Meso-Tetraphenylporphyrin Dimer Derivative as a Potential Photosensitizer in Photodynamic Therapy

Photochemistry and Photobiology

Volumn 66, Issue 4, 1997, Pages 405-412

  Faustino, Maria A F ^a   Neves, Maria G P M S ^a   Vicente, Maria G H ^a   Cavaleiro, José A S ^a   Neumann, Marcus ^b   Brauer, Hans D ^b   Jori, Giulio ^c  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b GOETHE UNIVERSITY   (Germany)

^c UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOSENSITIZING AGENT; PORPHYRIN;

ANIMAL; ARTICLE; BAGG ALBINO MOUSE; CHEMISTRY; DRUG DESIGN; FEMALE; FIBROSARCOMA; METHODOLOGY; MOUSE; PHOTOCHEMISTRY; PHOTOCHEMOTHERAPY;

ANIMALS; DRUG DESIGN; FEMALE; FIBROSARCOMA; MICE; MICE, INBRED BALB C; PHOTOCHEMISTRY; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; PORPHYRINS;

EID: 0031253680     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1997.tb03165.x     Document Type: Article

References (37)

1. Henderson, B. W. and T. J. Dougherty (1992) Photodynamic Therapy: Basic Principles and Clinical Applications. Marcel Dekker, New York.
2. Bonnett, R. (1995) Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy. Chem. Soc. Rev. 24, 19-33.
3. Schuitmaker, J. J., P. Bass, H. L. L. M. van Leengoed, F. W. van der Meulen, W. M. Star and N. van Zandwijk (1996) Photodynamic therapy: a promising new modality for the treatment of cancer. J. Photochem. Photobiol. B Biol. 34, 3-12.
4. Bommer, J. C. and B. F. Burnham (1990) Preparation of tetrapyrrolecarboxamide for use in tumor phototherapy. Chem. Abst. 112, 98293b
5. Woodburn, K. W., G. C. A. Bellinger, D. R. Phillips and J. A. Reiss (1992) Synthesis of porphyrins derived from the amidation of protoporphyrin IX for use as potential chemotherapeutic agents. Aust. J. Chem. 45, 1745-1751.
6. Boyle, R. W. and D. Dolphin (1996) Structure and biodistribution relationships of photodynamic sensitizers. Photochem. Photobiol. 64, 469-485.
7. Olmstedt, J. (1979) Calorimetric determination of absolute fluorescence quantum yields. J. Phys. Chem. 83, 2581-2584.
8. Grewer, C., C. Wirp, M. Neumann and H.-D. Brauer (1994) Evidence for competing electron and energy transfer for the fluorescence quenching of singlet oxigen sensitizers by molecular oxygen. Ber. Bunsenges. Phys. Chem. 98, 997-1003.
9. Sinn, E., K. Matthes and E. Naumann (1967) Experimentelle Untersuchungen über die Löslichkeit von Sauerstoff in flüssigen organischen Substanzen. Wiss. Z. Univ. Jena Math.-nat. R. 16, 523-529.
10. Dreeskamp, H., E. Koch and M. Zander (1974) Schweratominduzierte Fluoreszenzlöschung und Termschema von mehrkernigen aromatischen Kohlenwasserstoffen und Heterocyclen. Ber. Bunsenges. Phys. Chem. 78, 1328-1334.
11. g) in solution. J. Am. Chem. Soc. 111, 6983-6987.
12. Grewer, C., G. Schermann, R. Schmidt, A. Völcker and H.-D. Brauer (1991) Potential photosensitizers for photodynamic therapy - III. Photophysical properties of a lipophilic chlorin and its zinc and tin chelatcs. J. Photochem. Photobiol. B Biol. 11, 285-293.
13. g) sensitizers. J. Photochem. Photobiol. A Chem. 79, 11-17.
14. Grewer, C. and H.-D. Brauer (1993) Temperature dependence of the oxygen quenching of ππ*-singlet and ππ*-triplet states of singlet oxygen sensitizers. J. Phys. Chem. 97, 5001-5006.
15. Cuomo, V., G. Jori, B. Rihter, M. E. Keney and M. A. J. Rodgers (1990) Liposome-delivered Si (IV)-naphthalocyanine as a photodynamic sensitiser for experimental tumours: pharmacokinetic and phototherapeutic studies. Br. J. Cancer 62, 966-970.
16. Gouterman, M. (1979) Optical spectra and electronic structure of porphyrins and related rings. In The Porphyrins, Vol. 3 (Edited by D. Dolphin), pp. 1-165. Academic Press, New York.
