New hydroxypyridinone iron-chelators as potential anti-neurodegenerative drugs

Frontiers in Bioscience

Volumn 13, Issue 17, 2008, Pages 6763-6774

  Arduino, Daniela ^a   Silva, Daniel ^b   Cardoso, Sandra M ^a,c   Chaves, Silvia ^b   Oliveira, Catarina R ^a,c   Santos, M Amelia ^b  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b INSTITUTO SUPERIOR TÉCNICO   (Portugal)

^c UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

Apoptosis; Chelation; Hydroxypyridinone; Iron Chelator; Key Words: Alzheimer's disease; Neurodegeneration; Parkinson's Disease; Therapy

Indexed keywords

HYDROXYPYRIDINES; IRON CHELATING AGENT; PIPERAZINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE;

DEGENERATIVE DISEASE; HUMAN; PARKINSON DISEASE; REVIEW; TERATOCARCINOMA; TUMOR CELL LINE;

CELL LINE, TUMOR; HUMANS; IRON CHELATING AGENTS; NEURODEGENERATIVE DISEASES; PARKINSON DISEASE; PIPERAZINES; PYRIDINES; PYRIDONES; TERATOCARCINOMA;

EID: 52049107811     PISSN: 27686701     EISSN: 27686698     Source Type: Journal    
DOI: None     Document Type: Article

References (52)

