Water soluble aluminium phthalocyanine-polymer conjugates for PDT: Photodynamic activities and pharmacokinetics in tumour bearing mice

British Journal of Cancer

Volumn 80, Issue 10, 1999, Pages 1533-1541

  Brasseur, N ^a   Ouellet, R ^a   La Madeleine, C ^a   Van Lier, J ^a  

^a UNIVERSITY OF SHERBROOKE   (Canada)

Author keywords

Aluminium phthalocyanine; Colo 26 tumour; EMT 6 tumour; Photodynamic therapy; Polyethyleneglycol; Polyvinylalcohol

Indexed keywords

ALUMINUM DERIVATIVE; CREMOPHOR; DYE; MACROGOL; PHOTOSENSITIZING AGENT; PHTHALOCYANINE; POLYVINYL ALCOHOL;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BREAST TUMOR; CANCER GRAFT; COLON CARCINOMA; CONTROLLED STUDY; DRUG SOLUBILITY; EMULSION; HYDROPHOBICITY; LIGHT; MOUSE; NONHUMAN; PHOTODYNAMIC THERAPY; PHOTOTOXICITY; PRIORITY JOURNAL; RADIATION DOSE; TUMOR REGRESSION;

EID: 0033027572     PISSN: 00070920     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.bjc.6690557     Document Type: Article

References (54)

