Design and biological evaluation of new antioxidants for use in cerebrovascular disorders

Drugs of the Future

Volumn 21, Issue 10, 1996, Pages 1037-1046

  Marciniak, Gilbert ^a   Petty, Margaret A ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; MDL 74180; UNCLASSIFIED DRUG;

BRAIN ISCHEMIA; DRUG DESIGN; DRUG SYNTHESIS; ENANTIOMER; HEAD INJURY; MOUSE; NONHUMAN; RAT; REVIEW; STRUCTURE ACTIVITY RELATION; SUBARACHNOID HEMORRHAGE;

EID: 0029826798     PISSN: 03778282     EISSN: None     Source Type: Journal    
DOI: 10.1358/dof.1996.021.10.385490     Document Type: Review

References (75)

1. Krieglstein, J., Oberpichler, H. (Eds.). Pharmacology of Cerebral Ischemia. Wiss Verlag GmbH: Stuttgart 1990.
2. Bazan, N.G., Braquet, P., Ginsberg, M.D (Eds.). Neurochemical Correlates of Cerebral Ischemia. Advances in Neurochemistry, Vol. 7. Plenum Press: New York 1992.
3. Dunn, C.D.R. Stroke: Trends, treatments and markets. Scrip Reports, PJB Publications Ltd. 1995.
4. Hanin, I., Yoshida, M., Fisher, A. (Eds.). Alzheimer's and Parkinson's diseases: Recent developments. Advances in Behavioral Biology, Vol. 44. Plenum Press: New York 1995.
5. Dunn, C.D.R. Alzheimer's disease: Pathology and treatment. Scrip Reports, PJB Publications Ltd. 1996.
6. Peruche, B., Krieglstein, J. Mechanisms of drug actions against neuronal damage caused by ischemia - An overview. Prog Neuro-Psychopharmacol Biol Psychiat 1993, 17: 21-70.
7. Lees, G.J. Contributory mechanisms in the causation of neurodegenerative disorders. Neuroscience 1993, 54: 287-322.
8. Kontos, H.A. Oxygen radicals in CNS damage. Chem Biol Interact 1989, 72: 229-55.
9. Braughler, J.M., Hall, E.D. Central nervous system trauma and stroke: I. Biochemical considerations for oxygen radical formation and lipid peroxidation. Free Rad Biol Med 1989, 6: 289-301.
10. Hall, E.D., Braughler, J.M. Central nervous system trauma and stroke: II. Physiological and pharmacological evidence for involvement of oxygen radicals and lipid peroxidation. Free Rad Biol Med 1989, 6: 303-13.
11. Ikeda, Y., Long, D.M. The molecular basis of brain injury and brain oedema: The role of oxygen free radicals. Neurosurgery 1990, 27: 1-11.
12. Jesberger, J.A., Richardson, J.S. Oxygen free radicals and brain dysfunction. Int J Neurosci 1991, 57: 1-17.
13. Halliwell, B. Reactive oxygen species and the central nervous system. J Neurochem 1992, 59: 1609-23.
14. Gutteridge, J.M.C. Free radicals in disease processes: A compilation of cause and consequence, free Rad Res Commun 1993, 19: 141-58.
15. Jenner, P. Oxidative damage in neurodegenerative disease. Lancet 1994, 344: 796-8.
16. Simonian, N.A., Coyle, J.T. Oxidative stress in neurodegenerative diseases. Annu Rev Pharmacol Toxicol 1996, 36: 83-106.
17. Halliwell, B., Gutteridge, J.M.C. (Eds.). Free Radicals in Biology and Medicine, Second Edition. Clarendon Press: Oxford 1989.
18. Halliwell, B. Drug antioxidant effects: A basis for drug selection? Drugs 1991, 42: 569-605.
19. Evans, P.H. Free radicals in brain metabolism and pathology. Brit Med Bull 1993, 49: 577-87.
20. Kontos, H.A. Oxygen radicals in cerebral vascular injury. Circ Res 1985, 57: 508-16.
21. Siesjö, B.K., Ahardh, C.D., Bengtsson, F. Free radicals and brain damage. Cerebrovasc Brain Metab Rev 1989, 1: 165-211.
22. Cohen, G. Oxidative stress in the nervous system. In: Oxidative Stress, Sies, H. (Ed.). Academic Press: Orlando 1985, 383-402.
