Stability, disposition, and penetration of catalytic antioxidants Mn-porphyrin and Mn-salen and of methylprednisolone in spinal cord injury

Central Nervous System Agents in Medicinal Chemistry

Volumn 12, Issue 2, 2012, Pages 122-130

  Wu, Liqin ^a   Shan, Yichu ^a   Liu, Danxia ^a  

^a University of Texas Medical Branch School of Medicine   (United States)

Author keywords

Antioxidant therapy; Blood spinal cord barrier; EUK 134; Methylprednisolone; Mn containing catalytic antioxidants; MnTBAP; Spinal cord injury; Stability and disposition

Indexed keywords

ANTIOXIDANT; MANGANESE (III) 3 METHOXY N, N' BIS(SALICYCLIDENE)ETHYLENEDIAMINE CHLORIDE; MANGANESE (III) TETRAKIS(4 BENZOIC ACID)PORPHYRIN; MANGANESE N,N' ETHYLENEBIS(3 METHOXYSALICYLIDENEAMINE); METHYLPREDNISOLONE SODIUM SUCCINATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BLOOD; BLOOD SPINAL CORD BARRIER; CEREBROSPINAL FLUID; CONTROLLED STUDY; DRUG DISPOSITION; DRUG PENETRATION; DRUG STABILITY; IN VIVO STUDY; MALE; NONHUMAN; PERMEABILITY BARRIER; RAT; SPINAL CORD INJURY;

EID: 84862577216     PISSN: 18715249     EISSN: 18756166     Source Type: Journal    
DOI: 10.2174/187152412800792742     Document Type: Article

References (47)

