Skip to main content
SpringerLink
Log in

A Novel Squarylium Dye for Monitoring Oxidative Processes in Lipid Membranes

  • Original Paper
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

A novel squaraine probe SQ-1 has been found to be appropriate for monitoring the peroxidation processes in membrane systems. Formation of free radicals was triggered by methemoglobin (metHb) or cytochrome c (cyt c) binding to the model lipid membranes composed of zwitterionic lipid phosphatidylcholine (PC) and anionic lipid cardiolipin (CL). Protein association with the lipid vesicles was followed by drastic quenching of SQ-1 fluorescence. The observed spectral changes were suppressed in the presence of free radical scavengers, butylated hydroxytoluene (BHT) and thiourea (TM) suggesting that SQ-1 decolorization can be attributed to its reactions with lipid radicals.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Keil D, Hartmann H, Moschny T (1991) Synthesis and characterization of 1, 3-bis-(2-dialkylamino-5-thienyl)-substituted squaraines-a novel class of intensively coloured panchromatic dyes. Dyes Pigments 17:19–27. doi:10.1016/0143-7208(91)85025-4

    Article  CAS  Google Scholar 

  2. Ramaiah D, Eckert I, Arun KT, Weidenfeller L, Epe B (2004) Squaraine dyes for photodynamic therapy: mechanism of cytotoxicity and DNA damage induced by halogenated squaraine dyes plus light (&gt;600 nm). Photochem. Photobiol. 79:99–104. doi:10.1562/0031-8655(2004)79<99:SDFPTM>2.0.CO;2

    Article  CAS  PubMed  Google Scholar 

  3. Law KY, Bailey FC (1987) Squaraine chemistry: effect of synthesis on the morphological and xerographic properties of photoconductive squaraines. J. Imag. Sci. 31:172–175

    CAS  Google Scholar 

  4. Polaroid Corporation: US Patent 5795981.

  5. Merritt VY, Hovel HJ (1976) Organic solar cells of hydroxysquarylium. Appl. Phys. Lett. 29:414–416. doi:10.1063/1.89101

    Article  CAS  Google Scholar 

  6. Lakowicz JR (1999) Principles of fluorescent spectroscopy, 2nd edn. Kluwer Academic/Plenum, New York

    Google Scholar 

  7. Ioffe VM, Gorbenko GP, Deligeorgiev T, Gadjev N, Vasilev A (2007) Fluorescence study of protein-lipid complexes with a new symmetric squarylium probe. Biophys. Chem. 128:75–86. doi:10.1016/j.bpc.2007.03.007

    Article  CAS  PubMed  Google Scholar 

  8. Setsukinai K, Urano Y, Kakinuma K, Majima HJ, Nagano T (2003) Development of novel fluorescence probes that can reliably detect reactive oxygen species and distinguish specific species. J. Biol. Chem. 278:3170–3175. doi:10.1074/jbc.M209264200

    Article  CAS  PubMed  Google Scholar 

  9. Henry TD, Archer SL, Nelson D, Weir EK, From AH (1990) Enhanced chemiluminescence as a measure of oxygen-derived free radical generation during ischemia and reperfusion. Circ. Res. 67:1453–1461

    CAS  PubMed  Google Scholar 

  10. Dikalova AE, Kadiiska MB, Mason RP (2001) An in vivo ESR spin-trapping study: Free radical generation in rats from formate intoxication-role of the Fenton reaction. Proc. Natl. Acad. Sci. USA 98:13549–13553. doi:10.1073/pnas.251091098

    Article  CAS  PubMed  Google Scholar 

  11. Khramtsov VV, Reznikov VA, Berliner LJ, Litkin AK, Grigorev IA, Clanton TL (2001) NMR spin trapping: detection of free radical reactions with a new fluorinated DMPO analog. Free Radic. Biol. Med. 30:1099–1107. doi:10.1016/S0891-5849(01)00505-6

    Article  CAS  PubMed  Google Scholar 

  12. Hempel SL, Buettner GR, O’Malley YQ, Wessels DA, Flaherty DM (1999) Dihydrofluorescein diacetate is superior for detecting intracellular oxidants: comparison with 2′, 7′-dichlorodihydrofluorescein diacetate, 5(and 6)-carboxy-2′, 7′-dichlorodihydrofluorescein diacetate, and dihydrorhodamine 123. Free Radic. Biol. Med. 27:146–159. doi:10.1016/S0891-5849(99)00061-1

    Article  CAS  PubMed  Google Scholar 

  13. Akasaka K (1995) Development of phosphine reagents for fluorometric determination of lipid hydroperoxides. Tohoku J. Agricul. Res. 45:111–119

    CAS  Google Scholar 

  14. Wolfbeis OS, Durkop A, Wu M, Lin Z (2002) A europium-ion-based luminescent sensing probe for hydrogen peroxide. Angew. Chem. 41:4495–4498. doi:10.1002/1521-3773(20021202)41:23<4495::AID-ANIE4495>3.0.CO;2-I

    Article  CAS  Google Scholar 

  15. Mui B, Chow L, Hope MJ (2003) Extrusion technique to generate liposomes of defined size. Methods Enzymol. 367:3–14. doi:10.1016/S0076-6879(03)67001-1

