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Chemical Compound Review

argininate     2-amino-5- (diaminomethylideneamino) pentanoate

Synonyms: AC1NUTTA, arginine anion, arg(-), CHEBI:32695, 2-amino-5-guanidinopentanoate, ...
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Disease relevance of arginine

  • This study demonstrates that treatment with rabbit anti-human C5a des arg antibodies attenuates ARDS and some of the systemic manifestations of sepsis in nonhuman primates [1].
  • A competitive inhibitor of leukotriene slow-reacting substance of anaphylaxis, FPL 55712, blocked in a dose-response fashion LTB4-, C5a des arg-, and FMLP-triggered LAI [2].
  • Human recombinant gamma-interferon (rhu-IFN-gamma) and human recombinant alpha-interferon (rhu-IFN-alpha 2 arg) with a chemical purity of over 95% were compared for their antiproliferative and HLA-DR-inducing activity in five human breast cancer cell lines (BT 20, ZR 75.1, MCF 7, 734B, Hs578T) [3].
  • Here we show that mAb PAb421 when microinjected into human SW480 colorectal carcinoma cells restores the transcription activation function to the resident mutant p53 (arg to his 273, pro to ser 309) [4].
  • Novel (cys152 > arg) missense mutation in an Arab patient with Canavan disease [5].

Psychiatry related information on arginine


High impact information on arginine

  • The second sequence (val ser arg lys192 arg pro arg) may be structurally related to the SV40 signal, although it has little sequence homology and falls in a region of the protein that has no counterpart in SV40 large-T [7].
  • Arg is most abundant in adult mouse brain, especially in synapse-rich regions. arg(-/-) mice develop normally but exhibit multiple behavioral abnormalities, suggesting that arg(-/-) brains suffer from defects in neuronal function [8].
  • First, using leukocyte aggregometry, we demonstrated that the addition of a recently developed rabbit anti-human polyclonal antibody to C5a des arg to endotoxin-activated plasma prevented leukocyte aggregation in vitro [1].
  • Purified C5a and C5a des arg were essentially equal in their ability to enhance neutrophil adherence, in contrast to the previously described greater in vitro potency of C5a compared with C5a des arg in stimulating neutrophil chemotaxis and enzyme release [9].
  • Addition of either purified complement fragment C5a des arg, or formyl-methionyl-leucyl-phenylalanine (FMLP), in concentrations ranging from 10(-10) to 10(-6) M, increased neutrophil adherence to endothelium in a dose-dependent manner [9].

Chemical compound and disease context of arginine

  • In this longitudinal study of patients with CNS vasculitis, we detected C activation by highly sensitive and specific assays that are capable of identifying breakdown products formed after C activation: C3a des arg, C4a des arg, C5a des arg, C1rC1s-C1-inhibitor complex, and terminal C complex (C5b-9) [10].
  • Erwinia sp. donors harboring pULB113 complemented mutations in various biosynthetic and catabolic genes (arg, gal, his, leu, met, pro, pur, thy) in Escherichia coli recA strains [11].
  • Extent of genetic lesions of the arginine and pyrimidine biosynthetic pathways in Lactobacillus plantarum, L. paraplantarum, L. pentosus, and L. casei: prevalence of CO(2)-dependent auxotrophs and characterization of deficient arg genes in L. plantarum [12].
  • In previous studies, we have shown the clinical significance of arg tyrosine kinases in a colorectal cancer progression model [13].
  • Two of five PDC cases and one papillary carcinoma revealed point mutations in exon 8 as follows; GTG (val) to CTG (leu) at codon 272 in case 23T, CGA (arg) to CCA (pro) at codon 306 in case of 30T, and CGG (arg) to AGG (arg) at codon 282 in case 28T [14].

Biological context of arginine

  • Neutrophil-endothelial cell interactions. Modulation of neutrophil adhesiveness induced by complement fragments C5a and C5a des arg and formyl-methionyl-leucyl-phenylalanine in vitro [9].
  • The more common arg/arg genotype in whites may explain why whites are more prone to develop cardiac cancer, whereas the more common proline allele in blacks may explain why they are more prone to develop antral cancers [15].
  • Phosphorylation and glycosylation alterations in the arg mutant keratins may account for some of the potential changes in the cellular function of these proteins [16].
  • We have previously described partial genomic sequences of arg, a human gene related to c-abl, and shown that it is expressed as a 12-kilobase transcript and is located at chromosome position 1q24-25 [17].
  • To understand the relevance of p53 missense mutations in vivo, we generated a mouse containing an arg-to-his substitution at p53 amino acid 172, which corresponds to the R175H hot-spot mutation in human tumors by homologous recombination [18].

