Abstract
Plant flavonols, and related compounds of the flavonoid group, are attracting enormous attention as novel therapeutic drugs for free radical mediated and other human diseases. Their high potency and low systemic toxicity make them viable alternatives to conventional therapeutics. On a different scenario, from the spectroscopic context, flavonols have emerged as one of the best known class of molecules exhibiting ultrafast excited state intramolecular proton transfer (ESIPT) leading to ‘two color’ fluorescence emissions which are exquisitely sensitive to environmental perturbations. Regarding therapeutic aspects of flavonols, the question of their physiological targets and the mode of interaction with such targets loom large This article presents perspectives, illustrating the potential usefulness of flavonols as their own fluorescent ‘reporters’ for noninvasive sensing of their interactions with representative biologically relevant targets encompassing carrier proteins, duplex and quadruplex DNA, and model and natural biomembranes. Representative and recent findings from our laboratory, exemplifying novel uses of flavonols as multiparametric fluorescence probes, are appropriately highlighted.
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References
Lakowicz JR (2006) Principles of fluorescence spectroscopy, 3rd edn. Springer, New York Inc.
Demchenko AP Introduction to fluorescence Sensing, 2nd ed. Springer 2015
Demchenko AP, Klymchenko AS, Pivovarenko VG, Ercelen S (2002) In: Krayenhof R, Visser AJWG, HC G (eds) Fluorescence spectroscopy, imaging and probes-new tools in chemical, physical and life sciences, Springer series on fluorescence methods and applications, vol 2. Springer, Heidelberg, Germany
Krasieva TB, Ehren J, O’Sullivan T, Tromberg BJ, Maher P (2015) Cell and brain tissue imaging of the flavonoid fisetin using label-free two-photon microscopy. Neurochem Int 89:243–248
Chaudhuri S, Sengupta B, Taylor J, Pahari B, Sengupta PK (2013) Interactions of dietary flavonoids with proteins: insights from fluorescence spectroscopy and other related biophysical studies. Curr Drug Metab 14:491–503 and references cited therein
Protti S, Mezzetti A (2012) Any color you like. Excited state and ground state proton transfer in flavonols and applications. In: Albini A (ed) Photochemistry, Vol, vol 40, pp 295–322
Sengupta PK, Banerjee A, Sengupta B 2006 Exploring the interactions of therapeutically active plant flavonoids with biological targets: Insights from fluorescence spectroscopy. In: Satoshi K (ed) Photoelectrochemistry and photobiology in the environment, energy & fuel, Research Signpost. Chap.5, 20–226, and references cited therein
Andersen OM, Markham KR (eds) (2006) Flavonoiids: chemistry, biochemistry and applications. CRC Press, Boca Raton
Rice-Evans CA, Diplock AT (1993) Current status of antioxidant therapy. Free Radic Biol Med 15:77–96
Havsteen BH (2002) The biochemistry and medical significance of the flavonoids. Pharmacol Therapeut 96:67–202
Pahari B, Sengupta B, Chakraborty S, Thomas B, McGowan D, Sengupta PK (2013) Contrasting binding of fisetin and daidzein in gamma-cyclodextrin nanocavity. J Photochem Photobiol B:Biology 118:33–41
Banerjee A, Basu K, Sengupta PK (2008) Interaction of 7-hydroxyflavone with serum albumin: a spectroscopic study. J Photochem Photobiol B Biol 90:33–40
Chaudhuri S, Pahari BP, Sengupta PK (2009) Ground- and excited-state proton transfer and antioxidant activity of 7-hydroxyflavone in model membranes: absorption and fluorescence spectroscopic studies. Biophys Chem 139:29–36
Rusznyák S, Szent-Görgyi A, Vitamin P (1936) flavonols as vitamins. Nature 138:27–27
Sengupta PK, Kasha M (1979) Excited state proton-transfer spectroscopy of 3-hydroxyflavone and quercetin. Chem Phys Lett 68:382–385
Demchenko AP, Heldt J, Waluk J, Chou P-T, Sengupta PK, Brizhnik L, del Valle JC (2014) From photochemistry and flowers to spectroscopy and music: the unique and diverse achievements of Michael Kasha. Angew Chem 53:14316–14324
Kasha M (1986) Proton-transfer spectroscopy: perturbation of the tautomerization potential. J Chem Soc Faraday Trans 2 82:2379–2392
Ameer-Beg S, Ormson SM, Brown RG, Matousek P, Towrie M, Nibbering ETJ, Foggi P, Neuwahl FVR (2001) Ultrafast Measurements of Excited State Intramolecular Proton Transfer (ESIPT) in room temperature solutions of 3-hydroxyflavone and derivatives. J Phys Chem A 105:3709–3718