23. Rice-Evans, C., Diplock, A.T. Current status of antioxidant therapy. Free Rad Biol Med 1993, 15: 77-96.
24. Jacobsen, E.J., McCall, J.M., Ayer, D.E. et al. Novel 21-aminosteroids that inhibit iron-dependent lipid peroxidation and protect against central nervous system trauma. J Med Chem 1990, 33: 1145-51.
25. Clark, W.M., Hazel, J.S., Coull, B.M. Lazaroids: CNS pharmacology and current research. Drugs 1995, 50: 971-83.
26. Hall, E.D., Braughler, J.M., Yonkers, P.A. et al. U-78517F: A potent inhibitor of lipid peroxidation with activity in experimental brain injury and ischemia. J Pharmacol Exp Ther 1991, 258: 688-94.
27. Jacobsen, E.J., VanDoornik, F.J., Ayer, D.E. et al. 2-(Aminomethyl)chromans that inhibit iron-dependent lipid peroxidation and protect against central nervous system trauma. J Med Chem 1992, 35: 4464-72.
28. Oshiro, Y., Sakurai, Y., Tanaka, T., Kikuchi, T., Hirose, T., Tottori, K. Novel cerebroprotective agents with central nervous system stimulating activity. 2. Synthesis and pharmacology of 1-(acylamino)-7-hydroxyindan derivatives. J Med Chem 1991, 34: 2014-23.
29. Clemens, J.A., Saunders, R.D., Ho, P.P., Phebus, L.A., Panetta, J.A. The antioxidant LY231617 reduces global ischemic neuronal injury in rats. Stroke 1993, 24: 716-23.
30. Van Acker, S.A.B.E., Koymans, L.M.H., Bast, A. Molecular pharmacology of vitamin E: Structural aspects of antioxidant activity. Free Rad Biol Med 1993, 15: 311-28.
31. McCay, P.B., King, M.M. Vitamin E: Its role as a biological free radical scavenger and its relationship to the microsomal mixed-function oxidase system. In: Vitamin E, a Comprehensive Treatise. Machlin, L.J. (Ed.). Marcel Dekker: New York 1980, 289-317.
32. Burton, G.W., Ingold, K.U. Autoxidation of biological molecules. 1. The antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vitro. J Amer Chem Soc 1981, 103: 6472-7.
33. Burton, G.W., Ingold, K.U. Vitamin E: Application of the principles of physical organic chemistry to the exploration of its structure and function. Acc Chem Res 1986, 19: 194-201.
34. Buettner, G.R. The pecking order of free radicals and antioxidants: Lipid peroxidation, α-tocopherol and ascorbate. Arch Biochem Biophys 1993, 300: 535-43.
35. Grisar, J.M., Bolkenius, F.N., Petty, M.A., Verne, J. 2,3-Dihydro-1-benzofurano-5-ols as analogues of α-tocopherol that inhibit in vitro and in vivo brain lipid autoxidation and protect mice against central nervous system trauma. J Med Chem 1995, 38: 453-8.
36. Bolkenius, F.N., Verne-Mismer, J., Wagner, J., Grisar, J.M. Amphiphilic α-tocopherol analogues as inhibitors of brain lipid peroxidation. Eur J Pharmacol 1996, 298: 37-43.
37. Grisar, J.M., Petty, M.A., Bolkenius, F.N. et al. A cardioselective, hydrophilic N,N,N-trimethylethanaminium alpha-tocopherol analogue that reduces myocardial infarction. J Med Chem 1991, 34: 257-60.
38. Dow, J., Petty, M.A., Grisar, J.M., Wagner, E.R., Haegele, K.D. Cardioselectivity of α-tocopherol analogues, with free radical scavenger activity, in the rat. Drug Metab Dispos 1991, 19: 1040-5.
39. Mukai, K., Okabe, K., Hosose, H. Synthesis and stopped-flow investigation of antioxidant activity of tocopherols. Finding of new tocopherol derivatives having the highest antioxidant activity among phenolic antioxidants. J Org Chem 1989, 54: 557-60.
