Novel electrochemical approach to enhanced toxicity of 4-oxo-2-nonenal vs. 4-hydroxy-2-nonenal (role of imine): Oxidative stress and therapeutic modalities

Medical Hypotheses

Volumn 67, Issue 1, 2006, Pages 151-156

  Kovacic, Peter ^a  

^a SAN DIEGO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICARBONYL DERIVATIVE; 4 HYDROXYNONENAL; 4 OXO 2 NONENAL; ACROLEIN; ALDEHYDE DERIVATIVE; ANTIOXIDANT; CARBOXYLIC ACID; CROTONALDEHYDE; CYSTEINE; GLUTATHIONE TRANSFERASE M1; HISTIDINE; HYDROPEROXIDE; IMINE; METHYLGLYOXAL; REACTIVE OXYGEN METABOLITE; SCHIFF BASE; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID;

AGING; ARTICLE; DISEASE ASSOCIATION; ELECTROCHEMISTRY; ELECTRON TRANSPORT; HUMAN; MEDICAL RESEARCH; METABOLITE; MICHAEL ADDITION; NONHUMAN; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PRIORITY JOURNAL;

ACROLEIN; ALDEHYDES; BIOCHEMISTRY; ELECTROCHEMISTRY; ELECTRON TRANSPORT; IMINES; MODELS, BIOLOGICAL; MODELS, CHEMICAL; OXIDATION-REDUCTION; OXIDATIVE STRESS; REACTIVE OXYGEN SPECIES;

EID: 33646097467     PISSN: 03069877     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mehy.2005.10.034     Document Type: Article

References (35)