Bader AN, Ariese F, Gooijer C (2002) Proton transfer in 3-Hydroxyflavone studied by high-resolution 10 K laser-excited Shpol’skii spectroscopy. J Phys Chem A 106:2844–2849
Demchenko AP, Tang K-C, Chou P-T (2013) Excited-state proton coupled charge transfer modulated by molecular structure and media polarization. Chem Soc Rev 42:1379–1408
Guharay J, Sengupta B, Sengupta PK (2001) Protein–flavonol interaction: fluorescence spectroscopic study. Proteins: structure, function. Genetics 43:75–81 and references cited therein
Pahari B, Chaudhuri S, Chakraborty S, Sengupta PK (2015) Ground and excited state proton transfer of the bioactive plant flavonol robinetin in a protein environment. J Phys Chem B 119:2533–2545
Sengupta B, Sengupta PK (2002) The interaction of quercetin with human serum albumin: a fluorescence spectroscopic study. Biochem Biophys Res Commun 299:400–403
Sengupta B, Sengupta PK (2003) Binding of quercetin with human serum albumin: a critical spectroscopic study. Biopolymers 72:427–434
Sengupta B, Pahari B, Blackmon L, Sengupta PK (2013) Prospect of bioflavoinoid fisetin as a quadruplex DNA ligand: a biophysical approach. PLoS One 8(6):e65383. doi:10.1371/journal.pone.0065383
Pahari B, Chakraborty S, Chaudhuri S, Sengupta B, Sengupta PK (2012) Binding and antioxidant properties of therapeutically important plant flavonoids in biomembranes: Insights from spectroscopic and quantum chemical studies. Chem Phys Lipids 165:488–496
Pahari B, Chakraborty S, Sengupta PK (2011) Encapsulation of 3-hydroxyflavone in gamma- cyclodextrin nanocavities: excited state proton transfer fluorescence and molecular docking studies. J Mol Struct 1006:483–488
Chaudhuri S, Chakraborty S, Sengupta PK (2011) Probing the interactions of hemoglobin with antioxidant flavonoids via fluorescence spectroscopy and molecular modeling studies. Biophys Chem 154(2011):26–34
Chaudhuri S, Pahari BP, Sengupta B, Sengupta PK (2010) Binding of the bioflavonoid robinetin with model membranes and hemoglobin: Inhibition of lipid peroxidation and protein glycosylation. J Photochem Photobiol B:Biology 98:12–19
Sengupta PK, Chaudhuri S (2010) “Interactions of therapeutically active plant flavonols with biological targets: insights from fluorescence spectroscopic studies” (Invited article). J Indian Chem Soc 2010(87):213–220
Chaudhuri S, Basu K, Sengupta B, Banerjee A, Sengupta PK (2008) Ground and excited state proton transfer and antioxidant activity of 3-hydroxyflavone in egg yolk phosphatidylcholine liposomes: absorption and fluorescence spectroscopic studies. Luminescence 23:l397–l403
Banerjee A, Basu K, Sengupta PK (2007) Effect of beta-cyclodextrin nanocavity confinement on the photophysics of robinetin. J Photochem Photobiol B Biol 89:88–97
Chaudhuri S, Banerjee A, Basu K, Sengupta B, Sengupta PK (2007) Interaction of flavonoids with red blood cell membrane lipids and proteins: antioxidant and antihemolytic effects. Int J Biol Macromol 2007(41):42–48
Banerjee A, Sengupta PK (2006) Encapsulation of 3-hydroxyflavone and fisetin in beta-cyclodextrins: Excited state proton transfer fluorescence and molecular mechanics studies. Chem Phys Lett 424:379–386
Sengupta B, Banerjee A, Sengupta PK (2005) Interactions of the plant flavonoid fisetin with macromolecular targets: insights from fluorescence spectroscopic studies. J Photochem Photobiol B Biol 80:79–86
Sengupta B, Banerjee A, Sengupta PK (2004) Investigations on the binding and antioxidant properties of the plant flavonoid fisetin in model biomembranes. FEBS Lett 570(2004):77–81
Sengupta B, Banerjee A, Sengupta PK (2005) Interactions of the plant flavonoid fisetin with macromolecular targets: insights from fluorescence spectroscopic studies. J Photochem Photobiol B Biol 80:79–86
Gutzeit HO, Henker Y, Kind B, Franz A (2004) Specific interactions of quercetin and other flavonoids with target proteins are revealed by elicited fluorescence. Biochem Biophys Res Commun 318:490–495
Mohapatra M, Mishra AK (2011) Photophysical behavior of fisetin in dimyristoylphosphatidylcholine liposome membrane. J Phys Chem B 115:9962–9970
Shyamala T, Mishra AK (2004) Ground- and excited-state proton transfer reaction of 3-hydroxyflavone in dimyristoylphosphatidylcholine liposome membrane. Photochem Photobiol 80:309–315
Jana B, Senapati S, Ghosh D, Bose D, Chattopadhyay N (2012) Spectroscopic exploration of mode of binding of ctDNA with 3-hydroxyflavone: a contrast to the mode of binding with flavonoids having additional hydroxyl groups. J Phys Chem B 116:639–645
