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Kinetics of singlet oxygen sensing using 9-substituted anthracene derivatives\(^{\#}\)

  • Devika Sasikumar
  • Reiko Kohara
  • Yuta TakanoEmail author
  • Ken-ichi Yuyama
  • Vasudevanpillai BijuEmail author
Regular Article
  • 105 Downloads

Abstract

Singlet oxygen (\(^{1}\hbox {O}_{2}\)), the lowest excited-state of molecular oxygen receives great attention in basic research and clinical and industrial settings. Despite several spectroscopic methods available for \(^{1}\hbox {O}_{2}\) sensing, fluorescence sensing receives great attention, for which many fluorogenic sensors based on substituted anthracene are reported. Nonetheless, the roles of substituents on the sensing efficiency, in terms of detection time, remain largely unknown. In this work, we examine the \(^{1}\hbox {O}_{2}\) sensing efficiency of a fluorescence sensor based on a coumarin–anthracene conjugate, which is an electron donor-acceptor dyad, and compare the efficiency with that of 9-methylanthracene. Here, \(^{1}\hbox {O}_{2}\) is generated using the standard photosensitizer Rose Bengal, which is followed by estimation of the rate of reaction of \(^{1}\hbox {O}_{2}\) to the sensor and 9-methylanthracene. The second order reaction rate of the sensor is an order of magnitude less than that of 9-methylanthracene. The lower reactivity of the sensor to \(^{1}\hbox {O}_{2}\) suggests that the roles of substituents, such as electronic interactions, steric interactions and the reactivity of precursor complexes, on sensing efficiency should be carefully considered during construction of fluorogenic molecular sensors.

Graphical Abstract

SYNOPSIS The kinetics of singlet oxygen sensing using a 9-substituted anthracene derivative is studied by comparing the photooxidation rates of a conjugate between 9-methyl anthracene and a coumarin dye. The singlet oxygen sensing rate points out that the electronic interaction and steric effect induced by the substituents on anthracene influence the kinetics of sensing.

Keywords

Singlet oxygen fluorescence sensing photochemistry athracene reaction kinetics 

Notes

Acknowledgements

D. S. acknowledges support under the English Program of Environmental Earth Science (EPEES) and a Scholarship by the Japan Student Services Organization (JASSO). V. B. acknowledges financial support (17H05243) from MEXT under the JSPS Grant-in-Aid for Scientific Research on Innovative Areas.

