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Chemical Compound Review

A1332_SIGMA     azane; 2-hydroxypropane-1,2,3...

Synonyms: AC1O5KKG, LS-54362, FT-0624617, FT-0634868, ST51037174, ...
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Disease relevance of citric acid


High impact information on citric acid

  • Growth factor stimulation of DNA synthesis and electron transport are restored by addition of di- or trivalent iron to the cells in the form of ferric ammonium citrate, ferrous ammonium sulfate, or diferric transferrin [6].
  • After adding iron as ferric ammonium citrate to the medium, latent ferritin H- and L-mRNAs were extensively transferred to polyribosomes, accompanied by increased uptake of [35S]methionine into ferritin protein [7].
  • Furthermore, cytoplasmic or mitochondrial Fe loading of induced Friend cells with ferric ammonium citrate, or the heme synthesis inhibitor, succinylacetone, respectively, also had no effect on frataxin expression [8].
  • Similarly, treatment with soluble iron as ferric ammonium citrate did not increase steady state levels of PKC-beta mRNA, despite producing a marked increase in cellular ferritin content [9].
  • The levels of receptor were reduced by at least 50 and 35% of that of the control in cells treated with diferric Tf and ferric ammonium citrate, respectively [10].

Chemical compound and disease context of citric acid


Biological context of citric acid

  • The regulation of ferritin synthesis by iron was examined in the reticulocytes of bullfrog tadpoles where the induction was 40- to 50-fold, increasing from 0.17 +/- 0.05% of total protein synthesis ([3H]leucine incorporation in cell suspension) to 7.4 +/- 1.6% following intraperitoneal injection of ferric ammonium citrate [15].
  • Intraperitoneal LD50 of the luxSVv mutant increased by 10- and 750-fold in ferric ammonium citrate-non-overloaded and ferric ammonium citrate-overloaded mice respectively [16].
  • Competition studies with unlabelled ligand or impermeable ferric ammonium citrate gave an IC50 of 1-15 micrograms Fe3+/ml for this process [17].
  • Effect of hemoglobin and of ferric ammonium citrate on the virulence of periodontopathic bacteria [18].
  • The effect of iron loading on membrane potential and cellular contractility was examined in cultured heart cells obtained from newborn rat ventricles exposed to ferric ammonium citrate at iron concentrations of 20, 40, and 80 micrograms/ml for 24 hours [19].

Anatomical context of citric acid


Associations of citric acid with other chemical compounds


Gene context of citric acid

  • These data conclusively demonstrate that two entirely different mechanisms of iron uptake from Tf exist in melanoma cells and that ferric ammonium citrate may be a useful experimental tool to further characterize the specific and nonspecific mechanisms of Fe uptake from Tf [1].
  • Significantly, the effect of chelation on reducing nuclear p21(CIP1/WAF1) was reversed by the Fe donor ferric ammonium citrate, indicating that p21(CIP1/WAF1) translation was dependent on intracellular Fe levels [29].
  • In contrast, these tonB mutants were able to utilize an iron chelate (ferric ammonium citrate) for growth [30].
  • The growth of pathogenic and non-pathogenic strains of V. parahaemolyticus on iron-limited agar plates was stimulated by ferritin, lactoferrin and transferrin at 30 microM, and also by hemin, hemoglobin and ferric ammonium citrate at 100 microM [31].
  • Treatment of murine J774 macrophages with increasing concentrations of ferric ammonium citrate significantly enhanced the amount of MMP-9 secreted [32].

Analytical, diagnostic and therapeutic context of citric acid

  • These results suggest that ammonium sulphate and ammonium citrate might be very suitable precipitants for crystallization studies of the ternary complex [33].
  • By addition of Fe3+ (50 microM ferric ammonium citrate) to an acidified aqueous mobile phase, we have successfully separated a series of hydroxypyridones-including CP20-and the related pyrones maltol and ethylmaltol by HPLC on microBondapak C18 [34].
  • M0s in culture were exposed to iron as either ferric ammonium citrate or iron dextran, and ferritin synthesis was determined by measurement of 3H-leucine incorporation after isolation of ferritin by a quantitative immunoadsorbent technique [35].