Sengupta B, MR S, DE D Jr, Harris K, RM W, Ward D, D’Asia G, Hampton C (2015) Excited state proton transfer of natural flavonoids and their chromophores in duplex and tetraplex DNAs. J Phys Chem B 119:2546–2556
Sytnik A, Gormin D, Kasha M (1994) Interplay between excited-state intramolecular proton transfer and charge transfer in flavonols and their use as protein-binding-site fluorescence probes. Proc Natl Acad Sci U S A 91:11968–11972
Böhl M, Zupalla C, Takalov SV, Hoflack B, Gutzeit HO (2005) Identification of actin as quercetin-binding protein: an approach to identify target molecules for specific ligands. Anal Biochem 34:295–299
Wybranowski T, Kruszewski S (2014) Optical spectroscopy study of the interaction between quercetin and human serum albumin. Acta Phys Pol A 125:A-57–A-60
Mishra B, Barik A, Priyadarshini KI, Mohan H (2005) Fluorescence spectroscopic studies on binding of a flavonoid antioxidant quercetin to serum albumins. J Chem Sci 117:641–647
Böhl M, Tietze S, Sokoll A, Madathil S, Pfennig F, Apostolakis J, Fahmy K, Gutzeit HO (2007) Flavonoids affect actin functions in cytoplasm and nucleus. Biophys J 93:2767–2780
Voicescu M, Ionescu S, Nistor C (2017) Spectroscopic study of 3-hydroxyflavone-protein interactions in lipidic bi-layers immobilized on silver nanoparticles. Spectrochim Acta A 170:1–8 (in press)
Voicescu M, Ionescu S (2015) 3-hydroxyflavone-Bovine serum albumin interaction in dextran medium. J Serb Chem Soc 80:517–528
Voicescu M, Bandula R (2015) 3,6-dihydroxyflavone/ Bovine serum albumin interaction in cyclodextrin medium: absorption and emission monitoring. Spectrochim Acta A 138:628–636
Latruffe N, Menzel M, Delmas D, Buchet R, Lancon A (2014) Compared binding properties between resveratrol and other polyphenols to plasmatic albumin: consequences for the health protecting effect of dietary plant microcomponents. Molecules 19:17066–17077
Falkovskaia E, Sengupta PK, Kasha M (1998) Photophysical induction of dual fluorescence of quercetin and related hydroxyflavones upon intermolecular H-bonding to solvent matrix. Chem Phys Lett 297:109–114
Rolinski OJ, Martin A, Birch DJS (2008) Human serum albumin-flavonoid interactions monitored by means of tryptophan kinetics. Ann N Y Acad Sci 1130:314–319
Rolinski OJ, Martin A, Birch JSD (2007) Human serum albumin and quercetin interactions monitored by time-resolved fluorescence: evidence for enhanced discrete rotamer conformations. J Biomed Opt 12(3):034013 -1–034013-7
Dufour C, Dangles O (2005) Flavonoid –serum albumin complexation: determination of binding constants and binding sites by fluorescence spectroscopy. Biochim Biophys Acta 172:164–173
Singha Roy A, Dinda AK, Dasgupta S (2012) Study of the interaction between fisetin and human serum albumin: a biophysical approach. Protein Pept Lett 19:604–615
Xiao J, Kai G (2012) A review of dietary polyphenol-plasma protein interactions: characterization, influence on the bioactivity, and structure-affinity relationship. Crit Rev Food Sci Nutr 52:85–101
Carter DC, He XM (1992) Atomic structure and chemistry of human serum albumin. Nature 358:209–215
S N, Balasubramanian S (2006) Quadruplex Nucleic acids. RSC, Cambridge, U.K.
Wang Y, Y H, Wu T, Zhou X, Shao Y (2015) Trigegered excited-state intramolecular proton transfer fluorescence for selective triplex DNA recognition. Anal Chem 87(23):11620–11624
Acknowledgements
The author gratefully acknowledges all his students, post doctoral associates, and collaborators whose dedicated inputs over the years led to the development and successful growth and progress of the research highlighted in this article. He is thankful to the University Grants Commission (UGC), India for award of an Emeritus Fellowship, and to the Department of Biophysics, Molecular Biology and Bioinformatics, University of Calcutta for facilities and invaluable support during preparation of this manuscript.
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Sengupta, P.K. (2017). Pharmacologically Active Plant Flavonols as Proton Transfer Based Multiparametric Fluorescence Probes Targeting Biomolecules: Perspectives and Prospects. In: Geddes, C. (eds) Reviews in Fluorescence 2016. Reviews in Fluorescence. Springer, Cham. https://doi.org/10.1007/978-3-319-48260-6_4
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