Orally available Mn porphyrins with superoxide dismutase and catalase activities

Journal of Biological Inorganic Chemistry

Volumn 14, Issue 6, 2009, Pages 979-991

  Rosenthal, Rosalind A ^a   Huffman, Karl D ^a   Fisette, Leslie W ^d   Damphousse, Christy A ^a   Callaway, Wyeth B ^b   Malfroy, Bernard ^c   Doctrow, Susan R ^a  

^a BOSTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Frontier Scientific Inc   (United States)

^c MindSet Rx Inc   (United States)

^d Proteome Systems   (United States)

Author keywords

Apoptosis; EUK 400 series compounds; Manganese porphyrins; Oxidative stress; Superoxide dismutase catalase mimetics

Indexed keywords

ANTIOXIDANT; CATALASE; EUK 189; EUK 207; EUK 400; EUK 418; EUK 423; EUK 425; EUK 450; EUK 451; EUK 452; EUK 453; MANGANESE DERIVATIVE; PEROXIDASE; PORPHYRIN DERIVATIVE; STAUROSPORINE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL CELL CULTURE; ANIMAL EXPERIMENT; ANTIOXIDANT ACTIVITY; ARTICLE; CELL DEATH; CELL STRAIN; DRUG BIOAVAILABILITY; ENZYME ACTIVITY; IN VITRO STUDY; NONHUMAN; PHEOCHROMOCYTOMA; PRIORITY JOURNAL; RAT; STOMACH JUICE;

ADMINISTRATION, ORAL; ANIMALS; BIOCATALYSIS; BIOLOGICAL AVAILABILITY; BIOMIMETIC MATERIALS; CATALASE; CELL DEATH; CELL LINE, TUMOR; MANGANESE; METALLOPORPHYRINS; PC12 CELLS; RATS; STAUROSPORINE; SUPEROXIDE DISMUTASE;

ANIMALIA; RATTUS;

EID: 70349290574     PISSN: 09498257     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00775-009-0550-4     Document Type: Article

References (61)

