Novel synthesized aminosteroidal heterocycles intervention for inhibiting iron-induced oxidative stress

European Journal of Medicinal Chemistry

Volumn 40, Issue 12, 2005, Pages 1283-1294

  Elmegeed, Gamal A ^a   Ahmed, Hanaa H ^a   Hussein, Jihan S ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

Aminosteroids; Erythrocyte; Heterocycles; Iron induced; Oxidative stress

Indexed keywords

17BETA ACETOXY 5' AMINOTHIENO[2',3':2,3] 5ALPHA ANDROSTAN 4' CARBONITRILE; 17BETA ACETOXY 6'' AMINOPYRIMIDINO[5'',4'':4',5']THIENO[2',3':2,3] 5ALPHA ANDROSTANE; 3BETA ACETOXY 17 (4' AMINO 2' IMINO 6' PHENYLPYRIMIDIN 5' YLIDENO) 5ALPHA ANDROSTANE; 3BETA ACETOXY 17 (5' AMINO 1',3' DIPHENYLPYRAZOL 4' YLIDENO) 5ALPHA ANDROSTANE; ADENOSINE TRIPHOSPHATASE; CHOLESTEROL; FERRITIN; HETEROCYCLIC STEROID; IRON; LEPTIN; NITRIC OXIDE; PHOSPHOLIPID; TRIACYLGLYCEROL; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; CHOLESTEROL BLOOD LEVEL; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFICACY; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME ACTIVITY; ERYTHROCYTE GHOST; ERYTHROCYTE MEMBRANE; FERRITIN BLOOD LEVEL; IRON BLOOD LEVEL; IRON OVERLOAD; LIPID BLOOD LEVEL; LIPID METABOLISM; LIPID PEROXIDATION; MALE; NONHUMAN; OXIDATIVE STRESS; PROTEIN BLOOD LEVEL; PROTEIN DETERMINATION; PROTEIN FUNCTION; RAT;

ADENOSINE TRIPHOSPHATASES; ADMINISTRATION, ORAL; ANIMALS; DISEASE MODELS, ANIMAL; DOSE-RESPONSE RELATIONSHIP, DRUG; ERYTHROCYTE MEMBRANE; IRON; IRON OVERLOAD; IRON, DIETARY; MALE; MEMBRANE LIPIDS; MOLECULAR CONFORMATION; OXIDATIVE STRESS; RATS; RATS, SPRAGUE-DAWLEY; STEROIDS, HETEROCYCLIC; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 27744507164     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2005.07.012     Document Type: Article

References (88)

