Photodynamic studies of metallo 5,10,15,20-tetrakis(4-methoxyphenyl) porphyrin: Photochemical characterization and biological consequences in a human carcinoma cell line

Photochemistry and Photobiology

Volumn 74, Issue 1, 2001, Pages 14-21

  Milanesio, M E ^a   Alvarez, M G ^a   Yslas, E I ^a   Borsarelli, C D ^b   Silber, J J ^a   Rivarola, V ^a   Durantini, E N ^a  

^a DEPARTAMENTO DE QUÍMICA   (Argentina)

^b UNIVERSIDAD NACIONAL DE SANTIAGO DEL ESTERO   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

5,10,15,20 TETRAKIS(4 METHOXYPHENYL)PORPHYRIN; CADMIUM DERIVATIVE; COPPER DERIVATIVE; DOCUSATE SODIUM; HEPTANE; OXYGEN; PORPHYRIN DERIVATIVE; TETRAHYDROFURAN; TRYPTOPHAN; UNCLASSIFIED DRUG; WATER; ZINC DERIVATIVE;

ARTICLE; CARCINOMA CELL; CELL SURVIVAL; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; HUMAN; HUMAN CELL; LARYNX CARCINOMA; LIGHT EXPOSURE; PHOTOCHEMISTRY; PHOTODYNAMICS; PHOTOOXIDATION; PHOTOSENSITIZATION; QUANTUM YIELD; REVERSE MICELLE; TEMPERATURE;

CELL SURVIVAL; HUMANS; OXYGEN; PHOTOCHEMISTRY; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; PORPHYRINS; SINGLET OXYGEN; TUMOR CELLS, CULTURED;

EID: 0035413193     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2001)074<0014:PSOMTM>2.0.CO;2     Document Type: Article

References (44)