Anatomical context of arginine

  • This finding suggested that those monocytes stimulated to adhere by C5a des arg were the same subpopulation responding to FMLP [19].
  • The fixation of endothelial cell monolayers prior to the adherence assay did not alter the degree of spontaneous, C5a des arg-stimulated, or FMLP-stimulated monocyte adherence [19].
  • In addition, the adhesion-dependent stimulation of p190RhoGAP phosphorylation observed in wild-type cells is not observed in arg(-/-) fibroblasts and neurons [20].
  • Transfection of an arg construct lacking the PTS-1 directed the synthesis of an arg that mislocalized to the cytosol and notably also complemented the genetic lesion and restored polyamine prototrophy to the Deltaarg parasites [21].
  • C5a des arg or FMLP stimulated monocytes to adhere to monolayers of human vascular smooth muscle cells, human dermal fibroblasts, or serum-coated plastic wells in a comparable fashion as to endothelial cells [19].

Associations of arginine with other chemical compounds

  • Indomethacin (10(-5) M), piroxicam (10(-6) M), and aspirin, cyclooxygenase antagonists, negated LTB4-, C5a des arg-, and FMLP-induced LAI [2].
  • Integrin-mediated adhesion promotes relocalization of p190 and p120 to the cell periphery in wild-type fibroblasts, but not in arg(-/-) fibroblasts [22].
  • Phosphoamino acid analysis of the arg gene product following an immune complex autokinase reaction revealed tyrosine phosphorylation and established that it possesses tyrosine kinase activity [23].
  • Gel mobility shift and 1,25-dihydroxyvitamin D3-stimulated transcription assays verified that an hVDR-GR DBD chimera is functional on the rat osteocalcin VDRE with only the conservative change of lys-49 to arg, and of the negatively charged glu-53 to a basic amino acid (lys or arg) [24].
  • In HLMC preparations expressing beta2-adrenoceptors with arg (wild-type) or gly (mutant) at position 16, desensitization was 71 +/- 5% (n = 18) or 43 +/- 5%, (n = 26), respectively, whereas the desensitization was 59 +/- 6% (n = 28) for heterozygotes at this position [25].

Gene context of arginine

  • The argR control region contains two promoters, one of which overlaps the operator site and, as with other arg genes, consists of two adjacent palindromic sequences ("ARG boxes") [26].
  • The sequence of TAP2 gene identified a single mutation, a C to T substitution changing the CGA arg codon at amino acid 220 into TGA stop codon in exon 3 [27].
  • In vitro deletion of part of the vector's trp promoter did not affect complementation of the argB and C auxotrophs, implying that the S. coelicolor A3(2) arg genes may be expressed from their own promoter [28].
  • Association between the p21 codon 31 A1 (arg) allele and lung cancer [29].
  • Ultrasonic extracts of a range of clinical isolates of P. gingivalis cells and purified arg- and lys-gingipains were also assessed for their ability to activate pro-MMP-2 [30].

Analytical, diagnostic and therapeutic context of arginine

  • The effect of hemodialysis and C5a des arg on neutrophil subpopulations [31].
  • Heat lability and gel filtration HPLC characteristics suggested that the major chemokinetically active material in aqueous extracts of psoriatic scale is different from C5a des arg [32].
  • The recombinant arg protein was detected in bacterial lysates by immunoblotting and exhibited a molecular mass of 145 kDa [23].
  • This result was confirmed by extensive analysis of 50 additional matched sets of normal colon and colon-tumor specimens, using arg-specific primers and RT-PCR reactions [33].
  • N-terminal sequence analysis of the truncated 35,000-M(r) protein X fragment locates the site of cleavage by arg C at the extreme N-terminal boundary of a putative E3-binding domain and corresponds to the release of a 15,000-M(r) N-terminal fragment comprising both the lipoyl and linker sequences [34].