1. R.S. Britton, K.L. Leicster, and B.R. Bacon Int. J. Hematol. 76 2002 219 228
2. M.L. Harris, H.J. Shiller, P.M. Reilly, M. Donowitz, M.B. Grisham, and G.B. Bulkley Pharmaceutic. Ther. 53 1992 375 408
3. S.J. Klebanoff J.I. Gally I.M. Goldstein R. Snyderman Oxygen metabolities from phagocytes 1992 Raven Pres New York, NY 541 588
4. M.B. Grisham, and D.N. Granger Dig. Dis. Sci. 33 1998 6S 15S
5. J. Lehotsky, P. Kaplan, M. Matejovicova, R. Murin, P. Racay, and L. Raeymaekers Gen. Physiol. Biophys. 21 2002 31 37
6. P.A. Baeuerle, and T. Henkle Annu. Rev. Immunol. 12 1994 141 179
7. E.D. Hall, J.M. McCall, and E.D. Means Adv. Pharmacol. 28 1994 221 268
8. B.M. Taylor, W.E. Fleming, C.W. Benjamin, Y. Wu, W.R. Mathews, and F.F. Sun J. Pharmacol. Exp. Ther. 276 1996 1224 1231
9. Y. Wang, W.R. Mathews, D.M. Guido, and H. Jaeschke J. Pharmacol. Exp. Ther. 277 1996 714 720
10. R. Fiscella, D.A. Gagliano, N.S. Peachey, R. Feist, R. Dunn, and T.T. Lam Ophthalmic Surg. 22 1991 740 744
11. J.M. McCall, J.M. Braughler, and E.D. Hall Acta Anaesthesiol. Belg. 38 1987 417 420
12. N. Noguchi, M. Takahashi, J. Tsuchiya, H. Yamashita, E. Komuro, and E. Niki Biochem. Pharmacol. 55 1998 785 791
13. The Chemistry of Estrogens and Antiestrogens Relationships between Structure, Receptor Binding and Biological Activity J.A. McLachlan Estrogens in the Environment 1980 Elsevier New York 46 49
14. D.P. Jindal, P. Piplani, H. Fajrak, C. Prior, and I.G. Marshall Eur. J. Med. Chem. 36 2001 195 202
15. R.M. Hoyte, J. Zhong, R. Lerum, A. Oluyemi, P. Persaud, C. O'Connor, D.C. Labaree, and R.B. Hochberg J. Med. Chem. 45 24 2002 5397 5405
16. D.J. Harvey, W.A. Laurie, and R.I. Reed Org. Mass Spectrom. 5 1971 1183
17. Roussel-UCLAF Agents for the Treatment of Hypercholesterolemia. Fr. M. 4 741, 1967, Feb. 13 Chem. Abstr. 69 1968 96965s
18. G.P. Baraldi, and P.C.T. Int Appl. Wo, 21, 617 (1999) Chem. Abstr. 130 1999 296427h
19. R.S. Brittion, G.A. Ramm, J. Olynyk, R. Singh, R. O'Neill, and B.R. Bacon Adv. Exp. Med. Biol. 356 1994 239 253
20. B. Halliwell, and J.M.C. Gutteridge Arch. Biochem. Biophys. 246 1986 501 514
21. R. Pakala, R. Pakala, and C.R. Benedict J. Cardiovasc. Pharmacol. 25 1995 871 879
22. J.A. Araujo, E.L. Romano, B.E. Brito, V. Parth́, M. Romano, M. Bracho, and R.F. Montaüo Cardier J. Arterioscl Throm. Vasc. Biol. 15 1995 1172 1180
23. M.L. Silvana, T. Ribeiro, M.E. Sliva, D.A. Chianca, H.D. Paula, L.M. Cardoso, E. Colombari, and L. Pedrosa J. Nutr. 133 2003 15 20
24. A. Pietrangelo, E. Rocchi, L. Schiaffonati, E. Ventura, and G. Cairo Hepato. 11 1990 798 804
25. L.G. Jr Valerio, and D.R. Petersen Exp. Mol. Pathol. 68 2000 1 12
26. A.M. Gressner, B. Lahme, and A. Brenzel Hepatol. 22 1995 1507 1518
27. G.A. Ramm, D.H. Crawford, L.W. Powell, N.I. Walker, L.M. Fletcher, and J.W. Halliday J. Hepatol. 26 1997 284 292