1. Selkoe, D.J.: Clearing the brain's amyloid cobwebs. Neuron 32, 177-80 (2001) (Pubitemid 33030186)
2. Roman, M.J., D.C. Delis, J.V. Filoteo, T.L. Demadura, J. Paulsen, N.R. Swerdlow, M.R. Swenson, D. Salmon, N. Butters & C. Shults: Is there a "subcortical" profile of attentional dysfunction? A comparison of patients with Huntington's and Parkinson's diseases on a global-local focused attention task. J Clin Exp Neuropsychol 20, 873-84 (1998) (Pubitemid 29284462)
3. Forno, L.S.: Neuropathology of Parkinson's disease. J Neuropathol Exp Neurol 55, 259-72 (1996) (Pubitemid 26085575)
4. Cardoso, S.M., P.I. Moreira, P. Agostinho, C. Pereira & C.R. Oliveira: Neurodegenerative pathways in Parkinson's disease: therapeutic strategies. Curr Drug Targets CNS Neurol Disord 4, 405-19 (2005) (Pubitemid 41086758)
5. Pereira, C., P. Agostinho, P.I. Moreira, S.M. Cardoso & C.R.Oliveira: Alzheimer's disease-associated neurotoxic mechanisms and neuroprotective strategies. Curr Drug Targets CNS Neurol Disord 4, 383-403 (2005) (Pubitemid 41086757)
6. Butterfield, D.A., J. Drake, C. Pocernich & A. Castegna: Evidence of oxidative damage in Alzheimer's disease brain: central role for amyloid beta-peptide. Trends Mol Med. 7, 548-54 (2001) (Pubitemid 33127140)
7. Pratico, D., C.M. Clark, V.M. Lee, J.Q. Trojanowski, J. Rokach & G.A. FitzGerald: Increased 8,12-isoiPF2alpha-VI in Alzheimer's disease: correlation of a noninvasive index of lipid peroxidation with disease severity. Ann Neurol 48, 809-12 (2000)
8. Crichton, R.R. & R.J. Ward: Metal-based Neurodegeneration. John Wiley & Sons Lda, Chichester, pp 62-87 (2006).
9. Smith, M.A., P.L. Harris, L.M. Sayre & G. Perry: Iron accumulation in Alzheimer disease is a source of redox-generated free radicals. Proc Natl Acad Sci USA 94, 9866-9868 (1997) (Pubitemid 27408156)
10. Dexter, D.T., C.J. Carter, F.R. Wells, F. Javoy-Agid, Y. Agid, A. Lees, P. Jenner & C.D. Marsden: Basal lipid peroxidation in substantia nigra is increased in Parkinson's disease. J Neurochem 52, 381-9 (1989) (Pubitemid 19037600)
11. Floor, E., M.G. Wetzel: Increased protein oxidation in human substantia nigra pars compacta in comparison with basal ganglia and prefrontal cortex measured with an improved dinitrophenylhydrazine assay. J Neurochem 70, 268-75 (1998) (Pubitemid 28020852)
12. Saggu, H., J. Cooksey, D. Dexter, F.R. Wells, A. Lees, P. Jenner & C.D. Marsden: A selective increase in particulate superoxide dismutase activity in parkinsonian substantia nigra. J Neurochem 53, 692-7 (1989) (Pubitemid 19207359)
13. Ben-Shachar, D., P. Riederer & M.B. Youdim: Ironmelanin interaction and lipid peroxidation: implications for Parkinson's disease. J Neurochem 57, 1609-14 (1991) (Pubitemid 21922796)
14. Graham, D.G.: Oxidative pathways for catecholamines in the genesis of neuromelanin and cytotoxic quinones. Mol Pharmacol 14, 633-43 (1978) (Pubitemid 8402469)
15. Maker, H.S., C. Weiss, D.J. Silides & G. Cohen: Coupling of dopamine oxidation (monoamine oxidase activity) to glutathione oxidation via the generation of hydrogen peroxide in rat brain homogenates. J Neurochem 36, 589-93 (1981) (Pubitemid 11190630)
16. Schindowski, K., T. Kratzsch, J. Peters, B. Steiner, S. Leutner, N. Touchet, K. Maurer, C. Czech, L. Pradier, L. Frölich, W.E. Müller & A. Eckert: Impact of aging: sporadic and genetic risk factors on vulnerability to apoptosis in Alzheimer's disease. Neuromolecular Med 4, 161-78 (2003)
17. Tatton, N.A., A. Maclean-Fraser, W.G. Tatton, D.P. Perl & C.W. Olanow: A fluorescent double-labelling method to detect and confirm apoptotic nuclei in Parkinson's disease. Ann Neurol 44, S142-8 (1998) (Pubitemid 28423841)
18. Hartmann, A., S. Hunot, P.P. Michel, M.P. Muriel, S. Vyas, B.A. Faucheux, A. Mouatt-Prigent, H. Turmel, A. Srinivasan, M. Ruberg, G.I. Evan, Y. Agid & E.C. Hirsch: Caspase-3: A vulnerability factor and final effector in apoptotic death of dopaminergic neurons in Parkinson's disease. Proc Natl Acad Sci USA 14; 97, 2875-80 (2000) (Pubitemid 30159265)
19. Tatton, N.A.: Increased caspase 3 and Bax immunoreactivity accompany nuclear GAPDH translocation and neuronal apoptosis in Parkinson's disease. Exp Neuro 166, 29-43 (2000)
20. Paschen, W.: Endoplasmic reticulum: a primary target in various acute disorders and degenerative diseases of the brain. Cell Calcium 34, 365-83 (2003) (Pubitemid 37021230)
21. Ryu, E.J., H.P. Harding, J.M. Angelastro, O.V. Vitolo, D. Ron & L.A. Greene: Endoplasmic reticulum stress and the unfolded protein response in cellular models of Parkinson's disease. J Neurosc 22, 10690-8 (2002) (Pubitemid 36005143)
22. Yamamuro, A., Y. Yoshioka, K. Ogita & S. Maeda: Involvement of endoplasmic reticulum stress on the cell death induced by 6-hydroxydopamine in human neuroblastoma SH-SY5Y cells. Neurochem Res 31, 657-64 (2006) (Pubitemid 43886413)
23. Hoozemans, J.J., E.S. van Haastert, P. Eikelenboom, R.A. de Vos, J. M. Rozemuller & W. Scheper: Activation of the unfolded protein response in Parkinson's disease. Biochem Biophys Res Commun 354, 707-11 (2007) (Pubitemid 46186242)
24. Hider, R.C., G.J. Kontoghiorghes & J. Silver: Pharmaceutical compositions. UK PATENT gb2118176, 1983
25. Kontoghiorghes, G.J., M.A. Aldouri, L. Sheppard & A.V. Hoffbrand: 1,2-dimethyl-3-hydroxypyrid-4-one, an orally active chelator for treatment of iron overload. Lancet 1 (8545), 1294-1295 (1987) (Pubitemid 17072195)
