.53 , pp. 3292-3301
    • Wyman, J.1
  • 42
    • 0000841283 scopus 로고
    • Evaluation of the relative effectiveness of different water-soluble β-cyclodextrin media to function as fluorescence enhancement agents
    • R.P. Frankewich, K.N. Thimmaiah, and W.L. Hinze Evaluation of the relative effectiveness of different water-soluble β-cyclodextrin media to function as fluorescence enhancement agents Anal. Chem. 63 1991 2924 2933
    • (1991) Anal. Chem. , vol.63 , pp. 2924-2933
    • Frankewich, R.P.1    Thimmaiah, K.N.2    Hinze, W.L.3
  • 43
    • 36448986041 scopus 로고    scopus 로고
    • Effect of b-cyclodextrin nanocavity confinement on the photophysics of robinetin
    • A. Banerjee, K. Basu, and P.K. Sengupta Effect of b-cyclodextrin nanocavity confinement on the photophysics of robinetin J. Photochem. Photobiol. B Biol. 89 2007 88 97
    • (2007) J. Photochem. Photobiol. B Biol. , vol.89 , pp. 88-97
    • Banerjee, A.1    Basu, K.2    Sengupta, P.K.3
  • 44
    • 0038341696 scopus 로고    scopus 로고
    • Induced circular dichroism by chiral molecular interaction
    • S. Allenmark Induced circular dichroism by chiral molecular interaction Chirality 15 2003 409 422
    • (2003) Chirality , vol.15 , pp. 409-422
    • Allenmark, S.1
  • 45
    • 80054020584 scopus 로고    scopus 로고
    • UV/Visible spectra of natural polyphenols: A time-dependent density functional theory study
    • E.H. Anouar, J. Gierschner, J.-L. Duroux, and P. Trouillas UV/Visible spectra of natural polyphenols: a time-dependent density functional theory study Food Chem. 131 2012 79 89
    • (2012) Food Chem. , vol.131 , pp. 79-89
    • Anouar, E.H.1    Gierschner, J.2    Duroux, J.-L.3    Trouillas, P.4
  • 46
    • 0025337885 scopus 로고
    • Inclusion complexes of purine nucleosides with cyclodextrins. II. Investigation of inclusion complex geometry and cavity microenvironment
    • T.X. Xiang, and B.D. Anderson Inclusion complexes of purine nucleosides with cyclodextrins. II. Investigation of inclusion complex geometry and cavity microenvironment Int. J. Pharm. 59 1990 45 55
    • (1990) Int. J. Pharm. , vol.59 , pp. 45-55
    • Xiang, T.X.1    Anderson, B.D.2


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