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Fluorescence Characteristics of some Flavones Probes in Different Micellar Media

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Abstract

The fluorescence characteristics of five hydroxiflavones (HFs) (some typical models of flavonols), (3 - HF, 6 - HF, 7-HF, 3, 6 - diHF and 3, 7-diHF) in the micellar media of non-ionic surfactant (Triton X-100), anionic surfactant (SDS) and the block copolymer Pluronic F127, have been investigated by means of UV–Vis and steady-state and time resolved fluorescence spectroscopies. Attention is paid to both excited-state intra-molecular proton transfer (ESIPT) as well as ground-state intermolecular proton transfer. The influence of the -OH groups as well as the effect of temperature on the dual fluorescence emission, the Normal and Tautomer emissions, are also investigated. The fluorescence quantum yield of the HFs in mentioned micellar media has been also determined. The results are discussed with relevance to the local environment of HFs as sensitive fluorescence probe in biological membrane systems.

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References

  1. Sengupta PK, Kasha M (1979) Exited state proton- transfer spectroscopy of 3-hydroxyflavone and quercetin. Chem Phys Lett 68:382–385

    Article  CAS  Google Scholar 

  2. Guharay J, Sengupta B, Sengupta PK (2001) Protein-flavonol interaction: fluorescence spectroscopy study. Proteins 43:75–81

    Article  CAS  PubMed  Google Scholar 

  3. McMorrow D, Kasha M (1984) Intramolecular excited state proton transfer in 3-hydroxiflavone, hydrogen—bonding, solvent perturbation. J Phys Chem 88:2235–2243

    Article  CAS  Google Scholar 

  4. Strandjord AJG, Courtney SH, Friedrich DM, Barbara PF (1983) Excited state dynamics of 3-hydroxyflavone. J Mc Phys Chem 87:1125–1133

    Article  CAS  Google Scholar 

  5. Quaranta A, Carturan S, Maggioni G, Ceccato R, Della Mea G (2003) Probing the chemical environment of 3-hydroxyflavone doped ormosils by a spectroscopic study of excited state intramolecular proton transfer. J Non-Cryst Solids 322:1–6

    Article  CAS  Google Scholar 

  6. Shyamala T, Mishra AK (2004) Ground- and excited-state proton transfer reaction of 3-Hydroxyflavone in dimyristoylphosphatidylcholine liposome membrane. J Photochem Photobiol 80:309–315

    Article  CAS  Google Scholar 

  7. Shynkar VV, Klymchenko AS, Kunzelmann C, Duportail G, Muller CD, Demchenko AP, Freyssinet J-M, Mely Y (2007) Fluorescent biomembrane probe for ratiometric detection of apoptosis. J Am Chem Soc 129:2187–2193

    Article  CAS  PubMed  Google Scholar 

  8. Shvadehak VV, Klymchenko AS, De Rocquigny H, Mely Y (2009) Sensing peptide-oligonucleotide interactions by a two-color fluorescence label: applications to the HIV-1 nucleocapsid protein. Nucleic Acids Res 37:e25

    Article  Google Scholar 

  9. Wolfbeis OS, Shulman SG (Ed.) (1985) Molecular luminescence spectroscopy: Methods and applications Part –I, Wiley, New York

  10. Sengupta B, Guharay J, Sengupta PK (1998) Reverse micelles of TX-100 in mixed solvents of benzene and n-hexane: fluorescence studies using 7-hydroxiflavone as probe. J Surf Sci Technol 14:150–156

    CAS  Google Scholar 

  11. Dennison SM, Guharay J, Sengupta PK (1999) Intramolecular excited proton—transfer and charge transfer fluorescence of a 3-hydroxiflavone derivative in micellar media. Spectrochim Acta, Part A 55:903–909

    Article  Google Scholar 

  12. Dennison SM, Guharay J, Sengupta PK (1999) Excited-state intramolecular proton transfer (ESIPT) and charge transfer (CT) fluorescence probe for model membranes. Spectrochim Acta, Part A 55:1127–1132

    Article  Google Scholar 

  13. Guharay J, Dennison SM, Sengupta PK (1999) Influence of different environments on the excited—state proton transfer and dual fluorescence of fisetin. Spectrochim Acta, Part A 55:1091–1099

