Porphyrin-carbohydrate conjugates: Impact of carbohydrate moieties in photodynamic therapy (PDT)

Anti-Cancer Agents in Medicinal Chemistry

Volumn 8, Issue 3, 2008, Pages 241-268

  Zheng, Xiang ^a   Pandey, Ravindra K ^a  

^a ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

Carbohydrate Porphyrin conjugates; Photodynamic therapy; Photofrin ; Porphyrin

Indexed keywords

BACTERIOCHLORIN; BENZOCHOLIN; CARBOHYDRATE DERIVATIVE; CELLOBIOSE; CHLORIN DERIVATIVE; CHLOROPHYLL; CYCLODEXTRIN; CYTOTOXIC AGENT; DISACCHARIDE; GALACTOSE; GLUCOSE; HEMATOPORPHYRIN; HEMATOPORPHYRIN DERIVATIVE; HEMIN; LACTOSE; MALTOSE; MESOPORPHYRIN; MONOSACCHARIDE; OCTAETHYLPORPHYRIN DERIVATIVE; PHOTOFRIN; PHOTOSENSITIZING AGENT; PORPHYRIN DERIVATIVE; PROTOPORPHYRIN; PYROPHEOPHORBIDE DERIVATIVE; RIBOSE; TEMOPORFIN; TETRAGLYCOSYLPORPHYRIN DERIVATIVE; TETRAPHENYLPORPHYRIN DERIVATIVE; UNINDEXED DRUG; XYLOSE; CARBOHYDRATE; CHLORIN; PORPHYRIN;

APOPTOSIS; CANCER CELL; CATALYSIS; CELL DEATH; CLINICAL TRIAL; CRYSTAL STRUCTURE; DNA DAMAGE; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG EFFICACY; DRUG PENETRATION; DRUG SAFETY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; DRUG UPTAKE; FIBROSARCOMA; GLUCOSE TRANSPORT; GLYCOSYLATION; GYNECOLOGIC CANCER; HEAD AND NECK CANCER; HUMAN; HYDROLYSIS; LIPOPHILICITY; MALIGNANT NEOPLASTIC DISEASE; NONHUMAN; PHOTODYNAMIC THERAPY; PHOTOSENSITIZATION; PHOTOTOXICITY; RESPIRATORY TRACT CANCER; REVIEW; ULTRAVIOLET RADIATION; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; NEOPLASM; PHOTOCHEMOTHERAPY; STRUCTURE ACTIVITY RELATION;

ANIMALS; CARBOHYDRATES; HUMANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NEOPLASMS; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; PORPHYRINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 43549101994     PISSN: 18715206     EISSN: None     Source Type: Journal    
DOI: 10.2174/187152008783961897     Document Type: Review

References (102)

