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Chemical Compound Review

arginine     (2S)-2-amino-5- (diaminomethylideneamino)pe...

Synonyms: Argamine, Arginina, Argivene, Levargin, Argininum, ...
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Disease relevance of arginine

  • The E. coli dnaY gene encodes an arginine transfer RNA [1].
  • We treated 10 patients with severe beta-thalassemia or sickle cell disease with arginine butyrate at an initial dose of 500 mg per kilogram of body weight per day (final dose, 2000 mg per kilogram per day), 6 days per week, for a mean (+/- SD) of 10 +/- 1.2 weeks (range, 9 to 13) [2].
  • Islet function was assessed by measuring the plasma insulin responses to intravenous glucose and arginine and the plasma glucagon responses to hypoglycemia and arginine [3].
  • CONCLUSIONS: Infants with persistent pulmonary hypertension have low plasma concentrations of arginine and nitric oxide metabolites [4].
  • Effect of L-arginine on plasminogen-activator inhibitor in hypertensive patients with hypercholesterolemia [5].
  • Parenteral L-arginine monotherapy was markedly harmful in animals with septic shock [6].
  • This suggests that L-arginine can block the formation and development of colorectal tumors, and this effect might be related to the increased serum NO concentration and decreased ODC activity [7].
  • It details the processes by which intracellular and extracellular levels of l-arginine may influence nitric oxide production and further documents the imbalance that is evident in various cardiovascular disease states [8].
  • Potential mechanisms for beneficial effects of exogenous arginine in sepsis include enhanced (protein) metabolism, improved microcirculation and organ function, effects on immune function and antibacterial effects, improved gut function, and an antioxidant role of arginine [9].
  • While caution in the face of a lack of evidence for benefit in sepsis is commended, well-defined studies examining arginine monotherapy in the context of full nutritional support should be carried out so as to define the possible clinical uses of arginine in critically ill and septic patients [10].

Psychiatry related information on arginine


High impact information on arginine


Chemical compound and disease context of arginine


Biological context of arginine


Anatomical context of arginine


Associations of arginine with other chemical compounds


Gene context of arginine

  • Here we demonstrate arginine methylation of STAT1 by the protein arginine methyl-transferase PRMT1 as a novel requirement for IFNalpha/beta-induced transcription [39].
  • The results show that the leader peptide, the product of the upstream open reading frame, plays an essential, negative role in the specific repression of CPA1 by arginine [40].
  • Arginine methylation of STAT1 modulates IFNalpha/beta-induced transcription [39].
  • This inhibition arises from impaired STAT1-DNA binding due to an increased association of the STAT inhibitor PIAS1 with phosphorylated STAT1 dimers in the absence of arginine methylation [39].
  • The ARFGAP molecule binds to switch 2 and helix alpha3 to orient ARF1 residues for catalysis, but it supplies neither arginine nor other amino acid side chains to the GTPase active site [41].
  • Deletion of GCN4 (gcn4-Delta), in combination with btn1-Delta, results in a very specific growth requirement for arginine [42].
  • PRMT1 also does not prefer substrates already containing one or more singly or doubly methylated arginine residues [43].

Analytical, diagnostic and therapeutic context of arginine

  • Deletion of arginine 156 resulted in a peptide that was shown to be greatly superior in both dose response titrations and in its rate of association with cells to form targets [44].
  • Surprisingly, OAT-deficient mice produced by gene targeting exhibit neonatal hypoornithinaemia and lethality, rescuable by short-term arginine supplementation [45].
  • Using genome-wide linkage mapping and a positional candidate approach in a Saudi Arabian family affected with autosomal recessive SCAN1, we identified a homozygous mutation in TDP1 (A1478G) that results in the substitution of histidine 493 with an arginine residue [26].
  • Site-directed mutagenesis reveals role of mobile arginine residue in lactate dehydrogenase catalysis [46].
  • During a 30-minute period of perfusion with glucose and arginine, pancreases from vitamin D-deficient rats exhibited a 48 percent reduction in insulin secretion compared to that for pancreases from vitamin D-deficient rats that had been replenished with vitamin D. Vitamin D status had no effect on pancreatic glucagon secretion [47].