1. MEC Robbins W Zhao 2004 In J Radiat Biol 80 251 259
2. A Reynolds C Laurie R Lee Mosley HE Gendelman 2007 Int Rev Neurobiol 82 297 325
3. Halliwell B, Gutteridge JMC (1999) Free radicals in biology and medicine. Oxford University Press, Oxford
4. SR Doctrow K Huffman CB Marcus G Tocco E Malfroy CA Adinolfi H Kruk K Baker N Lazarowych J Mascarenhas B Malfroy 2002 J Med Chem 45 4549 4558
5. KM Faulkner SI Liochev I Fridovich 1994 J Biol Chem 269 23471 23476
6. BJ Day I Fridovich JD Crapo 1997 Arch Biochem Biophys 347 256 262
7. JP Crow 2000 Free Radic Biol Med 28 1487 1494
8. R Shimanovich S Hannah V Lynch N Gerasimchuk TD Mody D Magda J Sessler JT Groves 2001 J Am Chem Soc 123 3613 3614
9. MA Sharpe R Ollosson VC Stewart JB Clark 2002 Biochem J 366 97 107
10. J Peng FF Stevenson SR Doctrow JK Andersen 2005 J Biol Chem 280 29194 29198
11. C Jung Y Rong S Doctrow M Baudry B Malfroy Z Xu 2001 Neurosci Lett 304 157 160
12. S Melov N Wolf D Strozyk SR Doctrow AI Bush 2005 Free Radic Biol Med 38 258 261
13. K Baker C Bucay-Marcus C Huffman H Kruk B Malfroy SR Doctrow 1998 J Pharmacol Exp Ther 284 215 221
14. R Liu IY Liu X Bi RF Thompson SR Doctrow B Malfroy M Baudry 2003 Proc Natl Acad Sci USA 100 8526 8531
15. S Melov SR Doctrow JA Schneider J Haberson M Patel PE Coskun K Huffman DC Wallace B Malfroy 2001 J Neurosci 21 8348 8353
16. AR Langan MA Khan IW Yeung J Van Dyk RP Hill 2006 Radiother Oncol 79 231 238
17. V Srinivasan S Doctrow VK Singh MH Whitnall 2008 Immunopharmacol Immunotoxicol 30 271 290
18. B Gauter-Fleckenstein K Fleckenstein K Owzar C Jiang I Batinic-Haberle Z Vujaskovic 2008 Free Radic Biol Med 44 982 989
19. Z Vujaskovic I Batinic-Haberle ZN Rabbani QF Feng SK Kang I Spasojevic TV Samulski I Fridovich MW Dewhirst MS Anscher 2002 Free Radic Biol Med 33 857 863
20. M Patel BJ Day 1999 Trends Pharmacol Sci 20 359 364
21. JH Lee YM Lee JW Park 2005 Biochem Biophys Res Commun 334 298 305
22. ZN Rabbani I Batinic-Haberle MS Anscher J Huang BJ Day E Alexander MW Dewhirst Z Vujaskovic 2007 Int J Radiat Oncol Biol Phys 67 573 580
23. RA Rosenthal E Vorotnikova L Fisette S Braunhut K Huffman M Tries SR Doctrow 2006 Free Radic Biol Med 41 S159 S160
24. JP Crow NY Calingasan J Chen JL Hill MF Beal 2005 Ann Neurol 58 258 265
25. SS Sharma S Gupta 2007 Eur J Pharmacol 561 72 79
26. GB Mackensen M Patel H Sheng CL Calvi I Batinic-Haberle BJ Day LP Liang I Fridovich JD Crapo RD Pearlstein DS Warner 2001 J Neurosci 21 4582 4592
27. LP Liang J Huang R Fulton BJ Day M Patel 2007 J Neurosci 27 4326 4333
28. RA Rosenthal LW Fisette K Huffman CA Damphousse WB Callaway B Malfroy S Doctrow 2007 Free Radic Biol Med 43 S188 S189
29. Meunier B, Cosledan F (2006) Office UPaT, 20060241095, 26 October 2006
30. D Lahaye K Muthukumaran CH Hung D Gryko JS Reboucas I Spasojevic I Batinic-Haberle JS Lindsey 2007 Bioorg Med Chem 15 7066 7086
31. MP Trova PJ Gauuan AD Pechulis SM Bubb SB Bocckino JD Crapo BJ Day 2003 Bioorg Med Chem 11 2695 2707
32. BJ Littler MA Miller CH Hung RW Wagner DF O'Shea PD Boyle JS Lindsey 1999 J Org Chem 64 1391 1396
33. Falk JE, Smith KM (eds) (1975) Porphyrins and metalloporphyrins. Elsevier, New York
34. S Neya N Funasaki 1997 J Heterocycl Chem 34 689 690
35. GMP Giblin PC Box IB Campbell AP Hancock S Roomans GI Mills C Molloy GE Tranter AL Walker SR Doctrow K Huffman B Malfroy 2001 Bioorg Med Chem Lett 11 1367 1370
36. FDA (2000) Waiver of in vivo bioavailability and bioequivalence studies for immediate-release solid oral dosage forms based on a biopharmaceutics classification system. http://www.fda.gov/Cder/guidance/3618fnl.htm
37. JS Reboucas I Spasojevic I Batinic-Haberle 2008 J Biol Inorg Chem 13 289 302
38. K Pong SR Doctrow K Huffman CA Adinolfi M Baudry 2001 Exp Neurol 171 84 97
39. C Hansch JP Bjorkroth A Leo 1987 J Pharm Sci 76 663 687
40. MC Gres B Julian M Bourrie V Meunier C Roques M Berger X Boulenc Y Berger G Fabre 1998 Pharm Res 15 726 733
41. S Yee 1997 Pharm Res 14 763 766
42. CL Stoner A Cleton K Johnson DM Oh H Hallak J Brodfuehrer N Surendran HK Hans 2004 Int J Pharm 269 241 249
43. Y Song RE Haddad SL Jia S Hok MM Olmstead DJ Nurco NE Schore J Zhang JG Ma KM Smith S Gazeau J Pecaut JC Marchon CJ Medforth JA Shelnutt 2005 J Am Chem Soc 127 1179 1192
44. Reboucas JS, Spasojevic I, Tjahjono DH, Richaud A, Mendez F, Benov L, Batinic-Haberle I (2008) Dalton Trans 1233-1242
45. CR Schlieve CJ Lieven LA Levin 2006 Invest Ophthalmol Vis Sci 47 3878 3886
46. M Shayeghi GO Latunde-Dada JS Oakhill AH Laftah K Takeuchi N Halliday Y Khan A Warley FE McCann RC Hider DM Frazer GJ Anderson CD Vulpe RJ Simpson AT McKie 2005 Cell 122 789 801
47. S Cohen R Margalit 1990 Biochem J 270 325 330
48. AY Abramov A Scorziello MR Duchen 2007 J Neurosci 27 1129 1138
49. BI Lee PH Chan GW Kim 2005 Stroke 36 2712 2717
50. JS Tauskela E Brunette N O'Reilly G Mealing T Comas TF Gendron R Monette P Morley 2005 FASEB J 19 1734 1736
51. Y Shan J Pepe TH Lu KK Elbirt RW Lambrecht HL Bonkovsky 2000 Arch Biochem Biophys 380 219 227
52. EA Konorev S Kotamraju H Zhao S Kalivendi J Joseph B Kalyanaraman 2002 Free Radic Biol Med 33 988
53. S Pfeiffer A Schrammel D Koesling K Schmidt B Mayer 1998 Mol Pharmacol 53 795 800
54. A Verma JS Nye SH Snyder 1987 Proc Natl Acad Sci USA 84 2256 2260
55. JG Pastorino G Simbula E Gilfor JB Hoek JL Farber 1994 J Biol Chem 269 31041 31046
56. F Bono I Lamarche V Prabonnaud G Le Fur JM Herbert 1999 Biochem Biophys Res Commun 265 457 461
57. N Leducq F Bono T Sulpice V Vin P Janiak GL Fur SE O'Connor JM Herbert 2003 J Pharmacol Exp Ther 306 828 837
58. Malfroy-Camine B, Doctrow S (2008) Application UP, 2008033444, 20 March 2008
59. RW Orrell 2006 Curr Opin Investig Drugs 7 70 80
60. JD Piganelli SC Flores C Cruz J Koepp I Batinic-Haberle J Crapo B Day R Kachadourian R Young B Bradley K Haskins 2002 Diabetes 51 347 355
61. NL Lubbers JS Polakowski JD Crapo CD Wegner BF Cox 2003 J Cardiovasc Pharmacol 41 714 719