17. Gouterman, M. and G. E. Khalil (1974) Porphyrin free base phosphorescence. J. Mol. Spectrosc. 53, 88-100.
18. Garner, A. and F. Wilkinson (1977) Quenching of triplet states by molecular oxygen and the role of charge-transfer interactions. Chem. Phys. Lett. 45, 432-435.
19. Dougherty, T. J. (1987) Photosensitizers: therapy and detection of malignant tumours. Photochem. Photobiol. 45, 879-889.
20. Biolo, R., G. Jori, M. Soncin, R. Pratesi, M. E. Kenney and M. A. J. Rodgers (1994) Photodynamic therapy of B16 pigmented melanoma with liposome-delivered Si(IV)-naphthalocyanine. Photochem. Photobiol. 59, 362-365.
21. Dougherty, T. J. (1993) Photodynamic therapy. Photochem. Photobiol. 58, 895-900.
22. Reddi, E., G. Lo Castro, R. Biolo and G. Jori (1987) Pharmacokinetic studies with Zn (II)-phthalocyanine in tumour-bearing mice. Br. J. Cancer 56, 597-600.
23. Jori, G. and E. Reddi (1991) Second generation photosensitizers for the photodynamic therapy of tumours. In Light in Biology and Medicine, Vol. 2 (Edited by R. H. Douglas, J. Moan and G. Ronto), pp. 253-266. Plenum Press, London.
24. Segalla, A., C. Milanesi, G. Jori, H. G. Capraro, U. Isele and K. Schieweck (1994) A liposomal Ge (IV)-phthalocyanine bearing two axially ligated cholesterol moieties: a new potential agent for photodynamic therapy of tumours. Br. J. Cancer 69, 817-825.
25. Soncin, M., L. Polo, E. Reddi, G. Jori, B. D. Rihter, M. E. Kenney and M. A. J. Rodgers (1995) Unusually high affinity of Zn (II)-tetradibenzobarreleno-octabutoxyphthalocyanine for low density lipoproteins in a tumour-bearing mice. Photochem. Photobiol. 61, 310-312.
26. Jori, G. (1990) Factors controlling the selectivity and efficiency of tumour damage in photodynamic therapy. Lasers Med. Sci. 5, 115-120.
27. Kessel, D., P. Thompson, S. Saatio and K. D. Nantwi (1987) Tumour localization and photosensitization by sulfonated derivatives of tetraphenylporphine. Photochem. Photobiol. 45, 787-789.
28. Van Lier, J. E. and J. D. Spikes (1989) The chemistry, photophysics and photosensitizing properties of phthalocyanines. In Photosensitizing Compounds: Their Chemistry, Biology and Clinical Use (Edited by G. Bock and S. Harnett), pp. 17-32. Ciba Foundation Symposium, J. Wiley & Sons, Chichester.
29. Kessel, D. (1986) Porphyrin-lipoprotein association as a factor in porphyrin localization. Cancer Lett. 33, 183-188.
30. Zhou, C. (1989) Mechanisms of tumour necrosis induced by photodynamic therapy. J. Photochem. Photobiol. B Biol. 3, 299-318.
31. Kongshaug, M. (1992) Distribution of tetrapyrrole photosensitizers among human plasma proteins. Int. J. Biochem. 24, 1239-1265.
32. Reddi, E. and G. Jori (1988) Steady state and time-resolved spectroscopic studies of photodynamic sensitizers: porphyrins and phthalocyanines. Rev. Chem. Int. 10, 241-268.
33. Jori, G. and E. Reddi (1993) The role of lipoproteins in the delivery of tumour-targeting photosensitizers. Int. J. Biochem. 25, 1369-1375.
34. Ometto, C., C. Fabris, C. Milanesi, G. Jori, M. J. Cook and D. A. Russell (1996) Tumour-localising and -photosensitizing properties of a novel zinc (II)-octadecylphthalocyanine. Br. J. Cancer 74, 1891-1899.
35. Henderson, B. W. and T. J. Dougherty (1992) How does photodynamic therapy work? Photochem. Photobiol. 55, 145-147.
36. Soncin, M., L. Polo, E. Reddi, G. Jori, M. E. Kenney, G. Cheng and M. A. J. Rodgers (1995) Effect of the delivery system on the biodistribution of Ge (IV)-octabutoxyphthalocyanines in tumour-bearing mice. Cancer Lett. 89, 101-106.
37. Cuomo, V., G. Jori, B. Rihter, M. E. Kenney and M. A. J. Rodgers (1991) Tumour-localising and -photosensitising properties of liposome-delivered Ge (IV)-octabutoxyphthalocyanine. Br. J. Cancer 64, 93-95.