Photophysical properties of porphycene derivatives (18π porphyrinoids)

Journal of Photochemistry and Photobiology B: Biology

Volumn 40, Issue 3, 1997, Pages 191-198

  Braslavsky, Silvia E ^a   Müller, Martin ^a   Mártire, Daniel O ^a   Pörting, Sigrid ^a   Bertolotti, Sonia G ^a   Chakravorti, Sankar ^a   Koç Weier, Gül ^a   Knipp, Bernd ^a   Schaffner, Kurt ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

Author keywords

Photodynamic therapy; Porphyrins; Sensitization; Singlet oxygen; Triplet

Indexed keywords

PORPHYRIN DERIVATIVE; SINGLET OXYGEN;

ABSORPTION SPECTROSCOPY; ARTICLE; FLUORESCENCE SPECTROSCOPY; PHOTODYNAMIC THERAPY; PHOTOSENSITIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 3142692503     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(97)00075-4     Document Type: Review

References (49)

1. C.J. Gomer, Preclinical examination of first and second generation photosensitizers used in photodynamic therapy, Photochem. Photobiol.,54(199l) 1093-1107.
2. D.V. Ash, S.B. Brown, New drugs and future developments in photodynamic therapy, Eur. J. Cancer, 29A (1993) 1781-1783.
3. R.W. Boyle, D. Dolphin, Structure and biodistribution relationships of photodynamic sensitizers, Photochem. Photobiol., 64 (1996) 469-485.
4. E. Vogel, M. Köcher, H. Schmickler, J. Lex, Porphycene - a novel porphin isomer, Angew. Chem., 98 (1986) 262-264; Angew. Chem. Int. Ed. Engl., 25 (1986) 257-259.
5. E. Vogel, M. Köcher, H. Schmickler, J. Lex, Porphycene - a novel porphin isomer, Angew. Chem., 98 (1986) 262-264; Angew. Chem. Int. Ed. Engl., 25 (1986) 257-259.
6. E. Vogel, Novel porphyrinoids, Pure Appl. Chem., 62 (1986) 557-564.
7. E. Vogel, M. Köcher, J. Lex, O. Ermer, Steric modulation of the porphycene system by alkyl substituents: 9,10,19,20-tetraalkyl-porphycenes, Isr. J. Chem., 29 (1989) 257-266.
8. M. Guardiano, R. Biolo, G. Jori, K. Schaffner, Tetra-n-propyl-porphycene as a tumour localizer: pharmacokinetic and phototherapeutic studies in mice, Cancer Lett., 44 (1989) 1-6.
9. C. Milanesi, R. Biolo, G. Jori, K. Schaffner, Experimental photodynamic therapy with tetrapropyl-porphycene: ultrastructural studies on the mechanism of tumour photodamage, Lasers Med. Sci.,6 (1991) 437-442.
10. M. Dellian, C. Richert, F. Gamarra, A.E. Goetz, Tumor growth following PDT with functionalized porphycenes and Photofrin II, in: P. Spinelli, M. Dal Fante, R. Marchensini (eds.), Photodynamic Therapy and Biomedical Lasers, Int. Congr. Ser. 1011, Elsevier, Amsterdam, 1992, pp. 467-469.
11. T. Sassy, C. Richert, R. Baumgartner, D. Jocham, E. Unsöld, Comparative study of the photodynamic effects of porphycenes and photofrin II on SSK2 fibrosarkoma of mice, Lasers Med. Sci.,7 (1992) 255.
12. K. Schaffner, E. Vogel, G. Jori, Porphycenes as photodynamic therapy agents, in: E.G. Jung, M.F. Holick, Biologic Effects of Light 1993, Walter de Gruyter, Berlin, 1994, pp. 312-321.
13. A. Aicher, K. Miller, E. Reich, R. Hautmann, Photodynamic therapy of human bladder carcinoma cells in vitro with pH-sensitive liposomes as carriers for 9-acetoxy-tetra-n-propylporphycene, Urol. Res., 22 (1994) 25-32.
14. A. Aicher, K. Miller, E. Reich, R. Hautmann, Photosensitization of human bladder cancer cells in vitro by 9-acetoxy-tetra-n-propylporphycene (ATPPn) bound to liposomes from soya phosphatidylcholine, Opt. Eng., 32 (1993) 342-346.
