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Chemical Compound Review

pyridoxamine     4-(aminomethyl)-5- (hydroxymethyl)-2-methyl...

Synonyms: Pyridoxylamine, SureCN30408, AGN-PC-00H10N, CHEMBL593019, AG-F-78709, ...
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Disease relevance of pyridoxamine


Psychiatry related information on pyridoxamine


High impact information on pyridoxamine


Chemical compound and disease context of pyridoxamine


Biological context of pyridoxamine

  • Evidence for an essential histidyl residue at the active site of pyridoxamine (pyridoxine)-5'-phosphate oxidase from rabbit liver [14].
  • When the phosphorylation of [3H]PN was reduced by adding 160 microM unlabeled PN, PL, PM, or 4'-deoxypyridoxine, the cell:medium concentration ratio for 3H did not exceed unity [15].
  • A membrane potential is not required for transport of pyridoxamine, and an artificially generated potential does not drive uptake in this organism [16].
  • Accumulation of pyridoxamine requires an exogenous energy source and is inhibited by glycolysis inhibitors [16].
  • Pyridoxamine (pyridoxine)-5'-phosphate oxidase (EC from rabbit liver is inactivated by diethylpyrocarbonate in an all-or-none fashion with first order kinetics with respect to modifier concentration [14].

Anatomical context of pyridoxamine

  • Erythrocytes take up PN by passive diffusion as indicated by the fact that the initial influx process is nonsaturable and is not affected by pyridoxamine (PM), PL, or 4'-deoxypyridoxine [15].
  • Pyridoxamine improves functional, structural, and biochemical alterations of peritoneal membranes in uremic peritoneal dialysis rats [17].
  • Collagen preparations were incubated in the presence or absence of AGE-breakers or PM in phosphate buffer, pH 7.4, for 24h at 37 degrees C. These treatments did not decrease the half-time for solubilization of diabetic skin collagen by pepsin or increase the acid solubility of diabetic tail tendon collagen [18].
  • Interestingly, pyridoxamine (PM), which had no effect in rat aorta and endothelial cell assays, also exerted a significant suppressive effect in this model [19].
  • Anti-angiogenic effect of pyridoxal 5'-phosphate, pyridoxal and pyridoxamine on embryoid bodies derived from mouse embryonic stem cells [19].

Associations of pyridoxamine with other chemical compounds


Gene context of pyridoxamine

  • Mouse brain ornithine decarboxylase (ODC) was purified to near-homogeneity by using (NH4)2SO4 precipitation and chromatography on heparin-Sepharose, pyridoxamine phosphate-agarose and DEAE-cellulose [24].
  • Here, two transamination catalysts were designed via computer modeling and assembled by chemically conjugating a pyridoxamine moiety within the large cavity of intestinal fatty acid binding protein [23].
  • The HPLC method was able to identify PLP, 4-PA, PM, PL, PN, and PMP from all other compounds in plasma in an analytical run of 46 min [25].
  • We have developed a HPLC-based method able to quantify the B6 vitamers pyridoxal 5'-phosphate (PLP), pyridoxal (PL), pyridoxamine 5'-phosphate (PMP), pyridoxine (PN), and pyridoxamine (PM) and the degradation product 4-pyridoxic acid (4-PA) [25].
  • Previous work has shown ALBP to be a good protein scaffold for exploring enantio- and stereoselective reactions; two constructs, ALBP attached to either a pyridoxamine or a phenanthroline group at C117, have been chemically characterized [26].