  1. Two mechanisms of iron uptake from transferrin by melanoma cells. The effect of desferrioxamine and ferric ammonium citrate. Richardson, D., Baker, E. J. Biol. Chem. (1992) [Pubmed]
  2. Iron accumulation, iron-mediated toxicity and altered levels of ferritin and transferrin receptor in cultured astrocytes during incubation with ferric ammonium citrate. Hoepken, H.H., Korten, T., Robinson, S.R., Dringen, R. J. Neurochem. (2004) [Pubmed]
  3. Hypoxia alters iron homeostasis and induces ferritin synthesis in oligodendrocytes. Qi, Y., Jamindar, T.M., Dawson, G. J. Neurochem. (1995) [Pubmed]
  4. Mycobacteria with a growth requirement for ferric ammonium citrate, identified as Mycobacterium haemophilum. Dawson, D.J., Jennis, F. J. Clin. Microbiol. (1980) [Pubmed]
  5. Studies of iron overload. Rat liver siderosome ferritin. Richter, G.W. Lab. Invest. (1984) [Pubmed]
  6. Iron reverses impermeable chelator inhibition of DNA synthesis in CCl 39 cells. Alcain, F.J., Löw, H., Crane, F.L. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  7. Translation of ferritin light and heavy subunit mRNAs is regulated by intracellular chelatable iron levels in rat hepatoma cells. Rogers, J., Munro, H. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  8. Erythroid differentiation and protoporphyrin IX down-regulate frataxin expression in Friend cells: characterization of frataxin expression compared to molecules involved in iron metabolism and hemoglobinization. Becker, E.M., Greer, J.M., Ponka, P., Richardson, D.R. Blood (2002) [Pubmed]
  9. Induction of protein kinase C mRNA in cultured lymphoblastoid T cells by iron-transferrin but not by soluble iron. Alcantara, O., Javors, M., Boldt, D.H. Blood (1991) [Pubmed]
  10. Effects of alterations in cellular iron on biosynthesis of the transferrin receptor in K562 cells. Rao, K.K., Shapiro, D., Mattia, E., Bridges, K., Klausner, R. Mol. Cell. Biol. (1985) [Pubmed]
  11. Regulation of sinefungin biosynthesis by the wild-type strain and mutants of Streptomyces incarnatus. Malina, H., Robert-Gero, M. Appl. Environ. Microbiol. (1988) [Pubmed]
  12. Glutathione peroxidase 1 and glutathione are required to protect mouse astrocytes from iron-mediated hydrogen peroxide toxicity. Liddell, J.R., Hoepken, H.H., Crack, P.J., Robinson, S.R., Dringen, R. J. Neurosci. Res. (2006) [Pubmed]
  13. Enzymic synthesis of the 4Fe-4S clusters of Clostridium pasteurianum ferredoxin. Bonomi, F., Pagani, S., Kurtz, D.M. Eur. J. Biochem. (1985) [Pubmed]
  14. Reduction of ferric iron by Listeria monocytogenes and other species of Listeria. Deneer, H.G., Boychuk, I. Can. J. Microbiol. (1993) [Pubmed]
  15. Translational control of ferritin synthesis by iron in embryonic reticulocytes of the bullfrog. Shull, G.E., Theil, E.C. J. Biol. Chem. (1982) [Pubmed]
  16. Regulation of Vibrio vulnificus virulence by the LuxS quorum-sensing system. Kim, S.Y., Lee, S.E., Kim, Y.R., Kim, C.M., Ryu, P.Y., Choy, H.E., Chung, S.S., Rhee, J.H. Mol. Microbiol. (2003) [Pubmed]
  17. Fe3+(2)-transferrin and Fe3+(2)-asialotransferrin deliver iron to hepatocytes by an identical mechanism. Sharma, R.J., Grant, D.A. Eur. J. Biochem. (1991) [Pubmed]
  18. Effect of hemoglobin and of ferric ammonium citrate on the virulence of periodontopathic bacteria. Mukherjee, S., Murphy, R.A., Wawszkiewcz, E.J. Oral Microbiol. Immunol. (1988) [Pubmed]