1. Allémann E, Brasseur N, Kudrevich SV, La Madeleine C and van Lier JE (1997) Photodynamic activities and biodistribution of fluorinated zinc phthalocyanine derivatives in the murine EMT-6 tumor model. Int J Cancer 72: 289-294
2. Bullemo C, Jori G, Rihter BD, Kenney ME and Rodgers MAJ (1992) Si(IV)-naphthalocyanine: modulalion of its pharmacokinetic properties through the use of hydrophilic axial ligands. Cancer Lett 65: 145-150
3. Ben-Hur E and Rosenthal I (1986) Photosensitization of chinese hamster cells by water-soluble phthalocyanines. Photochem Photobiol 43: 615-619
4. Berg K, Bommer JC and Moan J (1989) Evaluation of sulfonated aluminum phthalocyanines for use in photochemotherapy. A study on the relative efficiencies of photoinactivation. Photochem Photobiol 49: 587-594
5. Brasseur N, Ali H, Langlois R and van Lier JE (1987) Biological activities of phthalocyanines - VII. Photoinactivation of V-79 chinese hamster cells by selectively sulfonated gallium phthalocyanines. Photochem Photobiol 46: 739-744
6. Brasseur N, Ali H, Langlois R and van Lier JE (1988) Biological activities of phthalocyanines IX. Photosensitization of V-79 chinese hamster cells and EMT-6 mouse mammary tumor by selectively sulfonated zinc phthalocyanines. Photochem Photobiol 47: 705-711
7. Brasseur N, Nguyen T-L, Langlois R, Ouellet R, Marengo S, Houde D and van Lier JE (1994) Synthesis and photodynamic activities of silicon 2,3-naphthalocyanine derivatives. J Med Chem 37: 415-420
8. IRITc-MIBI following photodynamic therapy. Photochem Photobiol 64: 702-706
9. Casnati A, Ferdani R, Pochini A and Angaro R (1997) p-(Benzyloxy) calix[8] arene: one-pot synthesis and functionalization. J Org Chem 62: 6236-6239
10. Chan W-S, Marshall JF, Svensen R, Phillips D and Hart IR (1987) Photosensitising activity of phthalocyanine dyes screened against tissue culture cells. Photochem Photobiol 45: 757-761
11. Chan W-S, Marshall JF, Svensen R, Bedwell J and Hart IR (1990) Effect of sulfonation on the cell and tissue distribution of the photosensitizer aluminum phthalocyanine. Cancer Res 50: 4533-4538
12. Chan W-S, West CML, Moore JV and Hart IR (1991) Photocytotoxic efficacy of sulphonated species of aluminum phthalocyanine against cell monolayers, multicellular spheroids and in vivo tumours. Br J Cancer 64: 827-832
13. Chan W-S, Brasseur N, La Madeleine C and van Lier JE (1996) Evidence for different mechanisms of EMT-6 tumor necrosis by photodynamic therapy with disulfonated aluminum phthalocyanine or photofrin: tumor cell survival and blood flow. Anticancer Res 16: 1887-1892
14. Chan W-S, Brasseur N, La Madeleine C, Ouellet R and van Lier JE (1997) Efficacy and mechanism of aluminum phthalocyanine and its sulphonated derivatives mediated photodynamic therapy on murine tumours. Eur J Cancer 33(11): 1855-1859
15. Cuomo V, Jori G, Rihter B, Kenney ME and Rodgers MAJ (1990) Liposome-delivered Si(IV)-naphthalocyanine as a photodynamic sensitizer for experimental tumors: pharmacokinetic and phototherapeutic studies. Br J Cancer 62: 966-970
16. Davis N, Liu D, Jain AK, Jiang S-Y, Jiang F, Richter A and Levy JG (1993) Modified polyvinyl alcohol-benzoporphyrin derivative conjugates as phototoxic agents. Photochem Photobiol 57: 641-647
17. Daziano JP, Steenken S, Chabannon C, Mannoni P, Chanon M and Julliard M (1996) Photophysical and redox properties of a series of phthalocyanines. Relation with their photodynamic activities on TF-I and Daudi leukemic cells. Photochem Photobiol 64: 712-719
18. Dereski MO, Madigan L and Chopp M (1994) Brain response to photodynamic therapy with Photofrin, monosulfonated aluminum phthalocyanine and tin purpurin. Proc Spie 2371: 579-584
19. Dye D and Watkins J (1980) Suspected anaphylactic reaction to Cremophor EL. Br Med J 280: 1353
20. Egan LP (1972) Synthesis and acid-catalyzed hydrolysis of 3-O-glycosyl-i -serine and -threonine. Carbohydrate Res 23: 261-273
21. Fields R (1972)The rapid determination of amino groups with TNBS. Methods Enzymol 25: 464-468
22. Hamblin MR, Miller JL, Rizvi I, Ortel B, Maytin EV and Hasan T (1998) Mechanism of differential phototoxicity after pegylation of poly-L-lysine chlorin E6 conjugates. Proceedings of the 26th Annual Meeting of the American Society for Photobiology, Snowbird, Utah, July 1998; 24S
23. Henderson BW, Waldow SM, Mang TS, Potter WR, Malone PB and Daugherty TJ (1985) Tumor destruction and kinetics of tumor cell death in two experimental mouse tumors following photodynamic therapy. Cancer Res 45: 572-576
24. Hu M, Brasseur N, Yildiz SZ, van Lier JE and Leznoff CC (1998) Hydroxyphthalocyanines as potential photodynamic agents for cancer therapy. J Med Chem 41: 1789-1802
25. Isele U, Schieweck K, Kessler R, Van Hoogevest P and Capraro HG (1995) Pharmacokinetics and body distribution of liposomal zinc phthalocyanine in tumour-bearing mice: influence of aggregation state, particle size, and composition. J Pharm Sci 84: 166-173
26. Jiang FN, Jiang S, Liu D, Richter A and Levy JG (1990) Development of technology for linking photosensitizers to a model monoclonal antibody. J Immunol Methods 134: 139-149
27. Kessel D (1996) Photodynamic therapy of neoplastic disease. Drugs of Today 32: 385-396
28. Krinick NL, Sun Y, Joyner D, Spikes JD, Straight RC and Kopecek J (1994) A polymeric drug delivery system for the simultaneous delivery of drugs activatable by enzymes and/or light. J Biomater Sci Polymer Edu 5: 303-324
