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Chemical Compound Review

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

Synonyms: D-Arginin, D-Arginine, D-Arg, H-D-Arginine, H-D-Arg-OH, ...
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Disease relevance of arginine


Psychiatry related information on arginine


High impact information on arginine

  • L-NAME-induced constriction was completely reversed by adding 10(-3) M L-arginine (the precursor of nitric oxide) but not D-arginine (an inactive isomer) to the macula densa perfusate [7].
  • The shortening effect of L-NMMA on bleeding time was completely reversed by giving the animals the NO precursor L-arginine, but not D-arginine, which is not a precursor of NO [8].
  • METHODS: L-Glutamate, L-arginine, D-arginine, the NO donor S-nitroso-N-acetyl-penicillamine, and the NO synthase inhibitor NG-nitro-L-arginine-methyl ester were unilaterally microinjected into the rostral dorsal motor nucleus of anesthetized cats, and antral and pyloric motility were monitored using extraluminal force transducers [9].
  • Both these actions of L-NMMA were reversed by L-arginine (300, but not by D-arginine (300, indomethacin (1, prazosin (0.3, or by vagotomy [10].
  • Further studies in isolated adult rat cardiac myocytes elicited similar results, in that 50 mmol/L of L- and D-arginine equally decreased contraction amplitude and the underlying cytosolic calcium transient [11].

Chemical compound and disease context of arginine


Biological context of arginine


Anatomical context of arginine

  • L-NAME, or L- or D-arginine was continuously infused into the left anterior descending coronary artery (LAD) starting just prior to reperfusion, whereas SOD was intravenously injected before occlusion [21].
  • Pretreatment of the endothelium with the inactive stereoisomer D-arginine had no effect on neutrophil deposition [22].
  • To study the role of nitric oxide (NO), HC rats were treated with an infusion of L-arginine or D-arginine (150 mg via femoral artery) in a 50 mg bolus before RC administration and the remaining dose continuously for a period of one hour [23].
  • Endothelial pretreatment with D-arginine, or with L-arginine, in the absence or presence of L-NAME, did not significantly influence platelet interaction with the thrombogenic arterial media at intermediate and high shear rates [22].
  • Furthermore, we found that D-ArgGal (1) penetrated cell membranes more rapidly than its precursor D-arginine, (2) released arginine more slowly and in greater amounts than L-ArgGal, and (3) produced much higher levels of DAF-2 monitored NO and nitrite than did L-ArgGal under the same experimental conditions [24].

Associations of arginine with other chemical compounds


Gene context of arginine

  • Administration of L-arginine, but not D-arginine (100 mg/kg), used as a substrate for basal NO synthesis and which did not by itself alter the activity of the hypothalamic-pituitary-adrenal (HPA) axis, blunted IL-1-induced ACTH secretion, and reversed the interaction between L-NAME and IL-1 beta [30].
  • 2+/-15.8 pmol/mm per minute (P<0.01) in C57BL/6J wild-type mice, whereas addition of D-Arginine had no effects on J(Cl.) In contrast, addition of 0.5 mmol/L L-Arg to the bath did not alter J(Cl) of THALs from eNOS knockout mice [31].
  • This is in contrast to rat and murine CAT-3 proteins that have been reported to display a very low activity and to be inhibited by neutral and anionic L-amino acids as well as D-arginine (Hosokawa, H., et al. (1997) J. Biol. Chem. 272, 8717-8722; Ito, K., and Groudine, M. (1997) J. Biol. Chem. 272, 26780-26786) [32].
  • IL-1 beta-induced NOx production and intracellular cyclic GMP formation were similarly blocked by an NO synthase inhibitor, NG-monomethyl-L-arginine (LNMMA), whose effect was reversed by L-arginine, but not by D-arginine [33].
  • A shift of the guanido group further away from the backbone (D-arginine to D-homoarginine) resulted in a loss of tPA activating properties [34].