26. Hubálek, F., C. Binda, M. Li, J. Sterling, D.E. Edmondson & A. Mattevi: Inactivation of purified human recombinant monoamine oxidases A and B by rasagiline and its analogues. J Med Chem 47, 1767-1774 (2004)
27. Youdim, M.B.H. & Y.S. Bakhle: Monoamine oxidase: isoforms and inhibitors in Parkinson's disease and depressive illness. British J Pharmacol 147, 287-296 (2006)
28. Armarego, W.L.F. & D.D. Perring (eds) Purification of Laboratory Chemicals 4rd ed., Butterworth-Heinemann Press, Oxford (1999).
29. Santos, M.A., R. Grazina, A.Q. Neto, G. Cantinho, L. Gano & L. Patricio: Synthesis, chelating properties towards gallium and biological evaluation of two N-substituted 3- Hydroxy-4-Pyridinones. J Inorg Biochem 78, 303-311 (2000)
30. Leo, A., C. Hansch & D. Elkins: Partition coefficients and their uses. Chem Rev 71, 526-616 (1971).
31. Cardoso, S.M. & C.R. Oliveira: The role of calcineurin in amyloid-beta-peptides-mediated cell death. Brain Res 1050, 1-7 (2005) (Pubitemid 40922711)
32. Mosmann, T.: Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65, 55-63 (1983) (Pubitemid 14203433)
33. Cregan, S.P., J.G. MacLaurin, C.G. Craig, G.S. Robertso, D.W. Nicholson, D.S. Park & R.S. Slack: Baxdependent caspase-3 activation is a key determinant in p53-induced apoptosis in neurons. J Neurosc 19, 7860-9 (1999) (Pubitemid 30225784)
34. (a) Santos, M.A.: Hydroxypyridinone complexes with aluminium. In vitro studies and in vivo perspectives. Coord Chem Rev 228, 187-203 (2002)
35. (b) Santos, M.A.: Recent developments on 3-hydroxy-4-pyridinones in view of clinical applications. Mono and combined ligand approaches. Coord Chem Rev (2008)
36. Hider, R.C. & Z.D. Liu: Emerging understanding of the advantage of small molecules such as hydroxypyridinones in the treatment of iron overload. Curr Med Chem 10, 1051-1064 (2003) (Pubitemid 36582248)
37. Florence, A.L., A. Gauthier, R.J. Ward & R.R. Crichton. Influence of hydroxypyridones and desferrioxamine on the mobilization of aluminium from tissues of aluminium-loaded rats. Neurodegeneration 4, 449-455 (1995) (Pubitemid 26016591)
38. Santos, M.A., M. Gil, L. Gano, S. Chaves: Bifunctional 3-hydroxy-4-pyridinone derivatives as potential pharmaceuticals. Synthesis, complexation with Fe (III), Al (III) and Ga (III), and in vivo evaluation with 67Ga. J Bio Inorg Chem 10, 564-580 (2005)
39. Chang, H.Y. & X. Yang: Proteases for cell suicide: functions and regulation of caspases. Microbiol Mol Biol Rev 64, 821-846 (2000) (Pubitemid 32475932)
40. Troy, C.M. & M.L. Shelanski: Caspase-2 redux. Cell Death Differ 10, 101-7 (2003) (Pubitemid 36511835)
41. Nakagawa, T., H. Zhu, N. Morishima, E. Li, J. Xu, B.A. Yankner & J. Yuan: Caspase-12 mediates endoplasmic-reticulum-specific apoptosis and cytotoxicity by amyloid-beta. Nature 403, 98-103 (2000) (Pubitemid 30038529)
42. Hitomi, J., T. Katayama, Y. Eguchi, T. Kudo, M. Taniguchi, Y. Koyama, T. Manabe, S. Yamagishi, Y. Bando, K. Imaizumi, Y. Tsujimoto & M. Tohyama: Involvement of caspase-4 in endoplasmic reticulum stressinduced apoptosis and Abeta-induced cell death. J Cell Biol 165, 347-56 (2004) (Pubitemid 38649910)
43. Cardoso, S.M., R.H. Swerdlow & C.R. Oliveira: Induction of cytochrome c-mediated apoptosis by amyloid beta 25-35 requires functional mitochondria. Brain Res 931, 117-25 (2002) (Pubitemid 34230515)
44. Youdim, M.B., M. Fridkin & H. Zheng: Novel bifunctional drugs targeting monoamine oxidase inhibition and iron chelation as an approach to neuroprotection in Parkinson's disease and other neurodegenerative diseases. J Neural Transm 111, 1455-1471 (2004) (Pubitemid 39468399)
45. Sterling, J., Y. Herzig, T. Goren, N. Finkelstein, D. Lerner, W. Goldenberg, I. Miskolczi, S. Molnar, F. Rantal, T. Tamas, G. Toth, A. Zagyva, A. Zekany, J. Finberg, G. Lavian, A. Gross, R. Friedman, M. Razin, W. Huang, B. Krais, M. Chorev, M. B. Youdim & M. Weinstock,: Novel dual inhibitors of AChE and MAO derived from hydroxyl aminoindan and phenethylamine as potential treatment for Alzheimer's disease. J Med Chem 45, 5260-5279 (2002) (Pubitemid 35429165)
46. Zheng, H., L.M. Weiner, O. Bar-Am, S. Epsztejn, Z.I. Cabantchik, A. Warshawsky, M.B. Youdim & M. Fridkin: Design, synthesis, and evaluation of novel bifunctional iron-chelators as potential agents for neuroprotection in Alzheimer's, Parkinson's, and other neurodegenerative diseases. Bioorg Med Chem 13, 773-783 (2005)
47. Cardoso, S.M., S. Santos, R. H. Swerdlow & C. R. Oliveira: Functional mitochondria are required for amyloid beta-mediated neurotoxicity. FASEB J 15, 1439-1441 (2001)
48. Rogers J.T. & D. K. Lahiri: Metal and inflammatory targets for Alzheimer's disease. Curr Drug Targets 5, 535-551 (2004). (Pubitemid 39004428)
49. Lovell, M.A., J. D. Robertson, W.J. Teesdale, J.L. Campbell & W.R. Markesbery: Copper, iron and zinc in Alzheimer's disease senile plaques. J Neurol Sci 158, 47-52 (1998) (Pubitemid 28277534)
50. Moreira, P., C. Pereira, M.S. Santos & C. Oliveira: Effect of zinc ions on the cytotoxicity induced by the amyloid beta-peptide. Antioxi Redox Signal 2, 317-325 (2000) (Pubitemid 30445942)
51. Hicks, S.W. & C.E. Machamer: Golgi structure in stress sensing and apoptosis. Biochim Biophys Acta 1744, 406-14 (2005) (Pubitemid 40848258)
52. S. Canário, S. Chaves, M.L. Mira & M.A. Santos: Antioxidant properties of O,O- and O,S-Donor Ligands with pyrone and pyridinone molecular scaffolds. In Press