    Article  Google Scholar 

  14. Kasha M (1987) Proton transfer spectroscopy and proton transfer lasers. Acta Phys Pol, A 71:717–729

    Google Scholar 

  15. Itoh M, Adachi T (1984) Transient absorption and two-step laser excitation fluorescence studies of the excited-state proton transfer and relaxation in the methanol solution of 7- hydroxyflavone. J Am Chem Soc 106:4320–4324

    Article  CAS  Google Scholar 

  16. Sarkar M, Sengupta PK (1991) Influence of different micellar environments on teh excited-state proton transfer luminescence of 3-hydroxiflavone. Chem Phys Lett 179:68–72

    Article  CAS  Google Scholar 

  17. Sarkar M, Ray GJ, Sengupta KP (1996) Effect of reverse micelles on the intramolecular excited state transfer (ESPT) and dual luminescence behavior of 3-hydroxiflavone. Spectrochim Acta A 52:275–278

    Article  Google Scholar 

  18. Sarkar M, Ray GJ, Sengupta KP (1996) Luminescence behaviour of 7-hydroxyflavone in aerosol OT reverse micelles: excited-state proton transfer and red-edge excitation effects. J Photochem Photobiol 95:157–160

    Article  CAS  Google Scholar 

  19. Kasha M (1986) Proton-transfer spectroscopy: perturbation of tautomeric potential. J Chem Soc, Faraday Trans 82:2379–2392

    Article  CAS  Google Scholar 

  20. Klymchenko AS, Demchenko AP (2002) Probing AOT reverse micelles with two-color fluorescence dyes based on 3-hydroxychromone. Langmuir 18:5637–5639

    Article  CAS  Google Scholar 

  21. Guharay J, Chaudhuri R, Chakrabarti A, Sengupta PK (1997) Excited state proton transfer fluorescence of 3-hydroxyflavone in model membranes. Spectrochim Acta A 53:457–462

    Article  Google Scholar 

  22. Mondal S, Basu S, Mandal D (2009) Ground –and excited-state proton-transfer reaction of 3-hydroxyflavone in aqueous micelles. Chem Phys Lett 479:218–223

    Article  CAS  Google Scholar 

  23. Demchenko AP, Klymchenko AS, Pivovarenko VG, Ercelen S, Duportail G, Mely Y (2003) Multiparametric color-changing fluorescence probes. J Fluoresc 13:291–295

    Article  CAS  Google Scholar 

  24. Basu S, Mondal S, Mandal D (2010) Proton transfer reactions in nanoscopic polar domains:3-hydroxyflavone in AOT reverse micelles. J Chem Phys 132:034701–1/6

    Article  PubMed  Google Scholar 

  25. Voicescu M, Ionescu S, Gatea F (2013) Photophysical properties of some flavone probes in homogeneous media. J Fluoresc. doi:10.1007/s10895-013-1272-0

    Google Scholar 

  26. Melhuish WH (1961) Quantum efficiencies of fluorescence of organic substances: effect of solvent and concentration of the fluorescent solute. J Phys Chem 65:229–235

    Article  CAS  Google Scholar 

  27. Lakowicz JR (1983) Principles of fluorescence spectroscopy. Plenum Press, New York

    Book  Google Scholar 

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Acknowledgments

This work was supported by a grant of the Romanian National Authority for Scientific Research, CNCS – UEFISCDI, project number PN-II-RU-TE-2012-3-0055.

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Authors and Affiliations

  1. Institute of Physical Chemistry “Ilie Murgulescu”, Romanian Academy, Splaiul Independentei 202, 060021, Bucharest, Romania

    Mariana Voicescu

  2. Department of Physical Chemistry, University of Bucharest, Bd Regina Elisabeta 4-12, Bucharest, 030018, Romania

    Sorana Ionescu

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  1. Mariana Voicescu
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  2. Sorana Ionescu
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Correspondence to Mariana Voicescu.

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Voicescu, M., Ionescu, S. Fluorescence Characteristics of some Flavones Probes in Different Micellar Media. J Fluoresc 24, 735–743 (2014). https://doi.org/10.1007/s10895-013-1346-z

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  • DOI: https://doi.org/10.1007/s10895-013-1346-z

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