CGP 55398, a liposomal Ge(IV) phthalocyanine bearing two axially ligated cholesterol moieties: A new potential agent for photodynamic therapy of tumours

British Journal of Cancer

Volumn 69, Issue 5, 1994, Pages 817-825

  Segalla, A ^a   Milanesi, C ^a   Jori, G ^a   Capraro, H G ^b   Isele, U ^b   Schieweck, K ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b Ciba Geigy Ltd ^*  (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CGP 55398; CHOLESTEROL; LIPOPROTEIN; LIPOSOME; PHTHALOCYANINE DERIVATIVE; SINGLET OXYGEN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; FEMALE; FIBROSARCOMA; INTRAVENOUS DRUG ADMINISTRATION; MOUSE; NONHUMAN; PHOTODYNAMIC THERAPY; PRIORITY JOURNAL; TUMOR; TUMOR NECROSIS;

ANIMAL; DRUG CARRIERS; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; INDOLES; LIPOSOMES; MICE; MICE, INBRED BALB C; NEOPLASMS; ORGANOMETALLIC COMPOUNDS; PHOTOCHEMOTHERAPY; RABBITS; RADIATION-SENSITIZING AGENTS; SPECTRUM ANALYSIS;

EID: 0028325834     PISSN: 00070920     EISSN: 15321827     Source Type: Journal    
DOI: 10.1038/bjc.1994.160     Document Type: Article

References (41)