40. Kagan, V.E., Serbinova, R.A., Bakalova, Ts.S. et al. Mechanisms of stabilization of biomembranes by α-tocopherol - The role of the hydrocarbon chain in the inhibition of lipid peroxidation. Biochem Pharmacol 1990, 40: 2403-13.
41. Barclay, L.R.C., Vinqvist, M.R. Membrane peroxidation: Inhibiting effects of water-soluble antioxidants on phospholipids of different charge types. Free Rad Biol Med 1994, 16: 779-88.
42. Grisar, J.M., Petty, M.A., Bolkenius, F.N. New benzofuran derivative are free radical scavengers for treating stroke, nervous system trauma and reperfusion damage. W0 9320057-A1.
43. Marciniak, G., Ayers, T.A., Krysan, D.J., Schnettler, R.A. Novel process for preparing derivatives of 2,2,4,6,7-pentaalkyl-2,2-dihydrobenzofuranols. EP 95400518.
44. Marciniak, G., Leborgne, J.F., Grisar, J.M. An alternative synthesis of 5-hydroxy-3-[(4-methylpiperazino)-methyl]-2,2,4,6,7-pentamethyl-2,3-dihydro-1- benzofuran and of the corresponding enantiomers, as potent α-tocopherol analogues. Submitted for publication.
45. Ayers, T.A., Schnettler, R.A., Marciniak, G. et al. Enzymatic resolution for an improved enantioselective synthesis of benzofuranyl derivatives: Precursors to a class of vitamin E related antioxidants. Submitted for publication.
46. Bolkenius, F.N., Monard, D. Inactivation of protease nexin-1 by xanthine oxidase-derived free radicals. Neurochem Int 1995, 26: 587-92.
47. Petty, M.A., Bolkenius, F.N., Dow, J., Marciniak, G. Design and biological evaluation of tissue directed α-tocopherol analogues. Handbook of Synthetic Antioxidants. Cadenas, E., Packer, L. (Eds.). Marcel Dekker: New York 1996, in press.
48. Kontos, H.A. Oxygen radicals in cerebral vascular injury. Circ Res 1985, 57: 508-16.
49. Watson, B.D., Busto, R., Goldberg, W.J., Santiso, M., Yoshida, S., Ginsberg, M.D. Lipid peroxidation in vivo induced by reversible global ischaemia in rat brain. J Neurochem 1984, 42: 268-74.
50. Yoshida, S., Busto, R., Watson, B.D., Santiso, M., Ginsberg, M.D. Postischaemic cerebral lipid peroxidation in vitro: Modification by dietary vitamin E. J Neurochem 1985, 44: 1593-601.
51. Bromont, C., Marie, C., Bralet, J. Increased lipid peroxidation in vulnerable brain regions after transient forebrain ischaemia in rats. Stroke 1989, 20: 918-24.
52. Martz, D., Rayos, G., Schielke, G.P., Setz, A.L. Allopurinol and dimethylthiourea reduce brain infarction following middle cerebral artery occlusion in rats. Stroke 1989, 20: 488-94.
53. Liu, T.H., Beckman, J.S., Freeman, B.A., Hogan, E.L., Hsu, C.Y. Polyethylene glycol-conjugated superoxide dismutase and catalase reduce ischaemic brain injury. Amer J Physiol 1989, 256: H589-93.
54. Xue, D., Slivka, A., Buchan, A.M. Tirilazad reduces cortical infarction after transient but not permanent focal cerebral ischaemia in rats. Stroke 1992, 23: 894-9.
55. Kinouchi, H., Epstein, C.J., Mizui, T., Carlson, E., Chen, S.F., Chan, P.H. Attenuation of focal cerebral ischaemic injury in transgenic mice overexpressing CuZn Superoxide dismutase. Proc Natl Acad Sci USA 1991, 88: 11158-62.
56. Yang, G., Chan, P.H., Chen, J. et al. Human copper-zinc superoxide dismutase transgenic mice are highly resistant to reperfusion injury after focal cerebral ischaemia. Stroke 1994, 25: 165-70.
57. Kirsch, J.R., Phelan, A.M., Lange, D.G., Traystaman, R.J. Reperfusion induced free radical formation following global ischaemia. Pediatr Res 1987, 21: 202A.