  1. Effects of anti-C5a antibodies on the adult respiratory distress syndrome in septic primates. Stevens, J.H., O'Hanley, P., Shapiro, J.M., Mihm, F.G., Satoh, P.S., Collins, J.A., Raffin, T.A. J. Clin. Invest. (1986) [Pubmed]
  2. Various authentic chemoattractants mediating leukocyte adherence inhibition. Thomson, D.M. J. Natl. Cancer Inst. (1984) [Pubmed]
  3. Effects of human recombinant alpha 2 arg-interferon and gamma-interferon on human breast cancer cell lines: dissociation of antiproliferative activity and induction of HLA-DR antigen expression. Gastl, G., Marth, C., Leiter, E., Gattringer, C., Mayer, I., Daxenbichler, G., Flener, R., Huber, C. Cancer Res. (1985) [Pubmed]
  4. Microinjection of monoclonal antibody PAb421 into human SW480 colorectal carcinoma cells restores the transcription activation function to mutant p53. Abarzúa, P., LoSardo, J.E., Gubler, M.L., Neri, A. Cancer Res. (1995) [Pubmed]
  5. Novel (cys152 > arg) missense mutation in an Arab patient with Canavan disease. Kaul, R., Gao, G.P., Michals, K., Whelan, D.T., Levin, S., Matalon, R. Hum. Mutat. (1995) [Pubmed]
  6. SULT1A1 polymorphism and esophageal cancer in males. Wu, M.T., Wang, Y.T., Ho, C.K., Wu, D.C., Lee, Y.C., Hsu, H.K., Kao, E.L., Lee, J.M. Int. J. Cancer (2003) [Pubmed]
  7. Nuclear location signals in polyoma virus large-T. Richardson, W.D., Roberts, B.L., Smith, A.E. Cell (1986) [Pubmed]
  8. Essential roles for the Abl and Arg tyrosine kinases in neurulation. Koleske, A.J., Gifford, A.M., Scott, M.L., Nee, M., Bronson, R.T., Miczek, K.A., Baltimore, D. Neuron (1998) [Pubmed]
  9. Neutrophil-endothelial cell interactions. Modulation of neutrophil adhesiveness induced by complement fragments C5a and C5a des arg and formyl-methionyl-leucyl-phenylalanine in vitro. Tonnesen, M.G., Smedly, L.A., Henson, P.M. J. Clin. Invest. (1984) [Pubmed]
  10. Plasma concentrations of complement-activation complexes correlate with disease activity in patients diagnosed with isolated central nervous system vasculitis. Langlois, P.F., Sharon, G.E., Gawryl, M.S. J. Allergy Clin. Immunol. (1989) [Pubmed]
  11. pULB113, an RP4::mini-Mu plasmid, mediates chromosomal mobilization and R-prime formation in Erwinia amylovora, Erwinia chrysanthemi, and subspecies of Erwinia carotovora. Chatterjee, A.K., Ross, L.M., McEvoy, J.L., Thurn, K.K. Appl. Environ. Microbiol. (1985) [Pubmed]
  12. Extent of genetic lesions of the arginine and pyrimidine biosynthetic pathways in Lactobacillus plantarum, L. paraplantarum, L. pentosus, and L. casei: prevalence of CO(2)-dependent auxotrophs and characterization of deficient arg genes in L. plantarum. Bringel, F., Hubert, J.C. Appl. Environ. Microbiol. (2003) [Pubmed]
  13. Arg tyrosine kinase expression in human gastric adenocarcinoma is associated with vessel invasion. Wu, C.W., Li, A.F., Chi, C.W., Huang, C.J., Huang, C.L., Lui, W.Y., Lin, W.C. Anticancer Res. (2003) [Pubmed]
  14. p53 gene mutation in thyroid carcinoma. Ho, Y.S., Tseng, S.C., Chin, T.Y., Hsieh, L.L., Lin, J.D. Cancer Lett. (1996) [Pubmed]
  15. Alterations in exon 4 of the p53 gene in gastric carcinoma. Shepherd, T., Tolbert, D., Benedetti, J., Macdonald, J., Stemmermann, G., Wiest, J., DeVoe, G., Miller, M.A., Wang, J., Noffsinger, A., Fenoglio-Preiser, C. Gastroenterology (2000) [Pubmed]
  16. Chronic hepatitis, hepatocyte fragility, and increased soluble phosphoglycokeratins in transgenic mice expressing a keratin 18 conserved arginine mutant. Ku, N.O., Michie, S., Oshima, R.G., Omary, M.B. J. Cell Biol. (1995) [Pubmed]
