Synthesis of glycosylated cationic porphyrins as potential agents in photodynamic therapy

Canadian Journal of Chemistry

Volumn 74, Issue 8, 1996, Pages 1550-1563

  Driaf, Khalid ^a   Granet, Robert ^a   Krausz, Pierre ^a   Kaouadji, Mourad ^a   Thomasson, François ^b   Chulia, Albert José ^a   Verneuil, Bernard ^a   Spiro, Marenglen ^c   Blais, Jean Claude ^c   Bolbach, Gérard ^c  

^a UNIVERSITY OF LIMOGES   (France)

^b UNIV GRENOBLE ALPES   (France)

^c SORBONNE UNIVERSITÉ   (France)

Author keywords

cancer; cationic; glycosylated; phototherapy; porphyrins

Indexed keywords

ALDEHYDES; DERIVATIVES; MOLECULAR STRUCTURE; ONCOLOGY; PHOTODYNAMIC THERAPY; POLYSACCHARIDES; SYNTHESIS (CHEMICAL);

GLYCOSYLATED CATIONIC PORPHYRINS; PROPIONIC ACIDS; PYRROLE;

DRUG PRODUCTS;

PORPHYRIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PHOTODYNAMIC THERAPY; SPECTROPHOTOMETRY;

EID: 10244244878     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-172     Document Type: Article

References (57)

