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Chemical Compound Review

Diose     2-hydroxyethanal

Synonyms: GLYCOALDEHYDE, Hydroxyethanal, glycolaldehyde, CCRIS 2613, AG-D-82559, ...
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Disease relevance of glycolaldehyde


High impact information on glycolaldehyde


Chemical compound and disease context of glycolaldehyde


Biological context of glycolaldehyde


Anatomical context of glycolaldehyde


Associations of glycolaldehyde with other chemical compounds

  • We prepared three immunochemically distinct AGE by incubating bovine serum albumin (BSA) with glucose, glyceraldehyde, or glycolaldehyde [23].
  • We studied the reaction of carbonyl compounds glyoxal (GO) and glycolaldehyde (GLA) with pyridoxamine (PM), a potent post-Amadori inhibitor of AGE formation in vitro and of development of renal and retinal pathology in diabetic animals [24].
  • PM also inhibited the modification of lysine residues and loss of enzymatic activity of RNase in the presence of GO and GLA and inhibited formation of the AGE/ALE N(epsilon)-(carboxymethyl)lysine during reaction of GO and GLA with bovine serum albumin [24].
  • In the course of investigating the chemistry of phosphonoacetaldehyde (PAL), an analogue of glycolaldehyde phosphate, we have observed a striking case of catalysis by the layered hydroxide mineral hydrotalcite ([Mg2Al(OH)6][Cl.nH2O]) [25].
  • The reaction of 3-hydroxymorpholine in aqueous solution, 25 degrees C, pH 6.6, yields (2-hydroxy-ethoxy)acetaldehyde (62%), acetaldehyde (26%), and glycolaldehyde (26%), based on analysis of the dintrophenylhydrazine derivatives [26].

