Receptor-mediated targeting of phthalocyanines to macrophages via covalent coupling to native or maleylated bovine serum albumin

Photochemistry and Photobiology

Volumn 69, Issue 3, 1999, Pages 345-352

  Brasseur, Nicole ^a   Langlois, Réjean ^a   La Madeleine, Carole ^a   Quellet, René ^a   Van Lier, Johan E ^a  

^a UNIVERSITY OF SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BOVINAE;

BOVINE SERUM ALBUMIN; IMMUNOGLOBULIN RECEPTOR; INDOLE DERIVATIVE; ORGANOMETALLIC COMPOUND; PHOTOSENSITIZING AGENT; SCAVENGER RECEPTOR; TETRASULFOPHTHALOCYANINE ALUMINUM;

ANIMAL; ARTICLE; CATTLE; CELL LINE; CHEMISTRY; DRUG EFFECT; MACROPHAGE; METABOLISM; MOUSE; PHOTOCHEMOTHERAPY;

ANIMALS; CATTLE; CELL LINE; INDOLES; MACROPHAGES; MICE; ORGANOMETALLIC COMPOUNDS; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; RECEPTORS, IMMUNOLOGIC; RECEPTORS, SCAVENGER; SERUM ALBUMIN, BOVINE;

EID: 0033091409     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1999.tb03297.x     Document Type: Article

References (46)

