Fine-tuning the amphiphilicity: A crucial parameter in the design of potent α-phenyl-N-tert-butylnitrone analogues

Journal of Medicinal Chemistry

Volumn 50, Issue 17, 2007, Pages 3976-3979

  Durand, Grégory ^a   Poeggeler, Burkhard ^b   Böker, Jutta ^b   Raynal, Simon ^a   Polidori, Ange ^a   Pappolla, Miguel A ^c   Hardeland, Rüdiger ^b   Pucci, Bernard ^a  

^a UNIVERSITY OF AVIGNON   (France)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

^c MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOXORUBICIN; LACTOBIONAMIDE; N TERT BUTYL ALPHA PHENYLNITRONE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CELL CULTURE; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROPHILICITY; LIPOPHILICITY; MITOCHONDRION;

ANIMALS; ANTIOXIDANTS; CELLS, CULTURED; CYCLIC N-OXIDES; DISACCHARIDES; DRUG DESIGN; ELECTRON TRANSPORT COMPLEX I; NITROGEN OXIDES; RATS; ROTIFERA; STRUCTURE-ACTIVITY RELATIONSHIP; SUBMITOCHONDRIAL PARTICLES; TROMETHAMINE;

EID: 34548131138     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0706968     Document Type: Article

References (37)

