Cationic porphyrins are reversible proteasome inhibitors

Journal of the American Chemical Society

Volumn 134, Issue 25, 2012, Pages 10451-10457

  Santoro, Anna Maria ^a   Lo Giudice, Maria Cristina ^b,d   D'Urso, Alessandro ^b   Lauceri, Rosaria ^a   Purrello, Roberto ^b,c   Milardi, Danilo ^a  

^a CNR   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

^c CNR   (Italy)

^d RADBOUD UNIVERSITY MEDICAL CENTER   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ANTICANCER PROPERTIES; AXIAL COORDINATION; CATIONIC PORPHYRIN; CENTRAL METALS; INHIBITION ACTIVITY; INHIBITION ASSAYS; INHIBITORY EFFECT; MACROCYCLES; METALLOPORPHYRINS; MICROMOLAR RANGE; MOLECULAR LEVELS; PEPTIDASE ACTIVITY; PROTEASE ACTIVITIES; PROTEASOME INHIBITORS; PROTEASOMES; SPECTROSCOPIC CHARACTERIZATION; UV-VIS SPECTRA; WATER-SOLUBLE PORPHYRIN;

DYES; METAL IONS; SCAFFOLDS;

PORPHYRINS;

ANION; ANTINEOPLASTIC AGENT; CATION; CATIONIC PORPHYRIN DERIVATIVE; MACROCYCLIC COMPOUND; METAL ION; PORPHYRIN DERIVATIVE; PROTEASOME; PROTEASOME INHIBITOR; PROTEINASE; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ARTICLE; CANONICAL ANALYSIS; CELL ASSAY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFECT; DRUG EFFICACY; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVITY; HUMAN; HUMAN CELL; MOLECULAR DOCKING; PROTEIN STRUCTURE; PROTEIN SUBUNIT; SPECTROSCOPY; STATIC ELECTRICITY; ULTRAVIOLET RADIATION;

CATIONS; ENZYME ACTIVATION; ENZYME INHIBITORS; HELA CELLS; HUMANS; MODELS, MOLECULAR; PORPHYRINS; PROTEASOME ENDOPEPTIDASE COMPLEX;

EID: 84863490720     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja300781u     Document Type: Article

References (50)