29. Krüger TC, Mettler D, Schouwink H, Altermatt HJ and Ris HB (1998) Experimental assessment of photodynamic therapy with a polyethylene glycol derivative of mTHPC. Proceeding of the 7th Biennial Congress of the International Photodynamic Association, Nantes, France, July 1998: 66
30. Larroque C, Pelegrin A and van Lier JE (1996) Serum albumin as a vehicle for zinc phthalocyanine: photodynamic activities in solid tumour models. Br J Cancer 74: 1886-1890
31. Margaron P, Grégoire M-J, Šcasnár V and Lier JE (1996a) Structure-photodynamic activity relationships of a series of 4-substituted zinc phthalocyanines. Photochem Photobiol 63: 217-223
32. Margaron P, Madarnas P, Ouellet R and van Lier JE (1996b) Biological activities of phthalocyanines. XVII. Histopathologic evidence for different mechanisms of EMT 6 tumour necrosis induced by photodynamic therapy with disulfonated aluminum phthalocyanine or Photofrin. Anticancer Res 16: 613-620
33. Morlet L, Vonarx V, Foultier MT, Gouyette A, Stewart C, Lenz P and Patrice T (1997) In vitro and in vivo spectrofluorometry of a water-soluble meta-(tetrahydroxyphenyl)chlorin (m-THPC) derivative. J Photochem Photobiol B: Biol 39: 249-257
34. Ochsner M (1997) Photophysical and photobiological processes in the photodynamic therapy of tumours. J Photochem Photobiol B: Biol 39: 1-18
35. Paquette B, Ali H, Langlois R and van Lier JE (1988) Biological activities of phthalocyanines - VIII. Cellular distribution in V-79 chinese hamster cells and phototoxicity of selectively sulfonated aluminum phthalocyanines. Photochem Photobiol 47: 215-220
36. Pomer S, Grashev G, Sinn H, Kälble T and Slachler G (1995) Laser induced fluorescence diagnosis and photodynamic therapy of human renal cell carcinoma. Urol Int 55: 197-201
37. Rasch MH, Tijssen K, vanSteveninck J and Dubbelman TMAR (1996) Synergistic interaction of photodynamic treatment with the sensitizer aluminum phthalocyanine and hyperthermia on loss of clonogenicity of CHO cells. Photochem Photobiol 64: 586-593
38. Rheinwald M, Wunder A, Sinn H, Haase T and Schlegel W (1998) Pharmacokinetic and photophysical properties of a polyethylene glycol derivative of mTHPC. Proceedings of the 7th Biennial Congress of the International Photodynamic Association, Nantes, France, July 1998; 67
39. Rizvi I and Hasan T (1998) Selective targeting of intraperitoneal tumors. Proceedings of the 7th Biennial Congress of the International Photodynamic Association, Nantes, France, July 1998: 107
40. Roberts WG, Smith KM, McCullough JL and Berns MW (1989) Skin photosensitivity and photodestruction of several potential photodynamic sensitizers. Photochem Photobiol 49: 431-438
41. Rosenthal I (1991) Phthalocyanines as photodynamic sensitizers. Yearly review. Photochem Photobiol 53: 859-870
42. Rovers J, Saarnak A, Sterenborg D, Terpstra O and Grahn M (1998) Biodistribution of mTHPC and its pegylated derivative SC 102 in a rat liver tumour model. Proceedings of the 7th Biennial Congress of the International Photodynamic Association, Nantes, France, July 1998: 67
43. Sharman WM, Allen CM and van Lier JE (1999) The role of activated oxygen species in photodynamic therapy. In: Singlet Oxygen UV-A and Ozone, Methods in Enzymology. Sies H and Packer L (eds). Academic Press: San Diego, CA
44. Soukos NS, Hamblin MR and Hasan T (1997) The effect of charge on cellular uptake and phototoxicity of polylysine chlorin e6 conjugates. Photochem Photobiol 65: 723-729
45. Spikes JE (1986) Yearly review: phthalocyanines as photosensitizers in biological systems and for the photodynamic therapy of tumors. Photochem Photobiol 43: 691-699
46. Svaasand O (1984) Optical dosimetry for direct and interstitial radiation therapy of malignant tumors. In: Porphyrin Localization and Treatment of Tumours, Doiron DR and Gomer CJ (eds), pp. 91-114. Alan R. Liss; New York
47. Tada HR, Shibo O, Kuroshima K, Koyama M and Tsukamoto K (1986) An improved colorimetric assay for interleukin 2. Immunol Methods 93: 157-165
48. Tralau CJ, Young AR, Walker NP, Vernon DI, Macrobert AJ, Brown SB and Brown SO (1989) Mouse skin photosensitivity with dihaematoporphyrin ether (DHE) and aluminium sulphonated phthalocyanine (AISPc): a comparative study. Photochem Photobiol 49: 305-312
49. Tsuruo T, Yamori T, Naganuma K, Tsukagoshi S and Sakurai Y (1983) Characterization of metastatic clones derived from a metastatic variant of mouse colon adenocarcinoma 26. Cancer Res 43: 5347-5442
50. van Lier JE (1990) Phthalocyanines as sensitizers for PDT of cancer. In: Photodynamic Therapy of Neoplastic Dieseases, Kessel D (ed), pp. 279-290. CRC Press: Boca Raton, FI.
51. Woodburn K, Chang CK, Lee B, Henderson B and Kessel D (1994) Biodistribution and PDT efficacy of a ketochlorin photosensitizer as a function of the delivery vehicle. Photochem Photobiol 60: 154-149
52. Wulff G and Röhle G (1974) Results and problems of O-glycoside synthesis. Angewandte Chemie 13: 157-170
53. Yamaoka T, Tabata Y and Ikada Y (1994) Distribution and tissue uptake of poly(ethylene glycol) with different molecular weights after intravenous administration to mice. J Pharmaceut Sci 83: 601-606
54. Zharkova NN, Kozlov DN, Smirnov VV, Sokolov VV, Chissov VI, Filonenko EV, Sukhin DG, Galpern MG and Vorozhtsov GN (1994) SPIE - Photodynamic Therapy of Cancer II 2325: 400