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Chemical Compound Review:

CCRIS 9201 (E)-4-hydroxyhex-2-enal

Synonyms: KB-02504, LS-75538, SBB069586, LMFA06000016, AKOS006273451, ...

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Disease relevance of LMFA06000016

Accumulation of protein-bound 4-hydroxy-2-hexenal in spinal cords from patients with sporadic amyotrophic lateral sclerosis [1].
The induction of chromosomal aberrations was significantly elevated at concentrations of > or = 10 microM and 10 microM for 4-hydroxyhexenal and 4-hydroxyundecenal, respectively [2].
METHODS: We immunohistochemically detected malondialdehyde (MDA)-, 4-hydroxy-2-nonenal (HNE)-, and 4-hydroxy-2-hexenal (HHE)-protein adducts in liver biopsy specimens from 55 patients with chronic hepatitis C [3].

High impact information on LMFA06000016

Negative ion chemical ionization mass spectroscopy of two major compounds that were identified were consistent with the structures of the fatty acid oxidation products 4-hydroxyhexenal and 4-hydroxynonenal [4].
Induction of endothelial iNOS by 4-hydroxyhexenal through NF-kappaB activation [5].
Lipid peroxidation and its end-product, 4-hydroxyhexenal (HHE), are known to affect redox balance during aging, which causes various degenerative processes including vascular alterations from endothelial cell deterioration [5].
Our findings showed that the transporting activity of ANT in intact mitochondria was inhibited by two unsaturated aldehydes, 4-hydroxynonenal (HNE) and 4-hydroxyhexenal (HHE) [6].
NF-kappaB activation mechanism of 4-hydroxyhexenal via NIK/IKK and p38 MAPK pathway [7].

Biological context of LMFA06000016

Induction of endothelial apoptosis by 4-hydroxyhexenal [8].

Anatomical context of LMFA06000016

To investigate whether peroxidative products of PUFAs induce apoptosis in retinal pigmented epithelial (RPE) cells and possibly contribute to ARMD, human retinal pigmented epithelial cells (ARPE-19) were exposed to micromolar concentrations of H2O2, 4-hydroxynonenal (HNE) and 4-hydroxyhexenal (HHE) [9].
The cytotoxic and genotoxic activities of 4-hydroxypentenal (HPE), 4-hydroxyhexenal (HHE), 4-hydroxyoctenal (HOE), 4-hydroxynonenal (HNE) and 4-hydroxyundecenal (HUE) were investigated in Chinese hamster ovary (CHO) cells [10].

Associations of LMFA06000016 with other chemical compounds

4-Hydroxyhexenal: a lipid peroxidation product derived from oxidized docosahexaenoic acid [11].

Gene context of LMFA06000016

Incubation with HNE or 4-hydroxy-2-hexenal (HHE) decreased GAPDH activity and GAPDH protein level, and increased the 23-kDa fragment, in time- and dose-dependent manners, but that with other aldehydes did not [12].
In addition, the tubulointerstitial expression of collagens type I and type IV, the p22-, p47- and p67-phox subunits of NADPH oxidase, 4-hydroxy-2-nonenal, and 4-hydroxy-2-hexenal lipid peroxidation products were assessed by immunohistochemistry [13].
Reduction of 4-hydroxynonenal and 4-hydroxyhexenal by retinal aldose reductase [14].

References

Accumulation of protein-bound 4-hydroxy-2-hexenal in spinal cords from patients with sporadic amyotrophic lateral sclerosis. Shibata, N., Yamada, S., Uchida, K., Hirano, A., Sakoda, S., Fujimura, H., Sasaki, S., Iwata, M., Toi, S., Kawaguchi, M., Yamamoto, T., Kobayashi, M. Brain Res. (2004) [Pubmed]
Genotoxic properties of 4-hydroxyalkenals and analogous aldehydes. Eckl, P.M., Ortner, A., Esterbauer, H. Mutat. Res. (1993) [Pubmed]
In situ detection of oxidized n-3 polyunsaturated fatty acids in chronic hepatitis C: correlation with hepatic steatosis. Kitase, A., Hino, K., Furutani, T., Okuda, M., Gondo, T., Hidaka, I., Hara, Y., Yamaguchi, Y., Okita, K. J. Gastroenterol. (2005) [Pubmed]
Hydroxyalkenal formation induced by advanced glycosylation of low density lipoprotein. Al-Abed, Y., Liebich, H., Voelter, W., Bucala, R. J. Biol. Chem. (1996) [Pubmed]
Induction of endothelial iNOS by 4-hydroxyhexenal through NF-kappaB activation. Lee, J.Y., Je, J.H., Jung, K.J., Yu, B.P., Chung, H.Y. Free Radic. Biol. Med. (2004) [Pubmed]
Inhibition of adenine nucleotide translocator by lipid peroxidation products. Chen, J.J., Bertrand, H., Yu, B.P. Free Radic. Biol. Med. (1995) [Pubmed]
NF-kappaB activation mechanism of 4-hydroxyhexenal via NIK/IKK and p38 MAPK pathway. Je, J.H., Lee, J.Y., Jung, K.J., Sung, B., Go, E.K., Yu, B.P., Chung, H.Y. FEBS Lett. (2004) [Pubmed]
Induction of endothelial apoptosis by 4-hydroxyhexenal. Lee, J.Y., Je, J.H., Kim, D.H., Chung, S.W., Zou, Y., Kim, N.D., Ae Yoo, M., Suck Baik, H., Yu, B.P., Chung, H.Y. Eur. J. Biochem. (2004) [Pubmed]
Toxicity and detoxification of lipid-derived aldehydes in cultured retinal pigmented epithelial cells. Choudhary, S., Xiao, T., Srivastava, S., Zhang, W., Chan, L.L., Vergara, L.A., Van Kuijk, F.J., Ansari, N.H. Toxicol. Appl. Pharmacol. (2005) [Pubmed]
Cytotoxicity, DNA fragmentation and sister-chromatid exchange in Chinese hamster ovary cells exposed to the lipid peroxidation product 4-hydroxynonenal and homologous aldehydes. Brambilla, G., Sciabà, L., Faggin, P., Maura, A., Marinari, U.M., Ferro, M., Esterbauer, H. Mutat. Res. (1986) [Pubmed]
4-Hydroxyhexenal: a lipid peroxidation product derived from oxidized docosahexaenoic acid. Van Kuijk, F.J., Holte, L.L., Dratz, E.A. Biochim. Biophys. Acta (1990) [Pubmed]
Degradation of glyceraldehyde-3-phosphate dehydrogenase triggered by 4-hydroxy-2-nonenal and 4-hydroxy-2-hexenal. Tsuchiya, Y., Yamaguchi, M., Chikuma, T., Hojo, H. Arch. Biochem. Biophys. (2005) [Pubmed]
Telmisartan inhibits both oxidative stress and renal fibrosis after unilateral ureteral obstruction in acatalasemic mice. Sugiyama, H., Kobayashi, M., Wang, D.H., Sunami, R., Maeshima, Y., Yamasaki, Y., Masuoka, N., Kira, S., Makino, H. Nephrol. Dial. Transplant. (2005) [Pubmed]
Reduction of 4-hydroxynonenal and 4-hydroxyhexenal by retinal aldose reductase. He, Q., Khanna, P., Srivastava, S., van Kuijk, F.J., Ansari, N.H. Biochem. Biophys. Res. Commun. (1998) [Pubmed]

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