  19. Effect of iron loading on transmembrane potential, contraction, and automaticity of rat ventricular muscle cells in culture. Link, G., Athias, P., Grynberg, A., Pinson, A., Hershko, C. J. Lab. Clin. Med. (1989) [Pubmed]
  20. Fluctuations of intracellular iron modulate elastin production. Bunda, S., Kaviani, N., Hinek, A. J. Biol. Chem. (2005) [Pubmed]
  21. Expression of transferrin receptors in phytohemagglutinin-stimulated human T-lymphocytes. Evidence for a three-step model. Pelosi, E., Testa, U., Louache, F., Thomopoulos, P., Salvo, G., Samoggia, P., Peschle, C. J. Biol. Chem. (1986) [Pubmed]
  22. Heme regulation of HeLa cell transferrin receptor number. Ward, J.H., Jordan, I., Kushner, J.P., Kaplan, J. J. Biol. Chem. (1984) [Pubmed]
  23. Iron loading of isolated rat hepatocytes inhibits asialoglycoprotein receptor dynamics and induces formation of rat hepatic lectin-1 [correction of leptin-1] (RHL-1) oligomers. McAbee, D.D., Ling, Y.Y., Stich, C. Biochem. J. (1998) [Pubmed]
  24. Human Abeta1-42 reduces iron-induced toxicity in rat cerebral cortex. Bishop, G.M., Robinson, S.R. J. Neurosci. Res. (2003) [Pubmed]
  25. Iron released by sodium nitroprusside contributes to heme oxygenase-1 induction via the cAMP-protein kinase A-mitogen-activated protein kinase pathway in RAW 264.7 cells. Kim, H.J., Tsoy, I., Park, M.K., Lee, Y.S., Lee, J.H., Seo, H.G., Chang, K.C. Mol. Pharmacol. (2006) [Pubmed]
  26. Improving spot homogeneity by using polymer substrates in matrix-assisted laser desorption/ionization mass spectrometry of oligonucleotides. Kim, Y., Hurst, G.B., Doktycz, M.J., Buchanan, M.V. Anal. Chem. (2001) [Pubmed]
  27. Direct determination of gentamicin components by capillary electrophoresis with potential gradient detection. Yuan, L., Wei, H., Li, S.F. Electrophoresis (2005) [Pubmed]
  28. Citrate therapy for polycystic kidney disease in rats. Tanner, G.A., Tanner, J.A. Kidney Int. (2000) [Pubmed]
  29. Potent iron chelators increase the mRNA levels of the universal cyclin-dependent kinase inhibitor p21(CIP1/WAF1), but paradoxically inhibit its translation: a potential mechanism of cell cycle dysregulation. Le, N.T., Richardson, D.R. Carcinogenesis (2003) [Pubmed]
  30. Utilization of transferrin-bound iron by Haemophilus influenzae requires an intact tonB gene. Jarosik, G.P., Maciver, I., Hansen, E.J. Infect. Immun. (1995) [Pubmed]
  31. Utilization of iron sources and its possible roles in the pathogenesis of Vibrio parahaemolyticus. Wong, H.C., Liu, C.C., Yu, C.M., Lee, Y.S. Microbiol. Immunol. (1996) [Pubmed]
  32. Dietary iron restriction increases plaque stability in apolipoprotein-e-deficient mice. Lee, H.T., Chiu, L.L., Lee, T.S., Tsai, H.L., Chau, L.Y. J. Biomed. Sci. (2003) [Pubmed]
  33. Stabilization of the ternary complex EF-Tu.GTP.valyl-tRNAval by ammonium salts. Antonsson, B., Leberman, R. Biochimie (1982) [Pubmed]
  34. Reversed-phase high-performance liquid chromatography of non-transferrin-bound iron and some hydroxypyridone and hydroxypyrone chelators. el-Jammal, A., Templeton, D.M. J. Chromatogr. B, Biomed. Appl. (1994) [Pubmed]
  35. Ferritin synthesis in peripheral blood monocytes in idiopathic hemochromatosis. Bassett, M.L., Halliday, J.W., Powell, L.W. J. Lab. Clin. Med. (1982) [Pubmed]
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