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Chemical Compound Review

CCRIS 4272     (4S,5R)-4,5,6-trihydroxy-2- oxo-hexanal

Synonyms: AG-F-45126, CHEBI:60777, KB-62892, LS-75671, CTK8F5042, ...
 
 
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Disease relevance of CCRIS 4272

 

High impact information on CCRIS 4272

 

Chemical compound and disease context of CCRIS 4272

 

Biological context of CCRIS 4272

 

Anatomical context of CCRIS 4272

 

Associations of CCRIS 4272 with other chemical compounds

 

Gene context of CCRIS 4272

  • Identity of a major 3-deoxyglucosone-reducing enzyme with aldehyde reductase in rat liver established by amino acid sequencing and cDNA expression [18].
  • Monkey 3-deoxyglucosone reductase: tissue distribution and purification of three multiple forms of the kidney enzyme that are identical with dihydrodiol dehydrogenase, aldehyde reductase, and aldose reductase [22].
  • Aldehyde reductase is a major protein associated with 3-deoxyglucosone reductase activity in rat, pig and human livers [23].
  • Early glycated albumin, but not advanced glycated albumin, methylglyoxal, or 3-deoxyglucosone increases the expression of PAI-1 in human peritoneal mesothelial cells [24].
  • HB-EGF, but not PDGF, is regulated at the transcriptional level by 3-deoxyglucosone (3-DG), a major and highly reactive intermediate in the glycation reaction [25].
 

