Tetra-2,3-pyrazinoporphyrazines with externally appended pyridine rings. 9. Novel heterobimetallic macrocycles and related hydrosoluble hexacations as potentially active photo/chemotherapeutic anticancer agents

Inorganic Chemistry

Volumn 50, Issue 16, 2011, Pages 7391-7402

  Donzello, Maria Pia ^a   Vittori, Daniela ^a   Viola, Elisa ^a   Manet, Ilse ^b   Mannina, Luisa ^a   Cellai, Luciano ^c   Monti, Sandra ^b   Ercolani, Claudio ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b Istituto per la Sintesi Organica e la Fotoreattività   (Italy)

^c CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; MACROCYCLIC COMPOUND; METALLOPORPHYRIN; PHOTOSENSITIZING AGENT; PYRAN DERIVATIVE; PYRIDINE DERIVATIVE; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; LIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUBILITY; SYNTHESIS;

ANTINEOPLASTIC AGENTS; LIGHT; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; METALLOPORPHYRINS; MOLECULAR STRUCTURE; PHOTOSENSITIZING AGENTS; PYRANS; PYRIDINES; SOLUBILITY; WATER;

EID: 80051496500     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic200498s     Document Type: Article

References (59)

1. Moreira, L. M.; Vieira dos Santos, F.; Pereira Lyon, J.; Maftoum-Costa, M.; Pacheco-Soares, C.; Soares da Silva, N. Aust. J. Chem. 2008, 61, 741-754
2. O'Connor, A. E.; Gallagher, W. M.; Byrne, A. T. Photochem. Photobiol. 2009, 85, 1053
3. Szacilowski, K.; Macyk, W.; Drzewiecka-Matuszek, A.; Brindell, M.; Stochel, G. Chem. Rev. 2005, 105, 2647-2694
4. Detty, M. R.; Gibson, S. L.; Wagner, S. J. J. Med. Chem. 2004, 47, 3897-3915
5. De Rosa, M. C.; Crutchley, R. J. Coord. Chem. Rev. 2002, 233-234, 351-371
6. Pandey, R. K.; Zheng, G. In The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R. Eds.; Academic Press, 2000; Vol. 6, Chapter 43, pp 157-230.
7. Dougherty, T. J.; Gomer, C. J.; Henderson, B. W.; Jori, G.; Kessel, D.; Korbelik, M.; Moan, J.; Peng, Q. J. Natl. Cancer Inst. 1998, 90, 889
8. Redmond, R. W.; Gamlin, J. N. Photochem. Photobiol. 1999, 70, 391
9. Ali, H.; van Lier, E. Chem. Rev. 1999, 99, 2379-2450
10. Sharman, W. M.; Allen, C. M.; van Lier, J. E. Drug Discovery Today 1999, 4, 507
11. Bellner, B. A.; Dougherty, T. J. J. Clin. Laser Med. Surg. 1996, 14, 311
12. Shinohara, H.; Tsaryova, O.; Schnurpfeil, G.; Wöhrle, D. J. Photochem. Photobiol., A 2006, 184, 50
13. Spiller, W.; Kliesch, H.; Wöhrle., D.; Hackbarth, S.; Röder, B.; Schnurpfeil, G. J. Porphyrins Phthalocyanines 1998, 2, 145
14. Schnurpfeil, G.; Sobbi, A. K.; Spiller, W.; Kliesch, H.; Wöhrle., D. J. Porphyrins Phthalocyanines 1997, 1, 159
15. Fernandez, D. A.; Awruch, J.; Dicelio, L. E. Photochem. Photobiol. 1996, 63, 784
16. Müller, S.; Mantareva, V.; Stoichkova, N.; Kliesch, H.; Sobbi, A.; Wöhrle., D.; Shopova, M. J. Photochem. Photobiol., B 1996, 35, 167
17. Maree, S. E.; Nyokong, T. J. Porphyrins Phthalocyanines 2001, 5, 782
18. Lawrence, D. S.; Whitten, D. G. Photochem. Photobiol. 1996, 64, 923
19. Donzello, M. P.; Viola, E.; Xiaohui, C.; Mannina, L.; Rizzoli, C.; Ricciardi, G.; Ercolani, C.; Kadish, K. M.; Rosa, A. Inorg. Chem. 2008, 47, 3903
20. Donzello, M. P.; Viola, E.; Bergami, C.; Dini, D.; Ercolani, C.; Giustini, M.; Kadish, K. M.; Meneghetti, M.; Monacelli, F.; Rosa, A; Ricciardi, G. Inorg. Chem. 2008, 47, 8757
21. Zimcik, P.; Novakova, V.; Miletin, M.; Kopecky, K. Macroheterocycles 2008, 1, 21
22. Mitzel, F.; Fitzgerald, S; Beeby, A.; Faust, R. Eur. J. Org. Chem. 2004, 1136
23. Baum, S. M.; Trabanco, A. A.; Montalban, A. G.; Micallef, A. S.; Zhong, C.; Meunier, H. G.; Suhling, K.; Phillips, D.; White, A. J. P.; Williams, D. J.; Barrett, A. G. M.; Hoffman, B. M. J. Org. Chem. 2003, 68, 1665