15. M. Leunig, C. Richert, F. Gamarra, W. Lumper, E. Vogel, D. Jocham, A.E. Goetz, Tumour localisation kinetics of photofrin and three synthetic porphyrinoids in an amelanotic membrane of the hamster, Br. J. Cancer, 68 (1993) 225-234.
16. C. Richert, J.M. Wessels, M. Müller, M. Kisters, T. Benninghaus, A.E. Goetz, Photodynamic antitumor agents: β-methoxyethyl groups give access to functionalized porphycenes and enhance cellular uptake and activity, J. Med. Chem., 37 (1994) 2797-2807.
17. S. Kimel, V. Gottfried, R. David, C. Averbuj, In vivo uptake and photodynamic activity of porphycenes, Proc. SPIE, 2078 (1994) 205-210.
18. V. Gottfried, R. Davidi, C. Averbuj, S. Kimel, In vivo damage to chorioallantoic membrane blood vessels by porphycene-induced photodynamic therapy, J. Photochem. Photobiol. B: Biol., 30 (1995) 115-121.
19. R. Davidi, V. Gottfried, S. Kimel, Uptake and photodynamic activity of porphycenes in tumor cells implanted on the chick chorioallantoic membrane (CAM), Proc. SPIE, 2625 (1996) 33-41.
20. M. Dellian, C. Richert, F. Gamarra, A.E. Goetz, Photodynamic eradication of amelanotic melanoma of the hamster with fast acting photosensitizers, Int. J. Cancer, 65 (1996) 246-248.
21. R.M. Szeimies, S. Karrer, C. Abels, P. Steinbach, S. Fickweiler, H. Messmann, W. Bäumler, M. Landthaler, 9-Acetoxy-2,7,12,17-tetrakis-(β-methoxyethyl)-porphycene (ATMPn), a Novel Photosensitizer for Photodynamic Therapy: Uptake Kinetics and Intracellular Localization, J. Photochem. Photobiol. B: Biol., 34 (1996) 67-72.
22. S. Karrer, C. Abels, R.M. Szeimis, W. Bäumler, M. Dellian, U. Hohenleutner, E. Goetz, M. Landthaler, Topical application of a first porphycene dye for photodynamic therapy. Penetration studies in human perilesional skin and basal cell carcinoma, Arch. Dermatol. Res., 289 (1997) 132-137.
23. A.D. Cross, Developing a sensitizer from laboratory to a clinical formulation, Proc. SPIE, 2625 (1996) 262-264.
24. K.W. Woodburn, N.J. Kaye, A.A. Reiss, D.R. Phillipps, Evaluation of porphyrin characteristics required for photodynamic therapy, Photochem. Photobiol., 55 (1992) 697-704.
25. P.E. Aramendía, R.W. Redmond, S. Nonell, W. Schuster, S.E. Braslavsky, K. Schaffner, E. Vogel, The photophysical properties of porphycene: potential photodynamic therapy agents, Photochem. Photobiol., 44 (1986) 555-559.
26. E. Vogel, M. Balci, K. Pramod, P. Koch, J. Lex, O. Ermer 2,7.12,17-Tetrapropylporphycene - counterpart of octaethylporphyrin in the porphycene series, Angew. Chem., 99 (1987) 909-912; Angew. Chem. Int. Ed. Engl., 26 (1987) 928-931.
27. E. Vogel, M. Balci, K. Pramod, P. Koch, J. Lex, O. Ermer 2,7.12,17-Tetrapropylporphycene - counterpart of octaethylporphyrin in the porphycene series, Angew. Chem., 99 (1987) 909-912; Angew. Chem. Int. Ed. Engl., 26 (1987) 928-931.
28. S. Nonell, P.F. Aramendía, K. Heihoff, R.M. Negri, S.E. Braslavsky, Laser-induced optoacoustics combined with near-infrared emission. An alternative approach for the determination of intersystem crossing quantum yields applied to porphycenes, J. Phys. Chem., 94 (1990) 5879-5883.
29. D.O. Mártire, N. Jux, P.F. Aramendía, R.M. Negri, J. Lex, S.E. Braslavsky, K. Schaffner, E. Vogel, Photophysics and Photochemistry of 22π and 26π acetylene-cumulene porphyrinoids, J. Am. Chem. Soc., 114(1990) 9969-9978.