1. Fisher, A. M., A. L. Murphee and C. J. Gomer (1995) Clinical and preclinical photodynamic therapy (review). Lasers Surg. Med. 17, 2-31.
2. Kessel, D. (1996) Photodynamic therapy of neoplastic disease (Review). Drugs of Today 32, 385-396.
3. Henderson, B. W. and T. J. Dougherty (1992) How does photodynamic therapy work? Photochem. Photobiol. 55, 145-157.
4. Brown, S. (1996) PDT comes of age (Editorial). Int. Photodyn. A PDT Forum 1, 1.
5. van Lier, J. E. (1990) Phthalocyanines as sensitizers for PDT of cancer. In Photodynamic Therapy of Neoplastic Disease (Edited by D. Kessel), pp. 279-290. CRC Press, Boca Raton, FL.
6. Rosenthal, I. (1991) Phthalocyanines as photodynamic sensitizers. Yearly review. Photochem. Photobiol 53, 859-870.
7. Mazière, J. C., P. Morlière and R. Santus (1991) New trends in photobiology (Invited review). The role of the low density lipoprotein receptor pathway in the delivery of lipophilic photosensitizers in the photodynamic therapy of tumours. J. Photochem. Photobiol. B Biol. 8, 351-360.
8. Klyashchilsky, B. A., I. S. Nechaeva and G. V. Ponomaryov (1994) Approaches to targetted photodynamic tumor therapy. Review. J. Controlled Release 29, 1-16.
9. Gordon, S. and S. Rabinowitz (1989) Macrophages as targets for drug delivery. Adv. Drug Delivery Rev. 4, 27-47.
10. Basu, S. K. (1990) Receptor-mediated endocytosis of macromolecular conjugates in selective drug delivery. Biochem. Pharmacol. 40, 1941-1946.
11. Milas, L., J. Wike, N. Hunter, J. Volpe and I. Basic (1987) Macrophage content of murine sarcomas and carcinomas: associations with tumor growth parameters and tumor radiocurability. Cancer Res. 47, 1069-1075.
12. 2 from cells by photodynamic treatment in vitro. Cancer Res. 49, 6896-6900.
13. Evans, S., W. Matthews, R. Perry, D. Fraker, J. Norton and H. I. Pass ( 1990) Effect of photodynamic therapy on tumor necrosis factor production by murine macrophages. J. Nail. Cancer Inst. 82, 34-39.
14. Yamamoto, N., J. K. Hoober, N. Yamamoto and S. Yamamoto (1992) Tumoricidal capacities of macrophages photodynamically activated with hematoporphyrin derivative. Photochem. Photobiol. 56, 245-250.
15. Korbelik, M. and G. Krosl (1994) Enhanced macrophage cytotoxicity against tumor cells treated with photodynamic therapy. Photochem. Photobiol. 60, 497-502.
16. Krosl, G., M. Korbelik and G. J. Dougherty (1995) Induction of immune cell infiltration into murine SCCVII tumour by Photofrin-based photodynamic therapy. Br. J. Cancer 71, 549-555.
17. Korbelik, M. (1992) Low density lipoprotein receptor pathway in the delivery of Photofrin: how much is it relevant for selective accumulation of the photosensitizers in tumors? J. Photochem. Photobiol. B Biol. 12, 107-109.
18. Korbelik, M., G. Krosl, P. L. Olive and D. J. Chaplin (1991) Distribution of photofrin between tumor cells and tumor associated macrophages. Br. J. Cancer 64, 508-512.
19. Hamblin, M. R. and E. L. Newman (1994) New trends in photobiology (Invited review). On the mechanism of the tumour-localising effect in photodynamic therapy. J. Photochem. Photobiol. B Biol. 23, 3-8.
20. Goldstein, J. L., Y. K. Ho, S. K. Basu and M. S. Brown (1979) Binding site on macrophages that mediates uptake and degradation of acetylated low density lipoprotein, producing massive cholesterol deposition. Proc. Natl. Acad. Sci. USA 76, 333-337.
21. Krieger, M., S. Acton, J. Ashkenas, A. Pearson, M. Penman and D. Resnick (1993) Molecular flypaper, host defense and atherosclerosis. Structure, binding properties and functions of macrophage scavenger receptors. Minireview. J. Biol. Chem. 268, 4569-4572.
22. Mukhopadhyay, A., G. Chaudhuri, S. K. Arora, S. Sehgal and S. K. Basu (1989) Receptor-mediated drug delivery to macrophages in chemotherapy of leishmaniasis. Science 244, 705-707.
23. Mukhopadhyay, A., B. Mukhopadhyay, R. K. Srivastava and S. K. Basu (1992) Scavenger-receptor mediated delivery of daunomycin elicits selective toxicity towards neoplastic cells of macrophage lineage. Biochem. J. 284, 237-241.
24. Mukhopadhyay, B., A. Mukhopadhyay and S. K. Basu (1993) Enhancement of tumouricidal activity of daunomycin by receptor-mediated delivery. In vivo studies. Biochem. Pharmacol. 46, 919-924.
25. Ali, H., R. Langlois, J. R. Wagner, N. Brasseur, B. Paquette and J. E. van Lier (1988) Biological activities of phthalocyanines - X. Syntheses and analyses of sulfonated phthalocyanines. Photochem. Photobiol. 47, 713-717.
26. Weber, J. H. and D. H. Busch (1965) Complexes derived from strong field ligands. XIX. Magnetic properties of transition metal derivatives of 4,4′,4″,4‴-tetrasulfophthalocyanine. Inorg. Chem. 4, 469-471.
27. Skorobogaty, A., T. D. Smith, G. Dougherty and J. R. Pilbrow (1985) Synthesis and physico-chemical properties of cationic derivatives of phthalocyaninatocopper (II). J. Chem. Soc. Dalton Trans. 651-658.
28. Zickendraht, C. and E. J. Koller (1959) New phthalocyanine dyestuffs. U.S. Patent 2,897,207 (C.A. 54: P2767e).
29. Staros, J. V., R. W. Wright and D. M. Swingle (1986) Enhancement by N-hydroxysulfosuccinimide of water-soluble carbodiimide-mediated coupling reactions. Anal Biochem. 156, 220-222.
30. Bradford, M. M. (1976) A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254.
31. Butler, P. J. G. and B. S. Hartley (1972) Maleylation of amino groups. Methods Enzymol. 25, 191-199.
32. Fraker, P. J. and J. C. Speck, Jr. (1978) Protein and cell membrane iodinations with a sparingly soluble chloroamide, 1,3,4,6-tetrachloro-3α,6α-diphenylglycoluril. Biochem. Biophys, Res. Commun. 80, 849-857.
33. Tada, H., O. Shiho, K. Kuroshima, M. Koyama and K. Tsukamoto (1986) An improved colorimetric assay for interleukin 2. J. Immunol. Methods 93, 157-165.
34. Haberland, M. E. and A. M. Fogelman (1985) Scavenger receptor-mediated recognition of maleyl bovine plasma albumin and the demaleylated protein in human monocyte macrophages. Proc. Natl. Acad. Sci. USA 82, 2693-2697.
35. Larroque, C., A. Pelegrin and J. E. van Lier (1996) Serum albumin as a vehicle for zinc phthalocyanine: photodynamic activities in solid tumor models. Br. J. Cancer 74, 1886-1890.
36. Spike, J. D. and J. C. Bommer (1986) Zinc tetrasulfophthalocyanine as a photodynamic sensitizer for biomolecules. Int. J. Radiat. Biol. 50, 41-45.
37. Wagner, J. R., H. Ali, R. Langlois, N. Brasseur and J. E. van Lier (1987) Biological activities of phthalocyanines - VI. Photooxidation of L-tryptophan by selectively sulfonated gallium phthalocyanines: singlet oxygen yields and effect of aggregation. Photochem. Photobiol. 45, 587-594.
38. Langlois, R., H. Ali, N. Brasseur, R. Wagner and J. E. van Lier (1986) Biological activities of phthalocyanines - IV. Type II sensitized photooxidation of L-lryptophan and cholesterol by sulfonated metallo phthalocyanines. Photochem. Photobiol. 44, 117-123.
39. Hamblin, M. R. and E. L. Newman (1994) Photosensitizer targeting in photodynamic therapy I. Conjugates of haematoporphyrin with albumin and transferrin. J. Photochem. Photobiol. B Biol. 26, 45-56.
40. Rohrer, L. (1991) The acetylated low-density lipoprotein receptor or macrophage scavenger receptor. Atherosclerosis Rev. 23, 123-129.
41. Margaron, P., M.-J. Grégoire, V. Šč asnár, H. Ali and J. E. van Lier (1996) Structure-photodynamic activity relationships of a series of 4-substituted zinc phthalocyanines. Photochem. Photobiol. 63, 217-223.
42. Brasseur, N., H. Ali, R. Langlois and J. E. van Lier (1987) Biological activities of phthalocyanines - VII. Photoinactivation of V-79 Chinese hamster cells by selectively sulfonated gallium phthalocyanines. Photochem. Photobiol. 46, 739-744.
43. Brasseur, N., H. Ali, R. Langlois and J. E. van Lier (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.
44. Paquette, B., H. Ali, R. Langlois and J. E. van Lier (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.
45. Peng, Q., G. W. Farrants, K. Madslien, J. C. Bommer, J. Moan, H. E. Danielsen and J. M. Nesland (1991) Subcellular localization, redistribution and photobleaching of sulfonated aluminum phthalocyanines in a human melanoma cell line. Int. J. Cancer 49, 290-295.
46. Hamblin, M. R., B. Penta, B. Ortel and T. Hasan (1998) Targeting phototoxicity to macrophages via albumin photosensitizer conjugates. Proceedings of the 26th Annual Meeting of the American Society for Photobiology. Snowbird, UT, USA, July 1998.