Analytical, diagnostic and therapeutic context of arginine


  1. Prolonged administration of L-arginine ameliorates chronic pulmonary hypertension and pulmonary vascular remodeling in rats. Mitani, Y., Maruyama, K., Sakurai, M. Circulation (1997) [Pubmed]
  2. Renal intramedullary infusion of L-arginine prevents reduction of medullary blood flow and hypertension in Dahl salt-sensitive rats. Miyata, N., Cowley, A.W. Hypertension (1999) [Pubmed]
  3. Cardiac enkephalins attenuate vagal bradycardia: interactions with NOS-1-cGMP systems in canine sinoatrial node. Farias, M., Jackson, K., Johnson, M., Caffrey, J.L. Am. J. Physiol. Heart Circ. Physiol. (2003) [Pubmed]
  4. Involvement of endogenous nitric oxide in the mechanism of bradykinin-induced peripheral hyperalgesia. Nakamura, A., Fujita, M., Shiomi, H. Br. J. Pharmacol. (1996) [Pubmed]
  5. Nitric oxide (NO) inhibits release of acetylcholine from nerves of isolated circular muscle of the canine ileum: relationship to motility and release of nitric oxide. Hryhorenko, L.M., Woskowska, Z., Fox-Threlkeld, J.A. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  6. Mediation by nitric oxide formation in the preoptic area of endotoxin and tumour necrosis factor-induced inhibition of water intake in the rat. Calapai, G., Mazzaglia, G., Cilia, M., Zingarelli, B., Squadrito, F., Caputi, A.P. Br. J. Pharmacol. (1994) [Pubmed]
  7. Evidence for the role of nitric oxide in macula densa control of glomerular hemodynamics. Ito, S., Ren, Y. J. Clin. Invest. (1993) [Pubmed]
  8. Role of endothelium-derived nitric oxide in the bleeding tendency of uremia. Remuzzi, G., Perico, N., Zoja, C., Corna, D., Macconi, D., Viganò, G. J. Clin. Invest. (1990) [Pubmed]
  9. Functional evidence for the presence of nitric oxide synthase in the dorsal motor nucleus of the vagus. Panico, W.H., Cavuto, N.J., Kallimanis, G., Nguyen, C., Armstrong, D.M., Benjamin, S.B., Gillis, R.A., Travagli, R.A. Gastroenterology (1995) [Pubmed]
  10. Role of endothelium-derived nitric oxide in the regulation of blood pressure. Rees, D.D., Palmer, R.M., Moncada, S. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  11. Physiological concentrations of nitric oxide do not elicit an acute negative inotropic effect in unstimulated cardiac muscle. Weyrich, A.S., Ma, X.L., Buerke, M., Murohara, T., Armstead, V.E., Lefer, A.M., Nicolas, J.M., Thomas, A.P., Lefer, D.J., Vinten-Johansen, J. Circ. Res. (1994) [Pubmed]
  12. Effect of L-arginine on endothelial injury and hemostasis in rabbit endotoxin shock. Wiel, E., Pu, Q., Corseaux, D., Robin, E., Bordet, R., Lund, N., Jude, B., Vallet, B. J. Appl. Physiol. (2000) [Pubmed]
  13. Acceleration of ulcer healing by cholecystokinin (CCK): role of CCK-A receptors, somatostatin, nitric oxide and sensory nerves. Brzozowski, T., Konturek, P.C., Konturek, S.J., Pajdo, R., Drozdowicz, D., Kwiecień, S., Hahn, E.G. Regul. Pept. (1999) [Pubmed]
  14. Catalepsy induced by intra-striatal administration of nitric oxide synthase inhibitors in rats. Del Bel, E.A., da Silva, C.A., Guimarães, F.S., Bermúdez-Echeverry, M. Eur. J. Pharmacol. (2004) [Pubmed]
  15. Arginine in burn injury improves cardiac performance and prevents bacterial translocation. Horton, J.W., White, J., Maass, D., Sanders, B. J. Appl. Physiol. (1998) [Pubmed]
  16. Effectiveness of D-arginine vasopressin in von Willebrand's disease. Bala, L., Boggio, L., Green, D. Current hematology reports. (2005) [Pubmed]
  17. Does acute improvement of endothelial dysfunction in coronary artery disease improve myocardial ischemia? A double-blind comparison of parenteral D- and L-arginine. Quyyumi, A.A. J. Am. Coll. Cardiol. (1998) [Pubmed]
  18. Renal vasodilation with L-arginine. Effects of dietary salt. Deng, X., Welch, W.J., Wilcox, C.S. Hypertension (1995) [Pubmed]
  19. Molecular basis for the antiproliferative effect of agmatine in tumor cells of colonic, hepatic, and neuronal origin. Wolf, C., Br??ss, M., H??nisch, B., G??thert, M., von K??gelgen, I., Molderings, G.J. Mol. Pharmacol. (2007) [Pubmed]