1. Lin D., Lee H.-G., Liu Q., Perry G., Smith M.A., and Sayre L.M. 4-Oxo 2-nonenal is both more neurotoxic and more protein reactive than 4-hydroxy-2-nonenal. Chem Res Toxicol 18 (2005) 1219-1231 (and references therein)
2. Kovacic P., and Becvar L.E. Mode of action of anti-infective agents: focus on oxidative stress and electron transfer. Curr Pharmaceut Des 6 (2000) 143-167
3. Kovacic P., and Osuna J.A. Mechanisms of anti-cancer agents: emphasis on oxidative stress and electron transfer. Curr Pharmaceut Des 6 (2000) 277-309
4. Kovacic P., and Jacintho J.D. Mechanisms of carcinogenesis: focus on oxidative stress and electron transfer. Curr Med Chem 8 (2001) 773-796
5. Kovacic P., and Jacintho J.D. Reproductive toxins: pervasive theme of oxidative stress and electron transfer. Curr Med Chem 8 (2001) 863-892
6. Kovacic P., Sacman A., and Wu-Weis M. Nephrotoxins: widespread role of oxidative stress and electron transfer. Curr Med Chem 9 (2002) 823-847
7. Poli G., Cheeseman K.H., Dianzani M.U., and Slater T.F. Free radicals in the pathogenesis of liver injury (1989), Pergamon, New York
8. Kovacic P., and Thurn L.A. Cardiovascular toxicity from the perspective of oxidative stress and electron transfer. Curr Vasc Pharmacol 3 (2005) 107-117
9. Kovacic P., and Somanathan R. Neurotoxicity: the broad framework of electron transfer, oxidative stress and protection of antioxidants. Curr Med Chem CNS Agents 5 (2005) 249-258
10. Kovacic P., Pozos R.S., Somanathan R., Shangari N., and O'Brien P.J. Mechanism of mitochondrial uncouplers, inhibitors, and toxins: focus on electron transfer, free radicals, and structure-activity relationships. Curr Med Chem 12 (2005) 2601-2623
11. Kovacic P., and Cooksy A.L. Unifying theme for toxicity and addiction by abused drugs: electron transfer and reactive oxygen species. Med Hypotheses 64 (2005) 357-366
12. Halliwell B., and Gutteridge J.M.C. Free radicals in biology and medicine (1999), Oxford University Press, New York
13. Kovacic P., and Cooksy A.L. Role of diacetyl metabolite in alcohol toxicity and addiction via electron transfer and oxidative stress. Arch Toxicol 79 (2005) 123-128
14. Wondrak G.T., Cervantes-Laurean D., Roberts M.G., Qrasem J.G., Kim M., Jacobson E.L., et al. Identification of α-dicarbonyl scavengers for cellular protection against oxidative stress. Biochem Pharmacol 63 (2002) 361-373
15. Montoya M.R., Zon M.A., and Mellado J.M.R. Investigation of the reduction of 1,2-cyclohexanedione and methylglyoxal on mercury electrodes under pure kinetic conditions by linear sweep voltammetry. J Electroanal Chem 353 (1993) 217-224
16. Mellado J.M.R., and Montoya M.R. CEC mechanisms in the electroreduction of α-dicarbonyl compounds on mercury electrodes. J Electroanal Chem 365 (1994) 71-78
17. Niufar N.N., Haycock F.L., Wesemann J.L., MacStay J.A., Heasley V.L., and Kovacic P. Reduction potentials of conjugated aliphatic ketones, oximes, and imines: correlation with structure and bioactivity. Rev Soc Quim Mex 46 (2002) 307-312
18. Opheim L.-N. Determination of crotonaldehyde in ethanol by differential pulse polarography. Anal Chim Acta 91 (1977) 331-334
19. Wu L. The pro-oxidant role of methylglyoxal in mesenteric artery smooth muscle cells. Can J Physiol Pharmacol 83 (2005) 63-68
20. Du J., Suzuki H., Nagase F., Akhand A.A., Ma X.Y., Yokoyama T., et al. Superoxide-mediated early oxidation and activation of ASKI are important for initiating methylglyoxal-induced apoptosis process. Free Rad Biol Med 31 (2001) 469-478
21. Choudhary D., Chandra D., and Kale R.K. Influence of methylglyoxal on antioxidant enzymes and oxidative damage. Toxicol Lett 93 (1997) 141-152
22. Schlichter L.C., Pahapill P.A., and Chung I. Dual action of 2,3-butanedione monoxime (BDM) on K+ current in human T lymphocytes. J Pharmacol Exp Ther 261 (1992) 438-446
23. Kovacic P. Mechanism of organophosphates (nerve gases and pesticides) and antiodotes: electron transfer and oxidative stress. Curr Med Chem 10 (2003) 2705-2709
24. Verter H. In: Zabicky J. (Ed). Chemistry of the carbonyl group vol. 2 (1970), Interscience 72-156 [Chapter 2]
25. Marinello A.J., Bansal A.K., Paul B., Koser P.L., Love J., Struck R.F., et al. Metabolism and binding of cyclophosphamide and its metabolite acrolein to rat hepatic microsomal cytochrome P-450. Cancer Res 44 (1984) 4615-4621
26. Picklo M.J., Montine T.J., Amaranth V., and Neely M.D. Carbonyl toxicology and Alzheimer's disease. Toxicol Appl Pharmacol 184 (2002) 187-197
27. Al-Abed Y., and Bucala R. Efficient scavenging of fatty acid oxidation products by aminoguanidine. Chem Res Toxicol 10 (1997) 875-879
28. Neely M.D., Zimmerman L., Picklo M.J., Ou J.J., Morales C.R., Montine K.S., et al. Congeners of N(alpha)-acetyl-l-cysteine but not aminoguanidine act as neuroprotectants from the lipid peroxidation product 4-hydroxy-2-nonenal. Free Rad Biol Med 29 (2000) 1028-1036
29. Xie C., Lovell M.A., and Markesbery W.R. Glutathione transferase protects neuronal cultures against 4-hydroxynonenal toxicity. Free Rad Biol Med 25 (1998) 979-988
30. Neely M.D., Amarath V., Weitlauf C., and Montine T.J. Synthesis and cellular effects of an intracellularly activated analogue of 4-hydroxynonenal. Chem Res Toxicol 15 (2002) 40-47
31. Hayes J.D., and McMahon M. Molecular basis for the contribution of the antioxidant responsive element in cancer chemoprevention. Cancer Lett 174 (2001) 103-113
32. Nakamura Y., Morimitsu Y., Uzu T., Ohigashi H., Murakami A., Naito Y., et al. A glutathione S-transferase inducer from papaya: rapid screening, identification, and structure-activity relationship of isothiocyanates. Cancer Lett 157 (2000) 193-200
33. Tsukagoshi H., Kawata T., Shimizu Y., Ishizuka T., Dobashi K., and Mori M. 4-Hydroxy-2-nonenal enhances fibronectin production by IMR-90 human lung fibroblasts partly via activation of epidermal growth factor receptor linked extracellular signal-related kinase p44/42 pathway. Toxicol Appl Pharmacol 184 (2002) 127-135
34. Watanabe T., Pakala R., Katagiri T., and Benedict C. Lipid peroxidation product 4-hydroxy-2-nonenal acts synergistically with serotonin in inducing vascular smooth muscle cell proliferation. Atherosclerosis 155 (2001) 37-44
35. Olsen A., Stripp C., Christense J., Thomasen B.L., Overvad K., and Tjonneland A. Fruit and vegetable intake and risk of major chronic disease. J Natl Canc Inst 97 (2005) 1307-1308