1. BELLEMO, C., JORI, G., RIHTER, B.D., KENNEY, M.E. & RODGERS, M.A.J. (1992). Si(IV)-naphthalocyanine: modulation of its pharmacokinetic properties through the use of hydrophilic axial ligands. Cancer Lett., 65, 145–150.
2. BELLNIER, D.A., HO, Y.K., PANDEY, R.K., MISSERT, J.R. & DOUGHERTY, T.J. (1989). Distribution and elimination of Photofrin II in mice. Photochem. Photobiol., 50, 221–225.
3. BELTRAMINI, M., FIREY, P.A., RICCHELLI, F., RODGERS, M.A.J. & JORI, G. (1987). Steady-state and time-resolved spectroscopic studies on the hematoporphyrin-lipoprotein complex, Biochemistry, 26, 6852–6858.
4. BEN-HUR, E. & ROSENTHAL, E. (1985). The phthalocyanines: a new class of mammalian cell photosensitisers with a potential for cancer phototherapy. Int. J. Radiat. Biol., 47, 145–147.
5. BONNETT, R. & BERENBAUM, M. (1990). Porphyrins as photosensitizers. In Photosensitizing Compounds: Their Chemistry, Biology and Clinical Use, Bock, G. & Harnett, S. (eds) pp. 40-59. Ciba Foundation Symposium 146, Wiley: Chichester.
6. CAPRARO, H.-G., SCHIEWECK, K., HILFIKER, R., ISELE, U., VAN HOOGEVEST, P., NAEF, R. & BAUMANN, M. (1994). Synthesis and biological evaluation of new germanium phthalocyanines incorporated into liposomes. Part I: Chemistry. In Photodynamic Therapy of Cancer, Jori, G. & Moan, J. (eds) Proceedings EOS/SPIE, Vol. 2078 (in press).
7. CHAPMAN, M.J. (1986). Comparative analysis of mammalian plasma lipoproteins. In Methods in Enzymology, Albens, J.J. & Segret, J.P. (eds) pp. 70-143. Academic Press: London.
8. CUOMO, V., JORI, G., RIHTER, B., KENNEY, M E. & RODGERS, M.A.J. (1991). Tumour-localizing and -photosensitizing properties of liposome-delivered Ge(IV)-octabutoxy-phthalocyanine. Br. J. Cancer, 64, 93–95.
9. DOUGHERTY, T.J. (1987). Photosensitizers: therapy and detection of malignant tumours. Photochem. Photobiol., 45, 879–889.
10. FOOTE, C.S. (1976). Photosensitized oxidation and singlet oxygen: consequences in biological systems. In Free Radicals in Biology, Vol. II, Pryor, J.A. (ed.) pp. 85-133. Academic Press: New York.
11. GINEVRA, F., BIFFANTI, S., PAGNAN, A., BIOLO, R., REDDI, E. & JORI, G. (1990). Delivery of the tumour photosensitizer Zn(II)-phthalocyanine to serum proteins by different liposomes: studies in vitro and in vivo. Cancer Lett., 49, 59–65.
12. GOLDSTEIN, J.L., BROWN, M.S., ANDERSON, R.G.W., RUSSELL, D.W. & SCHNEIDER, W.J. (1985). Receptor-mediated endocytosis: concepts emerging from the LDL receptor system. Ann. Rev. Cell Biol., 1, 1–39.
13. 6 in a mouse tumour model. Cancer Res., 50, 3985–3990.
14. GORMAN, A.A. & RODGERS, M.A.J. (1992). Current perspectives of singlet oxygen detection in biological environments. J. Photochem. Photobiol., B: Biol., 14, 159–176.
15. GOTTO, A.M., POWNALL, H.J. & HAVEL, R.J. (1986). Introduction to the plasma lipoproteins. In Methods in Enzymology, Segrest, J.P. & Albers, J.J. (eds) pp. 3-41. Academic Press: New York.
16. HENDERSON, B.W. & BELLNIER, D.A. (1989). Tissue localization of photosensitizers and the mechanism of photodynamic tissue destruction. In Photosensitizing Compounds: Their Chemistry, Biology and Clinical Use, Bock, G. & Harnett, S. (eds) pp. 112-130. Ciba Foundation Symposium 146, Wiley: Chichester.
17. ISELE, U., VAN HOOGEVEST, P., CAPRARO, H.-G. & SCHIEWECK, K. (1993). Pharmaceutical development of CGP 55 847, a liposomal zinc-phthalocyanine formulation using a controlled organic solvent dilution method. In Photodynamic Therapy of Cancer, Jori, G. & Moan, J. (eds) Proceedings EOS/SPIE, Vol. 2078 (in press).
18. JORI, G. (1987). Photodynamic therapy of solid tumours. Radiat. Phys. Chem., 30, 375–380.
19. JORI, G. (1992a). Low density lipoproteins-liposome delivery systems for tumour photosensitizers in vivo. In Photodynamic Therapy: Basic Principles and Clinical Application, Henderson, B.W. & Dougherty, T.J. (eds) pp. 173-186. Marcel Dekker: New York.
20. JORI, G. (1992b). Far-red absorbing photosensitizers: their use in the photodynamic therapy of tumours. J. Photochem. Photobiol., A: Chem., 62, 371–378.