58. Sakamoto, A., Ohnishi, S.T., Ohnishi, T., Ogawa, R. Relationship between free radical production and lipid peroxidation during ischemia-reperfusion injury in the rat brain. Brain Res 1991, 554: 186-92.
59. Oliver, C.N., Starke-Reed, P.E., Stadtman, E.R., Liu, G.J., Carney, J.M., Floyd, R.A. Oxidative damage to brain, loss of glutamine synthetase activity and production of free radicals during ischaemia/reperfusion-induced injury to gerbil brain. Proc Natl Acad Sci USA 1990, 87: 5144-7.
60. Cowley, D.J., Lukovic, L., Petty, M.A. MDL74180 reduces cerebral infarction and free radical concentrations in rats subjected to ischaemia and reperfusion. Eur J Pharmacol 1996, 298: 227-33.
61. Yoshida, S., Busto, R., Ginsberg, M. et al. Compression-induced brain oedema: Modification by prior depletion and supplementation of vitamin E. Neurology 1993, 33: 166-72.
62. Schettini, A., Lippman, R., Waish, E.K. Attenuation of decompressive hypoperfusion and cerebral oedema by superoxide dismutase. J Neurosurg 1989, 71: 578-87.
63. Levasseur, J.E., Patterson, J.L., Ghatak, N.R., Kontos, H.E., Choi, S.C. Combined effect of respirator-induced ventilation and superoxide dismutase in experimental brain injury. J Neurosurg 1989, 71: 573-7.
64. McIntosh, T.K., Thomas, M., Smith, D.F., Banbury, M. The novel 21-aminosteroid U74006F attenuates cerebral oedema and improves survival after brain injury in the rat. J Neurotrauma 1992, 9: 33-46.
65. Hall, E.D., Andrus, P.K., Yonkers, P.A. Brain hydroxyl radical generation in acute experimental head injury. J Neurochem 1993, 60: 588-94.
66. Smith, S.I., Andrus, P.K., Zhang, J.R., Hall, E.D. Direct measurement of hydroxyl radicals, lipid peroxidation and blood-brain barrier disruption following unilateral cortical impact head injury in the mice. J Neurotrauma 1994, 11: 393-404.
67. Muizelaar, J.P. Cerebral ischaemia-reperfusion injury after severe head injury and its possible treatment with polyethyleneglycol-superoxide dismutase. Ann Emerg Med 1993, 22: 1014-20.
68. Muizelaar, J.P., Mamarou, A., Young, H.F. et al. Improving the outcome of severe head injury with the oxygen radical scavenger PEG-SOD: A phase I trial. J Neurosurg 1993, 78: 375-82.
69. Hall, E.D., Yonkers, P.A., McCall, J.M., Braughler, J.M. Effects of the 21-aminosteroid U-74006F on experimental head injury in mice. J Neurosurg 1988, 68: 456-61.
70. Petty, M.A., Poulet, P., Haas, A., Namer, J., Wagner, J. Reduction of traumatic brain injury-induced cerebral oedema by a free radical scavenger. Eur J Pharmacol 1996, 307: 149-55.
71. Kukreja, R.C., Konlos, H.A., Hess, M.L., Ellis, E.F. PGH synthetase and lipoxygenase generate Superoxide in the presence of NADH or NADPH. Circ Res 1986, 59: 612-9.
72. Travis, MA, Yonkers, P.A., Hall, E.D. Attenuation of post-haemorrhagic and postischaemic cerebral hypoperfusion by the 21-aminosteroid U74006F, a potent inhibitor of iron-dependent lipid peroxidation. Neurosci Abst 1987, 13: 1494.
73. Hall, E.D., Travis, M.A. Attenuation of progressive brain hypoperfusion following experimental subarachnoid haemorrhage by large intravenous doses of methylprednisolone. Exp Neurol 1988, 99: 594-606.
74. Sano, K., Asano, T., Tanishima, T., Sasaki, T. Lipid peroxidation as a cause of cerebral vasospasm. Neurol Res 1980, 2: 253-72.
75. Hatake, K., Wakabayashi, I., Kakishita, E., Hishida, S. Impairment of endothelium dependent relaxation in human basilar artery after subarachnoid haemorrhage. Stroke 1992, 23: 1111-7.