1. Delattre, J.; Beaudeux, J.-L.; Bonnefont-Rousselot, D. Radicaux Libres et Stress Oxydant; Lavoisier: Paris, 2005.
2. Ames, B. N.; Shigenaga, M. K.; Hagen, T. M. Oxidants, antioxidants, and the neurodegenerative diseases of aging. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 7915-7922.
3. Novelli, G. P.; Angiolini, P.; Tani, R.; Consales, G.; Bordi, L. Phenyl-t-butyl-nitrone is active against traumatic shock in rats. Free Radical Res. Commun. 1986, 1, 321-327.
4. Hamburger, S. A.; McCay, P. B. Endotoxin-induced mortality in rats is reduced by nitrones. Circ. Shock 1989, 29, 329-334.
5. Jotti, A.; Paracchini, L.; Perletti, G.; Piccinini, F. Cardiotoxicity induced by doxorubicin in vivo: protective activity of the spin trap alpha-phenyl-tert-butyl nitrone. Pharmacol. Res. 1992, 26, 143-150.
6. Cao, X.; Phillis, J. W. α-Phenyl-tert-butyl-nitrone reduces cortical infarct and edema in rats subjected to focal ischemia. Brain Res. 1994, 644, 267-272.
7. Mori, H.; Arai, T.; Ishii, H.; Adachi, T.; Endo, N.; Makino, K.; Mori, K. Neuroprotective effects of pterin-6-aldehyde in gerbil global brain ischemia: comparison with those of α-phenyl-N-tert-butylnitrone. Neurosci. Lett. 1998, 241, 99-102.
8. Sack, C. A.; Socci, D. J.; Crandall, B. M.; Arendash, G. W. Antioxidant treatment with phenyl-a-tert-butyl nitrone (PBN) improves the cognitive performance and survival of aging rats. Neurosci. Lett. 1996, 205, 181-184.
9. Cheng, H. Y.; Liu, T.; Feuerstein, G.; Barone, F. C. Distribution of spin-trapping compounds in rat blood and brain: in vivo microdialysis determination. Free Radical Biol. Med. 1993, 14, 243-250.
10. Liu, K. J.; Kotake, Y.; Lee, M.; Miyake, M.; Sugden, K.; Yu, Z.; Swartz, H. M. High-performance liquid chromatography study of the pharmacokinetics of various spin traps for application to in vivo spin trapping. Free Radical Biol. Med. 1999, 27, 82-89.
11. Schaeffer, C. F.; Janzen, E. G.; West, M. S.; Poyer, J. L.; Kosane, S. T. Blood chemistry changes in the rat induced by high doses of nitronyl free radical spin traps. Free Radical Biol. Med. 1996, 21, 427-436.
12. Dhainaut, A.; Tizot, A.; Raimbaud, E.; Lockhart, B.; Lestage, P.; Goldstein, S. Synthesis, structure, and neuroprotective properties of novel imidazolyl nitrones. J. Med. Chem. 2000, 43, 2165-2175.
13. (a) Bernotas, R. C.; Thomas, C. E.; Carr, A. A.; Nieduzak, T. R.; Adams, G.; Ohlweiler, D. F.; Hay, D. A. Synthesis and radical scavenging activity of 3,3-dialkyl-3,4-dihydro-isoquinoline 2-oxides. - Bioorg. Med Chem. Lett. 1996, 6, 1105-1110.
14. (b) Thomas, C. E.; Ohlweiler, D. F.; Carr, A. A.; Nieduzak, T. R.; Hay, D. A.; Adams, G.; Vaz, R.; Bernotas, R. C. Characterization of the radical trapping activity of a novel series of cyclic nitrone spin traps. J. Biol. Chem. 1996, 271, 3097-3104.
15. (c) Thomas, C. E.; Ohlweiler, D. F.; Taylor, V. L.; Schmidt, C. J. Radical trapping and inhibition of iron-dependent CNS damage by cyclic nitrone spin traps. J. Neurochem. 1997, 68, 1173-1182.
16. (a) Becker, D. A. Highly sensitive colorimetric detection and facile isolation of diamagnetic free radical adducts of novel chromotropic nitrone spin trapping agents readily derived from guaiazulene. J. Am. Chem. Soc. 1996, 118, 905-906.
17. (b) Becker, D. A.; Ley, J. J.; Echegoyen, L.; Alvarado, R. Stilbazulenyl nitrone (STAZN): a nitronyl-substituted hydrocarbon with the potency of classical phenolic chain-breaking antioxidants. J. Am. Chem. Soc. 2002, 124, 4678-4684.
18. (c) Yang, L.; Calingasan, N. Y.; Chen, J.; Ley, J. J.; Becker, D. A.; Beal, M. F. A novel azulenyl nitrone antioxidant protects against MPTP and 3-nitropropionic acid neurotoxicities. Exp. Neurol. 2005, 191, 86-93.
19. (a) Marklund, N.; Lewander, F.; Clausen, F.; Hillered, L. Effects of the nitrone radical scavengers PBN and S-PBN on in vivo trapping of reactive oxygen species after traumatic brain injury in rats. J. Cereb. Blood Flow Metab. 2001, 21, 1259-1267.
