Skip to main content
SpringerLink
Log in

Photochemistry and Photophysics of Merocyanine 540

  • Chapter
Novel Chemotherapeutic Agents: Preactivation in the Treatment of Cancer and AIDS

Part of the book series: Medical Intelligence Unit ((MIU.LANDES))

  • 26 Accesses

Abstract

The instrumentation at the Center for Fast Kinetics Research was intended to monitor very fast processes, such as time-resolved fluorescence or pulse radiolysis, in an effort to identify important but highly reactive intermediates. Knowing the nature and fate of these intermediates is of great value for formulating reaction mechanisms and, once the mechanism is known, optimizing the process of interest. A few days spent with such equipment generates a great wealth of experimental data, often requiring a month or more to analyze and decipher. In three days, it is certainly possible to uncover many facets of a chemical or biochemical process. However, deep investigation into complex reaction mechanisms demands regular bursts of experimentation. Such equipment is extremely expensive, requiring constant attention by specialists, and can be difficult to operate properly. More often than not, more than one instrument is needed to tackle a particular research project. Data analysis brings additional difficulties and misinterpretations are common.

Every great advance in science has issued from a new audacity of imagination. —John Dewey (1859–1952) The Quest for Certainty, Ch. II

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

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Hamer FM. The Cyanine Dyes and Related Compounds. New York: Wiley Interscience, 1964: 706–42.

    Google Scholar 

  2. Harriman A, Shoute LCT, Neta P. Radiation chemistry of cyanine dyes: oxidation and reduction of merocyanine 540. J Phys Chem 1991; 95: 2415–20.

    Article  CAS  Google Scholar 

  3. Benniston AC, Harriman A, Gulliya KS. Photophysical properties of Merocyanine 540 derivatives. J Chem Soc, Faraday Trans 1994; 90: 953–61.

    Article  CAS  Google Scholar 

  4. Gordon AJ, Ford RA. The Chemist’s Companion. Chichester: Wiley-Interscience, 1972: 184.

    Google Scholar 

  5. Kushner KM, Smith CP. Resonance and polarity in the molecules of three colored compounds. J Am Chem Soc 1949; 71: 1401–40.

    Article  CAS  Google Scholar 

  6. Gulliya KS, Davila J, Harriman A. The mechanism of LDL-mediated increased uptake of Merocyanine 540 by HL-60 cells. The Cancer J 1990; 3: 360–65.

    CAS  Google Scholar 

  7. Gulliya KS, Mathews JL, Fay JW, Dowben RM. Increased survival of normal cells during laser photodynamic therapy; implications for ex-vivo autologous bone marrow purging. Life Sci 1988; 42: 2651–6.

    Article  PubMed  CAS  Google Scholar 

  8. Gulliya KS, Pervaiz S. Elimination of clonogenic tumor cells from HL-60, Daudi and U-937 cell lines by laser photoradiation therapy; implications for autologous bone marrow purging. Blood 1989; 73: 1059–65.

    PubMed  CAS  Google Scholar 

  9. Dragsten PR, Webb WW. Mechanism of the membrane potential sensitivity of the fluorescent membrane probe Merocyanine 540. Biochemistry 1978; 17: 5228–40.

    Article  PubMed  CAS  Google Scholar 

  10. Dixit NS, Mackay RA. Absorption and emission characteristics of Merocyanine 540 in microemulsions. J Am Chem Soc 1983; 105: 2928–29.

    Article  CAS  Google Scholar 

  11. Aramendia PH, Krieg M, Nitsch C, Bittersman E, Braslaysky SE. The photophysics of Merocyanine 540: A comparative study in ethanol and in liposomes. Photochem Photobiol 1988; 48: 187–94.

    Article  PubMed  CAS  Google Scholar 

  12. Aramendia PH, Duchowicz R, Schaffardi L, Tocho JO. Photo-physical characterization of a photochromic system; The case of Merocyanine 540. J Phys Chem 1990; 94: 1389–92.

    Article  CAS  Google Scholar 

  13. Hoebeke M, Piette J, Van der Vorst A. Viscosity-dependent isomerization and fluorescence yields of Merocyanine 540. J Photochem Photobiol, B Biol 1990; 4: 273–82.

    CAS  Google Scholar 

  14. Hoebeke M, Seret A, Piette J, Van der Vorst A. Singlet oxygen production and photoisomerization;competitive processes for Merocyanine 540 irradiated with visible light. J Photochem Photobiol, B Biol 1988; 1: 437–46.

    CAS  Google Scholar 

  15. Davila J, Gulliya KS, Harriman A. Inactivation of tumours and viruses via efficient photoisomerization. J Chem Soc, Chem Commun 1989; 1215–16.

    Google Scholar 

  16. Harriman A. Photoisomerization dynamics of merocyanine dyes in solution. J Photochem Photobiol, A Chem 1992; 65: 79–93.

    CAS  Google Scholar 

  17. Davila J, Harriman A, Gulliya KS. Photochemistry of Merocyanine 540: The mechanism of chemotherapeutic activity with cyanine dyes. Photochem Photobiol 1991; 53: 1–11.

    Article  PubMed  CAS  Google Scholar 

  18. Benniston AC, Harriman A. To be published.

    Google Scholar 

  19. Günter WHH, Searle R, Sieber F. Structure-activity relationships in the antiviral and antileukemic photoproperties of Merocyanine 540. Seminars in Hematology 1992; 29: 88–94.

    Google Scholar 

  20. Günter WHH, Searle R, Sieber F. Photosensitizing merocyanine dyes based on selenobarbituric acid. Phosphorus, Sulfur, and Silicon 1992; 67: 417.