Analytical, diagnostic and therapeutic context of pyridoxamine


  1. Modification of proteins in vitro by physiological levels of glucose: pyridoxamine inhibits conversion of Amadori intermediate to advanced glycation end-products through binding of redox metal ions. Voziyan, P.A., Khalifah, R.G., Thibaudeau, C., Yildiz, A., Jacob, J., Serianni, A.S., Hudson, B.G. J. Biol. Chem. (2003) [Pubmed]
  2. Pyruvoyl-dependent histidine decarboxylases. Mechanism of cleavage of the proenzyme from Lactobacillus buchneri. Recsei, P.A., Snell, E.E. J. Biol. Chem. (1985) [Pubmed]
  3. New potential agents in treating diabetic kidney disease : the fourth act. Williams, M.E. Drugs (2006) [Pubmed]
  4. Pyridoxamine lowers kidney crystals in experimental hyperoxaluria: a potential therapy for primary hyperoxaluria. Chetyrkin, S.V., Kim, D., Belmont, J.M., Scheinman, J.I., Hudson, B.G., Voziyan, P.A. Kidney Int. (2005) [Pubmed]
  5. Pre-steady-state kinetics of Escherichia coli aspartate aminotransferase catalyzed reactions and thermodynamic aspects of its substrate specificity. Kuramitsu, S., Hiromi, K., Hayashi, H., Morino, Y., Kagamiyama, H. Biochemistry (1990) [Pubmed]
  6. The effect of vitamin B6 on cognition. Malouf, R., Grimley Evans, J. Cochrane database of systematic reviews (Online) (2003) [Pubmed]
  7. The design of protein-based catalysts using semisynthetic methods. Distefano, M.D., Kuang, H., Qi, D., Mazhary, A. Curr. Opin. Struct. Biol. (1998) [Pubmed]
  8. Human Mitochondrial Branched Chain Aminotransferase Isozyme: STRUCTURAL ROLE OF THE CXXC CENTER IN CATALYSIS. Yennawar, N.H., Islam, M.M., Conway, M., Wallin, R., Hutson, S.M. J. Biol. Chem. (2006) [Pubmed]
  9. Crystal structure of pyridoxal kinase in complex with roscovitine and derivatives. Tang, L., Li, M.H., Cao, P., Wang, F., Chang, W.R., Bach, S., Reinhardt, J., Ferandin, Y., Galons, H., Wan, Y., Gray, N., Meijer, L., Jiang, T., Liang, D.C. J. Biol. Chem. (2005) [Pubmed]
  10. Tpn1p, the plasma membrane vitamin B6 transporter of Saccharomyces cerevisiae. Stolz, J., Vielreicher, M. J. Biol. Chem. (2003) [Pubmed]
  11. Pyridoxamine traps intermediates in lipid peroxidation reactions in vivo: evidence on the role of lipids in chemical modification of protein and development of diabetic complications. Metz, T.O., Alderson, N.L., Chachich, M.E., Thorpe, S.R., Baynes, J.W. J. Biol. Chem. (2003) [Pubmed]
  12. Pyridine analogs inhibit the glucosyltransferase of Streptococcus mutans. Thaniyavarn, S., Taylor, K.G., Singh, S., Doyle, R.J. Infect. Immun. (1982) [Pubmed]
  13. Reaction mechanism of Escherichia coli cystathionine gamma-synthase: direct evidence for a pyridoxamine derivative of vinylglyoxylate as a key intermediate in pyridoxal phosphate dependent gamma-elimination and gamma-replacement reactions. Brzović, P., Holbrook, E.L., Greene, R.C., Dunn, M.F. Biochemistry (1990) [Pubmed]
  14. Evidence for an essential histidyl residue at the active site of pyridoxamine (pyridoxine)-5'-phosphate oxidase from rabbit liver. Horiike, K., Tsuge, H., McCormick, D.B. J. Biol. Chem. (1979) [Pubmed]
  15. Transport and accumulation of pyridoxine and pyridoxal by erythrocytes. Mehansho, H., Henderson, L.M. J. Biol. Chem. (1980) [Pubmed]
  16. Transport and metabolism of vitamin B6 in lactic acid bacteria. Mulligan, J.H., Snell, E.E. J. Biol. Chem. (1977) [Pubmed]
  17. Pyridoxamine improves functional, structural, and biochemical alterations of peritoneal membranes in uremic peritoneal dialysis rats. Kakuta, T., Tanaka, R., Satoh, Y., Izuhara, Y., Inagi, R., Nangaku, M., Saito, A., Miyata, T. Kidney Int. (2005) [Pubmed]
  18. AGE-breakers cleave model compounds, but do not break Maillard crosslinks in skin and tail collagen from diabetic rats. Yang, S., Litchfield, J.E., Baynes, J.W. Arch. Biochem. Biophys. (2003) [Pubmed]
  19. Anti-angiogenic effect of pyridoxal 5'-phosphate, pyridoxal and pyridoxamine on embryoid bodies derived from mouse embryonic stem cells. Matsubara, K., Mori, M., Akagi, R., Kato, N. Int. J. Mol. Med. (2004) [Pubmed]
  20. NMR studies of 1H resonances in the 10-18-ppm range for cytosolic aspartate aminotransferase. Metzler, D.E., Metzler, C.M., Mollova, E.T., Scott, R.D., Tanase, S., Kogo, K., Higaki, T., Morino, Y. J. Biol. Chem. (1994) [Pubmed]
  21. N,N'-ethylenebis(pyridoxylideneiminato) and N,N'-ethylenebis(pyridoxylaminato): synthesis, characterization, potentiometric, spectroscopic, and DFT studies of their vanadium(IV) and vanadium(V) complexes. Correia, I., Costa Pessoa, J., Duarte, M.T., Henriques, R.T., Piedade, M.F., Veiros, L.F., Jakusch, T., Kiss, T., Dörnyei, A., Castro, M.M., Geraldes, C.F., Avecilla, F. Chemistry (Weinheim an der Bergstrasse, Germany) (2004) [Pubmed]
  22. Mechanisms of the inhibition of human erythrocyte pyridoxal kinase by drugs. Lainé-Cessac, P., Cailleux, A., Allain, P. Biochem. Pharmacol. (1997) [Pubmed]
  23. Enzymes by design: chemogenetic assembly of transamination active sites containing lysine residues for covalent catalysis. Häring, D., Distefano, M.D. Bioconjug. Chem. (2001) [Pubmed]
  24. Purification of mouse brain ornithine decarboxylase reveals its presence as an inactive complex with antizyme. Laitinen, P.H., Hietala, O.A., Pulkka, A.E., Pajunen, A.E. Biochem. J. (1986) [Pubmed]
  25. Determination of vitamin B6 vitamers and pyridoxic acid in plasma: development and evaluation of a high-performance liquid chromatographic assay. Bisp, M.R., Bor, M.V., Heinsvig, E.M., Kall, M.A., Nexø, E. Anal. Biochem. (2002) [Pubmed]
  26. Structural characterization of two synthetic catalysts based on adipocyte lipid-binding protein. Ory, J.J., Mazhary, A., Kuang, H., Davies, R.R., Distefano, M.D., Banaszak, L.J. Protein Eng. (1998) [Pubmed]
  27. Selective tryptic cleavage of native cytoplasmic aspartate transaminase holoenzyme. Iriarte, A., Hubert, E., Kraft, K., Martinez-Carrion, M. J. Biol. Chem. (1984) [Pubmed]
  28. Two homogeneous immunoassays for pyridoxamine. Brandon, D.L., Corse, J.W., Windle, J.J., Layton, L.L. J. Immunol. Methods (1985) [Pubmed]
  29. Modified purification of pyridoxamine (pyridoxine) 5'-phosphate oxidase from rabbit liver by 5'-phosphopyridoxyl affinity chromatography. Bowers-Komro, D.M., Hagen, T.M., McCormick, D.B. Meth. Enzymol. (1986) [Pubmed]
  30. 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]
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