    Article  CAS  PubMed  Google Scholar 

  16. Bartlett G (1959) Phosphorus assay in column chromatography. J. Biol. Chem. 234:466–468

    CAS  PubMed  Google Scholar 

  17. Arun KT, Ramaiah D (2005) Near-infrared fluorescent probes: synthesis and spectroscopic investigations of a few amphiphilic squaraine dyes. J. Phys. Chem. A 109:5571–5578. doi:10.1021/jp051338o

    Article  CAS  PubMed  Google Scholar 

  18. Itabe H, Kobayashi T, Inoue K (1988) Generation of toxic phospholipids during oxyhemoglobin-induced peroxidation of phosphatidylcholines. Biochim. Biophys. Acta 961:13–21

    CAS  PubMed  Google Scholar 

  19. Szebeni J, Winterbourn CC, Carrel RW (1984) Oxidative interactions between haemoglobin and membrane lipids. Biochem. J. 220:685–692

    CAS  PubMed  Google Scholar 

  20. Heimburg T, Marsh D (1993) Investigation of secondary and tertiary structural changes of cytochrome c in complexes with anionic lipids using amide hydrogen exchange measurements: an FTIR study. Biophys. J. 65:2408–2417. doi:10.1016/S0006-3495(93)81299-2

    Article  CAS  PubMed  Google Scholar 

  21. Rogers MS, Patel RP, Reeder BJ, Sarti P, Wilson MT, Alayash A (1995) Pro-oxidant effects of cross-linked haemoglobins explored using liposome and cytochrome c oxidase vesicle model membranes. Biochem. J. 310:827–833

    CAS  PubMed  Google Scholar 

  22. Sadrzadeh SM, Graf E, Panter SS, Hallaway PE, Eaton JW (1984) Hemoglobin. A biologic Fenton reagent. J. Biol. Chem. 259:14354–14356

    CAS  PubMed  Google Scholar 

  23. Tarazi L, Narayanan N, Sowell J, Patonay G, Strekowski L (2002) Investigation of the spectral properties of a squarylium near-infrared dye and its complexation with Fe(III) and Co(II) ions. Spectrochim. Acta [A] 58:257–264. doi:10.1016/S1386-1425(01)00542-X

    Article  Google Scholar 

  24. Wong-ekkabut J, Xu Z, Triampo W, Tang IM, Tieleman DP, Monticelli L (2007) Effect of lipid peroxidation on the properties of lipid bilayers: a molecular dynamics study. Biophys. J. 93:4225–4236. doi:10.1529/biophysj.107.112565

    Article  CAS  PubMed  Google Scholar 

  25. Wratten ML, Vanginkel G, Vantveld AA, Bekker A, Vanfaassen EE, Sevanian A (1992) Structural and dynamic effects of oxidatively modified phospholipids in unsaturated lipid membranes. Biochemistry 31:10901–10907. doi:10.1021/bi00159a034

    Article  CAS  PubMed  Google Scholar 

  26. Mason RP, Walter MF, Mason PE (1997) Effect of oxidative stress on membrane structure: small-angle X-ray diffraction analysis. Free Radic. Biol. Med. 23:419–425. doi:10.1016/S0891-5849(97)00101-9

    Article  CAS  PubMed  Google Scholar 

  27. Richter C (1987) Biophysical consequences of lipid peroxidation in membranes. Chem. Phys. Lipids 44:175–189. doi:10.1016/0009-3084(87)90049-1

    Article  CAS  PubMed  Google Scholar 

  28. Nicolescu AC, Li Q, Brown L, Thatcher GRJ (2006) Nitroxidation, nitration, and oxidation of a BODIPY fluorophore by RNOS and ROS. Nitric Oxide 15:163–176. doi:10.1016/j.niox.2006.01.010

    Article  CAS  PubMed  Google Scholar 

  29. Guivarch E, Trevin S, Lahitte C, Oturan MA (2003) Degradation of azo dyes in water by Electro-Fenton process. Environ. Chem. Lett. 1:38–44. doi:10.1007/s10311-002-0017-0

    Article  CAS  Google Scholar 

Download references

Acknowledgment

This work was supported by the grant № 4534 from the Science and Technology Center in Ukraine.

Author information

Authors and Affiliations

  1. Department of Biological and Medical Physics, V.N. Karazin Kharkov National University, 4 Svobody Sq., Kharkov, 61077, Ukraine

    Valeriya M. Trusova & Galyna P. Gorbenko

  2. Department of Applied Organic Chemistry, Faculty of Chemistry, University of Sofia, Sofia, 1164, Bulgaria

    Todor Deligeorgiev, Nikolai Gadjev & Aleksey Vasilev

  3. 66-82 Geroyev Truda St., Kharkov, 61121, Ukraine

    Valeriya M. Trusova

Authors
  1. Valeriya M. Trusova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Galyna P. Gorbenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Todor Deligeorgiev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nikolai Gadjev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Aleksey Vasilev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Valeriya M. Trusova.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Trusova, V.M., Gorbenko, G.P., Deligeorgiev, T. et al. A Novel Squarylium Dye for Monitoring Oxidative Processes in Lipid Membranes. J Fluoresc 19, 1017–1023 (2009). https://doi.org/10.1007/s10895-009-0501-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-009-0501-z

Keywords

Search

Navigation