Halogenated silicon(IV) phthalocyanines with axial poly(ethylene glycol) chains. Synthesis, spectroscopic properties, complexation with bovine serum albumin and in vitro photodynamic activities

New Journal of Chemistry

Volumn 28, Issue 3, 2004, Pages 348-354

  Huang, Jian Dong ^a,b   Wang, Shuangqing ^a   Lo, Pui Chi ^a   Fong, Wing Ping ^a   Ko, Wing Hung ^a   Ng, Dennis K P ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^b FUZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BOVINE SERUM ALBUMIN; DIMETHYL ETHER; HALOGEN; MACROGOL; PHTHALOCYANINE; SILICON; SODIUM HYDROXIDE; SOLVENT;

ANIMAL CELL; ARTICLE; CELL STRAIN; CELL STRAIN HEPG2; CELL STRAIN J 774; CHEMICAL ANALYSIS; COMPLEX FORMATION; CONJUGATION; FLUORESCENCE; HALOGENATION; HUMAN; HUMAN CELL; IN VITRO STUDY; MACROPHAGE; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR WEIGHT; NONHUMAN; PHOTOCHEMICAL QUENCHING; PHOTODYNAMICS; PHOTOTOXICITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; SYNTHESIS;

EID: 1642406285     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b307934a     Document Type: Article

References (47)