1. Maiti, N. C.; Mazumdar, S.; Periasamy, N. J. Phys. Chem. B 1998, 102, 1528-1538
2. Lauceri, R.; Raudino, A.; Monsù Scolaro, L; Micali, N; Purrello, R. J. Am. Chem. Soc. 2002, 124, 894-895
3. Segawa, H; Takehara, C; Honda, K; Shimidzu, T; Asahi, T; Mataga, N. J. Phys. Chem. 1992, 2, 503-506
4. Pasternack, R. F.; Francesconi, L.; Raff, D.; Spiro, E. Inorg. Chem. 1973, 11, 2606-2611
5. Pasternack, R. F.; Gibbs, E. J.; Villafranca, J. J. Biochemistry 1983, 22, 2406-2414
6. D'Urso, A.; Holmes, A. E.; Berova, N.; Balaz, M.; Purrello, R. Chem. Asian J. 2011, 6, 3104-3109
7. Shohei, S.; Atsuhiro, O. Angew Chem. Int. 2011, 50, 4342-4373
8. Dougherty, T. J.; Gomer, C. J.; Henderson, B. W.; Jori, G. J. Natl. Cancer. Inst. 1998, 90, 889-905
9. Pandey, R. K.; Zheng, G. In The porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press, Boston, 2000, 6, 157-230.
10. Celli, J. P.; Spring, B. Q.; Rizvi, I.; Evans, C. L.; Samkoe, K. S.; Verma, S.; Pogue, B. W.; Hasan, T. Chem. Rev. 2010, 110, 2795-2838
11. Barth, R. F.; Coderre, J. A.; Vicente, M. G.; Blue, T. E. Clin. Cancer Res. 2005, 11, 3987-4002
12. Soloway, A,H.; Tjarks, W.; Barnum, B. A.; Rong, F. G.; Barth, R. F.; Codogni, I. M.; Wilson, J. G. Chem. Rev. 1998, 98, 1515-1562
13. Dixon, I. M.; Lopez, F.; Estève, J.,P.; Tejera, A. M.; Blasco, M. A.; Pratviel, G.; Meunier, B. Chembiochem. 2005, 6, 123-132
14. Harley, C. B.; Futcher, A. B.; Greider, C.W. Nature 1990, 345, 458-460
15. Mergny, J. L.; Riou, J. F.; Mailliet, P. Nucleic Acids Res. 2002, 30, 839-865
16. Szokalska, A.; Makowski, M.; Nowis, D.; Wilczynski, G. M.; Kujawa, M.; Wójcik, C.; Młynarczuk-Biały, I.; Salwa, P.; Bil, J.; Janowska, S.; Agostinis, P.; Verfaillie, T.; Bugajski, M.; Gietka, J.; Issat, T.; Głodkowska, E.; Mrówka, P.; Stoklosa, T.; Hamblin, M. R.; Mróz, P.; Jakóbisiak, M.; Golab, J. Cancer Res. 2009, 69, 4235-4243
17. Gallastegui, N; Groll, M. Trends Biochem. Sci. 2010, 35, 634-642
18. Hershko, A.; Ciechanover, A. Annu. Rev. Biochem. 1998, 67, 425-479
19. Pickart, C. M.; Cohen, R. E. Nat. Rev. Mol. Cell Biol. 2004, 5, 177-87
20. Coux, O.; Tanaka, K.; Goldberg, A. L. Annu. Rev. Biochem. 1996, 65, 810-47
21. Kisselev, A. F.; Callard, A.; Goldberg, A. L. J. Biol. Chem. 2006, 281, 8582-8590
22. Matsuo, Y; Sawai, H; Ochi, N; Yasuda, A; Sakamoto, M; Takahashi, H; Funahashi, H; Takeyama, H; Guha, S. Dig. Dis. Sci. 2010, 55, 1167-76
23. Adams, J. Cancer Cell. 2004, 5, 417-421
24. Crawford, L. J.; Walker, B.; Ovaa, H.; Chauhan, D.; Anderson, K. C.; Morris, T. C.; Irvine, A. E. Cancer Res. 2006, 66, 6379-86
25. Milardi, D.; Arnesano, F.; Grasso, G.; Magrì, A.; Tabbì, G.; Scintilla, S.; Natile, G.; Rizzarelli, E. Angew. Chem Int. Ed. 2007, 46, 7993-7995
26. Arena, G.; Fattorusso, R.; Grasso, G.; Grasso, G. I.; Isernia, C.; Malgieri, G.; Milardi, D.; Rizzarelli, E. Chem.-Eur. J. 2011, 17, 11596-11603
27. Demo, S. D.; Kirk, C. J.; Aujay, M. A.; Buchholz, T. J.; Dajee, M.; Ho, M. N.; Jiang, J.; Laidig, G. J.; Lewis, E. R.; Parlati, F.; Shenk, K. D.; Smyth, M. S.; Sun, C. M.; Vallone, M. K.; Woo, T. M.; Molineaux, C. J.; Bennett, M. K. Cancer Res. 2007, 67, 6383-6391
28. Herrmansn, O.; Ehdi, H. U.; Orsin, A. Can. J. Chem. 1978, 56, 1084-1087
29. Rodgers, K. J.; Dean, R. T. Int. J. Biochem. Cell. Biol. 2003, 35, 716-727
30. Copeland, R. A. In Evaluation of Enzyme Inhibitors in Drug Discovery; Methods of Biochemical Analysis; Wiley Press: Hoboken, NJ, 2005, 46.
31. Trott, O.; Olson, A. J. J. Comput. Chem. 2010, 31, 455-461
32. Huey, R.; Morris, G. M.; Olson, A. J.; Goodsell, D. S. J. Comput. Chem. 2007, 28, 1145-1152
33. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909
34. De Bettignies, G.; Coux, O. Biochimie 2010, 92, 1530-1545
35. Portero-Otín, M.; Pamplona, R.; Ruiz, M. C.; Cabiscol, E.; Prat, J.; Bellmunt, M. J. Diabetes 1999, 48, 2215-2220
36. McNaught, K. S.; Olanow, C. W.; Halliwell, B; Isacson, O; Jenner, P Nat. Rev. Neur. 2001, 2, 589-594
37. Gaczynska, M.; Rock, K. L.; Spies, T.; Goldberg, A. L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 9213-9217
38. Kisselev, A. F.; Garcia-Calvo, M.; Overkleeft, H. S.; Peterson, E.; Pennington, M. W.; Ploegh, H. L.; Thornberry, N. A.; Goldberg, A. L. J. Biol. Chem. 2003, 278, 35869-35877
39. Fenteany, G.; Standaert, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726-731
40. Crawford, L. J.; Walker, B.; Ovaa, H.; Chauhan, D.; Anderson, K. C.; Morris, T. C.; Irvine, A. E. Cancer Res. 2006, 66, 6379-6386
41. Stauch, B.; Simon, B.; Basile, T.; Schneider, G.; Malek, N. P.; Kalesse, M.; Carlomagno, T. Angew. Chem. 2010, 122, 4026-4030
42. Parkinson, G. N.; Ghosh, R.; Neidle, S. Biochemistry 2007, 46, 2390-2397
43. Giordano, S.; Petrelli, A. Curr. Med. Chem. 2008, 15, 422-432
44. McMillin, D. R.; Shelton, A. H.; Bejune, S. A.; Fanwick, P. E.; Wall, R. K. Coord. Chem. Rev. 2005, 249, 1451-1459
45. Mita, H.; Ohyama, T.; Tanaka, Y.; Yamamoto, Y. Biochemistry 2006, 45, 6765-6772
46. Wang, K.; Zhang, Z.; Wu, L.; Li, Z.-Y. Chem. Biodiv 2007, 514-522
47. Jia, G.; Feng, Z.; Wei, C.; Zhou, J.; Wang, X.; Li, C. J. Phys. Chem.B 2009, 113, 16237-16245
48. Kornguth, S. E.; Kalinke, T.; Robins, H. I.; Cohen, J. D.; Turski, P. Cancer Res. 1989, 49, 6390-6395
49. Dick, L. R.; Fleming, P. E. Drug Discov. Today 2010, 15, 243-249
50. Blackburn, C.; Gigstad, K. M.; Hales, P.; Garcia, K.; Jones, M.; Bruzzese, F. J.; Barrett, C.; Liu, J. X.; Soucy, T. A.; Sappal, D. S.; Bump, N.; Olhava, E. J.; Fleming, P.; Dick, L. R.; Tsu, C.; Sintchak, M. D.; Blank, J. L. Biochem. J. 2010, 430, 461-476