    Article  Google Scholar 

  21. Benniston AC, Harriman A, Gulliya KS. To be published.

    Google Scholar 

  22. Redmond RW, Srichai MB, Bilitz JM, Schlomer DD, Krieg M. Merocyanine dyes: Effect of structural modifications on photophyical properties and biological activity. Photochem Photobiol 1994; 60: 348–55.

    Article  PubMed  CAS  Google Scholar 

  23. Feix JB, Kalyanaraman B. An electron spin resonance study of Merocyanine 540-mediated type I reactions in liposomes. Photochem Photobiol 1991; 53: 39–45.

    Article  PubMed  CAS  Google Scholar 

  24. Byers GW, Gross S, Henriches PM. Direct and sensitized photo-oxidation of cyanine dyes. Photochem Photobiol 1976; 23: 37–43.

    Article  PubMed  CAS  Google Scholar 

  25. Sieber F. Merocyanine 540. Photochem Photobiol 1987; 46: 1035–42.

    Article  PubMed  CAS  Google Scholar 

  26. O’Neil CH. Isolation and properties of the cell surface membrane of Amoeba Proteus. Expt Cell Res 1964; 35: 477–96.

    Article  Google Scholar 

  27. Kalyanaraman B, Feix JB, Sieber F, Thomas JP, Girotti AW. Photodynamic action of Merocyanine 540 on artificial and natural cell membranes: involvement of singlet molecular oxygen. Proc Natl Acad Sci 1987; 84: 2999–3003.

    Article  PubMed  CAS  Google Scholar 

  28. Feix JB, Kalyanaraman B, Chignell CF, Hall RD. Direct observation of singlet oxygen production by merocyanine 540 associated with phosphatidylcholine liposomes. J. Biol. Chem. 1988; 263: 17247–50.

    PubMed  CAS  Google Scholar 

  29. O’Brien JM, Montgomery RR, Burns WH, Gaffney DK, Sieber F. Evaluation of Merocyanine 540-sensitized photoirradiation as a means to inactivate enveloped viruses in blood products. J Lab Clin Med 1990; 116: 439–47.

    PubMed  Google Scholar 

  30. Gaffney DK, O’Brien JM, Sieber F. Modulation by thiols of the Merocyanine 540-sensitized photolysis of leukemia cells, red cells, and herpes simplex virus type I. Photochem Photobiol 1991; 53: 85–92.

    Article  PubMed  CAS  Google Scholar 

  31. Rodgers MAJ, Snowden PT. Lifetime of O2(’i) in liquid water as determined by time-resolved infra-red luminescence measurements. J Am Chem Soc 1982; 104: 5541–43.

    Article  CAS  Google Scholar 

  32. Moan J. On the diffusion length of singlet oxygen in cells and tissue. J Photochem Photobiol, B Biol 1990; 6: 343–44.

    CAS  Google Scholar 

  33. Gulliya KS, Mathews JL, Fay JW, Dowben RM. Effect of free radical quenchers on the dye-mediated laser light induced photo-sensitization of leukemic cells. Proc SPIE 1987; 847: 163–65.

    Article  Google Scholar 

  34. Gaffney DK, Schober SL, Sieber F. Merocyanine 540-sensitized photoinactivation of leukemic cells: role of oxygen and effects on plasma membrane integrity and mitochondrial respiration. Exp Hematol 1990; 18: 23–26.

    PubMed  CAS  Google Scholar 

  35. O’Brien JM, Siebe F. Merocyanine 540-sensitized photoinactivation of enveloped viruses and its application in the sterilization of blood products. In: Gorin NC, Douay L, eds. Experimental Hematology Today. New York: Springer, 1989: 26–30.

    Google Scholar 

  36. Franck B, Schneider U. Photooxidation products of merocyanine 540 formed under preactivation conditions for tumor therapy. Photochem Photobiol 1992; 56: 271–76.

    Article  PubMed  CAS  Google Scholar 

  37. Nagle JF. Theory of biomembrane phase transitions. J Chem Phys 1973; 58: 252–64.

    Article  CAS  Google Scholar 

  38. Srinivasan KR, Kay RL, Nagle JF. The pressure dependence of lipid bilayer phase transition. Biochemistry 1974; 13: 3494–96.

    Article  PubMed  CAS  Google Scholar 

  39. McEvoy L, Schlegel RA, Williamson P et al. Merocyanine 540 as flow cytometric probe of membrane lipid organization in leukocytes. J Leukocyte Biol 1988; 44: 337–44.

    PubMed  CAS  Google Scholar 

  40. Benniston AC, Harriman A. Photoinduced and thermal isomerization processes for bis-oxonols: Rotor volume, stereochemical and viscosity effects. J Chem Soc, Faraday Trans 1994; 90: 2627–34.

    Article  CAS  Google Scholar 

  41. Harriman A, Luengo G, Gulliya KS. In vitro photodynamic activity of kryptocyanine. Photochem Photobiol 1990; 52: 735–40.

    Article  PubMed  CAS  Google Scholar 

Download references

Authors
  1. Anthony A. Harriman
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

Copyright information

© 1996 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Harriman, A.A. (1996). Photochemistry and Photophysics of Merocyanine 540. In: Novel Chemotherapeutic Agents: Preactivation in the Treatment of Cancer and AIDS. Medical Intelligence Unit. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-22241-6_3

Download citation

  • DOI: https://doi.org/10.1007/978-3-662-22241-6_3

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-662-22243-0

  • Online ISBN: 978-3-662-22241-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation