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Spectroscopic Properties of some Hydroxylated 2-Stilbazole Derivatives

  • Alexander V. SemenovEmail author
  • Olga I. Balakireva
  • Irina V. Tarasova
  • Elena V. Semenova
  • Olga V. Minaeva
ORIGINAL ARTICLE
  • 30 Downloads

Abstract

The spectroscopic properties for a number of new hydroxylated 2-stilbazoles were studied by absorption and fluorescence spectroscopy. The maximum absorption and emission wavelengths, the molar extinction coefficients, and the Stokes shift values of derivatives were given. The dependence of the spectral characteristics on pH was shown. The possibility of creating molecular logic systems and fluorescent dyes for bioimaging based on these derivatives was demonstrated. The dependence of fluorescence on the medium redox properties was established for an one of derivatives. The possibility of a fluorescent probe creating on its basis to assess the oxidative state of living systems was demonstrated. The probe has good biocompatibility and can be successfully used for fluorescence imaging in cells.

Keywords

2-Stilbazoles Photophysical properties Fluorescent probe Cell imaging Logic gate 

Notes

Supplementary material

10895_2019_2445_MOESM1_ESM.docx (19.6 mb)
ESM 1 (DOCX 20093 kb)

References

  1. 1.
    Lipunova GN, Nosova EV, Trashakhova TV, Charushin VN (2011) Azinylarylethenes: synthesis and photophysical and photochemical properties. Russ Chem Rev 80:1115–1133.  https://doi.org/10.1070/RC2011v080n11ABEH004234 CrossRefGoogle Scholar
  2. 2.
    Baraldi I, Spalletti A, Vanossi D (2003) Rotamerism and electronic spectra of aza-derivatives of stilbene and diphenylbutadiene. A combined experimental and theoretical study. Spectrochim Acta A 59:75–86.  https://doi.org/10.1016/S1386-1425(02)00117-8 CrossRefGoogle Scholar
  3. 3.
    Haroutounian SA, Katzenellenboge JA (1988) Hydroxystilbazoles and hydroxyazaphenanthrenes: photocyclization and fluorescence studies. Photochem Photobiol 47:503–516.  https://doi.org/10.1111/j.1751-1097.1988.tb08838.x CrossRefGoogle Scholar
  4. 4.
    Waldeck DH (1991) Photoisomerization dynamics of stilbenes. Chem Rev 91:415–436.  https://doi.org/10.1021/cr00003a007 CrossRefGoogle Scholar
  5. 5.
    Han J, Burgess K (2010) Fluorescent indicators for intracellular pH. Chem Rev 110:2709–2728.  https://doi.org/10.1021/cr900249z CrossRefGoogle Scholar
  6. 6.
    Budyka MF (2017) Molecular switches and logic gates for information processing, the bottom-up strategy: from silicon to carbon, from molecules to supermolecules. Russ Chem Rev 86:181–210.  https://doi.org/10.1070/RCR4657 CrossRefGoogle Scholar
  7. 7.
    Krumova K, Cosa G (2013) Fluorogenic probes for imaging reactive oxygen species. Photochemistry 41:279–301.  https://doi.org/10.1039/9781849737722-00279 CrossRefGoogle Scholar
  8. 8.
    Semenov AV, Balakireva OI, Tarasova IV, Burtasov AA, Semenova EV, Petrov PS, Minaeva OV, Pyataev NA (2018) Synthesis, theoretical, and experimental study of radical scavenging activity of 3-pyridinol containing trans-resveratrol analogs. Med Chem Res 27:1298–1308.  https://doi.org/10.1007/s00044-018-2150-8 CrossRefGoogle Scholar
  9. 9.
    Brouwer AM (2011) Standards for photoluminescence quantum yield measurements in solution (IUPAC technical report). Pure Appl Chem 83:2213–2228.  https://doi.org/10.1351/PAC-REP-10-09-31 CrossRefGoogle Scholar
  10. 10.
    Würth C, Grabolle M, Pauli J, Spieles M, Resch-Genger U (2013) Relative and absolute determination of fluorescence quantum yields of transparent samples. Nat Protoc 8:1535–1550.  https://doi.org/10.1038/nprot.2013.087 CrossRefGoogle Scholar
  11. 11.
    Evangelio E, Hernando J, Imaz I, Bardají GG, Alibés R, Busqué F, Ruiz-Molina D (2008) Catechol derivatives as fluorescent Chemosensors for wide-range pH detection. Chem Eur J 14:9754–9763.  https://doi.org/10.1002/chem.200800722 CrossRefGoogle Scholar
  12. 12.
    Kan Y, Danner EW, Israelachvili JN, Chen Y, Waite JH (2014) Boronate complex formation with Dopa containing mussel adhesive protein retards pH-induced oxidation and enables adhesion to mica. PLoS One 9:e108869.  https://doi.org/10.1371/journal.pone.0108869 CrossRefPubMedPubMedCentralGoogle Scholar
  13. 13.
    Kannan N, Nguyen LV, Makarem M, Dong Y, Shih K, Eirew P, Raouf A, Emerman JT, Eaves CJ (2014) Glutathione-dependent and -independent oxidative stress-control mechanisms distinguish normal human mammary epithelial cell subsets. Proc Natl Acad Sci U S A 111:7789–7794.  https://doi.org/10.1073/pnas.1403813111 CrossRefPubMedPubMedCentralGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Physics and Chemistry InstituteNational Research Mordovia State UniversitySaranskRussia
  2. 2.Medicine InstituteNational Research Mordovia State UniversitySaranskRussia

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