1. Dolmans, D. E. J. G. J.; Fukumura, D.; Jain, R. K. Nat. Rev. Cancer, 2003, 3, 380.
2. Detty, M. R.; Gibson, S. L.; Wagner, S. J. J. Med Chem., 2 004, 47, 3897.
3. Brown, S. B.; Brown, E. A.; Walker, I. Lancet Oncol., 2004, 5, 497.
4. Huang, Z. Technol. Cancer Res. T., 2005, 4, 283.
5. Bonnett, R.; Martinez, G. Tetrahedron, 2001, 57, 9513.
6. Dougherty, T. J.; Gomer, C. J.; Henderson, B. W.; Jori, G. J. Natl. Cancer I., 1998, 90, 889.
7. MacDonald, I. J.; Dougherty, T. J. J. Porphyr. Phthalocya, 2001, 5, 105.
8. Henderson, B. W.; Dougherty, T. J. Photodynamic Therapy: Basic Principles and Clinical Application, Marcel Dekker, New York 1992.
9. Medina, R. A.; Owen, G. I. Biol. Res., 2002, 35.
10. Birnbaum, M. J.; Haspel, H. C; Rosen, O. M. Science, 1987, 235, 1495.
11. Liu, F. T.; Rabinovich, G. A. Nat Rev. Cancer, 2005, 5, 29.
12. Loris, R. Bba-Gen Subjects, 2002, 1572, 198.
13. Krzeslak, A.; Lipinska, A. Cell Mol. Biol. Lett., 2004, 9, 305.
14. Gillenwater, A.; Xu, X. C.; ElNaggar, A. K.; Clayman, G. L.; Lotan, R. Head Neck-J. Sci. Spec., 1996, 18, 422.
15. Xu, X. C.; Elnaggar, A. K.; Lotan, R. Am. J. Pathol., 1995, 147, 815.
16. Lotan, R.; Ito, H.; Yasui, W.; Yokozaki, H. Int. J. Cancer, 1994, 56, 474.
17. Bresalier, R. S.; Yan, P. S.; Byrd, J. C.; Lotan, R.; Raz, A. Cancer, 1997, 80, 776.
18. Bonnett, R.; Nizhnik, A. N.; Berenbaum, M. C. Chem. Commun., 1989, 1822.
19. Fulling, G.; Schroder, D.; Franck, B. Angew. Chem. Int. Edit., 1989, 28, 1519.
20. Kuroda, Y.; Hiroshige, T.; Sera., T.; Shiroiwa, Y. J. Am. Chem. Soc., 1989, 111, 1912.
21. Maillard, P.; Guerquinkern, J. L.; Momenteau, M.; Gaspard, S. J. Am. Chem. Soc., 1989, 111, 9125.
22. Maillard, P.; Guerquinkern, J. L.; Huel, C.; Momenteau, M. J. Org. Chem., 1993, 58, 2774.
23. Oulmi, D.; Maillard, P.; Guerquinkern, J. L.; Huel, C.Momenteau, M. J. Org. Chem., 1995, 60, 1554.
24. Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P. C.; Marguerettaz, A. M. J. Org. Chem., 1987, 52, 827.
25. Li, F.; Yang, K.; Tyhonas, J. S.; MacCrum, K. A.; Lindsey, J. S. Tetrahedron, 1997, 53, 12339
26. Pasetto, P.; Chen, X.; Drain, C. M.; Franck, R. W. Chem. Commun., 2001, 81.
27. Momenteau, M.; Oulmi, D.; Maillard, P.; Croisy, A. SPIE Preceedings, 1995, 2325, 13.
28. Kohata, K.; Higashio, H.; Yamaguchi, Y.; Koketsu, M.; Odashima, T. Bull. Chem. Soc. Jpn., 1994, 67, 668.
29. Hirohara, S.; Obata, M.; Saito. A.; Ogata, S. Photochem. Photobiol., 2004, 80, 301.
30. Driaf, K.; Krausz, P.; Verneuil, B.; Spiro, M. Tetrahedron Lett., 1993, 34, 1027.
31. Bourhim, A.; Gaud, O.; Granet, R.; Krausz, P.; Spiro, M. Synlett, 1993, 563.
32. Chaleix, V.; Sol, V.; Huang, Y. M.; Guilloton, M. Eur. J. Org. Chem., 2003, 2003, 1486.
33. Hombrecher, H. K.; Schell, C.; Thiem, J. Bioorg. Med. Chem. Lett., 1996, 6, 1199.
34. Schell, C.; Hombrecher, H. K. Bioorg. Med. Chem., 1999, 7, 1857.
35. Maillard, P.; Vilain, S.; Huel, C.; Momenteau, M. J. Org. Chem., 1994, 59, 2887.
36. Mikata, Y.; Onchi, Y.; Shibata, M.; Kakuchi, T. Bioorg. Med. Chem. Lett., 1998, 8, 3543.