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  2. Extended therapy with intravenous arginine butyrate in patients with beta-hemoglobinopathies. Sher, G.D., Ginder, G.D., Little, J., Yang, S., Dover, G.J., Olivieri, N.F. N. Engl. J. Med. (1995) [Pubmed]
  3. Preserved insulin secretion and insulin independence in recipients of islet autografts. Pyzdrowski, K.L., Kendall, D.M., Halter, J.B., Nakhleh, R.E., Sutherland, D.E., Robertson, R.P. N. Engl. J. Med. (1992) [Pubmed]
  4. Neonatal pulmonary hypertension--urea-cycle intermediates, nitric oxide production, and carbamoyl-phosphate synthetase function. Pearson, D.L., Dawling, S., Walsh, W.F., Haines, J.L., Christman, B.W., Bazyk, A., Scott, N., Summar, M.L. N. Engl. J. Med. (2001) [Pubmed]
  5. Effect of L-arginine on plasminogen-activator inhibitor in hypertensive patients with hypercholesterolemia. Korbut, R., Bieron, K., Gryglewski, R.J. N. Engl. J. Med. (1993) [Pubmed]
  6. Preclinical trial of L-arginine monotherapy alone or with N-acetylcysteine in septic shock. Kalil, A.C., Sevransky, J.E., Myers, D.E., Esposito, C., Vandivier, R.W., Eichacker, P., Susla, G.M., Solomon, S.B., Csako, G., Costello, R., Sittler, K.J., Banks, S., Natanson, C., Danner, R.L. Crit. Care Med. (2006) [Pubmed]
  7. L-arginine reduces cell proliferation and ornithine decarboxylase activity in patients with colorectal adenoma and adenocarcinoma. Ma, Q., Wang, Y., Gao, X., Ma, Z., Song, Z. Clin. Cancer Res. (2007) [Pubmed]
  8. L-arginine transporters in cardiovascular disease: a novel therapeutic target. Chin-Dusting, J.P., Willems, L., Kaye, D.M. Pharmacol. Ther. (2007) [Pubmed]
  9. Exogenous arginine in sepsis. Luiking, Y.C., Deutz, N.E. Crit. Care Med. (2007) [Pubmed]
  10. Use of exogenous arginine in multiple organ dysfunction syndrome and sepsis. Barbul, A., Uliyargoli, A. Crit. Care Med. (2007) [Pubmed]
  11. Abnormalities in plasma and cerebrospinal-fluid arginine vasopressin in patients with anorexia nervosa. Gold, P.W., Kaye, W., Robertson, G.L., Ebert, M. N. Engl. J. Med. (1983) [Pubmed]
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  13. The arginine/nitric oxide pathway modulates sphincter of Oddi motor activity in guinea pigs and rabbits. Mourelle, M., Guarner, F., Moncada, S., Malagelada, J.R. Gastroenterology (1993) [Pubmed]
  14. Cerebrospinal fluid vasopressin, oxytocin, somatostatin, and beta-endorphin in Alzheimer's disease. Raskind, M.A., Peskind, E.R., Lampe, T.H., Risse, S.C., Taborsky, G.J., Dorsa, D. Arch. Gen. Psychiatry (1986) [Pubmed]
  15. Elevated cerebrospinal fluid levels of oxytocin in obsessive-compulsive disorder. Comparison with Tourette's syndrome and healthy controls. Leckman, J.F., Goodman, W.K., North, W.G., Chappell, P.B., Price, L.H., Pauls, D.L., Anderson, G.M., Riddle, M.A., McSwiggan-Hardin, M., McDougle, C.J. Arch. Gen. Psychiatry (1994) [Pubmed]
  16. Hyperalimentation in cancer. Souba, W.W., Copeland, E.M. CA: a cancer journal for clinicians. (1989) [Pubmed]
  17. Nitric oxide in health and disease of the respiratory system. Ricciardolo, F.L., Sterk, P.J., Gaston, B., Folkerts, G. Physiol. Rev. (2004) [Pubmed]
  18. Regulation of amino acid and glucose transporters in endothelial and smooth muscle cells. Mann, G.E., Yudilevich, D.L., Sobrevia, L. Physiol. Rev. (2003) [Pubmed]
