New class of potent catalysts of O2−dismutation. Mn(iii) ortho-methoxyethylpyridyl- and di-ortho-methoxyethylimidazolylporphyrins

Journal of the Chemical Society. Dalton Transactions

Volumn 4, Issue 11, 2004, Pages 1696-1702

  Batinić Haberle, Ines ^a   Spasojević, Ivan ^a   Stevens, Robert D ^a   Hambright, Peter ^b   Neta, Pedatsur ^c   Okado Matsumoto, Ayako ^a   Fridovich, Irwin ^a  

^a DUKE UNIVERSITY MEDICAL CENTER   (United States)

^b HOWARD UNIVERSITY   (United States)

^c NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

Author keywords

Catalysts of O2 dismutation; Mn(iii) methoxyethylimidazolylporphyrins; Mn(iii) methoxyethylpyridylporphyrins; Sod mimics; Sod deficient E. coli

Indexed keywords

MANGANESE; METALLOPORPHYRIN; SUPEROXIDE; SUPEROXIDE DISMUTASE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ELECTROCHEMISTRY; ESCHERICHIA COLI; GROWTH, DEVELOPMENT AND AGING; KINETICS; METABOLISM; METHODOLOGY; MOLECULAR MIMICRY; OXIDATION REDUCTION REACTION; ULTRAVIOLET SPECTROPHOTOMETRY;

CATALYSIS; ELECTROCHEMISTRY; ESCHERICHIA COLI; KINETICS; MANGANESE; METALLOPORPHYRINS; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SPECTROPHOTOMETRY, ULTRAVIOLET; SUPEROXIDE DISMUTASE; SUPEROXIDES;

ANTIOXIDANTS; CATALYSTS; ELECTROSTATICS; ESCHERICHIA COLI; OXIDATION; POSITIVE IONS; RATE CONSTANTS; REDOX REACTIONS; SURFACE ACTIVE AGENTS; SYNTHESIS (CHEMICAL); TOXICITY;

LIPID PEROXIDATION; LIPOPHILICITY; OXIDATIVE STRESS;

OXYGEN;

EID: 2942731654     PISSN: 14779226     EISSN: None     Source Type: Journal    
DOI: 10.1039/b400818a     Document Type: Article

References (56)

