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Chemical Compound Review

AG-D-99549     (2S,3S)-3-[(1R)-1- hydroxyhexyl]oxirane-2...

Synonyms: AC1MIN0Q, CTK4C7407, LS-100996, 152322-55-9
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Disease relevance of trans-4-Hydroxy-2-nonenal


Psychiatry related information on trans-4-Hydroxy-2-nonenal


High impact information on trans-4-Hydroxy-2-nonenal


Biological context of trans-4-Hydroxy-2-nonenal


Anatomical context of trans-4-Hydroxy-2-nonenal


Associations of trans-4-Hydroxy-2-nonenal with other chemical compounds


Gene context of trans-4-Hydroxy-2-nonenal


Analytical, diagnostic and therapeutic context of trans-4-Hydroxy-2-nonenal


  1. Astrocytic biotransformation of trans-4-hydroxy-2-nonenal is dose-dependent. Kubatova, A., Murphy, T.C., Combs, C., Picklo, M.J. Chem. Res. Toxicol. (2006) [Pubmed]
  2. Acute toxicity of trans-4-hydroxy-2-nonenal in Fisher 344 rats [corrected]. Nishikawa, A., Sodum, R., Chung, F.L. Lipids (1992) [Pubmed]
  3. Long-chain adducts of trans-4-hydroxy-2-nonenal to DNA bases cause recombination, base substitutions and frameshift mutations in M13 phage. Kowalczyk, P., Cieśla, J.M., Komisarski, M., Kuśmierek, J.T., Tudek, B. Mutat. Res. (2004) [Pubmed]
  4. High molecular weight neurofilament proteins are physiological substrates of adduction by the lipid peroxidation product hydroxynonenal. Wataya, T., Nunomura, A., Smith, M.A., Siedlak, S.L., Harris, P.L., Shimohama, S., Szweda, L.I., Kaminski, M.A., Avila, J., Price, D.L., Cleveland, D.W., Sayre, L.M., Perry, G. J. Biol. Chem. (2002) [Pubmed]
  5. trans-4-Hydroxy-2-hexenal: a reactive metabolite from the macrocyclic pyrrolizidine alkaloid senecionine. Segall, H.J., Wilson, D.W., Dallas, J.L., Haddon, W.F. Science (1985) [Pubmed]
  6. Trans-4-hydroxy-2-nonenal inhibits nucleotide excision repair in human cells: a possible mechanism for lipid peroxidation-induced carcinogenesis. Feng, Z., Hu, W., Tang, M.S. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  7. Metabolic activation of trans-4-hydroxy-2-nonenal, a toxic product of membrane lipid peroxidation and inhibitor of P450 cytochromes. Kuo, C.L., Vaz, A.D., Coon, M.J. J. Biol. Chem. (1997) [Pubmed]
  8. Enantioselective metabolism of trans-4-hydroxy-2-nonenal by brain mitochondria. Honzatko, A., Brichac, J., Murphy, T.C., Reberg, A., Kubátová, A., Smoliakova, I.P., Picklo, M.J. Free Radic. Biol. Med. (2005) [Pubmed]
  9. Effect of enzyme-resistant starch on formation of 1,N(2)-propanodeoxyguanosine adducts of trans-4-hydroxy-2-nonenal and cell proliferation in the colonic mucosa of healthy volunteers. Wacker, M., Wanek, P., Eder, E., Hylla, S., Gostner, A., Scheppach, W. Cancer Epidemiol. Biomarkers Prev. (2002) [Pubmed]
  10. Potential role of lipid peroxidation derived DNA damage in human colon carcinogenesis: studies on exocyclic base adducts as stable oxidative stress markers. Bartsch, H., Nair, J. Cancer Detect. Prev. (2002) [Pubmed]
  11. Succinylpurinemic autism: increased sensitivity of defective adenylosuccinate lyase towards 4-hydroxy-2-nonenal. Salerno, C., Siems, W.G., Crifò, C. Biochim. Biophys. Acta (2000) [Pubmed]
  12. Analysis of HNE metabolism in CNS models. Kubatova, A., Honzatko, A., Brichac, J., Long, E., Picklo, M.J. Redox Rep. (2007) [Pubmed]
  13. Is the glutathione conjugate of trans-4-hydroxy-2-nonenal transported by the multispecific organic anion transporting-ATPase of human erythrocytes? Dygas, A., Makowski, P., Pikuła, S. Acta Biochim. Pol. (1998) [Pubmed]
  14. 2,3-epoxy-4-hydroxynonanal, a potential lipid peroxidation product for etheno adduct formation, is not a substrate of human epoxide hydrolase. Chen, H.J., Gonzalez, F.J., Shou, M., Chung, F.L. Carcinogenesis (1998) [Pubmed]
  15. The major lipid peroxidation product, trans-4-hydroxy-2-nonenal, preferentially forms DNA adducts at codon 249 of human p53 gene, a unique mutational hotspot in hepatocellular carcinoma. Hu, W., Feng, Z., Eveleigh, J., Iyer, G., Pan, J., Amin, S., Chung, F.L., Tang, M.S. Carcinogenesis (2002) [Pubmed]
  16. Detection and quantification of endogenous cyclic DNA adducts derived from trans-4-hydroxy-2-nonenal in human brain tissue by isotope dilution capillary liquid chromatography nanoelectrospray tandem mass spectrometry. Liu, X., Lovell, M.A., Lynn, B.C. Chem. Res. Toxicol. (2006) [Pubmed]
  17. Increased brain levels of 4-hydroxy-2-nonenal glutathione conjugates in severe Alzheimer's disease. Völkel, W., Sicilia, T., Pähler, A., Gsell, W., Tatschner, T., Jellinger, K., Leblhuber, F., Riederer, P., Lutz, W.K., Götz, M.E. Neurochem. Int. (2006) [Pubmed]
  18. High dietary omega-6 polyunsaturated fatty acids drastically increase the formation of etheno-DNA base adducts in white blood cells of female subjects. Nair, J., Vaca, C.E., Velic, I., Mutanen, M., Valsta, L.M., Bartsch, H. Cancer Epidemiol. Biomarkers Prev. (1997) [Pubmed]
  19. Nitrate-based vasodilators inhibit multiple vascular aldehyde dehydrogenases. Murphy, T.C., Arntzen, R., Picklo, M.J. Cardiovasc. Toxicol. (2005) [Pubmed]
  20. PTEN, Akt, and GSK3beta signalling in rat primary cortical neuronal cultures following tumor necrosis factor-alpha and trans-4-hydroxy-2-nonenal treatments. Rickle, A., Behbahani, H., Ankarcrona, M., Winblad, B., Cowburn, R.F. J. Neurosci. Res. (2006) [Pubmed]
  21. In vivo involvement of cytochrome P450 4A family in the oxidative metabolism of the lipid peroxidation product trans-4-hydroxy-2-nonenal, using PPARalpha-deficient mice. Guéraud, F., Alary, J., Costet, P., Debrauwer, L., Dolo, L., Pineau, T., Paris, A. J. Lipid Res. (1999) [Pubmed]
  22. Flow cytometry as a method for studying effects of stressors on primary rat neurons. Behbahani, H., Rickle, A., Concha, H., Ankarcrona, M., Winblad, B., Cowburn, R.F. J. Neurosci. Res. (2005) [Pubmed]
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