1. (a) R. Bonnett, Chemical Aspects of Photodynamic Therapy, Gordon and Breach, Amsterdam, 2000;
2. (b) I. J. MacDonald and T. J. Dougherty, J. Porphyrins Phthalocyanines, 2001, 5, 105;
3. (c) N. L. Oleinick, R. L. Morris and I. Belichenko, Photochem. Photobiol. Sci., 2002, 1, 1;
4. (d) M. B. Vrouenraets, G. W. M. Visser, G. B. Snow and G. A. M. S. van Dongen, Anticancer Res., 2003, 23, 505.
5. (a) H. Ali and J. E. van Lier, Chem. Rev., 1999, 99, 2379;
6. (b) R. Bonnett, J. Heterocycl. Chem., 2002, 39, 455.
7. (a) E. A. Lukyanets, J. Porphyrins Phthalocyanines, 1999, 3, 424;
8. (b) C. M. Allen, W. M. Sharman and J. E. van Lier, J. Porphyrins Phthalocyanines, 2001, 5, 161;
9. (c) A. C. Tedesco, J. C. G. Rotta and C. N. Lunardi, Curr. Org. Chem., 2003, 7, 187.
10. (a) Poly(ethylene glycol) Chemistry and Biological Applications, eds. J. M. Harris and S. Zalipsky, American Chemical Society, Washington, DC, 1997;
11. (b) G. Molineux, Cancer Treatment Rev., 2002, 28, 13;
12. (c) R. B. Greenwald, Y. H. Choe, J. McGuire and C. D. Conover, Adv. Drug Delivery Rev., 2003, 55, 217.
13. (a) S. W. Young, K. W. Woodburn, M. Wright, T. D. Mody, Q. Fan, J. L. Sessler, W. C. Dow and R. A. Miller, Photochem. Photobiol., 1996, 63, 892;
14. (b) F. Mitzel, S. FitzGerald, A. Beeby and R. Faust, Chem. Commun., 2001, 2596;
15. (c) F. Mitzel, S. FitzGerald, A. Beeby and R. Faust, Chem. Eur. J., 2003, 9, 1233.
16. (a) P. Westermann, T. Glanzmann, S. Andrejevic, D. R. Braichotte, M. Forrer, G. A. Wagnieres, P. Monnier, H. van den Bergh, J.-P. Mach and S. Folli, Int. J. Cancer, 1998, 76, 842;
17. (b) R. Hornung, M. K. Fehr, J. Monti-Frayne, B. J. Tromberg, M. W. Berns and Y. Tadir, Br. J. Cancer, 1999, 81, 631;
18. (c) H.-B. Ris, T. Krueger, A. Giger, C. K. Lim, J. C. M. Stewart, U. Althaus and H. J. Altermatt, Br. J. Cancer, 1999, 79, 1061;
19. (d) R. Hornung, M. K. Fehr, H. Walt, P. Wyss, M. W. Berns and Y. Tadir, Photochem. Photobiol., 2000, 72, 696;
20. (e) T. Reuther, A. C. Kübler, U. Zillmann, C. Flechtenmacher and H. Sinn, Lasers Surg. Med., 2001, 29, 314;
21. (f) T. Krueger, H. J. Altermatt, D. Mettler, B. Scholl, L. Magnusson and H.-B. Ris, Lasers Surg. Med., 2003, 32, 61.
22. (a) G. J. Clarkson, A. Cook, N. B. McKeown, K. E. Treacher and Z. Ali-Adib, Macromolecules, 1996, 29, 913;
23. (b) G. J. Clarkson, B. M. Hassan, D. R. Maloney and N. B. McKeown, Macromolecules, 1996, 29, 1854;
24. (c) T. Toupance, P. Bassoul, L. Mineau and J. Simon, J. Phys. Chem., 1996, 100, 11 704.
25. (a) C. Bellemo, G. Jori, B. D. Rihter, M. E. Kenney and M. A. J. Rodgers, Cancer Lett., 1992, 65, 145;
26. (b) N. Brasseur, R. Ouellet, C. La Madeleine and J. E. van Lier, Br. J. Cancer, 1999, 80, 1533.
27. (a) E. Allémann, N. Brasseur, O. Benrezzak, J. Rousseau, S. V. Kudrevich, R. W. Boyle, J.-C. Leroux, R. Gurny and J. E. van Lier, J. Pharm. Pharmacol., 1995, 47, 382;
28. (b) J. C. Leroux, E. Allémann, F. DeJaeghere, E. Doelker and R. Gurny, J. Controlled Release, 1996, 39, 339;
29. (c) E. Allémann, J. Rousseau, N. Brasseur, S. V. Kudrevich, K. Lewis and J. E. van Lier, Int. J. Cancer, 1996, 66, 821;
30. (d) A. Gijsens, A. Derycke, L. Missiaen, D. de Vos, J. Huwyler, A. Eberle and P. de Witte, Int. J. Cancer, 2002, 101, 78.
31. (a) T. Ngai, G. Zhang, X.-Y. Li, D. K. P. Ng and C. Wu, Langmuir, 2001, 17, 1381;
32. (b) Z. Sheng, X. Ye, Z. Zheng, S. Yu, D. K. P. Ng, T. Ngai and C. Wu, Macromolecules, 2002, 35, 3681.
33. A preliminary communication has appeared reporting the preparation and photophysical properties of three of these compounds (4b-d): P.-C. Lo, S. Wang, A. Zeug, M. Meyer, B. Röder and D. K. P. Ng, Tetrahedron Lett., 2003, 44, 1967.
34. 750 methyl ether to be exactly 550 and 750, respectively.
35. (a) J. Vacus and J. Simon, Adv. Mater., 1995, 7, 797;
36. (b) M. Kimura, K. Nakada, Y. Yamaguchi, K. Hanabusa, H. Shirai and N. Kobayashi, Chem. Commun., 1997, 1215;
37. (c) A. C. H. Ng, X.-Y. Li and D. K. P. Ng, Macromolecules, 1999, 32, 5292.
38. W. Spiller, H. Kliesch, D. Wöhrle, S. Hackbarth, B. Röder and G. Schnurpfeil, J. Porphyrins Phthalocyanines, 1998, 2, 145.
39. G. Stehle, A. Wunder, H. H. Schrenk, G. Hartung, D. L. Heene and H. Sinn, Anti-Cancer Drugs, 1999, 10, 785.
40. M. M. Bradford, Anal. Biochem., 1976, 72, 248.
41. N. Brasseur, R. Langlois, C. La Madeleine, R. Ouellet and J. E. van Lier, Photochem. Photobiol., 1999, 69, 345.
42. D. Wöhrle, M. Eskes, K. Shigehara and A. Yamada, Synthesis, 1993, 194.
43. C. C. Leznoff, Z. Li, H. Isago, A. M. D'Ascanio and D. S. Terekhov, J. Porphyrins Phthalocyanines, 1999, 3, 406.
44. C. W. Dirk, T. Inabe, K. F. Schoch, Jr. and T. J. Marks, J. Am. Chem. Soc., 1983, 105, 1539.
45. D. F. Eaton, Pure Appl. Chem., 1988, 60, 1107.
46. G. Ferraudi, in Phthalocyanines-Properties and Applications, eds. C. C. Leznoff and A. B. P. Lever, VCH, New York, 1989, vol. 1, p. 301.
47. MTT = 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide: H. Tada, O. Shiho, K. Kuroshima, M. Koyama and K. Tsukamoto, J. Immunol. Methods, 1986, 93, 157.