  19. Histone deimination antagonizes arginine methylation. Cuthbert, G.L., Daujat, S., Snowden, A.W., Erdjument-Bromage, H., Hagiwara, T., Yamada, M., Schneider, R., Gregory, P.D., Tempst, P., Bannister, A.J., Kouzarides, T. Cell (2004) [Pubmed]
  20. Arginine methylation of STAT1: a reassessment. Meissner, T., Krause, E., Lödige, I., Vinkemeier, U. Cell (2004) [Pubmed]
  21. Hemodynamic and coagulation responses to 1-desamino[8-D-arginine] vasopressin in patients with congenital nephrogenic diabetes insipidus. Bichet, D.G., Razi, M., Lonergan, M., Arthus, M.F., Papukna, V., Kortas, C., Barjon, J.N. N. Engl. J. Med. (1988) [Pubmed]
  22. Missense glucokinase mutation in maturity-onset diabetes of the young and mutation screening in late-onset diabetes. Stoffel, M., Patel, P., Lo, Y.M., Hattersley, A.T., Lucassen, A.M., Page, R., Bell, J.I., Bell, G.I., Turner, R.C., Wainscoat, J.S. Nat. Genet. (1992) [Pubmed]
  23. A single amino acid substitution within the matrix protein of a type D retrovirus converts its morphogenesis to that of a type C retrovirus. Rhee, S.S., Hunter, E. Cell (1990) [Pubmed]
  24. Ornithine transcarbamylase deficiency. Unsuccessful therapy of neonatal hyperammonemia with N-carbamyl-L-glutamate and L-arginine. Gelehrter, T.D., Rosenberg, L.E. N. Engl. J. Med. (1975) [Pubmed]
  25. Mutations in the active site of Escherichia coli phosphofructokinase. Hellinga, H.W., Evans, P.R. Nature (1987) [Pubmed]
  26. Mutation of TDP1, encoding a topoisomerase I-dependent DNA damage repair enzyme, in spinocerebellar ataxia with axonal neuropathy. Takashima, H., Boerkoel, C.F., John, J., Saifi, G.M., Salih, M.A., Armstrong, D., Mao, Y., Quiocho, F.A., Roa, B.B., Nakagawa, M., Stockton, D.W., Lupski, J.R. Nat. Genet. (2002) [Pubmed]
  27. The genetic basis of epidermolytic hyperkeratosis: a disorder of differentiation-specific epidermal keratin genes. Cheng, J., Syder, A.J., Yu, Q.C., Letai, A., Paller, A.S., Fuchs, E. Cell (1992) [Pubmed]
  28. Vascular dysmorphogenesis caused by an activating mutation in the receptor tyrosine kinase TIE2. Vikkula, M., Boon, L.M., Carraway, K.L., Calvert, J.T., Diamonti, A.J., Goumnerov, B., Pasyk, K.A., Marchuk, D.A., Warman, M.L., Cantley, L.C., Mulliken, J.B., Olsen, B.R. Cell (1996) [Pubmed]
  29. Altered platelet calcium metabolism as an early predictor of increased peripheral vascular resistance and preeclampsia in urban black women. Zemel, M.B., Zemel, P.C., Berry, S., Norman, G., Kowalczyk, C., Sokol, R.J., Standley, P.R., Walsh, M.F., Sowers, J.R. N. Engl. J. Med. (1990) [Pubmed]
  30. Non-type I cystinuria caused by mutations in SLC7A9, encoding a subunit (bo,+AT) of rBAT. Feliubadaló, L., Font, M., Purroy, J., Rousaud, F., Estivill, X., Nunes, V., Golomb, E., Centola, M., Aksentijevich, I., Kreiss, Y., Goldman, B., Pras, M., Kastner, D.L., Pras, E., Gasparini, P., Bisceglia, L., Beccia, E., Gallucci, M., de Sanctis, L., Ponzone, A., Rizzoni, G.F., Zelante, L., Bassi, M.T., George, A.L., Manzoni, M., De Grandi, A., Riboni, M., Endsley, J.K., Ballabio, A., Borsani, G., Reig, N., Fernández, E., Estévez, R., Pineda, M., Torrents, D., Camps, M., Lloberas, J., Zorzano, A., Palacín, M. Nat. Genet. (1999) [Pubmed]
  31. The zipper model of translational control: a small upstream ORF is the switch that controls structural remodeling of an mRNA leader. Yaman, I., Fernandez, J., Liu, H., Caprara, M., Komar, A.A., Koromilas, A.E., Zhou, L., Snider, M.D., Scheuner, D., Kaufman, R.J., Hatzoglou, M. Cell (2003) [Pubmed]
