Glycosylated derivatives of tetraphenyl porphyrin: Photophysical characterization, self-aggregation and membrane binding

Journal of Photochemistry and Photobiology B: Biology

Volumn 44, Issue 3, 1998, Pages 216-224

  Csik G ^a   Balog, E ^a   Voszka, I ^a   Tolgyesi F ^a   Oulmi, D ^b   Maillard, Ph ^b   Momenteau, M ^b  

^a SEMMELWEIS UNIVERSITY OF MEDICINE   (Hungary)

^b CNRS   (France)

Author keywords

Aggregation; Association constants; Fluorescence; Liposomes; Tetraphenyl porphyrins

Indexed keywords

LIPOSOME; PORPHYRIN DERIVATIVE;

ARTICLE; CELLULAR DISTRIBUTION; FLUORESCENCE SPECTROSCOPY; HYDROPHOBICITY; LIPID BILAYER; PHOTODYNAMIC THERAPY; PRIORITY JOURNAL;

EID: 0032584490     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1011-1344(98)00147-X     Document Type: Article

References (29)

1. [1] F. Ricchelli, G. Jori, S. Gobbo, M. Tronchin, Liposomes as models to study the distribution of porphyrins in cell membrane, Biochim. Biophys. Acta 1065 (1991) 42-48.
2. [2] F. Ricchelli, S. Gobbo, Porphyrins as fluorescent probes for monitoring phase transition of lipid domains in biological membranes. Factors influencing the microenvironment of hematoporphyrin and protoporphyrin in liposomes, J. Photochem. Photobiol. 29 (1995) 65-70.
3. [3] Q. Peng, G.W. Farrants, K. Madslien, J.C. Bommer, J. Moan, H.E. Danielsen, J.M. Nesland, Subcellular localization, redistribution and photobleaching of sulfonated aluminium phthalocyanines in a human melanoma cell line, Int. J. Cancer 49 (1991) 290-295.
4. [4] J.M. Wessels, W. Strauß, H.K. Seidlitz, A. Rück, H. Schneckenburger, Intracellular localization of mesotetraphenylporphine tetrasulfonate probed by time-resolved and microscopic fluorescence spectroscopy, J. Photochem. Photobiol. B: Biol. 12 (1992) 275-284.
5. [5] D. Oulmi, P. Maillard, J.-L. Guerquin-Kern, Ch. Huel, M. Momenteau, Glycoconjugated porphyrins 3. Synthesis of flat amphiphilic mixed meso-(glycosylated aryl)arylporphyrins and mixed meso-(glycosylated aryl)alkylporphyrins bearing some monosaccharide and disaccharide groups, J. Org. Chem. 60 (1995) 1554-1564.
6. [6] P. Maillard, J.-L. Guerquin-Kern, Ch. Huel, M. Momenteau, Glycoconjugated porphyrins 2. Synthesis of sterically constrained polyglycosylated compounds derived from tetraphenylporphyrins, J. Org. Chem. 58 (1993) 2774-2780.
7. [7] C. Tanielian, L. Golder, C. Wolff, Production and quenching of singlet oxygen by the sensitizer in dye-sensitized photo-oxygenations, J. Photochem. 25 (1984) 117-125.
8. [8] E. Zenkevich, E. Sagun, V. Knyukshto, A. Shulga, A. Mirinov, O. Efremova, R. Bonnett, S. Phinda Songea, M. Kassem, Photophysical and photochemical properties of potential porphyrin and chlorin photosensitizers for PDT, J. Photochem. Photobiol. B: Biol. 33 (1996) 171-180.
9. [9] M. Momenteau, D. Oulmi, P. Maillard, A. Croisy, in SPIE Proc., vol. 2325, Photodynamic Therapy of Cancer II. In Vitro Photobiological Activity of a New Series of Photosensitizers, The Glycoconjugated Porphyrins, 1994, pp. 13-23.
10. [10] R. Santus, J.F. Reyftmann, Photosensitization of membrane components, Biochimie 68 (1986) 843-848.