1. Balentine, J.D. Hypotheses in spinal cord trauma research, In: Central Nervous System Trauma Status Report. Becker, D.P.; Povlishock, J.T., Eds.; NIH, Bethesda, Maryland, 1985; pp. 455-461.
2. Young, W. Secondary injury mechanisms in acute spinal cord injury. J. Emerg. Med., 1993, 11, 13-22.
3. Genovese, T.; Cuzzocrea, S. Role of free radicals and poly(ADPribose) polymerase-1 in the development of spinal cord injury: new potential therapeutic targets. Curr. Med. Chem., 2008, 15, 477-487.
4. Lewen, A.; Matz, P.; Chan, P.H. Free radical pathways in CNS injury. J. Neurotrauma, 2000, 17, 871-890.
5. Chan, P. H. Reactive oxygen radicals in signaling and damage in the ischemic brain. J. Cerebr. Blood F. Met., 2001, 21, 2-14.
6. Liu, D.; Sybert, T.E.; Qian, H.; Liu, J. Superoxide production after spinal injury detected by microperfusion of cytochromec. Free Radic. Biol. Med., 1998, 25, 298-304.
7. Liu, D.; Liu, J.; Wen, J. Elevation of hydrogen peroxide after spinal cord injury detected by using the Fenton reaction. Free Radic. Biol. Med., 1999, 27, 478-482.
8. Liu, D.; Ling, X.; Wen, J.; Liu, J. The role of reactive nitrogen species in secondary spinal cord injury: formation of nitric oxide, peroxynitrite, and nitrated protein. J. Neurochem., 2000, 75, 2144-2154.
9. Liu, D.; Liu, J.; Sun, D.; Wen, J. The time course of hydroxyl radical formation following spinal cord injury: the possible role of the iron-catalyzed Haber-Weiss reaction. J. Neurotrauma, 2004, 21, 805-816.
10. Leski, M.L.; Bao, F.; Wu, L.; Qian, H.; Sun, D.; Liu, D. Protein and DNA oxidation in spinal injury: neurofilaments--an oxidation target. Free Radic. Biol. Med., 2001, 30, 613-624.
11. Springer, J.E.; Azbill, R.D.; Mark, R.J.; Begley, J.G.; Waeg, G.; Matson, M.P. 4-hydroxynonenal, a lipid peroxidation product, rapidly accumulates following traumatic spinal cord injury and inhibits glutamate uptake. J. Neurochem., 1997, 68, 2469-2476.
12. Scott, G.S.; Jakeman, L.B.; Stokes, B.T.; Szabo, C. Peroxynitrite production and activation of poly (adenosine diphosphate-ribose) synthetase in spinal cord injury. Ann. Neurol., 1999, 45, 120-124.
13. Carrico, KM.; Vaishnav, R.; Hall, ED. Temporal and spatial dynamics of peroxynitrite-induced oxidative damage after spinal cord contusion injury. J. Neurotrauma, 2009, 26, 1369-1378.
14. Aksenova, M.; Butterfield, D.; Zhang, S.; Underwood, M.; Geddes, J. Increased protein oxidation and decreased creatine kinase BB expression and activity after spinal cord contusion injury. J. Neurotrauma, 2002, 19, 491-502.
15. Genovese, T.; Mazzon, E.; Esposito, E.; Muià, C.; Rosanna, Di. Paola.; Bramanti, P.; Cuzzocrea, S. Beneficial effects of FeTSPP, a peroxynitrite decomposition catalyst, in a mouse model of spinal cord injury. Free Radic Biol. Med., 2007, 43, 763-780.
16. Genovese, T.; Mazzon, E.; Esposito, E.; Muià, C.; Rosanna, Di. Paola.; Murthy, K.; Neville, L.; Bramanti, P.; Cuzzocrea, S. Effects of a metalloporphyrinic peroxynitrite decomposition catalyst,ww- 85, in a mouse model of spinal cord injury. Free Rad. Biol. Med; 2009, 43, 631-645.
17. Titsworth, W.L.; Liu, N.K.; Xu, X.M. Role of secretory phospholipase A2 in CNS inflammation: Implications in traumatic spinal cord injury. CNS Neurol. Disord. Drug Targets, 2008, 7, 254-269.
18. Day, B.J. Catalytic antioxidants: a radical approach to new therapeutics. Drug Discov. Today., 2004, 9, 557-566.
19. Day, B.J. Catalase and glutathione peroxidase mimics. Biochem. Pharmacol., 2009, 77, 285-296.
20. Batinić-Haberle, I.; Rebouças, J.S.; Spasojević, I. Superoxide dismutase mimics: chemistry, pharmacology, and therapeutic potential. Antioxid. Redox Signal., 2010, 13, 877-918.
21. Day, B.J.; Fridovich, I.; Crapo, J.D. Manganic porphyrins possess catalase activity and protect endothelial cells against hydrogen peroxide-mediated injury. Arch. Biochem. Biophys., 1997, 347, 256-262.
22. Zingarelli, B.; Day, B.; Crapo, J. D.; Salzman, A. L.; Szabo, C. The potential role of peroxynitrite in the vascular contractile and cellular energetic failure in endotoxic shock. Br. J. Pharmacol., 1997, 120, 259-267.
23. Day, B.J.; Batinic-Haberle, I.; Crapo, J.D. Metalloporphyrins are potent inhibitors of lipid peroxidation. Free Radic. Biol. Med., 1999, 26, 730-736.
24. Liang, L.P.; Ho, Y.S.; Patel, M. Mitochondrial superoxide production in kainate induced hippocampal damage. Neuroscience, 2000, 101, 563-570.
25. Hachmeister, J.E.; Valluru, L.; Bao, F.; Liu, D. Mn (III) tetrakis (4- benzoic acid) porphyrin administered into the intrathecal space reduces oxidative damage and neuron death after spinal cord injury: a comparison with methylprednisolone. J. Neurotrauma, 2006, 23, 1766-1778.
26. Doctrow, S.R.; Huffman, K.; Marcus, C.B.; Musleh, W.; Bruce, A.; Baudry, M.; Malfroy, B. Salen-manganese complexes: combined superoxide dismutase/catalase mimics with broad pharmacological efficacy. Adv. Pharmacol., 1997, 38, 247-269.
27. Doctrow, S.R.; Huffman, K.; Marcus, C.B.; Tocco, G.; Malfroy, E.; Adinolfi, C.A.; Kruk, H.; Baker, K.; Lazarowych, N.; Mascarenhas, J.; Malfroy, B. Salen-manganese complexes as catalytic scavengers of hydrogen peroxide and cytoprotective agents: structure-activity relationship studies. J. Med. Chem., 2002, 45, 4549-4558.