  20. Kinetics, pharmacology, and autoradiographic distribution of L-[3H]nitroarginine binding sites in rat cerebellum. Rao, V.L., Butterworth, R.F. J. Neurochem. (1996) [Pubmed]
  21. Intra-coronary administration of L-arginine aggravates myocardial stunning through production of peroxynitrite in dogs. Mori, E., Haramaki, N., Ikeda, H., Imaizumi, T. Cardiovasc. Res. (1998) [Pubmed]
  22. Endothelium-derived nitric oxide decreases polymorphonuclear leukocyte interaction with the deeply injured arterial wall under intermediate and high shear conditions. Provost, P., Merhi, Y. Thromb. Haemost. (1997) [Pubmed]
  23. Hypercholesterolemia aggravates radiocontrast nephrotoxicity: protective role of L-arginine. Andrade, L., Campos, S.B., Seguro, A.C. Kidney Int. (1998) [Pubmed]
  24. Galactosyl derivatives of L-arginine and D-arginine: synthesis, stability, cell permeation, and nitric oxide production in pituitary GH3 cells. Melisi, D., Secondo, A., Montoro, P., Piacente, S., Rimoli, M.G., Minale, M., de Caprariis, P., Annunziato, L. J. Med. Chem. (2006) [Pubmed]
  25. Nitric oxide synthase inhibitors attenuate human monocyte chemotaxis in vitro. Belenky, S.N., Robbins, R.A., Rubinstein, I. J. Leukoc. Biol. (1993) [Pubmed]
  26. Supplemental L-arginine HCl augments bacterial phagocytosis in human polymorphonuclear leukocytes. Moffat, F.L., Han, T., Li, Z.M., Peck, M.D., Jy, W., Ahn, Y.S., Chu, A.J., Bourguignon, L.Y. J. Cell. Physiol. (1996) [Pubmed]
  27. Limited proteolysis and X-ray crystallography reveal the origin of substrate specificity and of the rate-limiting product release during oxidation of D-amino acids catalyzed by mammalian D-amino acid oxidase. Vanoni, M.A., Cosma, A., Mazzeo, D., Mattevi, A., Todone, F., Curti, B. Biochemistry (1997) [Pubmed]
  28. In vivo administration of D-arginine: effects on blood pressure and vascular function in angiotensin II-induced hypertensive rats. Wölkart, G., Stessel, H., Brunner, F. Atherosclerosis (2004) [Pubmed]
  29. L-arginine attenuates ketamine-induced increase in renal sympathetic nerve activity. Okamoto, H., Hoka, S., Kawasaki, T., Okuyama, T., Takahashi, S. Anesthesiology (1994) [Pubmed]
  30. In the rat, endogenous nitric oxide modulates the response of the hypothalamic-pituitary-adrenal axis to interleukin-1 beta, vasopressin, and oxytocin. Rivier, C., Shen, G.H. J. Neurosci. (1994) [Pubmed]
  31. eNOS mediates L-arginine-induced inhibition of thick ascending limb chloride flux. Plato, C.F., Shesely, E.G., Garvin, J.L. Hypertension (2000) [Pubmed]
  32. Human cationic amino acid transporter hCAT-3 is preferentially expressed in peripheral tissues. Vékony, N., Wolf, S., Boissel, J.P., Gnauert, K., Closs, E.I. Biochemistry (2001) [Pubmed]
  33. Interleukin-1 beta induces nitric oxide production by a mouse pituitary tumour cell line (AtT20/D16). Ohta, K., Hirata, Y., Imai, T., Marumo, F. J. Endocrinol. (1993) [Pubmed]
  34. Tissue plasminogen activator enhancing activity of vasopressin analogues in monkeys: structure-activity study. Vilhardt, H., Barth, T. J. Recept. Res. (1993) [Pubmed]
  35. The role of L-arginine in ameliorating reperfusion injury after myocardial ischemia in the cat. Weyrich, A.S., Ma, X.L., Lefer, A.M. Circulation (1992) [Pubmed]
  36. L-arginine may mediate the therapeutic effects of low protein diets. Narita, I., Border, W.A., Ketteler, M., Ruoslahti, E., Noble, N.A. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  37. Effects of L-arginine on forearm vessels and responses to acetylcholine. Imaizumi, T., Hirooka, Y., Masaki, H., Harada, S., Momohara, M., Tagawa, T., Takeshita, A. Hypertension (1992) [Pubmed]
  38. Protective effects of dietary L-arginine supplementation on chronic cyclosporine nephrotoxicity. Andoh, T.F., Gardner, M.P., Bennett, W.M. Transplantation (1997) [Pubmed]
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