  17. The complete coding sequence of arg defines the Abelson subfamily of cytoplasmic tyrosine kinases. Kruh, G.D., Perego, R., Miki, T., Aaronson, S.A. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  18. High metastatic potential in mice inheriting a targeted p53 missense mutation. Liu, G., McDonnell, T.J., Montes de Oca Luna, R., Kapoor, M., Mims, B., El-Naggar, A.K., Lozano, G. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  19. Human monocyte adherence: a primary effect of chemotactic factors on the monocyte to stimulate adherence to human endothelium. Doherty, D.E., Haslett, C., Tonnesen, M.G., Henson, P.M. J. Immunol. (1987) [Pubmed]
  20. Adhesion-dependent regulation of p190RhoGAP in the developing brain by the Abl-related gene tyrosine kinase. Hernández, S.E., Settleman, J., Koleske, A.J. Curr. Biol. (2004) [Pubmed]
  21. Arginase plays a pivotal role in polyamine precursor metabolism in Leishmania. Characterization of gene deletion mutants. Roberts, S.C., Tancer, M.J., Polinsky, M.R., Gibson, K.M., Heby, O., Ullman, B. J. Biol. Chem. (2004) [Pubmed]
  22. Integrin Signaling through Arg Activates p190RhoGAP by Promoting Its Binding to p120RasGAP and Recruitment to the Membrane. Bradley, W.D., Hern??ndez, S.E., Settleman, J., Koleske, A.J. Mol. Biol. Cell (2006) [Pubmed]
  23. Arg encodes a widely expressed 145 kDa protein-tyrosine kinase. Perego, R., Ron, D., Kruh, G.D. Oncogene (1991) [Pubmed]
  24. Two basic amino acids C-terminal of the proximal box specify functional binding of the vitamin D receptor to its rat osteocalcin deoxyribonucleic acid-responsive element. Hsieh, J.C., Whitfield, G.K., Jurutka, P.W., Haussler, C.A., Thatcher, M.L., Thompson, P.D., Dang, H.T., Galligan, M.A., Oza, A.K., Haussler, M.R. Endocrinology (2003) [Pubmed]
  25. Influence of genetic polymorphisms in the beta2-adrenoceptor on desensitization in human lung mast cells. Chong, L.K., Chowdry, J., Ghahramani, P., Peachell, P.T. Pharmacogenetics (2000) [Pubmed]
  26. Nucleotide sequence of the argR gene of Escherichia coli K-12 and isolation of its product, the arginine repressor. Lim, D.B., Oppenheim, J.D., Eckhardt, T., Maas, W.K. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  27. Molecular studies and NK cell function of a new case of TAP2 homozygous human deficiency. Matamoros, N., Milà, J., Llano, M., Balas, A., Vicario, J.L., Pons, J., Crespí, C., Martinez, N., Iglesias-Alzueta, J., López-Botet, M. Clin. Exp. Immunol. (2001) [Pubmed]
  28. Cloning and expression in Escherichia coli of a Streptomyces coelicolor A3(2) argCJB gene cluster. Hindle, Z., Callis, R., Dowden, S., Rudd, B.A., Baumberg, S. Microbiology (Reading, Engl.) (1994) [Pubmed]
  29. Association between the p21 codon 31 A1 (arg) allele and lung cancer. Själander, A., Birgander, R., Rannug, A., Alexandrie, A.K., Tornling, G., Beckman, G. Hum. Hered. (1996) [Pubmed]
  30. Activation of human matrix metalloproteinase 2 by gingival crevicular fluid and Porphyromonas gingivalis. Grayson, R., Douglas, C.W., Heath, J., Rawlinson, A., Evans, G.S. Journal of clinical periodontology. (2003) [Pubmed]
  31. The effect of hemodialysis and C5a des arg on neutrophil subpopulations. Klempner, M.S., Gallin, J.I., Balow, J.E., Van Kammen, D.P. Blood (1980) [Pubmed]
  32. Psoriatic skin lesions contain biologically active amounts of an interleukin 1-like compound. Camp, R.D., Fincham, N.J., Cunningham, F.M., Greaves, M.W., Morris, J., Chu, A. J. Immunol. (1986) [Pubmed]
  33. Comparative tyrosine-kinase profiles in colorectal cancers: enhanced arg expression in carcinoma as compared with adenoma and normal mucosa. Chen, W.S., Kung, H.J., Yang, W.K., Lin, W. Int. J. Cancer (1999) [Pubmed]
  34. Reconstitution of mammalian pyruvate dehydrogenase and 2-oxoglutarate dehydrogenase complexes: analysis of protein X involvement and interaction of homologous and heterologous dihydrolipoamide dehydrogenases. Sanderson, S.J., Khan, S.S., McCartney, R.G., Miller, C., Lindsay, J.G. Biochem. J. (1996) [Pubmed]
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