1. I. Spasojević, I. Batinić-Haberle, J.S. Reboucas, Y.M. Idemori, I. Fridovich: J. Biol. Chem. (2003), 278: 6831.
2. R.F. Pasternack, A. Banth, J.M. Pasternack, C.S. Johnson: J. Inorg. Biochem. (1981), 15: 261.
3. R.F. Pasternack, B. Halliwell: J. Am. Chem. Soc. (1979), 101: 1026.
4. I. Batinić-Haberle: Methods Enzymol. (2002), 349: 223.
5. I. Spasojević, I. Batinić-Haberle: Inorg. Chim. Acta (2001), 317: 230.
6. I. Batinić-Haberle, L. Benov, I. Spasojević, I. Fridovich: J. Biol. Chem. (1998), 273: 24521.
7. I. Batinić-Haberle, I. Spasojević, P. Hambright, L. Benov, A.L. Crumbliss, I. Fridovich: Inorg. Chem. (1999), 38: 4011.
8. R. Kachadourian, I. Batinić-Haberle, I. Fridovich: Inorg. Chem. (1999), 38: 391.
9. I. Batinić-Haberle, I. Spasojević, R.D. Stevens, P Hambright, I. Fridovich: J. Chem. Soc., Dalton Trans. (2002), 2689.
10. I. Spasojević, R. Menzeleev, P.S. White, I. Fridovich: Inorg. Chem. (2002), 41: 5874.
11. H. Sheng, J.J. Enghild, R. Bowler, M. Patel, I. Batinić-Haberle, C.L. Calvi, B.J. Day, R.D. Pearlstein, J.D. Crapo, D.S. Warner: Free Radic. Biol. Med. (2002), 33: 947.
12. Ž. Vujašković, I. Batinić-Haberle, Z.N. Rabbani, Q.-F. Feng, S.K. Kang, I. Spasojević, T.V. Samulski, I. Fridovich, M.W. Dewhirst, M.S. Anscher: Free Radical Biol. Med. (2002), 33: 857.
13. J.D. Piganelli, S.C. Flores, C. Cruz, J. Koepp, R. Young, B. Bradley, R. Kachadourian, I. Batinić-Haberle, K. Haskins: Diabetes (2002), 51: 347.
14. M. Aslan, T.M. Ryan, B. Adler, T.M. Townes, D.A. Parks, J.A. Thompson, A. Tousson, M.T. Gladwin, M.M. Tarpey, R.P. Patel, I. Batinić-Haberle, C.R. White, B.A. Freeman: Proc. Natl. Acad. Sci. USA (2001), 98: 15215.
15. H. Sheng, I. Spasojević, D.S. Warner, I. Batinić-Haberle: Free Radical Biol. Med. (2003), 35.
16. H. Sheng, I. Batinić-Haberle, I. Spasojević, I. Fridovich, D.S. Warner: Free Radical Biol. Med. (2002), 33.
17. H. Sheng, I. Spasojević, D.S. Warner, I. Batinić-Haberle: Neurosci. Lett. (2004).
18. R. Kachadourian, C.A. Johnson, E. Min, I. Spasojević, B.J. Day: Biochem. Pharmacol. (2004), 67: 77.
19. A. Trostchansky, G. Ferrer-Sueta, C. Batthyany, H. Botti, I. Batinić-Haberle, R Radi, H. Rubbo: Free Radical Biol. Med. (2003), 35: 1293.
20. A. Okado-Matsumoto, I. Batinić-Haberle, I. Fridovich: Free Radic. Biol. Med. (2004).
21. W.R. Waud, F.O. Brady, R.D. Wiley, K.V. Rajagopalan: Arch. Biochem. Biophys. (1975), 19: 695.
22. L.R. Milgrom, P.J.F. Dempsey, G. Yahiouglu: Tetrahedron (1996), 52: 9877.
23. I.M. Kolthof, W.J. Tomsicek: J. Phys. Chem. (1935), 39: 945.
24. I. Batinić-Haberle, R.D. Stevens, I. Fridovich: J. Porphyrins Phthalocyanines (2000), 4: 217.
25. I. Batinić-Haberle, I. Spasojević, R.D. Stevens, P. Hambright, A.N. Thorpe, J. Grodkowski, P. Neta, I. Fridovich: Inorg. Chem. (2001), 40: 726.
26. J.M. McCord, I. Fridovich: J. Biol. Chem. (1969), 244: 6049.
27. I. Batinić-Haberle, L. Benov, I. Fridovich: Anal. Biochem. (1999), 275: 267.
28. T. Maniatis, E.F. Fritsch and J Sambrook, Molecular Cloning: A Laboratory Manual, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, (1982).
29. K.M. Smith, Mass Spectrometry of Porphyrins and Metalloporphyrins in Porphyrins and Metalloporphyrins, ed. K.M. Smith, Elsevier Scientific Publishing Company, Amsterdam, (1975), p 388.
30. B. Halliwell and J. Gutteridge, Free Radicals in Biology and Medicine, New York, Oxford University Press, (1999).
31. G. Ferrer-Sueta, D. Vitturi, I. Batinić-Haberle, I. Fridovich, S. Goldstein, G. Czapski, R. Radi: J. Biol. Chem. (2003), 278: 27432.
32. P. Hambright, I. Batinić-Haberle, I. Spasojević: J. Porphyrins Phthalocyanines (2003), 7: 139.
33. J.H. Espenson, Chemical Kinetics and Reaction Mechanisms, McGraw-Hill Book Company, New York, (1981), p 172.
34. D.H. Tjahjono, T. Akutsu, N. Yoshioka, H. Inoue: Biochim, Biophys. Acta (1999), 1472: 333.
35. R.A. Marcus: Annu. Rev. Phys. Chem. (1964), 15: 155.
36. R.B. Jordan, Reaction Mechanisms of Inorganic and Organometallic Systems, 2nd edn, Oxford University Press, New York, (1998).
37. L.E. Bennet: Prog. Inorg. Chem. (1973), 18: 1-176.
38. C.K. Vance, A.-F. Miller: Biochemistry (2001), 40: 13079.
39. G.D. Lawrence, D.T. Sawyer: Biochemistry (1979), 18: 3045.
40. W.C. Barrette Jr., D.T. Sawyer, J.A. Free, K. Asada: Biochemistry (1983), 22: 624.
41. R.M. Ellerby, D.E. Cabelli, J.A. Graden, J.S. Valentine: J. Am. Chem. Soc. (1996), 118: 6556.
42. C.K. Vance, A.-F. Miller: J. Am. Chem. Soc. (1998), 120: 461.
43. D. Klug-Roth, I. Fridovich, J. Rabani: J. Am. Chem. Soc. (1973), 95: 2786.
44. I. Batinić-Haberle, S.I. Liochev, I. Spasojević, I. Fridovich: Arch. Biochem. Biophys. (1997), 343: 225.
45. R. Kachadourian, I. Batinić-Haberle, I. Fridovich: Free Radical Biol. Med. (1998), 25.
46. S. Cuzzocrea, E. Mazzon, L. Dugo, A.P. Caputi, K. Aston, D.P. Riley, D. Salvemini: Br. J. Pharmacol. (2001), 132: 19.
47. K. Aston, N. Rath, A. Naik, U. Slomczynska, O.F. Schall, D.P. Riley: Inorg. Chem. (2001), 40: 1779.
48. D.P. Riley: Adv. Supramol. Chem. (2000), 6: 217-244.
49. D.P. Riley, S.L. Henke, P.J. Lennon, R.H. Weiss, W.L. Neumann, W.J. Rivers Jr., K.W. Aston, K.R. Sample, H. Rahman, C.-S. Ling, J.-J. Shieh, D.H. Busch, W. Szulbinski: Inorg. Chem. (1996), 35: 5213.
50. D.P. Riley, R.H. Weiss: J. Am. Chem. Soc. (1994), 116: 387.
51. I.N. Hines, H. Harada, R. Wolf, M.B. Grisham: Curr. Med. Chem. (2003), 10: 2661.
52. H.M. Tse, M.J. Milton, J.D. Piganelli: Free Radical Biol. Med. (2004), 36: 233.
53. R. Bottino, A.N. Balamurugan, S. Bertera, M. Pietropaolo, M. Trucco, J.D. Piganelli: Diabetes (2002), 51: 2561.
54. R.P. Bowler, H. Sheng, J.J. Enghild, R.D. Pearlstein, D.S. Warner, J.D. Crapo: Free Radical Biol. Med. (2002), 33: 1141.
55. G. Ferrer-Sueta, C. Quijano, B. Alvarez, R. Radi: Methods Enzymol. (2002), 349: 23.
56. B.J. Moeller, I. Batinić-Haberle, I. Spasojević, Z.N. Rabbani, M.S. Anscher, M.W. Dewhirst and Ž. Vujašković, Proceedings of the 94th Annual Meeting of the American Association for Cancer Research, 2nd edn., (2003), 44:, 604.