30. G. Martínez, S.G. Bertolotti, O.E. Zimerman, D.O. Mártire, S.E. Braslavsky, N.A. García, A kinetic study of the photodynamic properties of the xanthene dye merbromin (mercurochrome) and its aggregates with amino acids in aqueous solution, J. Photochem. Photobiol. B: Biol., 17 (1993) 247-255.
31. K.I. Salokhiddinov, I.M Byteva, B.M. Dzhagarov, Duration of luminescence of singlet oxygen in solutions under pulsed laser excitation. Opt. Spectrosc., 47 (1979) 881-886.
32. K.I. Salokhiddinov, I.M. Byteva, G.P. Gurinovich, Lifetime of singlet oxygen in different solvents, J. Appl. Spectrosc., 34 (1979) 561-566.
33. I.M. Byteva, Pulsed spectroscopic study of luminescence of oxygen in solutions, J. Appl. Spectrosc., 31 (1979) 1041-1043.
34. E. Vogel., M. Bröring, P. Scholz, R. Deponte, J. Lex, H. Schmickler, K. Schaffner, S.E. Braslavsky, M. Müller, S Pörting, S.J. Weghorn, C. Fowler, J.L. Sessler, Angew. Chem., 109 (1997) 1725-1728; Angew. Chem. Int. Ed. Engl., 36 (1997) 1651-1654.
35. E. Vogel., M. Bröring, P. Scholz, R. Deponte, J. Lex, H. Schmickler, K. Schaffner, S.E. Braslavsky, M. Müller, S Pörting, S.J. Weghorn, C. Fowler, J.L. Sessler, Angew. Chem., 109 (1997) 1725-1728; Angew. Chem. Int. Ed. Engl., 36 (1997) 1651-1654.
36. R. Bensasson, C.R. Goldschmidt, E.J. Land, T.G. Truscott, Laser intensity and the comparative method for determination of triplet quantum yields, Photochem. Photobiol., 28 (1978) 277-281.
37. S.E. Braslavsky. G.E. Heibel, Time-resolved photothermal and photoacoustic methods applied to photoinducad processes in solution, Chem. Rev., 92 (1992) 1381-1410.
38. J.-L. Habib Jiwan, B. Wegewijs, M.T. Indelli, F. Scandola, S.E. Braslavsky, Volume changes associated with intramolecular electron transfer during MLCT state formation. Time-resolved photoacoustic studies of ruthenium cyano complexes, Recl. Trav. Chim. Pays-Bas, 114(1995) 542-548.
39. 2, Volume I, Physical-Chemical Aspects, CRC Press, Boca Raton, FL, 1985, pp. 1-12.
40. 8 = octa-β-halo-tetrakis (pentafluorophenyl) porphyrin; X = Cl, Br), J. Am. Chem. Soc., 116 (1994) 9730-9732.
41. R.W. Redmond, S.E. Braslavsky, Time-resolved thermal lensing and phosphorescence studies on photosensitized singlet molecular oxygen formation. Influence of the electronic configuration of the sensitizer on the sensitization efficiency, Chem. Phys. Lett., 148 (1988) 523-529.
42. E. Vogel, B. Binsack, Unpublished results (1991).
43. D. Gust, T.A. Moore, A.L. Moore, C. Devadoss, P.A. Liddell, R. Hermant, R.A. Nieman, L.J. Demanche, J.M. DeGraziano, I. Gouni, Triplet and singlet energy transfer in carotene-porphyrin dyads: role of the linkage bonds, J. Am. Chem. Soc., 114 (1992) 3590-3603.
44. A. Rahbar, Substitutions- und Folgereaktionen am 2,7,12.17-Tetra-n-propylporphycen. Ph.D. Thesis, Universität Köln, 1992.
45. M. Müller, Konzeption, Synthese und Eigenschaften funktionalisierter Porphycen, Ph.D. Thesis, Universität Köln, 1994.
46. E. Vogel, M. Müller, Unpublished results (1994).
47. E. Vogel, O. Halpern, Unpublished results (1995).
48. M. Hoppe, 9,10-Benzotetrapropylporphycen - Synthese und Eigenschaften, Ph.D. Thesis, Universität Köln, 1994.
49. D. Donnerstag, Benzoporphycene - neuartige tetrapyrrolische Porphyrinoide, Ph.D. Thesis, Universität Köln, 1993.