37. Laville, I.; Figueiredo, T.; Loock, B.; Pigaglio, S. Bioorg. Med. Chem., 2003, 11, 1643.
38. Hirohara, S.; Obata, M.; Ogata, S.; Ohtsuki, C. Photoch. Photobiol. B, 2005, 78, 7.
39. Di Stasio, B.; Frochot C.; Dumas, D.; Even, P. Eur. J. Med. Chem., 2005, 40, 1111.
40. Driaf, K.; Granet, R,; Krausz, P.; Kaouadji, M. Can. J. Chem., 1996, 74, 1550.
41. Asayama, S.; Mori, T.; Nagaoka, S.; Kawakami, H. J. Biomat. Sci.-Polym. E., 2003, 14, 1169.
42. Sol, V.; Blais, J. C.; Carre, V.; Granet, R. J. Org. Chem., 1999,6 4, 4431.
43. Chen, X.; Hui, L.; Foster, D. A.; Drain, C. M. Biochem., 2004, 43, 10919.
44. Ahmed, S.; Davoust, E.; Savoie, H.; Boa, A. N.; Boyle, R. W. Tetrahedron Lett., 2004, 45, 6045.
45. Tome, J. P. C.; Neves, M. G. P. M. S.; Tome, A. C.; Cavaleiro, J. A. S. Bioorg. Med. Chem.,2 005, 13, 3878.
46. Domingues, M. R. M.; Domingues, P.; Reis, A.; Correia, A. J. F. J. Mass Spectrom., 2004, 39, 158.
47. Maillard, P.; Huel, C.; Momenteau, M. Tetrahedron Lett.,1 992, 33, 8081.
48. Cornia, M.; Casiraghi, G.; Binacchi, S.; Zanardi, F.; Rassu, G. J. Org. Chem., 1994, 59, 1226.
49. Cornia, M.; Valenti C.; Capacchi, S.; Cozzini, P. Tetrahedron, Lett., 1998, 54, 8091.
50. Davoust, E.; Granet, R.; Krausz, P.; Carre, V.; Guilloton, M. Tetrahedron Lett., 1999, 40, 2513.
51. Kaldapa, C.; Blais, J. C.; Carre, V.; Granet, R. Tetrahedron Lett., 2000, 41, 331.
52. Sol, V.; Chaleix, V.; Champavier, Y.; Granet, R. Bioorg. Med. Chem., 2006, 14, 7745.
53. Bourhim, A.; Czernecki, S.; Krausz, P. J. Carbohyd. Chem., 1990, 9, 761.
54. Matsuo, T.; Nagai, H.; Hisaeda, Y.; Hayashi, T. Chem. Commun., 2006, 3131.
55. Fuhrhop, J. H.; Demoulin, C.; Boettcher, C.; Koning, J.; Siggel, U. J. Am. Chem. Soc., 1992, 114, 4159.
56. Zheng, G.; Graham, A.; Shibata. M.; Missert, J. R. Org. Chem., 2001, 66, 8709.
57. Pandey, S. K.; Zheng, X.; Morgan, J.; Missert, J. RJ. Mol. Pharm. In Press 2007.
58. Zheng, X.; Pandey, S. K.; Missert, J. R.; Camacho, S. Third International Conference on Porphyrins and Phthalocyanines, Society of Porphyrins & Phthalocyanines, New Orleans 2004.
59. Zhang, M.; Zhang, Z. H.; Blessington, D.; Li, H. Bioconj. Chem., 2003, 14, 709.
60. Adams, K. R.; Berenbaum, M. C.; Bonnett, R.; Nizhnik, A. N. J. Chem. Soc.-Perkin Trans. 1, 1992, 12, 1465.
61. Li, G. L.; Pandey, S. K.; Graham, A.; Dobhal, M. P.J. Org. Chem., 2004, 69, 158.
62. Silva, A. M. G.; Tome, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S. Tetr ahedron Lett., 2002, 43, 603.
63. Ono, N.; Bougauchi, M.; Maruyama, K. Tetrahedron Lett., 1992, 33, 1629.
64. Lee, P. P. S.; Lo, P. C.; Chan, E. Y. M.; Fong, W. P. Tetrahedron Lett., 2005, 46, 1551.
65. Alvarez-Mico, X.; Calvete, M. J. F.; Hanack, M.; Ziegler, T. Tetrahedron Lett., 2006, 47, 3283.
66. Ribeiro, A. O.; Tome, J. P. C.; Neves, M. G. P. M. S.; Tome, A. C. Tetrahedron Lett., 2006, 47, 9177.
67. He, Y. Y.; An, J. Y.; Jiang, L. J. Biochim. Biophys. Acta-General Subjects, 1999, 1472, 232.