24. Sakellariou, E. G.; Montalban, A. G.; Meunier, H.; Rumbles, G.; Philips, D.; Ostier, R. B.; Suhling, K.; Barrett, A. G. M.; Hoffman, B. M. Inorg. Chem. 2002, 41, 2182
25. Montalban, A. G.; Baum, S. M.; Barrett, A. G. M.; Hoffman, B. M. Dalton Trans. 2003, 2093
26. Michelsen, U.; Kliesch, H.; Schnurpfeil, G.; Sobbi, A. K.; Wöhrle, D. Photochem. Photobiol. 1996, 64, 694
27. Klein, A. V.; Hambley, T. W. Chem. Rev. 2009, 109, 4911-4920
28. Lu, Q.-B J. Med. Chem. 2007, 50, 2601
29. Crescenzi, E.; Chiavello, A.; Canti, G.; Reddi, E.; Veneziani, B. M.; Palombo, G. Mol. Cancer Therap. 2006, 5, 776
30. Crescenzi, E.; Varriale, E.; Iovino, M.; Veneziani, B. M.; Palumbo, G. Mol. Cancer Therap. 2004, 3, 537
31. Nonaka, M.; Ikeda, H.; Inokuchi, T. Cancer Lett. 2002, 184, 171
32. Lottner, C.; Knuechel, R.; Bernhardt, G.; Brunner, H. Cancer Lett. 2004, 203, 171
33. Brunner, H.; Arndt, M. R.; Treittinger, B. Inorg. Chim. Acta 2004, 357, 1649
34. Brunner, H.; Shellerer, K. -M. Inorg. Chim. Acta 2003, 350, 39
35. Song, R.; Kim, Y.-S.; Sohn, Y. S. J. Inorg. Biochem. 2002, 83, 83
36. Canti, G.; Nicolin, A.; Cubeddu, R.; Taroni, P.; Bandieramonte, G.; Valentini, G. Cancer Lett. 1998, 125, 39
37. Mao, J.; Zhang, Y.; Zhu, J.; Zhang, C.; Guo, Z. Chem Comm. 2009, 908
38. Nemykin, V. N.; Mytsyk, V. M.; Volkov, S. V.; Kobayashi, N. J. Porphyrins Phthalocyanines 2000, 4, 551
39. Donzello, M. P.; Ou, Z.; Monacelli, F.; Ricciardi, G.; Rizzoli, C.; Ercolani, C.; Kadish, K. M. Inorg. Chem. 2004, 43, 8626
40. Donzello, M. P.; Ou, Z.; Dini, D.; Meneghetti, M.; Ercolani, C.; Kadish, K. M. Inorg. Chem. 2004, 43, 8637
41. Villano, M.; Amendola, V.; Sandonà, G.; Donzello, M. P.; Ercolani, C.; Meneghetti, M. J. Phys. Chem. B 2006, 110, 24534
42. Bergami, C.; Donzello, M. P.; Ercolani, C.; Monacelli, F.; Kadish, K. M.; Rizzoli, C. Inorg. Chem. 2005, 44, 9852
43. Bergami, C.; Donzello, M. P.; Monacelli, F.; Ercolani, C.; Kadish, K. M. Inorg. Chem. 2005, 44, 9862
44. Manet, I.; Manoli, F.; Donzello, M. P.; Viola, E.; Andreano, G.; Masi, A.; Cellai, L.; Monti, S. Org. Biol. Chem. 2011, 9, 684
45. Manet, I., Manoli, F., Donzello, M. P., Ercolani, C., Vittori, D., Cellai, L., Masi, A., and Monti, S. Inorg. Chem. 2011, 50 DOI 10.1021/ic200514z
46. Kharasch, M. S.; Seyler, R. C.; Mayo, F. R. J. Am. Chem. Soc. 1938, 60, 882
47. Zimcik, P.; Miletin, M.; Musil, Z.; Kopecky, K.; Kubza, L.; Brault, D. J. Photochem. Photobiol., A 2006, 183, 59
48. Viola, E.; Donzello, M. P.; Giustini, M.; Monacelli, F.; Ercolani, C., to be submitted.
49. Donzello, M. P.; Viola, E.; Cai, X.; Mannina, L.; Ercolani, C.; Kadish, K. M. Inorg. Chem. 2010, 49, 2447
50. Stillman, M. J. In Phthalocyanines: Properties and Applications; Leznoff, C. C.; Lever, A. B. P., Eds.; VCH Publishers, Inc.: New York, 1989; Vol. 1, pp 133-289.
51. Mack, J.; Stillman, M. J. In The Porphyrin Handbook, Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: New York, 2003; Vol. 16, pp 43-116.
52. Gouterman, M. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. III, and references therein.
53. Cai, X.; Donzello, M. P.; Viola, E.; Rizzoli, C.; Ercolani, C.; Kadish, K. M. Inorg. Chem. 2009, 48, 7086
54. Ogunsipe, A.; Maree, D.; Nyokong, T. J. Mol. Struct. 2003, 650, 131
55. Musil, Z.; Zimcik, P.; Miletin, M.; Kopecky, K.; Petrik, P.; Lenco, J. J. Photochem. Photobiol., A 2007, 186, 316
56. Michelsen, U.; Kliesch, H.; Schnurpfeil, G.; Sobbi, A. K.; Wöhrle, D. Photochem. Photobiol. 1996, 64, 694
57. Zimcik, P.; Miletin, M.; Radilova, H.; Novakova, V.; Kopecky, K.; Svec, J.; Rudolf, E. Photochem. Photobiol. 2010, 86, 168
58. Novakova, V.; Mørkved, E. H.; Miletin, M.; Zimcik, P. J. Porphyrins Phthalocyanines 2010, 14, 582
59. Mørkved, E. H.; Afseth, N. K.; Zimcik, P. J. Porphyrins Phthalocyanines 2007, 11, 130