Analytical, diagnostic and therapeutic context of CCRIS 4272

References

  1. Identification of fructose 3-phosphate in the lens of diabetic rats. Szwergold, B.S., Kappler, F., Brown, T.R. Science (1990) [Pubmed]
  2. Teratogenicity of 3-deoxyglucosone and diabetic embryopathy. Eriksson, U.J., Wentzel, P., Minhas, H.S., Thornalley, P.J. Diabetes (1998) [Pubmed]
  3. Glycated and oxidized protein degradation products are indicators of fasting and postprandial hyperglycemia in diabetes. Ahmed, N., Babaei-Jadidi, R., Howell, S.K., Thornalley, P.J., Beisswenger, P.J. Diabetes Care (2005) [Pubmed]
  4. Relation between serum 3-deoxyglucosone and development of diabetic microangiopathy. Kusunoki, H., Miyata, S., Ohara, T., Liu, B.F., Uriuhara, A., Kojima, H., Suzuki, K., Miyazaki, H., Yamashita, Y., Inaba, K., Kasuga, M. Diabetes Care (2003) [Pubmed]
  5. Elevation of aldose reductase gene expression in rat primary hepatoma and hepatoma cell lines: implication in detoxification of cytotoxic aldehydes. Takahashi, M., Fujii, J., Miyoshi, E., Hoshi, A., Taniguchi, N. Int. J. Cancer (1995) [Pubmed]
  6. Immunohistochemical detection of imidazolone, a novel advanced glycation end product, in kidneys and aortas of diabetic patients. Niwa, T., Katsuzaki, T., Miyazaki, S., Miyazaki, T., Ishizaki, Y., Hayase, F., Tatemichi, N., Takei, Y. J. Clin. Invest. (1997) [Pubmed]
  7. Susceptibility to diabetic nephropathy is related to dicarbonyl and oxidative stress. Beisswenger, P.J., Drummond, K.S., Nelson, R.G., Howell, S.K., Szwergold, B.S., Mauer, M. Diabetes (2005) [Pubmed]
  8. Selective induction of heparin-binding epidermal growth factor-like growth factor by methylglyoxal and 3-deoxyglucosone in rat aortic smooth muscle cells. The involvement of reactive oxygen species formation and a possible implication for atherogenesis in diabetes. Che, W., Asahi, M., Takahashi, M., Kaneto, H., Okado, A., Higashiyama, S., Taniguchi, N. J. Biol. Chem. (1997) [Pubmed]
  9. Effect of pyridoxamine (K-163), an inhibitor of advanced glycation end products, on type 2 diabetic nephropathy in KK-A(y)/Ta mice. Tanimoto, M., Gohda, T., Kaneko, S., Hagiwara, S., Murakoshi, M., Aoki, T., Yamada, K., Ito, T., Matsumoto, M., Horikoshi, S., Tomino, Y. Metab. Clin. Exp. (2007) [Pubmed]
  10. Identification of 3-deoxyglucosone dehydrogenase as aldehyde dehydrogenase 1A1 (retinaldehyde dehydrogenase 1). Collard, F., Vertommen, D., Fortpied, J., Duester, G., Van Schaftingen, E. Biochimie (2007) [Pubmed]
  11. Induction of apoptotic cell death by methylglyoxal and 3-deoxyglucosone in macrophage-derived cell lines. Okado, A., Kawasaki, Y., Hasuike, Y., Takahashi, M., Teshima, T., Fujii, J., Taniguchi, N. Biochem. Biophys. Res. Commun. (1996) [Pubmed]
  12. Heterocyclization of 3-deoxy-D-erythro-hexos-2-ulose-1,2-bis(thiosemicarbazone). Crystal structure of the major diastereomer. Martins Alho, M.A., Baggio, R., Garland, M.T., D'Accorso, N.B., Varela, O. Carbohydr. Res. (2002) [Pubmed]
  13. Efficient in vitro lowering of carbonyl stress by the glyoxalase system in conventional glucose peritoneal dialysis fluid. Inagi, R., Miyata, T., Ueda, Y., Yoshino, A., Nangaku, M., van Ypersele de Strihou, C., Kurokawa, K. Kidney Int. (2002) [Pubmed]
  14. Heat-shock protein 27 is a major methylglyoxal-modified protein in endothelial cells. Schalkwijk, C.G., van Bezu, J., van der Schors, R.C., Uchida, K., Stehouwer, C.D., van Hinsbergh, V.W. FEBS Lett. (2006) [Pubmed]
  15. Selective vulnerability of spinal motor neurons to reactive dicarbonyl compounds, intermediate products of glycation, in vitro: implication of inefficient glutathione system in spinal motor neurons. Shinpo, K., Kikuchi, S., Sasaki, H., Ogata, A., Moriwaka, F., Tashiro, K. Brain Res. (2000) [Pubmed]
  16. Suppression of 3-deoxyglucosone and heparin-binding epidermal growth factor-like growth factor mRNA expression by an aldose reductase inhibitor in rat vascular smooth muscle cells. Li, W., Hamada, Y., Nakashima, E., Naruse, K., Kamiya, H., Akiyama, N., Hirooka, H., Takahashi, N., Horiuchi, S., Hotta, N., Oiso, Y., Nakamura, J. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  17. Effects of 3-deoxyglucosone on the Maillard reaction. Igaki, N., Sakai, M., Hata, H., Oimomi, M., Baba, S., Kato, H. Clin. Chem. (1990) [Pubmed]
  18. Identity of a major 3-deoxyglucosone-reducing enzyme with aldehyde reductase in rat liver established by amino acid sequencing and cDNA expression. Takahashi, M., Fujii, J., Teshima, T., Suzuki, K., Shiba, T., Taniguchi, N. Gene (1993) [Pubmed]
  19. Role of polyol pathway in nonenzymatic glycation. Hamada, Y., Araki, N., Horiuchi, S., Hotta, N. Nephrol. Dial. Transplant. (1996) [Pubmed]
  20. Effect of carbonyl compounds on red blood cells deformability. Iwata, H., Ukeda, H., Maruyama, T., Fujino, T., Sawamura, M. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  21. Detection of 3-deoxyfructose and 3-deoxyglucosone in human urine and plasma: evidence for intermediate stages of the Maillard reaction in vivo. Knecht, K.J., Feather, M.S., Baynes, J.W. Arch. Biochem. Biophys. (1992) [Pubmed]
  22. Monkey 3-deoxyglucosone reductase: tissue distribution and purification of three multiple forms of the kidney enzyme that are identical with dihydrodiol dehydrogenase, aldehyde reductase, and aldose reductase. Sato, K., Inazu, A., Yamaguchi, S., Nakayama, T., Deyashiki, Y., Sawada, H., Hara, A. Arch. Biochem. Biophys. (1993) [Pubmed]
  23. Aldehyde reductase is a major protein associated with 3-deoxyglucosone reductase activity in rat, pig and human livers. Kanazu, T., Shinoda, M., Nakayama, T., Deyashiki, Y., Hara, A., Sawada, H. Biochem. J. (1991) [Pubmed]
  24. Early glycated albumin, but not advanced glycated albumin, methylglyoxal, or 3-deoxyglucosone increases the expression of PAI-1 in human peritoneal mesothelial cells. Mandl-Weber, S., Haslinger, B., Schalkwijk, C.G., Sitter, T. Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis. (2001) [Pubmed]
  25. Involvement of glycation and oxidative stress in diabetic macroangiopathy. Taniguchi, N., Kaneto, H., Asahi, M., Takahashi, M., Wenyi, C., Higashiyama, S., Fujii, J., Suzuki, K., Kayanoki, Y. Diabetes (1996) [Pubmed]
  26. Presence of 3-deoxyglucosone, a potent protein crosslinking intermediate of Maillard reaction, in diabetic serum. Niwa, T., Takeda, N., Yoshizumi, H., Tatematsu, A., Ohara, M., Tomiyama, S., Niimura, K. Biochem. Biophys. Res. Commun. (1993) [Pubmed]
  27. 3-Deoxyglucosone, a promoter of advanced glycation end products in fluids for peritoneal dialysis. Linden, T., Forsbäck, G., Deppisch, R., Henle, T., Wieslander, A. Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis. (1998) [Pubmed]
  28. Quantitation of the glycation intermediate 3-deoxyglucosone by oxidation with rabbit liver oxoaldehyde dehydrogenase to 2-keto-3-deoxygluconic acid followed by high-performance liquid chromatography. Fujii, E., Iwase, H., Ishii-Karakasa, I., Yajima, Y., Hotta, K. J. Chromatogr. B, Biomed. Appl. (1994) [Pubmed]
  29. Characterisation of a novel AGE-compound derived from lysine and 3-deoxyglucosone. Skovsted, I.C., Christensen, M., Breinholt, J., Mortensen, S.B. Cell. Mol. Biol. (Noisy-le-grand) (1998) [Pubmed]
  30. Gas chromatographic-mass spectrometric analysis of erythrocyte 3-deoxyglucosone in hemodialysis patients. Tsukushi, S., Shimokata, K., Niwa, T. J. Chromatogr. B Biomed. Sci. Appl. (1999) [Pubmed]
 
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