28. Sharpe, M.A.; Ollosson, R.; Stewart, V.C.; Clark, J.B. Oxidation of nitric oxide by oxomanganese-salen complexes: a new mechanism for cellular protection by superoxide dismutase/catalase mimetics. Biochem. J., 2002, 366, 97-107.
29. Melov, S.; Doctrow, S.R.; Schneider, J.A.; Haberson, J.; Patel, M.; Coskun, P.E.; Huffman, K.; Wallace, D.C.; Malfroy, B. Lifespan extension and rescue of spongiform encephalopathy in superoxide dismutase 2 nullizygous mice treated with superoxide dismutasecatalase mimetics. J. Neurosci., 2001, 21, 8348-8353.
30. Jung, C.; Rong, Y.; Doctrow, S.; Baudry, M.; Malfroy, B.; Xu, Z. Synthetic superoxide dismutase/catalase mimetics reduce oxidative stress and prolong survival in a mouse amyotrophic lateral sclerosis model. Neurosci. Lett., 2001, 304, 157-160.
31. Baker, K.; Marcus, C.; Huffman, K.; Kru, H.; Malfroy, B.; Doctrow, S.R. Synthetic combined superoxide dismutase/catalase mimetics are protective as a delayed treatment in a rat stroke model: a key role for reactive oxygen species in ischemic brain injury. J. Pharmacol. Exp. Ther., 1998, 284, 215-221.
32. Melov, S.; Schneider, J.A.; Day, B.J.; Hinerfeld, D.; Coskun, P.; Mirra, S.S.; Crapo, J.D.; Wallace, D.C.; A novel neurological phenotype in mice lacking mitochondrial manganese superoxide dismutase. Nat. Genet., 1998, 18, 159-163.
33. Popovich, P.G.; Horner, P.J.; Mullin, B.B.; Stokes, B.T.; A quantitative spatial analysis of the blood-spinal cord barrier. I. Permeability changes after experimental spinal contusion injury. Exp. Neurol., 1996, 142, 258-275.
34. Whetstone, W.D.; Hsu, J.Y.; Eisenberg, M.; Werb, Z.; Noble- Haeusslein, L.J.; Blood-spinal cord barrier after spinal cord injury: relation to revascularization and wound healing. J. Neurosci. Res., 2003, 74, 227-239.
35. Cohen, D.M.; Patel, C.B.; Ahobila-Vajjula, P.; Sundberg, L.M.; Chacko, T.; Liu, S-J.; Narayana, P.A. Blood-spinal cord barrier permeability in experimental spinal cord injury: Dynamic contrastenhanced magnetic resonance imaging NMR. Biomed., 2009, 22, 332-341.
36. Ling, X.; Liu, D. Temporal and spatial profiles of cell loss after spinal cord injury: Reduction by a metalloporphyrin. J. Neurosci. Res., 2007, 85, 2175-2185.
37. Huang, Y.L.; Saljo, A.; Suneson, A.; Hansson, H.A. A new approach for multiple sampling of cisternal cerebrospinal fluid in rodents with minimal trauma and inflammation. J. Neurosci. Methods, 1995, 63, 13-22.
38. Bracken, M.B.; Shepard, M.J.; Holford, T.R.; Leo-Summers, L.; Aldrich, E.F.; Fazl, M.; Fehlings, M.; Herr, D.L.; Hitchon, P.W.; Marshall, L.F.; Nockels, R.P.; Pascale, V.; Perot, P.L.; Piepmeier, J.; Sonntag, V.K.; Wagner, F.; Wilberger, J.E.; Winn, H.R.; Young, W. Administration of methylprednisolone for 24 or 48 hours or tirilazad mesylate for 48 hours in the treatment of acute spinal cord injury. Results of the Third National Acute Spinal Cord Injury Randomized Controlled Trial. National Acute Spinal Cord Injury Study. JAMA, 1997, 277, 1597-1604.
39. De Ley, G.; Leybaert, L. Effect of flunarizine and methylprednisolone on functional recovery after experimental spinal injury. J. Neurotrauma, 1993, 10, 25-35.
40. Perez-Espejo, M.A, Haghighi, S.S, Adelstein, E.H, Madsen, R. The effects of taxol, methylprednisolone, and 4-aminopyridine in compressive spinal cord injury: A qualitative experimental study. Surg. Neurol., 1996, 46, 350-357.
41. Koc, R.K.; Akdemir, H.; Karakucuk, E.I.; Oktem, I.S.; Menku, A. Effect of methylprednisolone, tirilazad mesylate and vitamin E on lipid peroxidation after experimental spinal cord injury. Spinal Cord, 1999, 1, 29-32.
42. Oury, T.D.; Thakker, K.; Menache, M.; Chang, L.Y.; Crapo, J.D.; Day, B.J.; Attenuation of Bleomycin-Induced Pulmonary Fibrosis by a Catalytic Antioxidant Metalloporphyrin. Am. J. Respir. Cell Mol. Biol., 2001, 25, 164-169.
43. Kachadourian, R.; Menzleev, R.; Agha, B.; Bocckino, S.B.; Day, B.J. High-performance liquid chromatography with spectrophotometric and electrochemical detection of a series of manganese (I I I) cationic porphyrins. J. Chromatogr., 2002, 767, 61-67.
44. Smith, M.D. High-performance liquid chromatographic determination of hydrocortisone and methylprednisolone and their hemisuccinate esters in human serum J. Chromatogr., 1979, 164, 129-137.
45. Vree, T.B.; Lagerwerf, A.J.; Verwey-van Wissen, C.P.; Jongen, P.J. High-performance liquid chromatography analysis, preliminary pharmacokinetics, metabolism and renal excretion of methylprednisolone with its C6 and C20 hydroxy metabolites in multiple sclerosis patients receiving high-dose pulse therapy. J. Chromatogr., 1999, 732, 337-348.
46. Braughler, J.M.; Hall, E.D. Uptake and elimination of methylprednisolone from contused cat spinal cord following intravenous injection of the sodium succinate ester. J. Neurosurgery, 1983, 58, 538-542.
47. Segal, J.L.; Maltby, B.F.; Langdorf, M.I.; Jacobson, R.; Brunnemann, S.R.; Jusko, W.J. Methylprednisolone disposition kinetics in patients with acute spinal cord injury. Pharmacotherapy, 1998, 18, 16-22.