1. Milgrom, L. R. and F. O'Neill (1993) The chemistry of natural products. In Porphyrins, Chap. 8 (Edited by R. H. Thomson), pp. 329-376. Blackie, London.
2. Grossweiner, L. I. (1994) The science of phototherapy. In Photodynamic Therapy, Chap. 8, pp. 139-155. CRC Press, London.
3. McCaughan, J. S. Jr (1999) Photodynamic therapy. A review. Drugs Aging 15, 49-68.
4. Dougherty, T. J. (1993) Photodynamic therapy. Photochem. Photobiol. 58, 895-900.
5. Penning, L. C. and T. M. Dubbelman (1994) Fundamentals of photodynamic therapy: cellular and biochemical aspects. AntiCancer Drugs 5, 139-146.
6. Hombrecher, H. K., S. Ohm and D. Koli (1996) Synthesis of galactopyranosyl substituted porphyrins. Tetrahedron 52, 5441-5448.
7. Gaud, O., R. Granet, M. Kaouadji, P. Krausz, J. C. Blais and G. Bolbach (1996) Synthèse et analyse structurale de nouvelles méso-arylporphyrines glycosylées en vue de l'application en photothérapie des cancers. Can. J. Chem. 74, 481-499.
8. Driaf, K., R. Granet, P. Krausz, M. Kaouadji, F. Thomasson, A. J. Chulia, B. Verneuil, M. Spiro, J.-C. Blais and G. Bolbach (1996) Synthesis of glycosylated cationic porphyrin as potential agents in photodynamic therapy. Can. J. Chem. 74, 1550-1563.
9. Sol, V., J. C. Blais, V. Carré, R. Granet, M. Guilloton, M. Spíro and P. J. Krausz (1999) Synthesis, spectroscopy, and photocytotoxicity of glycosylated amino acid porphyrin derivatives as promising molecules for cancer phototheraphy. J. Org. Chem. 64, 4431-4444.
10. Durantini, E. N. (2000) Synthesis of meso-nitrophenylporphyrins covalently linked to a polyphenylene chain bearing methoxy groups. J. Phorphirins Phthalocyanines 4, 233-242.
11. Jori, G., L. Schindl, A. Schindl and L. Polo (1996) Novel approaches towards a detailed control of the mechanism and efficiency of photosensitized process in vivo. J. Photochem. Photobiol. A: Chem. 102, 101-107.
12. Star, W. M., H. P. C. Marijnissen, A. E. Berg-Blok, J. A. C. Versteeg, K. A. P. Franken and H. S. Reinhold (1986) Destruction of rat mammary tumor and normal tissue microcirculation by hematoporphyrin derivative observed in vivo in sandwich observation chambers. Cancer Res. 46, 2532-2540.
13. Moan, J., Q. Peng, R. Sorensen, V. Iani and J. M. Nesland (1998) The biophysical foundations of photodynamic therapy. Endoscopy 30, 387-391.
14. Katona, Z., A. Grofesik, P. Baranyai, I. Bitter, G. Grabner, M. Kubinyi and T. Vidoczy (1998) Triplet state spectroscopic studies on some 5.10,15,20-tetrakis(methoxyphenyl) porphyrins. J. Mol. Struct. 450, 41-45.
15. Alvarez, M. G., E. I. Yslas, V. Rivarola, G. Mori, M. La Penna, J. J. Silber and E. N. Durantini (2000) Photodynamic effect of 5,10,15,20-tetrakis(4-methoxyphenyl) porphine (TMP) on Hep2 cell lines. Molecules 5, 379-380.
16. Pineiro, M., A. L. Carvalho, M. M. Pereira, A. M. d'A. Rocha Gonsalves, L. G. Arnaut and S. J. Formosinho (1998) Photoacoustic measurements of porphyrin triplet-state quantum yields and singlet-oxygen efficiencies. Chem. Eur. J. 4, 2299-2307.
17. Mosinger, J., K. Losinska, T. Abrhamova, S. Veiserova, Z. Micka, I. Newcova and B. Mosinger (2000) Determination of singlet oxygen production and antibacterial effect of nonpolar porphyrins in heterogeneous systems. Anal. Lett. 33, 1091-1104.
18. Bonnett, R., S. Ioannou, A. G. James, C. W. Pitt and M. M. Z. Soe (1993) Synthesis and film-forming properties of metal complexes of octadecyl ethers of 5,10,15,20-tetrakis(4-hydroxyphenyl) porphyrin. J. Mater. Chem. 3, 793-799.
19. Garbo, G. M., V. H. Fingar, T. J. Wieman, E. B. Noakes III, P. S. Haydon, P. B. Cerrito, D. H. Kessel and A. R. Morgan (1998) In vivo and in vitro photodynamic studies with benzochlorin iminium salts delivered by a lipid emulsion. Photochem. Photobiol. 68, 561-568.
20. Faustino, M. A. F., M. G. P. M. S. Neves, J. A. S. Cavaleiro, M. Neumann, H.-D. Brauer and G. Jori (2000) Part 2. meso-Tetraphenylporphyrin dimmer derivatives as potential photosensitizers in photodynamic therapy. Photochem. Photobiol. 72, 217-225.
21. Ali, H. and J. E. van Lier (1999) Metal complexes as photo-and radiosensitizers. Chem. Rev. 99, 2379-2450.
22. Kimel, S., B. J. Tromberg, W. G. Roberts and M. W. Berns (1989) Singlet oxygen generation of porphyrlns, chlorines, and phthalocyanines. Photochem. Photobiol. 50, 175-183.