Gene context of glycolaldehyde


Analytical, diagnostic and therapeutic context of glycolaldehyde


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  2. Glycolaldehyde induces growth inhibition and oxidative stress in human breast cancer cells. Al-Enezi, K.S., Alkhalaf, M., Benov, L.T. Free Radic. Biol. Med. (2006) [Pubmed]
  3. Vinyl carbamate epoxide, a major strong electrophilic, mutagenic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate (urethane). Park, K.K., Liem, A., Stewart, B.C., Miller, J.A. Carcinogenesis (1993) [Pubmed]
  4. Pyridoxine-requiring mutants of Escherichia coli: glycolaldehyde dehydrogenase is not coded for by the pdxB gene. Shimizu, S., Dempsey, W.B. J. Bacteriol. (1978) [Pubmed]
  5. Aldehyde modification of peptide immunogen enhances protein-reactive antibody response to toxic shock syndrome toxin-1. Bavoso, A., Ostuni, A., De Vendel, J., Pollaro, F., Armentano, F., Knight, T., Makker, S., Tramontano, A. J. Pept. Sci. (2006) [Pubmed]
  6. The myeloperoxidase system of human phagocytes generates Nepsilon-(carboxymethyl)lysine on proteins: a mechanism for producing advanced glycation end products at sites of inflammation. Anderson, M.M., Requena, J.R., Crowley, J.R., Thorpe, S.R., Heinecke, J.W. J. Clin. Invest. (1999) [Pubmed]
  7. Glyoxal oxidase of Phanerochaete chrysosporium: its characterization and activation by lignin peroxidase. Kersten, P.J. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  8. Visualization of the interaction of native and modified lipoproteins with parenchymal, endothelial and Kupffer cells from human liver. Kleinherenbrink-Stins, M.F., van de Boom, J.H., Schouten, D., Roholl, P.J., Niels van der Heyde, M., Brouwer, A., van Berkel, T.J., Knook, D.L. Hepatology (1991) [Pubmed]
  9. Advanced glycation end product precursors impair ABCA1-dependent cholesterol removal from cells. Passarelli, M., Tang, C., McDonald, T.O., O'Brien, K.D., Gerrity, R.G., Heinecke, J.W., Oram, J.F. Diabetes (2005) [Pubmed]
  10. Production of N(epsilon)-(carboxymethyl)lysine is impaired in mice deficient in NADPH oxidase: a role for phagocyte-derived oxidants in the formation of advanced glycation end products during inflammation. Anderson, M.M., Heinecke, J.W. Diabetes (2003) [Pubmed]
  11. Ethylene glycol poisoning. Leth, P.M., Gregersen, M. Forensic Sci. Int. (2005) [Pubmed]
  12. TAGE (toxic AGEs) hypothesis in various chronic diseases. Takeuchi, M., Yamagishi, S. Med. Hypotheses (2004) [Pubmed]
  13. Ethylene glycol-mediated tubular injury: identification of critical metabolites and injury pathways. Poldelski, V., Johnson, A., Wright, S., Rosa, V.D., Zager, R.A. Am. J. Kidney Dis. (2001) [Pubmed]
  14. Effects of nonenzymatic glycosylation of mesangial matrix on proliferation of mesangial cells. Crowley, S.T., Brownlee, M., Edelstein, D., Satriano, J.A., Mori, T., Singhal, P.C., Schlondorff, D.O. Diabetes (1991) [Pubmed]
  15. Biosynthesis of vitamin B(6) in rhizobium. Tazoe, M., Ichikawa, K., Hoshino, T. J. Biol. Chem. (2000) [Pubmed]
  16. Inhibition of matrix-induced bone differentiation by advanced glycation end-products in rats. Fong, Y., Edelstein, D., Wang, E.A., Brownlee, M. Diabetologia (1993) [Pubmed]
  17. Identification of cis-ethanesemidione as the organic radical derived from glycolaldehyde in the suicide inactivation of dioldehydrase and of ethanolamine ammonia-lyase. Abend, A., Bandarian, V., Reed, G.H., Frey, P.A. Biochemistry (2000) [Pubmed]
  18. N-(2-hydroxyethyl)doxorubicin from hydrolysis of 3'-deamino-3'-(3-cyano-4-morpholinyl)doxorubicin. Acton, E.M., Tong, G.L., Smith, T.H., Taylor, D.L., Streeter, D.G., Peters, J.H., Gordon, G.R., Filppi, J.A., Wolgemuth, R.L., Giuliani, F.C. J. Med. Chem. (1986) [Pubmed]
  19. Hydrazine compounds inhibit glycation of low-density lipoproteins and prevent the in vitro formation of model foam cells from glycolaldehyde-modified low-density lipoproteins. Brown, B.E., Mahroof, F.M., Cook, N.L., van Reyk, D.M., Davies, M.J. Diabetologia (2006) [Pubmed]
  20. Increased uptake of alpha-hydroxy aldehyde-modified low density lipoprotein by macrophage scavenger receptors. Kawamura, M., Heinecke, J.W., Chait, A. J. Lipid Res. (2000) [Pubmed]
  21. Enhanced immunogenicity of aldehyde-bearing antigens: a possible link between innate and adaptive immunity. Allison, M.E., Fearon, D.T. Eur. J. Immunol. (2000) [Pubmed]
  22. The role of advanced glycation end products in retinal microvascular leukostasis. Moore, T.C., Moore, J.E., Kaji, Y., Frizzell, N., Usui, T., Poulaki, V., Campbell, I.L., Stitt, A.W., Gardiner, T.A., Archer, D.B., Adamis, A.P. Invest. Ophthalmol. Vis. Sci. (2003) [Pubmed]
  23. Advanced glycation end product-induced apoptosis and overexpression of vascular endothelial growth factor and monocyte chemoattractant protein-1 in human-cultured mesangial cells. Yamagishi, S., Inagaki, Y., Okamoto, T., Amano, S., Koga, K., Takeuchi, M., Makita, Z. J. Biol. Chem. (2002) [Pubmed]
  24. A post-Amadori inhibitor pyridoxamine also inhibits chemical modification of proteins by scavenging carbonyl intermediates of carbohydrate and lipid degradation. Voziyan, P.A., Metz, T.O., Baynes, J.W., Hudson, B.G. J. Biol. Chem. (2002) [Pubmed]
  25. Mineral catalysis of a potentially prebiotic aldol condensation. De Graaf, R.M., Visscher, J., Xu, Y., Arrhenius, G., Schwartz, A.W. J. Mol. Evol. (1998) [Pubmed]
  26. Reexamination of the aqueous chemistry of N-Nitroso-3-hydroxymorpholine, a metabolite of the carcinogen N-nitrosomorpholine. Kim, H.J., Fishbein, J.C. Chem. Res. Toxicol. (2003) [Pubmed]
  27. Glycolaldehyde induces apoptosis in a human breast cancer cell line. Al-Maghrebi, M.A., Al-Mulla, F., Benov, L.T. Arch. Biochem. Biophys. (2003) [Pubmed]
  28. Glycolaldehyde-modified bovine serum albumin downregulates leptin expression in mouse adipocytes via a CD36-mediated pathway. Unno, Y., Sakai, M., Sakamoto, Y., Kuniyasu, A., Nagai, R., Nakayama, H., Horiuchi, S. Ann. N. Y. Acad. Sci. (2005) [Pubmed]
  29. Glycolaldehyde, a reactive intermediate for advanced glycation end products, plays an important role in the generation of an active ligand for the macrophage scavenger receptor. Nagai, R., Matsumoto, K., Ling, X., Suzuki, H., Araki, T., Horiuchi, S. Diabetes (2000) [Pubmed]
  30. One-substrate transketolase-catalyzed reaction. Bykova, I.A., Solovjeva, O.N., Meshalkina, L.E., Kovina, M.V., Kochetov, G.A. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  31. Molecular cloning and kinetic characterization of an aldehyde dehydrogenase gene in Klebsiella pneumoniae. Ma, L.C., Lee, S.L., Lee, C.Z., Yin, S.J., Wang, J.T. J. Formos. Med. Assoc. (2005) [Pubmed]
  32. Influence of ligation state and concentration of hemoglobin A on its cross-linking by glycolaldehyde: functional properties of cross-linked, carboxymethylated hemoglobin. Manning, L.R., Manning, J.M. Biochemistry (1988) [Pubmed]
  33. Glycolaldehyde causes DNA-protein crosslinks: a new aspect of ethylene oxide genotoxicity. Hengstler, J.G., Fuchs, J., Gebhard, S., Oesch, F. Mutat. Res. (1994) [Pubmed]
  34. Development of a polyclonal antibody with broad epitope specificity for advanced glycation endproducts and localization of these epitopes in Bruch's membrane of the aging eye. Farboud, B., Aotaki-Keen, A., Miyata, T., Hjelmeland, L.M., Handa, J.T. Mol. Vis. (1999) [Pubmed]
  35. Studies on the resuscitative efficacy of polymerized bovine hemoglobin. Bu, F., Wang, H., Zhu, X. Artificial cells, blood substitutes, and immobilization biotechnology. (2000) [Pubmed]
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