  32. Vascular endothelial cells synthesize nitric oxide from L-arginine. Palmer, R.M., Ashton, D.S., Moncada, S. Nature (1988) [Pubmed]
  33. Anticystinuric effects of glutamine and of dietary sodium restriction. Jaeger, P., Portmann, L., Saunders, A., Rosenberg, L.E., Thier, S.O. N. Engl. J. Med. (1986) [Pubmed]
  34. Autosomal dominant and recessive osteochondrodysplasias associated with the COL11A2 locus. Vikkula, M., Mariman, E.C., Lui, V.C., Zhidkova, N.I., Tiller, G.E., Goldring, M.B., van Beersum, S.E., de Waal Malefijt, M.C., van den Hoogen, F.H., Ropers, H.H. Cell (1995) [Pubmed]
  35. Mutations in the gene for transglutaminase 1 in autosomal recessive lamellar ichthyosis. Russell, L.J., DiGiovanna, J.J., Rogers, G.R., Steinert, P.M., Hashem, N., Compton, J.G., Bale, S.J. Nat. Genet. (1995) [Pubmed]
  36. Primary structure of the human splicing factor ASF reveals similarities with Drosophila regulators. Ge, H., Zuo, P., Manley, J.L. Cell (1991) [Pubmed]
  37. Receptor-mediated activation of nitric oxide synthesis by arginine in endothelial cells. Joshi, M.S., Ferguson, T.B., Johnson, F.K., Johnson, R.A., Parthasarathy, S., Lancaster, J.R. Proc. Natl. Acad. Sci. U.S.A. (2007) [Pubmed]
  38. Recovery of endothelial function in severe falciparum malaria: relationship with improvement in plasma L-arginine and blood lactate concentrations. Yeo, T.W., Lampah, D.A., Gitawati, R., Tjitra, E., Kenangalem, E., McNeil, Y.R., Darcy, C.J., Granger, D.L., Weinberg, J.B., Lopansri, B.K., Price, R.N., Duffull, S.B., Celermajer, D.S., Anstey, N.M. J. Infect. Dis. (2008) [Pubmed]
  39. Arginine methylation of STAT1 modulates IFNalpha/beta-induced transcription. Mowen, K.A., Tang, J., Zhu, W., Schurter, B.T., Shuai, K., Herschman, H.R., David, M. Cell (2001) [Pubmed]
  40. The leader peptide of yeast gene CPA1 is essential for the translational repression of its expression. Werner, M., Feller, A., Messenguy, F., Piérard, A. Cell (1987) [Pubmed]
  41. Structural and functional analysis of the ARF1-ARFGAP complex reveals a role for coatomer in GTP hydrolysis. Goldberg, J. Cell (1999) [Pubmed]
  42. Absence of Btn1p in the yeast model for juvenile Batten disease may cause arginine to become toxic to yeast cells. Vitiello, S.P., Wolfe, D.M., Pearce, D.A. Hum. Mol. Genet. (2007) [Pubmed]
  43. Type I Arginine Methyltransferases PRMT1 and PRMT-3 Act Distributively. Kölbel, K., Ihling, C., Bellmann-Sickert, K., Neundorf, I., Beck-Sickinger, A.G., Sinz, A., Kühn, U., Wahle, E. J. Biol. Chem. (2009) [Pubmed]
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  45. Mice lacking ornithine-delta-aminotransferase have paradoxical neonatal hypoornithinaemia and retinal degeneration. Wang, T., Lawler, A.M., Steel, G., Sipila, I., Milam, A.H., Valle, D. Nat. Genet. (1995) [Pubmed]
  46. Site-directed mutagenesis reveals role of mobile arginine residue in lactate dehydrogenase catalysis. Clarke, A.R., Wigley, D.B., Chia, W.N., Barstow, D., Atkinson, T., Holbrook, J.J. Nature (1986) [Pubmed]
  47. Vitamin D deficiency inhibits pancreatic secretion of insulin. Norman, A.W., Frankel, J.B., Heldt, A.M., Grodsky, G.M. Science (1980) [Pubmed]
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