Effects of peripheral chloro substitution on the photophysical properties and in vitro photodynamic activities of galactose-conjugated silicon(IV) phthalocyanines

ChemMedChem

Volumn 3, Issue 7, 2008, Pages 1110-1117

  Lo, Pui Chi ^a   Fong, Wing Ping ^a   Ng, Dennis K P ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Galactose; Heavy atom effect; Photodynamic therapy; Photosensitisers; Phthalocyanines

Indexed keywords

CHLORINE; FORMAMIDE DERIVATIVE; GALACTOSE; INDOLE DERIVATIVE; N,N DIMETHYLFORMAMIDE; N,N-DIMETHYLFORMAMIDE; ORGANOSILICON DERIVATIVE; PHOTOSENSITIZING AGENT; PHTHALOCYANINE; SILICON; SINGLET OXYGEN;

ARTICLE; CELL STRAIN HT29; CHEMISTRY; COLORECTAL TUMOR; FLUORESCENCE; HUMAN; METABOLISM; PATHOLOGY; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; CHLORINE; COLORECTAL NEOPLASMS; FLUORESCENCE; FORMAMIDES; GALACTOSE; HT29 CELLS; HUMANS; INDOLES; ORGANOSILICON COMPOUNDS; PHOTOSENSITIZING AGENTS; SILICON; SINGLET OXYGEN; SPECTRUM ANALYSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 54849204100     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200800042     Document Type: Article

References (39)