23. Wefers, H. (1987) Singlet oxygen in biological systems. Bioelectrochemistry and bioenergetics. J. Electroanal. Chem. 232, 91-104.
24. Segalla, A., C. Milanesi, G. Jori, H.-G. Capraro, U. Isele and K. Schieweck (1994) CGP 55398, 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. Rodgers, M. A. J. and P. C. Lee (1984) Singlet molecular oxygen in micellar system. 2. Quenching behavior in AOT reverse micelles. J. Phys. Chem. 88, 3480-3484.
26. Gandini, S. C. M., V. E. Yushmanov, I. E. Borissevitch and M. Tabak (1999) Interaction of tetra (4-sulfonatophenyl) porphyrin with ion surfactants: aggregation and location in micelles. Langmuir 15, 6233-6243.
27. Borsarelli, C. D., E. N. Durantini and N. A. Garcia (1996) Singlet molecular oxygen-mediated photooxidation of nitrophenolic compounds in water-in-oil microemulsions. J. Chem. Soc. Perkin Trans. 2 2009-2013.
28. Lindsey, S. J., I. C. Schreiman, H. C. Hsu, P. C. Kearney and A. M. Marguerettaz (1987) Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions. J. Org. Chem. 52, 827-836.
29. Alvarez, M. G., M. La Penna, E. I. Yslas, V. Rivarola and E. N. Durantini (2000) Photodamaging effects of porphyrin in a human carcinoma cell line. Chem. Educator 5, 24-26.
30. Correa, N. M., E. D. Durantini and J. J. Silbier (1998) Binding of nitrodiphenylamines to reverse micelles of AOT in n-hexane and carbon tetrachloride: solvent and substituent effects. J. Colloid Interface Sci. 208, 96-103.
31. Demas, J. N. and G. A. Crosby (1971) The measurement of photoluminescence quantum yields. J. Phys. Chem. 75, 991-1024.
32. Tatman, D., P. A. Liddel, T. A. Moore, D. Gust and A. L. Moore (1998) Carotenohematoporphyrins as tumor-imaging dyes. Synthesis and in vitro photophysical characterization. Photochem. Photobiol. 68, 459-466.
33. g). J. Phys. Chem. 94, 4377-4378.
34. Valduga, G., S. Nonell, E. Reddi, G. Jori and S. E. Braslavsky (1988) The production of singlet molecular oxygen by zinc(II) phthalocyanine in ethanol and in unilamellar vesicles. Chemical quenching and phosphorescence studies. Photochem. Photobiol. 48, 1-5.
35. Kremer, J. M. H., M. W. J. van der Esker, C. Pathmanoharan and P. H. Wiersema (1977) Vesicles of variable diameter prepared by a modified injection method. Biochemistry 16, 3932-3935.
36. Ginevra, F., S. Biffanti, A. Pagnan, R. Biolo, E. Reddi and G. Jori (1990) Delivery of the photosensitizer zinc(II)-phthalocyanine to serum proteins by different liposomes: studies in vitro and in vivo. Cancer Lett. 49, 59-65.
37. Kostenich, G., T. Babushkina, A. Lavi, Y. Langzam, Z. Malik, A. Orenstein and B. Ehrenberg (1998) Photosensitization by the near-IR-absorbing photosensitizer lutetium texaphyrin: spectroscopic, in vitro and in vivo studies. J. Porphyrins Phthalocyanines 2, 383-390.
38. Hadjur, C., N. Lange, J. Rebsteim P. Monnier, H. van den Bergh and G. J. Wagnières (1998) Spectroscopic studies of photobleaching and photoproduct formation of meta(tetrahydroxyphenyl) chlorin (m-THPC) used in photodynamic therapy. The production of singlet oxygen by m-THPC. J. Photochem. Photobiol. B: Biol. 45, 170-178.
39. Belitchenko, I., V. Melnikova, L. Bezdetnaya, H. Rezzoug, J. L. Merlin, A. Potapenko and F. Guillemin (1988) Characterization of photodegradation of meta-tetra (hydroxyphenyl) chlorin (mTHPC) in solution: biological consecuences in human tumor cells. Photochem. Photobiol. 67, 584-590.
40. Jori, G. and E. Reddi (1993) The role of lipoproteins in the delivery of tumour-targeting photosensitizers. Int. J. Biochem. 25, 1369-1375.
41. Lissi, E. A., M. V. Encinas, S. A. Bertolotti, J. J. Cosa and C. M. Previtali (1990) Fluorescence quenching of indolic compounds in reverse micelles of AOT. Photochem. Photobiol. 51, 53-58.
42. Edrei, R., V. Gottfried, J. E. van Lier and S. Kimel (1998) Sulfonated phthalocyanines: photophysical properties, in vitro cell uptake and structure-activity relationships. J. Porphyrins Phthalocyanines 2, 191-199.
43. Aveline, B. M. and R. W. Redmond (1998) Exclusive free radical mechanisms of cellular photosensitization. Photochem. Photobiol. 68, 266-275.
44. Aveline, B. M. and R. W. Redmond (1999) Can cellular phototoxicity be accurately predicted on the basis of sensitizer photophysics? Photochem. Photobiol. 69, 306-316.