Skip to main content
Log in

An explanation to the high efficiency ofm-THPC (temporfin) used in photodynamic therapy

  • Notes
  • Published:
Chinese Science Bulletin

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

Meso-tetrahydroxylphenyl chlorin (m-THPC) is one of the most efficient prospective sensitizers used in photodynamic therapy (PDT). ESR spectroscopy, fluorescence quenching experiments and cyclic voltammogram measurement were used to study its redox properties. The results showed that the ability of m-THPC generating superoxide radical anions was very strong, and the rate constant ofm-THPC fluorescence quenching by oxygenk q (O2)=1.46×1010 mol−1 · s−1. The values of fluorescence quenching rate constant of m-THPC by some other electron acceptors, such as methyl viologen (MV2+) and anthraquinone (An), were also measured. And they were kq(MV2+)=5.51×109 mol−1 · s−1, kq (An)=7.81×109 mol−1 · s−1. The oxidation potential ofm-THPC was examined to be +0.62 V (vs. NHE) in acetonitrile. All these suggested thatm-THPC should be a much stronger electron donor than photofrin, the currently used in clinical photodrug, and may react easily through electron transfer with biological matter to yield various radicals. So it seemed reasonable that the type I reaction may play an important role in the high activity ofm-THPC-PDT.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Dougherty, T. J., Photosensitizers: therapy and detection of malignant tumors, Photochemistry and Photobiology, 1987, 45: 879.

    Article  PubMed  CAS  Google Scholar 

  2. Agarwal, R., Athar, M., Elmets, C. A. et al., Photodynamic therapy of chemically and ultraviolet B radiation-induced murine skin papillomas by chloroaluminum phthalocyanine tetrasulfonate, Photochemistry and Photobiology, 1992, 56: 43.

    Article  PubMed  CAS  Google Scholar 

  3. Bergh, V. D., Photodynamic therapy and photodetection of early cancer in the upper aerodigestive tract, the tracheobronchial tree, the oesphagus and the urinary bladder, Hadrontherapy in Oncology, 1994, 557.

  4. Bonnett, R., White, R. D., Winfield, U. J. et al., Hydroporphyrins of the meso-tetra(hydroxyphenyl)porphyrin series as tumour photosensitizers, Journal of Biochemistry, 1989, 261: 277.

    CAS  Google Scholar 

  5. Berenbaum, M. C., Bonnett, R., Cheveretton, E. B. et al., Selectivity of meso-tetra(hydroxyphenyl)porphyrins and chlorines and of photofrin II in causing photodamage in tumor, skin, muscle and bladder: The concept of cost-benefit in analyzing the results, Lasers Mde. Sci., 1994, 8: 235.

    Article  Google Scholar 

  6. Ris, H-B., Altermatt, H. J., Nachbur, et al., Intraoperative photodynamic therapy with m-tetrahydroxy-phenylchlorin for chest malignancies, Lasers Surg. Med., 1996, 18: 39.

    Article  PubMed  CAS  Google Scholar 

  7. Tanielian, C., Wolff, C., Esch, M., Singlet oxygen production in water: aggregation and charge-transfer effects, Journal of Physical Chemistry, 1996, 100: 6555.

    Article  CAS  Google Scholar 

  8. Bonnett, R., Studies on 5,10,15,20-tetrakis(m-hydroxyphenyl) chlorin, m-THPC (TEMOPORFIN), Proc. SPIE-Int. Soc. Opt. Eng., 1995, 2371: 31.

    CAS  Google Scholar 

  9. Moan, J., Wold, E., Detection of singlet oxygen production by ESR, Nature, 1979, 279: 450.

    Article  PubMed  CAS  Google Scholar 

  10. Diwu, Z., Lown, J. W., Photosensitization by anticancer agents (12): Perylene quinonoid pigments, a novel type of singlet oxygen sensitizer, Journal of Photochemistry and Photobiology, Ser. A: Chemistry, 1992, 64: 273.

    Article  CAS  Google Scholar 

  11. John, R. H., Hair, M. L., Detection of superoxide ions in nonaqueous media: Generation by photolysis of pigment dispersions, Journal of Physical Chemistry, 1978, 82(12): 1397.

    Article  Google Scholar 

  12. Maning, L. E., Kramer, M. K., Foote, C. S., Interception ofO 2 by benzoquinone in cyanoaromatic-sensitized photooxygenations, Tetrahedron Letters, 1984, 84(25): 2523.

    Article  Google Scholar 

  13. Weng, M., Zhang, M.-H., Shen, T., Electron transfer interaction between hypocrellin A and biological substrates and quantitative analysis of superoxide anion radicals, Journal of Chemistry Society, Perkin Transaction 2, 1997,2393.

  14. Gibson, S. L., Cohen, H. J., Hilf, R., Evidence against the production of superoxide by photoirradiation of hematoporphyin derivative, Photochemistry and Photobiology, 1984, 40(4): 441.

    Article  PubMed  CAS  Google Scholar 

  15. Howe, L., Sucheta, A., Einarsdottir, O. et al., Time-resolved studies of the excited-state dynamics of meso-tetra(hydroxylphenyl)chlorin in solution, Photochemistry and Photobiology, 1999, 69(6): 617.

    Article  PubMed  CAS  Google Scholar 

  16. Sawyer, D. T., Valentine, J. S., How super is superoxide? Acc. Chem.Res., 1981, 14: 393.

    Article  CAS  Google Scholar 

  17. Karamos, G. J., Turro, N. J., Photosensitization by reversible electron transfer: theories, experimental evidence, and examples, Chemical Reviews, 1986, 86: 401.

    Article  Google Scholar 

  18. Franlkner, L. R., Tachkikawa, H., Bard, A. J., Electrogenerated chemiluminescence (VII)—The influence of an external magnetic field on luminescence intensity, Journal of American Chemical Society, 1972, 94: 691.

    Article  Google Scholar 

  19. Bonnett, R., Charlesworth, P., Djelal, B. D. et al., Photophysical properties of 5,10,15,20-tetrakis(m-hydroxyphenyl)porphyrin (mTHPP), 5, 10, 15, 20-tetrakis(m-hydroxyphenyl)chlorin(m-THPC) and 5, 10, 15, 20-tetrakis(m-hydroxyphenyl)bacteriochlorin (mTHPBC): a comparative study, Journal of Chemical Society, Perkin Transaction 2, 1999, 325.

  20. Cheng, N. L., Handbook of Solvents (2nd ed.) (in Chinese), Beijing: Chemical Engineering Press, 1994, 288.

    Google Scholar 

  21. Meites, L., Zuman, P., CRC Handbook Series in Organic Eletrocchemistry, Vol. 1, Boca Raton, FL: CRC Press.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Manhua Zhang.

About this article

Cite this article

Chen, Y., Li, L., Zhang, M. et al. An explanation to the high efficiency ofm-THPC (temporfin) used in photodynamic therapy. Chin.Sci.Bull. 46, 823–827 (2001). https://doi.org/10.1007/BF02900431

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02900431

Keywords

Navigation