Manganese(III) complexes of bis(hydroxyphenyl)dipyrromethenes are potent orally active peroxynitrite scavengers

Journal of the American Chemical Society

Volumn 133, Issue 12, 2011, Pages 4200-4203

  Rausaria, Smita ^a   Kamadulski, Andrew ^a   Rath, Nigam P ^c   Bryant, Leesa ^b   Chen, Zhoumou ^b   Salvemini, Daniela ^b   Neumann, William L ^a  

^a SOUTHERN ILLINOIS UNIVERSITY EDWARDSVILLE   (United States)

^b SAINT LOUIS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARRAGEENANS; ELECTRON MECHANISM; HYPERALGESIA; LC-MS METHODS; NEW SERIES; ORALLY ACTIVE; PEROXYNITRITES;

X RAY CRYSTALLOGRAPHY;

MANGANESE;

ACETYLSALICYLIC ACID; ANALGESIC AGENT; ANTIOXIDANT; BIS(HYDROXYPHENYL)DIPYRROMETHENE; CARRAGEENAN; IBUPROFEN; MANGANESE; PARACETAMOL; PEROXYNITRITE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HYPERALGESIA; LIQUID CHROMATOGRAPHY; MASS SPECTROMETER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RAT; ULTRAVIOLET RADIATION; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; FREE RADICAL SCAVENGERS; MANGANESE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PEROXYNITROUS ACID; PORPHOBILINOGEN; STEREOISOMERISM;

EID: 79953045403     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja110427e     Document Type: Article

References (40)