20. (b) Green, R. A.; Ashwood, T.; Odergren, T.; Jackson, D. M. Nitrones as neuroprotective agents in cerebral ischemia with particular reference to NXY-059. Pharmacol. Ther. 2003, 100, 195-214.
21. (c) Wang, C. X.; Shuaib, A. NXY-059: a neuroprotective agent in acute stroke. Int. J. Clin. Pract. 2004, 58, 964-969.
22. Lenaz, G.; Fato, R.; Genova, M. L.; Bergamini, C.; Bianchi, C.; Biondi, A. Mitochondrial complex I: structural and functional aspects. Biochim. Biophys. Acta 2006, 1757, 1406-1420.
23. (a) Coulter, C. V.; Kelso, G. F.; Lin, T.-S.; Smith, R. A. J.; Murphy, M. P. Mitochondrially targeted antioxidants and thiol reagents. Free Radical Biol. Med. 2000, 28, 1547-1554.
24. (b) Kelso, G. F.; Porteous, C. M. Coulter, C. V.; Hughes, G.; Porteous, W. K.; Ledgerwood, E. C.; Smith, R. A. J.; Murphy, M. P. Selective targeting of a redoxactive ubiquinone to mitochondria within cells. J. Biol. Chem. 2001, 276, 4588-4596.
25. (c) Murphy, M. P.; Echtay, K. S.; Blaikie, F. H.; Asin-Cayuela, J.; Cocheme, H. M.; Green, K.; Buckingam, J. A.; Taylor, E. R.; Hurrell, F.; Hughes, G.; Miwa, S.; Cooper, C. E.; Svitunenko, D. A.; Smith, R. A. J.; Brand, M. D. Superoxide activates uncoupling proteins by generating carbon-centered radicals and initiating lipid peroxidation. J. Biol. Chem. 2003, 278, 48534-48545.
26. (d) Smith, R. A. J.; Porteous, C. M.; Gane, A. M.; Murphy, M. P. Delivery of bioactive molecules to mitochondria in vivo. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 5407-5412.
27. Ouari, O.; Polidori, A.; Pucci, B.; Tordo, P.; Chalier, F. Synthesis of a glycolipidic amphiphilic nitrone as a new spin trap. J. Org. Chem. 1999, 64, 3554-3556.
28. (a) Durand, G.; Polidori, A.; Salles, J.-P.; Pucci, B. Synthesis of a new family of glycolipidic nitrones as potential drugs for neurodegenerative disorders. Bioorg. Med. Chem. Lett. 2003, 13, 859-862.
29. (b) Durand, G.; Polidori, A.; Salles, J. P.; Prost, M.; Durand, P.; Pucci, B. Synthesis and antioxidant efficiency of a new amphiphilic spin-trap derived from PBN and lipoic acid. Bioorg. Med. Chem. Lett. 2003, 13, 2673-2676.
30. (c) Durand, G.; Polidori, A.; Ouari, O.; Tordo, P.; Geromel, V.; Rustin, P.; Pucci, B. Synthesis and preliminary biological evaluations of ionic and nonionic amphiphilic α-phenyl-N-tert-butylnitrone derivatives. J. Med. Chem. 2003, 46, 5230-5237.
31. Ortial, S.; Durand, G.; Poeggeler, B.; Polidori, A.; Pappolla, M. A.; Boker, J.; Hardeland, R.; Pucci, B. Fluorinated amphiphilic amino acid derivatives as antioxidant carriers: a new class of protective agents. J. Med. Chem. 2006, 49, 2812-2820.
32. Poeggeler, B.; Durand, G.; Polidori, A.; Pappolla, M. A.; Vega-Naredo, I.; Conto-Montes, A.; Böker, J.; Hardeland, R.; Pucci, B. Mitochondrial medicine: neuroprotection and life extension by the new amphiphilic nitrone LPBNAH acting as a highly potent antioxidant agent. J. Neurochem. 2005, 95, 962-973.
33. Ouari, O.; Chalier, F.; Bonaly, R.; Pucci, B.; Tordo, P. Synthesis and spin-trapping behaviour of glycosylated nitrones. J. Chem. Soc., Perkin Trans. 2 1998, 2299-2307.
34. Tanguy, S.; Durand, G.; Reboul, C.; Polidori, A.; Pucci, B.; Dauzat, M.; Obert, P. Protection against reactive oxygen species injuries in rat isolated perfused hearts: effect of LPBNAH, a new amphiphilic spin-trap derived from PBN. Cardiovasc. Drugs Ther. 2006, 20, 147-149.
35. Polidori, A.; Pucci, B.; Zarif, L.; Lacombe, J.-M.; Riess, J.-G.; Pavia, A. A. Vesicles and other supramolecular systems made from double-tailed synthetic glycolipids derived from galactosylated tris(hydroxymethyl) aminomethane. Chem. Phys. Lipids 1995, 77, 225-251.
36. Moreno-Sanchez, R.; Hogue, B. A.; Bravo, C.; Newman, A. H.; Basile, A. S.; Chiang, P. K. Inhibition of substrate oxidation in mitochondria by the peripheral-type benzodiazepine receptor ligand AHN 086. Biochem. Pharmacol. 1991, 41, 1479-1484.
37. Kotamraju, S.; Konorev, E. A.; Joseph, J.; Kalyanaraman, B. Doxorubicin-induced apoptosis in endothelial cells and cardiomyocytes is ameliorated by nitrone spin traps and ebselen. J. Biol. Chem. 2000, 275, 33585-33592.