28. K.R. Bridle, D.H.G. Crawford, L.M. Fletcher, J.L. Smith, L.W. Powell, and G.A. Ramm J. Hepatol. 38 2003 426 433
29. E.S. Fox, J.C. Kim, and T.F. Tracy J. Surg. Res. 72 1997 129 134
30. A. Dunger, J.M. Cunningham, C.A. Delaney, J.E. Lowe, M.H.L. Green, A.J. Bone, and I.C. Green Diabetes 45 1996 183 189
31. C.F. Nathan FASEB J. 6 1992 3051 3064
32. M. Galleano, M. Simontacchi, and S. Puntarulo Mol. Aspects Med. 25 2004 141 154
33. S.M. Sadrzadeh, and A.A. Naji J. Pharmacol. Exp. Ther. 284 1998 406 412
34. C. Lehmann, K. Egerer, A. Georgiew, M. Weber, T. Grune, and W.J. Kox Crit. Care Med. 27 1999 1164 1167
35. J.M. Palma-Vargas, A.H. Toledo, F.J. Garcia-Criado, K. Misawa, F. Lopez-Neblina, and L.H. Toledo-Pereyra J. Surg. Res. 66 1996 131 137
36. A.J. Dabbagh, T. Mannion, S.M. Lynch, and B. Frei Biochem. J. 300 1994 799 803
37. S. Brunet, L. Thibault, E. Delvin, W. Yotov, M. Bendayan, and E. Levy Hepatol. 29 1999 1809 1817
38. M. Fisher, P.H. Levine, E.M. Doyle, M.M. Arpano, and J.J. Hoogasian Atherosclerosis 90 1991 197 202
39. A. Khalil, A. Fortun, S. H́bert, J. Jay-Gerin, A. El Abbouyi, J. Wallach Jr., and T. Fülöp Life Sci. 63 1998 769 779
40. M. Markova, M. Haluzik, J. Jiskra, D. Haluzikova, J. Svobodova, and M. Rosicka Cas. Lek. Cesk. 140 2001 767 769
41. D.D. Mcabee, Y.Y. Ling, and C. Stich Biochem. J. 331 1998 719 726
42. R. Buettner, L.C. Bollheimer, B. Zietz, W. Drobnik, K. Lackner, G. Schmitz, and K.D. Paltitzsch J.Endocrino. 175 2002 745 756
43. J.G. Fischer, H.P. Glauert, T. Yin, M.L. Sweeney-Reeves, N. Larmonier, and M.C. Black J. Nut. 132 2002 2525 2531
44. M. Ferrali, C. Signorini, L. Ciccoli, and M. Comporti Biochem. J. 285 1992 295 301
45. A.C. Fernandes, P.M. Filipe, and C.F. Manso Eur. J. Pharmacol. 220 1992 211 216
46. A.K. Salahudeen, C. Wang, and V.K. Kanji Free Rad. Biol. Med. (Paris) 21 1996 691 697
47. J. Malmstrom, M. Jonsson, I.A. Cotgreave, L. Hammarstrom, M. Sjodin, and L. Engman J. Am. Chem. Soc. 123 2001 3434 3440
48. A. Kuno, Y. Sugiyama, K. Katsuta, H. Sakai, and H. Takasugi Chem. Pharm. Bull. (Tokyo) 40 1992 2423 2431
49. A. Kuno, K. Katsuta, H. Sakai, M. Ohkubo, Y. Sugiyama, and H. Takasugi Chem. Pharm. Bull. (Tokyo) 41 1993 139 147
50. L.G. Sultatos J. Pharmacol. Exp. Ther. 246 1988 946 949
51. B. Saniova Bratisl. Lek. Listy 98 1997 339 342
52. W.M. Clark, J.S. Hazel, and B.M. Coull Drugs 50 1995 971 983
53. I.M. London, and H. Schwarz J. Clin. Invest. 32 1953 1248 1252
54. A. Pietrangelo, R. Grandi, A. Tripodi, A. Tomasi, D. Ceccarelli, E. Ventura, and A. Masini Biochem. Pharmacol. 39 1990 123 128
55. C.M. Smuts, H.Y. Tichelaar, P.J. Van Jaarsveld, C.J. Badenhorst, M. Kruger, R. Laubsc, E.P. Mansvelt, and A.J. Benade Prostaglandins Leukot. Essent. Fatty Acids 52 1995 59 67
56. J.S. Hinzmann, R.L. Mckenna, T.S. Pierson, F. Han, F.J. Kezdy, and D.E. Epps Chem. Phys. Lipids 62 1992 123 138
57. T.T. Rohn, T.R. Hinds, and F.F. Vincenzi Biochem. Pharmacol. 46 1993 525 534