References

  1. 1.
    Prein M and Adam W 1996 The Schenck ene reaction: diastereoselective oxyfunctionalization with singlet oxygen in synthetic applications Angew. Chem. 35 477CrossRefGoogle Scholar
  2. 2.
    Ghogare A A and Greer A 2016 Using singlet oxygen to synthesize natural products and drugs Chem. Rev. 116 9994CrossRefGoogle Scholar
  3. 3.
    Ohloff G 1975 Singlet oxygen: A reagent in organic synthesis Pure Appl. Chem. 43 481CrossRefGoogle Scholar
  4. 4.
    Dougherty T J, Grindey G B, Fiel R, Weishaupt K R and Boyle D G 1975 Photoradiation therapy. II. Cure of animal tumors with hematoporphyrin and light J. Natl. Cancer Inst. 55 115CrossRefGoogle Scholar
  5. 5.
    Dougherty T J 1984 Photodynamic therapy (PDT) of malignant tumors Crit. Rev. Oncol. Hematol. 2 83CrossRefGoogle Scholar
  6. 6.
    Dolmans D E, Fukumura D and Jain R K 2003 Photodynamic therapy for cancer Nat. Rev. Cancer 3 380CrossRefGoogle Scholar
  7. 7.
    Kim H, Kim W, Mackeyev Y, Lee G S, Kim H J, Tachikawa T, Hong S, Lee S, Kim J, Wilson L J and Majima T 2012 Selective oxidative degradation of organic pollutants by singlet oxygen-mediated photosensitization: tin porphyrin versus \(\text{ C }_{60}\) aminofullerene systems Environ. Sci. Technol. 46 960Google Scholar
  8. 8.
    Phonsy P D, Anju S G, Jyothi K, Yesodharan S and Yesodharan E P 2015 Semiconductor Mediated Photocatalytic Degradation of Plastics and Recalcitrant Organic Pollutants in Water: Effect of Additives and Fate of Insitu Formed \(\text{ H }_{2}\text{ O }_{2}\) J. Adv. Oxid. Technol. 18 85Google Scholar
  9. 9.
    Gryglik D, Miller J S and Ledakowicz S 2007 Singlet molecular oxygen application for 2-chlorophenol removal J. Hazard. Mater. 146 502CrossRefGoogle Scholar
  10. 10.
    D’Autréaux B and Toledano M B 2007 ROS as signalling molecules: mechanisms that generate specificity in ROS homeostasis Nat. Rev. Mol. Cell Biol. 8 813CrossRefGoogle Scholar
  11. 11.
    Ray P D, Huang B W and Tsuji Y 2012 Reactive oxygen species (ROS) homeostasis and redox regulation in cellular signaling Cell Signal. 24 981CrossRefGoogle Scholar
  12. 12.
    Choi M H, Lee I K, Kim G W, Kim B U, Han Y H, Yu D Y, Park H S, Kim K Y, Lee J S, Choi C and Bae Y S 2005 Regulation of PDGF signalling and vascular remodelling by peroxiredoxin II Nature 435 347CrossRefGoogle Scholar
  13. 13.
    Petrou A L and Terzidaki A 2017 A meta-analysis and review examining a possible role for oxidative stress and singlet oxygen in diverse diseases Biochem. J. 474 2713CrossRefGoogle Scholar
  14. 14.
    Ames B N, Shigenaga M K and Hagen T M 1993 Oxidants, antioxidants, and the degenerative diseases of aging Proc. Natl. Acad. Sci. U. S. A. 90 7915CrossRefGoogle Scholar
  15. 15.
    Smith M A, Rottkamp C A, Nunomura A, Raina A K and Perry G 2000 Oxidative stress in Alzheimer’s disease Biochim. Biophys. Acta Mol. Basis Dis. 1502 139CrossRefGoogle Scholar
  16. 16.
    Davies M J 2003 Singlet oxygen-mediated damage to proteins and its consequences Biochem. Biophys. Res. Commun. 305 761CrossRefGoogle Scholar
  17. 17.
    Sies H and Menck C F 1992 Singlet oxygen induced DNA damage Mutat. Res. 275 367CrossRefGoogle Scholar
  18. 18.
    Laloi C and Havaux M 2015 Key players of singlet oxygen-induced cell death in plants Front. Plant Sci. 6 39CrossRefGoogle Scholar
  19. 19.
    DeRosa M C and Crutchley R J 2002 Photosensitized singlet oxygen and its applications Coord. Chem. Rev. 233 351CrossRefGoogle Scholar
  20. 20.
    Lion Y, Delmelle M and Van de Vorst A 1976 New method of detecting singlet oxygen production Nature 263 442CrossRefGoogle Scholar
  21. 21.
    Jiménez-Banzo A, Ragas X, Kapusta P and Nonell S 2008 Time-resolved methods in biophysics. 7. Photon counting vs. analog time-resolved singlet oxygen phosphorescence detection Photochem. Photobiol. Sci. 7 1003CrossRefGoogle Scholar
  22. 22.
    Niedre M, Patterson M S and Wilson B C 2002 Direct near-infrared luminescence detection of singlet oxygen generated by photodynamic therapy in cells in vitro and tissues in vivo J. Photochem. Photobiol. 75 382CrossRefGoogle Scholar
  23. 23.
    Oelckers S, Ziegler T, Michler I and Röder B 1999 Time-resolved detection of singlet oxygen luminescence in red-cell ghost suspensions: concerning a signal component that can be attributed to \(^{1}\text{ O }_{2}\) luminescence from the inside of a native membrane J. Photochem. Photobiol. B Biol. 53 121CrossRefGoogle Scholar
  24. 24.
    Tanaka K, Miura T, Umezawa N, Urano Y, Kikuchi K, Higuchi T and Nagano T 2001 Rational design of fluorescein-based fluorescence probes. Mechanism-based design of a maximum fluorescence probe for singlet oxygen J. Am. Chem. Soc. 123 2530CrossRefGoogle Scholar
  25. 25.
    Kim S, Tachikawa T, Fujitsuka M and Majima T 2014 Far-red fluorescence probe for monitoring singlet oxygen during photodynamic therapy J. Am. Chem. Soc. 136 11707CrossRefGoogle Scholar
  26. 26.
    Pedersen S K, Holmehave J, Blaikie F H, Gollmer A, Breitenbach T, Jensen H H and Ogilby P R 2014 Aarhus sensor green: a fluorescent probe for singlet oxygen J. Org. Chem. 79 3079CrossRefGoogle Scholar
  27. 27.
    Flors C, Fryer M J, Waring J, Reeder B, Bechtold U, Mullineaux P M, Nonell S, Wilson M T and Baker N R 2006 Imaging the production of singlet oxygen in vivo using a new fluorescent sensor, Singlet Oxygen Sensor Green\(^{{\textregistered }}\) J. Exp. Bot. 57 1725CrossRefGoogle Scholar
  28. 28.
    Kohara R, Yuyama K I, Shigeri Y and Biju V 2017 Blue-Emitting electron-donor/acceptor dyads for naked-eye fluorescence detection of singlet oxygen ChemPhotoChem 1 299CrossRefGoogle Scholar
  29. 29.
    Song B, Wang G, Tan M and Yuan J 2006 A europium (III) complex as an efficient singlet oxygen luminescence probe J. Am. Chem. Soc. 128 13442CrossRefGoogle Scholar
  30. 30.
    Zoltan T, Vargas F and Izzo C 2007 UV-Vis spectrophotometrical and analytical methodology for the determination of singlet oxygen in new antibacterials drugs  Anal. Chem. Insights 2 111CrossRefGoogle Scholar
  31. 31.
    Li M Y, Cline C S, Koker E B, Carmichael H H, Chignell C F and Bilski P 2001 Quenching of singlet molecular oxygen (\(^{1}\text{ O }_{2})\) by azide anion in solvent mixtures Photochem. Photobiol. 74 760CrossRefGoogle Scholar
  32. 32.
    Aubry J M, Pierlot C, Rigaudy J and Schmidt R 2003 Reversible binding of oxygen to aromatic compounds Acc. Chem. Res. 36 668CrossRefGoogle Scholar
  33. 33.
    Davidson R S and Trethewey K R 1977 Factors affecting dye-sensitised photo-oxygenation reactions J. Chem. Soc., Perkin Trans. 2 2 169CrossRefGoogle Scholar
  34. 34.
    Wilkinson F and Brummer J G 1981 Rate constants for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution J. Phys. Chem. Ref. Data 10 809CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 2019

Authors and Affiliations

  1. 1.Research Institute for Electronic Science and Graduate School of Environmental ScienceHokkaido UniversitySapporoJapan

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