1. a) D. E. J. G. J. Dolmans, D. Fukumura, R. K. Jain, Nat. Rev. Cancer 2003, 3, 380-387;
2. b) S. B. Brown, E. A. Brown, I. Walker, Lancet Oncol. 2004, 5, 497-508;
3. c) A. P. Castano, P. Mroz, M. R. Hamblin, Nat. Rev. Cancer 2006, 6, 535-545.
4. a) H. Ali, J. E. van Lier, Chem. Rev. 1999, 99, 2379-2450;
5. b) M. R. Detty, S. L. Gibson, S. J. Wagner, J. Med. Chem. 2004, 47, 3897-3915;
6. c) E. S. Nyman, P. H. Hynninen, J. Photochem. Photobiol. B 2004, 73, 1-28.
7. M. R. Detty, P. B. Merkel, J. Am. Chem. Soc. 1990, 112, 3845-3855.
8. M. Krieg, J. M. Bilitz, M. B. Srichai, R. W. Redmond, Biochim. Biophys. Acta Gen. Subj. 1994, 1199, 149-156.
9. a) E. Zenkevich, E. Sagun, V. Knyukshto, A. Shulga, A. Mironov, O. Efremova, R. Bonnett, S. P. Songca, M. Kassem, J. Photochem. Photobiol. B 1996, 33, 171-180;
10. b) N. Rubio, F. Prat, N. Bou, J. I. Borrell, J. Teixidó, T. Villanueva, Á. Juarranz, M. Cañete, J. C. Stockert, S. Nonell, New J. Chem. 2005, 29, 378-384.
11. a) M. Roslaniec, H. Weitman, D. Freeman, Y. Mazur, B. Ehrenberg, J. Photochem. Photobiol. B 2000, 57, 149-158;
12. b) R. A. Obermüller, K. Hohenthanner, H. Falk, Photochem. Photobiol. 2001, 74, 211-215.
13. M. Pineiro, A. M. d'A. R. Gonsalves, M. M. Pereira, S. J. Formosinho, L. G. Arnaut, J. Phys. Chem. A 2002, 106, 3787-3795.
14. a) P.-C. Lo, S. Wang, A. Zeug, M. Meyer, B. Röder, D. K. P. Ng, Tetrahedron Lett. 2003, 44, 1967-1970;
15. b) A. Ogunsipe, T. Nyokong, J. Porphyrins Phthalocyanines 2005, 9, 121-129;
16. c) W. Chidawanyika, A. Ogunsipe, T. Nyokong, New J. Chem. 2007, 31, 377-384.
17. a) D. Ramaiah, A. Joy, N. Chandrasekhar, N. V. Eldho, S. Das, M. V. George, Photochem. Photobiol. 1997, 65, 783-790;
18. b) E. Arunkumar, P. K. Sudeep, P. V. Kamat, B. C. Noll, B. D. Smith, New J. Chem. 2007, 31, 677-683.
19. a) D. M. Guldi, T. D. Mody, N. N. Gerasimchuk, D. Magda, J. L. Sessler, J. Am. Chem. Soc. 2000, 122, 8289-8298;
20. b) A. Drzewiecka-Matuszek, A. Skalna, A. Karocki, G. Stochel, L. Fiedor, J. Biol. Inorg. Chem. 2005, 10, 453-462.
21. a) J. Killoran, L. Allen, J. F. Gallagher, W. M. Gallagher, D. F. O'Shea, Chem. Commun. 2002, 1862-1863;
22. b) A. Gorman, J. Killoran, C. O'Shea, T. Kenna, W. M. Gallagher, D. F. O'Shea, J. Am. Chem. Soc. 2004, 126, 10619-10631;
23. c) W. M. Gallagher, L. T. Allen, C. O'Shea, T. Kenna, M. Hall, A. Gorman, J. Killoran, D. F. O'Shea, Br. J. Cancer 2005, 92, 1702-1710.
24. B. M. Aveline, R. W. Redmond, Photochem. Photobiol. 1999, 69, 306-316.
25. H. Y. Liu, P. Y. Guo, P. W. Kong, X. Ying, S. J. Liao, N. K. Mak, C. K. Chang, Chem. J. Chin. Univ. 2006, 27, 1363-1365.
26. a) J.-D. Huang, S. Wang, P.-C. Lo, W.-P. Fong, W.-H. Ko, D. K. P. Ng, New J. Chem. 2004, 28, 348-354;
27. b) P.-C. Lo, C. M. H. Chan, J.-Y. Liu, W.-P. Fong, D. K. P. Ng, J. Med. Chem. 2007, 50, 2100-2107.
28. a) A. Huygens, D. Huyghe, G. Bormans, A. Verbruggen, A. R. Kamuhabwa, T. Roskams, P. A. M. de Witte, Photochem. Photobiol. 2003, 78, 607-614;
29. b) D. Ramaiah, I. Eckert, K. T. Arun, L. Weidenfeller, B. Epe, Photochem. Photobiol. 2004, 79, 99-104.
30. a) P. P. S. Lee, P.-C. Lo, E. Y. M. Chan, W.-P. Fong, W.-H. Ko, D. K. P. Ng, Tetrahedron Lett. 2005, 46, 1551-1554;
31. b) P.-C. Lo, S. C. H. Leung, E. Y. M. Chan, W.-P. Fong, W.-H. Ko, D. K. P. Ng, Photodiag. Photodyn. Ther. 2007, 4, 117-123.
32. M. D. Maree, N. Kuznetsova, T. Nyokong, J. Photochem. Photobiol. A 2001, 140, 117-125.
33. H. M. Shen, C. Y. Shi, Y. Shen, C. N. Ong, Free Radical Biol. Med. 1996, 21, 139-146.
34. a) S. Linder, M. C. Shoshan, Drug Resist. Updates 2005, 8, 199-204;
35. b) C. Tardy, P. Codogno, H. Autefage, T. Levade, N. Andrieu-Abadie, Biochim. Biophys. Acta Rev. Cancer 2006, 1765, 101-125.
36. D. F. Eaton, Pure Appl. Chem. 1988, 60, 1107-1114.
37. G. Ferraudi in Phthalocyanines - Properties and Applications, Vol. 1 (Eds.: C. C. Leznoff, A. B. P. Lever), VCH, Weinheim, 1989, p. 301.
38. W. Spiller, H. Kliesch, D. Wöhrle, S. Hackbarth, B. Röder, G. Schnurpfeil, J. Porphyrins Phthalocyanines 1998, 2, 145-158.
39. H. Tada, O. Shiho, K. Kuroshima, M. Koyama, K. Tsukamoto, J. Immunol. Methods 1986, 93, 157-165.