68. Hirohara, S.; Obata, M.; Ogura, S.; Okura, I. J. Porphyr. Phthalocya., 2004, 8, 1289.
69. Kuroda, Y.; Sera, T.; Ogoshi, H. J. Am. Chem. Soc., 1991, 113, 2793.
70. Kuroda, Y.; Ito, M.; Sera, T.; Ogoshi, H. J. Am. Chem. Soc., 1993, 115, 7003.
71. Weber, L.; Imiolczyk, I.; Haufe, G.; Rehorek, D.; Hennig, H. Chem. Commun., 1992, 301.
72. Hombrecher, H. K.; Ohm, S.; Koll, D. Tetrahedron, 1996, 52, 5441.
73. Laville, I.; Pigaglio, S.; Blais, J. C.; Loock, B. Bioorg. Med. Chem., 2004, 12, 3673.
74. Casiraghi, G.; Cornia, M.; Zanardi, F.; Rassu, G. Org. Chem., 1994, 59, 1801.
75. Stepanek, P.; Dukh, U; Saman, D.; Moravcova, J. Org. Biomol. Chem., 2007, 5, 960.
76. Prinsep, M. R.; Caplan, F. R.; Moore, R. E.; Patterson, G. M. L.; Smith, C. D. J. Am. Chem. Soc., 1992, 114, 385.
77. Cornia, M.; Menozzi, M.; Ragg, E.; Mazzini, S. Tetr ahedron, 2000, 56, 3977.
78. Sylvain, I.; Benhaddou, R.; Carre, V.; Cottaz, S. J. Porphyr. Phthalocya., 1999, 3, 1.
79. Sylvain, I.; Zerrouki, R.; Granet, R.; Huang, Y. M. Bioorg. Med. Chem., 2002, 10, 57.
80. Fujimoto, K.; Miyata, T.; Aoyoma, Y. J. Am. Chem. Soc., 2000, 122, 3558.
81. Barel, A.; Jori, G.; Perin, A.; Romandini, P. Cancer Lett., 1986, 32, 117.
82. Allison, B. A.; Pritchard, P. H.; Levy, J. G. Br. J. Cancer, 1994, 69, 833.
83. Shulok, J. R.; Wade, M. H. Photochem. Photobiol., 1990, 51, 451.
84. Aveline, B. M.; Hasan, T.; Redmond, R. W. J. Photoch. Photobiol. B, 1995, 30, 161.
85. Redmond, R. W.; Land, E. J. Adv. Exp. Med. Biol., 1985, 193, 293.
86. Mikata, Y.; Onchi, Y.; Tabata, K.; Ogura, S. Tetrahedron Lett., 1998, 39, 4505.
87. Carre, V.; Gaud, O.; Sylvain, I.; Bourdon, O. J. Photoch. Photobiol. B, 1999, 48, 57.
88. Gabor, F.; Szolnoki, J.; Toth, K.; Fekete, A. Photochem. Photobiol., 2001, 73, 304.
89. Ballardini, R.; Colonna, B.; Gandolfi, M. T.; Kalovidouris, S. A. Eur. J. Org. Chem., 2003, 288.
90. Sol, V.; Branland, P.; Granet, R.; Kaldapa, C. Bioorg. Med. Chem. Lett., 1998, 8, 3007.
91. Csik, G.; Balog, E.; Voszka, I.; Tolgyesi, F. J. Photoch. Photobiol. B, 1998, 44, 216.
92. Hirohara, S.; Obata, M.; Ogata, S.; Kajiwara, K. J. Photoch. Photobiol. B, 2006, 84, 56.
93. Asayama, S.; Mizushima, K.; Nagaoka, S.; Kawakami, H. Bioconjugate Chem., 2004, 15, 1360.
94. Brewer, C. F.; Miceli, M. C.; Baum, L. G. Curr. Opin. Struc. Biol., 2002, 12, 616.
95. Pieters, R. J. Chembiochem., 2006, 7, 721.
96. Ahmad, N.; Gabius, H. J.; Andre, S.; Kaltner, H. J. Biol. Chem., 2004, 279, 10841.
97. Vrasidas, I.; Andre, S.; Valentini, P.; Bock, C. Org. Biomol. Chem., 2003, 1, 803.
98. Goel, M.; Damai, R. S.; Sethi, D. K.; Kant, K. J. Biochem., 2005, 44, 5588.
99. Komath, S. S.; Kavitha, M.; Swamy, M. J. Org. Biomol. Chem., 2006, 4, 973.
100. Griegel, S.; Rajewsky, M. F.; Ciesiolka, T.; Gabius, H. J. Anticancer Res., 1989, 9, 723.
101. Laville, I.; Pigaglio, S.; Blais, J. C.; Doz, F. J. Med. Chem., 2006, 49, 2558.
102. Sol, V.; Charmot, A.; Krausz, P.; Trombotto, S.; Queneau, Y. J. Carbohyd. Chem., 2006, 25, 345.