11. [11] D. Kessel, K. Woodburn, B.W. Henderson, C.K. Chang, Sites of photodamage in vivo and in vitro by cationic porphyrin, Photochem. Photobiol. 62 (1995) 875-881.
12. [12] A.D. Munday, A. Sriratana, J.S. Hills, S.B. Kahl, P. Nagley, Mitochondria are the functional intracellular target for a photosensitizing boronated porphyrin, Biochim. Biophys, Acta 1311 (1996) 1-4.
13. [13] B. Ehrenberg, E. Pevzener, Spectroscopic properties of the potentiometric Merocyanine 40 in solutions and liposomes, Photochem. Photobiol. 57 (1993) 228-234.
14. [14] P. Sekher, G. Garbo, Spectroscopic studies of tin ethyl etiopurpurin in homogeneous and heterogeneous systems, J. Photochem. Photobiol. B: Biol. 20 (1993) 117-125.
15. [15] Ch.R. Cantor, P.R. Schimmel, Biophysical Chemistry II. Freeman, San Francisco, 1980.
16. [16] J.N. Demas, G.A. Crosby, The measurement of photoluminescence quantum yields. A review, J. Phys. Chem. 75 (1971) 991-1024.
17. [17] R. Margalit, N. Shaklai, S. Cohen, Fluorimetric studies on the dimerization equilibrium of protoporphyrin IX and its haemato derivative, Biochem. J. 209 (1983) 547-552.
18. [18] B.M. Aveline, T. Hasan, R.W. Redmond, The effects of aggregation, protein binding and cellular incorporation on the photophysical properties of benzoporphyrin derivative monoacid ring A (BPDMA), J. Photochem. Photobiol. B: Biol. 30 (1995) 161-169.
19. [19] R.J. Clarke, H.-J. Appel, A stopped-flow kinetic study of the interaction of potential-sensitive oxonol dyes with lipid vesicles, Biophys. Chem. 34 (1989) 225-237.
20. [20] R. Margalit, M. Rotenberg, Thermodynamics of porphyrin dimerization in aqueous solutions, Biochem. J. 219 (1984) 445-450.
21. [21] D. Brault, C. Vever-Bizet, T. Le Doan, Spectrofluorimetric study of porphyrin incorporation into membrane models - evidence for pH effects, Biochim. Biophys. Acta 857 (1986) 238-250.
22. [22] I. Martín, I. Haro, F. Reig, M.A. Alsina, Synthesis and physicochemical study of hepatitis A viral-VP1 protein peptides, Langmuir 10 (1994) 784-789.
23. [23] R. Bonnett, S. Ioannou, R.D. White, U.-J. Winfield, M.C. Berenbaum, Meso-tetra(hydroxyphenyl)porphyrins as tumour photosensitisers: chemical and photochemical aspects, Photobiochem. Photobiophys. S (1987) 45-56.
24. [24] G.J. Smith, The effect of aggregation on the fluorescence and triplet state yield of hematoporphyrin, Photochem. Photobiol. 41 (1985) 123-126.
25. [25] D. Kessel, E. Rossi, Determinants of porphyrin-sensitized photooxidation characterized by fluorescence and absorption spectra, Photochem. Photobiol. 35 (1982) 37-41.
26. [26] E. Reddi, G. Jori, Steady-state and time-resolved spectroscopic studies of photodynamic sensitizers: porphyrins and phthalocyanines, Rev. Chem. Intermed. 10 (1988) 241-268.
27. [27] J. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum, New York, 1983, pp. 16-17.
28. [28] J. Yguerabide, M.C. Foster, Fluorescence spectroscopy of biological membranes, in: E. Grell (Ed.), Membrane Spectroscopy, Springer, Berlin, 1981, pp. 199-269.
29. [29] B. Paquette, H. Ali, R. Langloise, I.E. van Lier, Biological activities of phthalocyanines - VIII. Cellular distribution in V-79 Chinese hamster cells and phototoxicity of selectively sulfonated aluminium phthalocyanines, Photochem. Photobiol. 47 (1988) 215-220.