21. JORI, G. & REDDI, E. (1993). The role of lipoproteins in the delivery of tumour-targeting photosensitisers. Int. J. Biochem., 25, 1369–1375.
22. JORI, G., BIOLO, R., MILANESI, C., REDDI, E. & VALDUGA, G. (1991). Zinc(II)-phthalocyanine as a second generation photosensitizing agent in tumour phototherapy. In Photobiology, Riklis, E. (ed.) pp. 839-845. Plenum Press: New York.
23. KESSEL, D., THOMPSON, P., SAATIO, S. & NANTWI, K.D. (1987). Tumour localization and photosensitization by sulphonated derivatives of tetraphenylporphine. Photochem. Photobiol., 45, 787–789.
24. KONGSHAUG, M., MOAN, J., RIMINGTON, C. & EVENSEN, J. (1990). Binding of PDT photosensitizers to human plasma studied by ultracentrifugation. In Photodynamic Therapy of Neoplastic Disease, Vol. II, Kessel, D. (ed.) pp. 43-62. CRC Press: Boca Raton.
25. MAGDE, D., BRANNON, J.H., CREMERS, T.L. & OLMSTED, J. (1979). Triphenylmethane dyes as fluorescence standards. J. Phys. Chem., 83, 666–670.
26. MARCUS, L. (1992). Photodynamic therapy of human cancer. Proc. IEEE, 80, 869–889.
27. MOAN, J. & BERG, K. (1992). Photochemotherapy of cancer: experimental research. Photochem. Photobiol., 6, 931–948.
28. POLO, L., REDDI, E., GARBO, G.M., MORGAN, A. & JORI, G. (1992). The distribution of the tumour photosensitizers Zn(II)-phthalocyanine and Sn(IV)-etiopurpurin among rabbit plasma proteins. Cancer Lett., 66, 217–223.
29. REDDI, E. & JORI, G. (1988). Steady-state and time-resolved spectroscopic studies of photodynamic sensitizers: porphyrins and phthalocyanines. Rev. Chem. Interm., 10, 214–268.
30. REDDI, E., RODGERS, M.A.J., SPIKES, J.D. & JORI, G. (1984). The effect of medium polarity on the hematoporphyrin-sensitized photooxidation of L-tryptophan. Photochem. Photobiol., 40, 415–421.
31. REDDI, E., LO CASTRO, G., BIOLO, R. & JORI, G. (1987). Pharmacokinetic studies with Zn(II)-phthalocyanine in tumour-bearing mice. Br. J. Cancer, 56, 597–600.
32. REDDI, E., ZHOU, C., BIOLO, R., MENEGALDO, E. & JORI, G. (1990). Liposome-or LDL-administered Zn(II)-phthalocyanine as a photodynamic agent for tumours. I. Pharmacokinetic properties and phototherapeutic efficiency. Br. J. Cancer, 61, 407–411.
33. REED, M.W.R., MILLER, F.N., WIEMAN, T.J., TSENG, M.T. & PIETSCH, C.G. (1988). The effect of photodynamic therapy on the microcirculation. J. Surg. Res., 45, 452–459.
34. RUDEL, L.L., LEE, J.A., MORRIS, M.D. & FELTS, J.M. (1974). Characterization of plasma lipoproteins separated and purified by agarose-column chromatography. Biochem. J., 139, 80–85.
35. SCHERPHOF, G.L., SPANJER, H.H., DERKSEN, J.T.P., LAZAR, G. & ROERDINK, F.H. (1989). Targeting of liposomes to liver cells. In Drug Carrier Systems, Roerdink, F.H. & Kroon, A.M. (eds) pp. 281-291. Wiley: Chichester.
36. SCHIEWECK, K., JORI, G., BATT, E., VAN HOOGEVEST, P. & BIOLO, R. (1990). CGP 48127, a new liposomal Zn(II)-phthalocyanine formulation for photodynamic therapy of tumours. Abstracts of the 3rd Biennial Meeting of the International Photodynamic Association, Henderson, B. (ed.) Buffalo, USA. Abstract XXII/4.
37. SMITH, P.K., KROHN, R.I., HERMANSON, G.T., MALLIA, A.K., GARTNER, F.H., PROVENZANO, M.D., FUJIMOTO, E.K., GOEKE, N.M., OLSON, B.J. & KLENK, D.C. (1985). Measurement of protein using bicinchoninic acid. Anal. Biochem., 150, 76–85.
38. SPIKES, J.D. (1986). Phthalocyanines as photosensitizers in biological systems and for the photodynamic therapy of tumours. Photochem. Photobiol, 43, 691–699.
39. VAN LIER, J.E. & SPIKES, J.D. (1989). The chemistry, photophysics and photosensitizing properties of phthalocyanines. In Photosensitizing Compounds: Their Chemistry, Biology, and Clinical Use, Bock, G. & Harnett, S. (eds) pp. 17-32. Ciba Foundation Symposium 146. Wiley: Chichester.
40. ZHOU, C. (1989). Mechanisms of tumour necrosis induced by photodynamic therapy. J. Photochem. Photobiol., B: Biol., 3, 299–318.
41. ZHOU, C., MILANESI, C. & JORI, G. (1988). An ultrastructural comparative evaluation of tumours photosensitizd by porhyrins administered in aqueous solution, bound to liposomes or to lipoproteins. Photochem. Photobiol., 48, 487–492.