1. Batinic-Haberle, I.; Reboucas, J. S.; Spasojevic, I. Antioxid. Redox Signaling 2010, 13, 877
2. Ferrer-Sueta, G.; Radi, R. ACS Chem. Biol. 2009, 4, 161
3. Szabo, C.; Ischiropoulos, H.; Radi, R. Nat. Rev. Drug Discovery 2007, 6, 662
4. Salvemini, D.; Neumann, W. Life Sci. 2010, 86, 604
5. Salvemini, D.; Neumann, W. L. Trends Pharmacol. Sci. 2009, 30, 194
6. Salvemini, D. Arch. Biochem. Biophys. 2009, 484, 238
7. Groves, J. T.; Marla, S. S. J. Am. Chem. Soc. 1995, 117, 9578
8. Stern, M. K.; Jensen, M. P.; Kramer, K. J. Am. Chem. Soc. 1996, 118, 8735
9. Lee, J.; Hunt, J. A.; Groves, J. T. J. Am. Chem. Soc. 1998, 120, 6053
10. Ferrer-Sueta, G.; Vitturi, D.; Batinic-Haberle, I.; Fridovich, I.; Goldstein, S.; Czapski, G.; Radi, R. J. Biol. Chem. 2003, 278, 27432
11. Mahammed, A.; Gross, Z. Angew. Chem., Int. Ed. 2006, 45, 6544
12. Kupershmidt, L.; Okun, Z.; Amit, T.; Mandel, S.; Saltsman, I.; Mahammed, A.; Bar-Am, O.; Gross, Z.; Youdim, M. B. J. Neurochem. 2010, 113, 363
13. Gershman, Z.; Goldberg, I.; Gross, Z. Angew. Chem., Int. Ed. 2007, 46, 4320
14. Okun, Z.; Kupershmidt, L.; Amit, T.; Mandel., S.; Bar-Am, O.; Youdim, M. B. H.; Gross, Z. ACS Chem. Biol. 2009, 4, 910
15. Kanamori, A.; Catrinescu, M.-M.; Mahammed, A.; Gross, Z.; Levin, L. A. J. Neurochem. 2010, 114, 488
16. Haber, A.; Mahammaed, A.; Fuhrman, B.; Volkova, N.; Coleman, R.; Hayek, T.; Aviram, M.; Gross, Z. Angew. Chem., Int. Ed. 2008, 47, 7896
17. Drel, V. R.; Pacher, P.; Vareniuk, I.; Pavlov, I.; Ilnytska, O.; Lyzogubov, V. V.; Tibrewala, J.; Groves, J. T.; Obrosova, I. G. Eur. J. Pharmacol. 2007, 569, 48
18. Vareniuk, I.; Pavlov, I. A.; Drel, V. R.; Lyzogubov, V. V.; Ilnytska, O.; Bell, S. R.; Tibrewala, J.; Groves, J. T.; Obrosova, I. G. Exp. Neurol. 2007, 205, 425
19. Kim, H.; Burghart, A.; Welch, M. B.; Reibenspies, J.; Burgess, K. Chem. Commun. 1999, 1889
20. Burghart, A.; Kim, H.; Welch, M. B.; Thoresen, L. H.; Reibenspies, J.; Burgess, K. J. Org. Chem. 1999, 64, 7813
21. May, D. A., Jr.; Lash, T. D. J. Org. Chem. 1992, 57, 4820
22. Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P. C.; Marguerettaz, A. M. J. Org. Chem. 1987, 52, 827
23. Littler, B. J.; Ciringh, Y.; Lindsey, J. S. J. Org. Chem. 1999, 64, 2864
24. Parhi, A. K.; Kung, M. P.; Ploessl, K.; Kung, H. F. Tetrahedron Lett. 2008, 49, 3395
25. Loudet, A.; Bandichhor, R.; Burgess, K.; Palma, A.; McDonnell, S. O.; Hall, M. J.; O'Shea, D. F. Org. Lett. 2008, 10, 4771
26. Similar behavior was observed for the Mn(V)O corrolazines. See: Mandimutsira, B. S.; Ramdhanie, B.; Todd, R. C.; Wang, H.; Zareba, A. A.; Czernuszewicz, R. S.; Goldberg, D. P. J. Am. Chem. Soc. 2002, 124, 15170
27. Lansky, D. E.; Mandimutsira, B. S.; Ramdhanie, B.; Clausen, M.; Penner-Hahn, J.; Zvyagin, S. A.; Telser, J.; Kryzstek, J.; Zhan, R.; Ou, Z.; Kadish, K. M.; Zakharov, L.; Rheingold, A. L.; Goldberg, D. P. Inorg. Chem. 2005, 44, 4485
28. Goldberg, D. P. Acc. Chem. Res. 2007, 40, 626
29. Uppu, R. M.; Pryor, W. A. Anal. Biochem. 1996, 236, 242
30. Liu, H. Y.; Yam, F.; Xie, Y. T.; Li, X. Y.; Chang, C. K. J. Am. Chem. Soc. 2009, 131, 12890
31. Sikora, A.; Zielonka, J.; Lopez, M.; Joseph, J.; Kalyanaraman, B. Free Radical Biol. Med. 2009, 47, 1401
32. Hunt, J. A.; Lee, J.; Groves, J. T. Chem. Biol. 1997, 4, 845
33. Differences in pH (7.2 vs 7.4) for the boronate assay vs the stopped-flow experiments are in part responsible for the minor differences in the kinetic data.
34. Lieb, D.; Zahl, A.; Shubina, T. E.; Ivanovic-Burmazovic, I. J. Am. Chem. Soc. 2010, 132, 7282
35. Hoogenraad, M.; Ramkisoensing, K.; Driessan, W. L.; Kooijman, H.; Spek, A. L.; Brouwman, E.; Haasnoot, J. G.; Reedijk, J. Inorg. Chim. Acta 2001, 320, 117
36. Lodge, K. J. Chem. Eng. Data 1999, 4, 1321
37. For measurement of paw-withdrawl latency from a thermal stimulus (paw withdrawl from a warm surface), see: Hargreaves, K.; Dubner, R.; Brown, F.; Flores, C.; Joris, J. Pain 1988, 32, 77
38. Salvemini, D.; Wang, Z. Q.; Bourdon, D. M.; Stern, M. K.; Currie, M. G.; Manning, P. T. Eur. J. Pharmacol. 1996, 303, 217
39. Kos, I.; Benov, L.; Spasojevic, I.; Reboucas, J. S.; Batinic-Haberle, I. J. Med. Chem. 2009, 52, 7868
40. Batinic-Haberle, I.; Ndengele, M. M.; Cuzzocrea, S.; Reboucas, J. S.; Spasojevic, I.; Salvemini, D. Free Radical Biol. Med. 2009, 46, 212