1. (a) T.J. Dougherty, G. Lawrence, J.H. Kaufman, D. Boyle, K.R. Weishaupt, and A. Goldfarb. J. Natl. Cancer Inst. 62, 231 (1979);
2. (b) D. Kessel. Photochem. Photobiol. 39, 851 (1984);
3. (c) D. Kessel and E. Spikes. Photochem. Photobiol. 40, 59 (1984);
4. (d) J.R. Spears, J. Srub, D. Shropshire, and S.J. Paulin. Clin. Invest. 71, 395 (1983).
5. (a) D.W. Dixon, L.G. Marzilli, and R. Schinazi. Ann. N.Y. Acad. Sci. 616, 511 (1990);
6. (b) M. Asanaka, T. Kurimura, H. Toya, J. Ogaki, and Y. Kato. AIDS (London), 3, 403 (1989);
7. (c) R.D. Levere, Y.F. Gong, A. Kappas, D.J. Bucher, G.P. Wormser, and N.G. Abraham. Proc. Natl. Acad. Sci. U.S.A. 88, 1756 (1991);
8. (d) J.L. Sessler, M.J. Cyr, B.G. Maiya, M. Judy, J.T. Newman, H.L. Skiles, R. Boriak, J.L. Mattews, and T.C. Chanh. Proc. SPIE-Int. Soc. Opt. Eng. 1203, 233 (1990);
9. (e) D.W. Dixon, M.S. Kim, V. Kumar, G. Obara, L.G. Marzilli, and R.F. Schinazi. Antiviral Chem. Chemother. 3, 279 (1992).
10. (a) D. Kessel. Biochem. Pharmacol. 33, 1389 (1984);
11. (b) J. Moan. Photochem. Photobiol. 43, 681 (1986);
12. (c) H. Van der Berg. Chem. Br. 430 (1986);
13. (d) J.J. Crute, A.F. Walul, R.A. Bambara, R.S. Murant, S.L. Gibson, and R. Hilf. Cancer Res. 46, 153 (1986);
14. (e) R.M. Bôhmer and G. Morstyn. Cancer Res. 45, 5328 (1985), and references therein;
15. (f) B. Paquette and J.E. Van Lier. In Photodynamic therapy of neoplastic disease. Vol. 1. Edited by B.W. Henderson and T.J. Dougherty. Marcel Dekker, New York. 1992. p. 145;
16. (g) I. Rosenthal. Photochem. Photobiol. 53, 859 (1991);
17. (h) B.W. Henderson and T.J. Dougherty. Photochem. Photobiol. 55, 145 (1992).
18. G.G. Meng, B.R. James, K.A. Skov, and M. Korbelik. Can. J. Chem. 72, 1894 (1994).
19. C. Kieda and M. Monsigny. Invasion & Metastasis, 6, 347 (1986).
20. (a) A. Gabizon and D. Papahadjopoulos. Proc. Natl. Acad. Sci. U.S.A. 85, 6949 (1988);
21. (b) A.L. Klibanov, K. Maruyama, V.P. Torchilin, and L. Huang. FEBS Lett. 268, 235 (1990).
22. (a) E.J. Gibbs and R.F. Pasternack. Semin. Hematol. 26, 77 (1989);
23. (b) R.J. Fiel. J. Biomol. Struct. Dyn. 6, 1259 (1989);
24. (c) R.J. Fiel, J.C. Howard, E.H. Mark, and N. Datta-Gupta. Nucleic Acids Res. 6, 3093 (1979);
25. (d) R.J. Fiel and B.R. Munson. Nucleic Acids Res. 8, 2835 (1980);
26. (e) R.J. Fiel, M.J. Carvlin, E.H. Mark, and J.C. Howard. Nucleic Acids Res. 11, 6141 (1983);
27. (f) R.F. Pasternack, E.J. Gibbs, and J.J. Villafranca. Biochemistry, 22, 2406 (1983);
28. (g) R.F. Pasternack, E.J. Gibbs, and J.J. Villafranca. Biochemistry, 22, 5409 (1983);
29. (h) R.J. Fiel. J. Biolmol. Struct. Dyn. 6, 1259 (1989);
30. (i) L.G. Marzilli. New J. Chem. 14, 409 (1990);
31. (j) M. Rodriguez and A. Bard. J. Inorg. Chem. 31, 1129 (1992).
32. (a) J.B. Verlhac, A. Gaudemer, and I. Kraljic. Nouv. J. Chim. 8, 401 (1984);
33. (b) D. Praseuth, A. Gaudemer, J.B. Verlhac, I. Kraljic, I. Sissoëf, and E. Guillé. Photochem. Photobiol. 44, 717 (1986), and references therein.
34. L. Ding, J. Balzarihi, D. Schols, B. Meunier, and E. De Clercq. Biochem. Pharmacol. 44, 1675 (1992).
35. (a) L. Ding, C. Casas, G. Etemad-Moghadam, and B. Meunier. New J. Chem. 14, 421 (1990);
36. (b) L. Ding, G. Etemad-Moghadam, S. Cros, C. Auclair, and B. Meunier. J. Med. Chem. 34, 900 (1991).
37. (a) J.T. Groves and T.P. Farrell. J. Am. Chem. Soc. 111, 4998 (1989);
38. (b) G. Pratviel, M. Pitié, J. Bernadou, and B. Meunier. Nucleic Acids Res. 19, 6283 (1991);
39. (c) G. Gasmi, M. Pasdeloup, G. Pratviel, M. Pitié, J. Bernadou, and B. Meunier. Nucleic Acids Res. 19, 2835 (1991); M. Pitié, G. Pratviel, J. Bernadou, and B. Meunier. Proc. Natl. Acad. Sci. U.S.A. 89, 3967 (1992);
40. (c) G. Gasmi, M. Pasdeloup, G. Pratviel, M. Pitié, J. Bernadou, and B. Meunier. Nucleic Acids Res. 19, 2835 (1991); M. Pitié, G. Pratviel, J. Bernadou, and B. Meunier. Proc. Natl. Acad. Sci. U.S.A. 89, 3967 (1992);
41. (e) V.V. Vlassov, E.A. Deeva, and G.V. Ivanova. Nucleosides Nucleotides, 10, 641 (1991);
42. (f) T. Le Doan, D. Praseuth, L. Perrouault, M. Chassignol, N.T. Thuong, and C. Hélène. Bioconjugate Chem. 1, 108 (1990).
43. A.F. Mironov, G.M. Isaeva, V.I. Chvets, R.P. Evstigneeva, A.N. Stepanov, A.A. Perov, and S.E. Koupriyanov. Bioorg. Khim. 4, 1410 (1978).
44. (a) V.J. Lee, X. Zhang, J.A. Ibers, and J.I. Brauman. J. Am. Chem. Soc. 115, 3834 (1993);
45. (b) J.H. Fuhrhop, C. Demoulin, C. Boettcher, J. Koning, and U. Siggel. J. Am. Chem. Soc. 114, 4159 (1992);
46. N. Ono, M. Bougauchi, and K. Maruyama. Tetrahedron Lett. 33, 1629 (1992).
47. K. Driaf, P. Krausz, B. Verneuil, M. Spiro, J.C. Biais, and G. Bolbach. Tetrahedron Lett. 34, 1027 (1993).
48. R.G. Little, J.A. Anton, P.A. Loach, and J.A. Ibers. J. Heterocycl. Chem. 12, 343 (1975).
49. J.S. Lindsey, H.C. Hsu, and I.C. Scheirman. Tetrahedron Lett. 22, 931 (1986).
50. P. Maillard, J.L. Guerquin-Ken, C. Huel, and M. Momenteau. J. Org. Chem. 58, 2774 (1993).
51. K. Anzai and K. Hatano. Chem. Pharm. Bull. 32, 1273 (1984).
52. M. Spiro, J.C. Biais, G. Bolbach, F. Fournier, J.C. Tabet, K. Driaf, O. Gaud, R. Granet, and P. Krausz. Int. J. Mass Spectrom. Ion Processes, 134, 229 (1994).
53. G. Bolbach, K. Riahi, M. Spiro, A. Brunot, F. Breton, and J.C. Biais. Analusis, 21, 383 (1993).
54. R.W. Jeanloz and P.J. Stoffyn. Methods Carbohydr. Chem. 1, 221 (1962).
55. Y. Tsuzuki, S. Kataoka, M. Funayama, and K. Satsumabayashi. Bull. Chem. Soc. Jpn. 44, 526 (1971).
56. B. Schuster, M. Winter, and K. Herrmann. Z. Naturforsch. 41, 511 (1986).
57. D.H. Brauns. J. Am. Chem. Soc. 51, 1820 (1927).