58. M.A. Sochaski, W.J. Bartfay, S.R. Thorpe, J.W. Baynes, E. Bartfay, D.C. Lehotay, and P.P. Liu Metabolism 51 2002 645 651
59. K.A. Schwartz, J. Fisher, and E.T. Adams Toxicol. Pathol. 21 1993 311 320
60. H. Monyer, D.M. Hartley, and D.W. Choi Neuron 5 1990 121 126
61. J.K. Raison J. Bioenerg. 4 1973 285 309
62. L. Leclerc, C. Vasseur, E. Bursaux, M. Marden, and C. Poyart Biochim. Biophys. Acta 946 1988 49 56
63. L. Leclerc, F. Girard, F. Galacteros, and C. Poyart Biochim. Biophys. Acta 897 1987 33 40
64. L. Leclerc, M. Marden, and C. Poyart Biochim. Biophys. Acta 1062 1991 35 38
65. A. Zaidi, M.C. Marden, C. Poyart, and L. Leclerc Eur. J. Pharmacol. 290 1995 133 139
66. L.J. Bellamy The infrared spectra of complex molecules N.S. Bhacca D.H. William Application of NMR Spectroscopy in Organic chemistry 1964 Holden Day San Fransisco (John Wiley, New York, 1958)
67. IUPAC Joint Commission on Biochemical Nomenclature (JCBN) Pure Appl. Chem. 61 (1989); 1783-822 Eur. J. Biochem. 186 1989 429 458
68. A.O.A.C. Official Methods of Analysis, 16th ed 1995 Association of Official Analysis Washington, DC
69. D. Kondziolka, S. Somaza, A.J. Martinez, J. Jacobsohn, A. Maitz, L.D. Lunsford, and J.C. Flickinger Neurosurgery 41 1997 203 208
70. J. Carrier, E. Aghdassi, J. Cullen, and J.P. Allard J. Nutr. 132 2002 3146 3150
71. S. Schermer The Blood Morphology of Laboratory Animals, third ed 1967 F.A. Philadelphia Davi Co p. 42
72. B. Roelofsen, and J. DeGeir Van Deenenl, J. Cell. Physiol. 63 1964 233 243
73. E.G. Bligh, and W.J. Dyer Can J. Biochem. Physiol. 37 1959 911 915
74. J.T. Dodge, C. Mitchell, and D.J. Hanahan Arch. Biochem. Biophys. 100 1963 119 130
75. N. Weissman, and V.J. Pileggi R.J. Henry Clinical Chemistry Principals and Techniques, second ed 1974 Hagestwon, Harper and Row 692 693
76. E. Engvall H. Vanvunakis J.J. Langone Methods in Enzymology 70 1980 Academic Press New York p. 419
77. A. Corti, J. Fassino, F. Marcucci, E. Barbenti, and G. Cassani Biochem. J. 284 1992 905 910
78. H. Moshage, B. Rok, J.R. Huizenga, and P.L.M. Jansen Clin. Chem. 41 1995 892 896
79. W. Richmond Clin. Chem. 19 1973 1350 1356
80. M. Takayama, S. Itoh, T. Nagasaki, and I. Tanimizu Clin. Chim. Acta 79 1977 93 98
81. N. Zollner, and M. Tacconi Z. Gesamte Exp. Med. 145 1968 326 334
82. G. Bucolo, and H. David Clin. Chem. 19 1973 476 482
83. J.M. Friedman, and J.L. Halaas Nature 395 1998 763 770
84. S.P. Sharma, and R. Wadhwa Mech. Ageing Dev. 23 1983 67 71
85. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and P.T. Randall J. Biol. Chem. 193 1951 265 275
86. C.A. Alper N. Engl. J. Med. 291 1974 287 290
87. R.L. Post, C.R. Merritt, C.R. Kinsolving, and C.D. Albright J. Biol. Chem. 235 1960 1796 1802
88. G.W. Senedecor, and W.G. Cochran Statistical Methods, seventh ed 1980 Iowa State University Press Ames, Iowa 334 364