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Chemical Compound Review

Arsonic acid     dihydroxy-oxo-arsenic

Synonyms: AC1NUSF0, AR-1H7577, AR-1H7578, AC1Q5A7Y, dihydroxy(oxo)arsenic
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Disease relevance of Arsonate

  • In vivo administration of neutralizing anti-NGF antibodies caused strong reduction in the titer of specific IgG in mice immunized with tetanus toxoid, nitrophenol, or arsonate and reduced numbers of surface IgG or IgA B lymphocytes [1].
  • Some of these VH J558+ autoantibodies shared crossreactive idiotypes with VH J558+ antibodies directed against foreign antigens such as influenza virus hemagglutinin, poly(Glu60,Ala30,Tyr10), arsonate, and dextran [2].
  • Arsonate-specific murine T cell clones. II. Delayed-type hypersensitivity induced by P-azobenzenearsonate-L-tyrosine (ABA-Tyr) [3].
  • A series of 12 organic arsonic acid compounds has been synthesized and evaluated against human B-lineage (NALM-6) and T-lineage (MOLT-3) acute lymphoblastic leukemia (ALL) cell lines [4].

Psychiatry related information on Arsonate

  • The normal immune response of A/J mice against arsonate coupled to hemocyanin is characterized by a major recurrent cross-reactive Id, the CRIA [5].

High impact information on Arsonate


Chemical compound and disease context of Arsonate


Biological context of Arsonate


Anatomical context of Arsonate

  • Inhibition may result from competition of these analogs with arsonate at a site on the T cell [15].
  • Hence the specificities of these clones may reflect their intrinsic recognition of arsonate and its analogues, rather than more efficient presentation of certain analogues than of others by antigen-presenting cells, or differential recognition of associated MHC epitopes by the clones [11].
  • Idiotype connectance in the immune system. I. Expression of a cross-reactive idiotype on induced anti-p-azophenylarsonate antibodies and on endogenous antibodies not specific for arsonate [16].
  • In this report, we show that lethal irradiation of A/J mice followed by reconstitution with autologous or syngeneic lymphoid cells results in loss of major CRIA Id expression in the response to arsonate [5].
  • Comparison of the CRI+ arsonate-nonbinding 1F6 sequence with the CRI+ germ-line VH gene sequence reveals that the 1F6 heavy chain differs from the germ-line-encoded amino acid sequence at seven positions within VH [Siekevitz, M., Gefter, M. L., Brodeur, P., Riblet, R., & Marshak-Rothstein, A. (1982) Eur. J. Immunol. 12, 1023-1032] [17].

Associations of Arsonate with other chemical compounds

  • The hapten- and carrier-specific T lymphocyte clone D5 and a T hybridoma (D5h) derived from D5 cells recognize several different protein Ag conjugated with p-azobenzenearsonate (arsonate) presented by the class II MHC protein I-Ad [18].
  • Analytical procedures are elaborated for the sequential allotment of azobenzene arsonate binding sites in proteins and peptides [19].
  • The patterns of stimulation segregated the clones into two specificity groups and indicated that the epitope recognized by the T-cell included the arsonate group and elements in the side chain of tyrosine [20].
  • Thus, hepatic MT was examined in channel catfish treated with the herbicide monosodium methyl arsonate (MSMA) and compared to equal doses of trivalent and pentavalent arsenic [21].
  • The cellular proteins from KB cells bound to arsonic acid moieties were eluted by 50 mM sodium arsenate in Tris-HCl buffer (50 mM, pH 7.6) [22].

Gene context of Arsonate

  • Analysis of sera from AXC Igh recombinant mice maps the 91A3 marker to the left of Igh-Dex, consistent with the location of the VH genes controlling the arsonate CRI [23].
  • Upon Ag stimulation, an arsonate-specific murine T cell clone exhibited a rapid but transient increase in cell adhesion to collagen, fibronectin, and laminin [24].
  • 9 of 20 antibodies bound to foreign antigens such as bacterial polysaccharides, poly(Glu50, Tyr50), poly(Glu54,Lys37,Phe9), arsonate, and lysozyme, known to interact with antibodies encoded by genes from the VH J558 family [2].
  • To investigate this issue, we created FcgammaRIIB-deficient versions of two previously described targeted BCR-transgenic lines of mice that contain follicular B cells with specificity for the hapten arsonate, but with different levels of antinuclear autoantigen reactivity [25].
  • The Ig produced by cells transfected with both the chimeric H chain and parental L chains genes expressed the NP epitope but lost the original arsonate binding activity [26].

Analytical, diagnostic and therapeutic context of Arsonate

  • The availability of cloned T cell lines that produce antigen-specific idiotype-positive I region-containing products should facilitate a more thorough dissection of the interrelationships of T-B interctions in the arsonate idiotypic system [27].
  • Analysis of the specific ARS-binding molecules by sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE) indicated that these animals were capable of producing both high molecular-weight (presumably IgM) and low molecular-weight antibodies to the ARS hapten [28].
  • However, after treatment with rabbit polyclonal anti-CRIA antibodies (Ab2 or anti-idiotypic antibodies) and arsonate, BALB/c mice are able to synthesize a CRIA-like idiotype [29].
  • Biological activity of the approximately 50-kDa MAb HC polypeptide was demonstrated by arsonate affinity matrix binding as determined by Western blot analysis [30].
  • 1. In order to obtain an effective ligand for affinity chromatography of the low molecular weight acid phosphatase (orthophosphoric-monoester phosphohydrolase (acid optimum), EC from human red cells nine phosphonic and two arsonic acid substrate analogues were investigated as potential inhibitors [31].


  1. Nerve growth factor is an autocrine survival factor for memory B lymphocytes. Torcia, M., Bracci-Laudiero, L., Lucibello, M., Nencioni, L., Labardi, D., Rubartelli, A., Cozzolino, F., Aloe, L., Garaci, E. Cell (1996) [Pubmed]
  2. Autoantibodies of various specificities encoded by genes from the VH J558 family bind to foreign antigens and share idiotopes of antibodies specific for self and foreign antigens. Monestier, M., Bonin, B., Migliorini, P., Dang, H., Datta, S., Kuppers, R., Rose, N., Maurer, P., Talal, N., Bona, C. J. Exp. Med. (1987) [Pubmed]
  3. Arsonate-specific murine T cell clones. II. Delayed-type hypersensitivity induced by P-azobenzenearsonate-L-tyrosine (ABA-Tyr). Morita, C.T., Goodman, J.W., Lewis, G.K. J. Immunol. (1985) [Pubmed]
  4. Organic phenyl arsonic acid compounds with potent antileukemic activity. Liu, X.P., Narla, R.K., Uckun, F.M. Bioorg. Med. Chem. Lett. (2003) [Pubmed]
  5. Loss of a major idiotype (CRIA) after repopulation of irradiated mice. Willems, F., Vansanten-Urbain, G., De Wit, D., Slaoui, M., Urbain, J. J. Immunol. (1990) [Pubmed]
  6. The T cell receptor V alpha 3 gene segment is associated with reactivity to p-azobenzenearsonate. Tan, K.N., Datlof, B.M., Gilmore, J.A., Kronman, A.C., Lee, J.H., Maxam, A.M., Rao, A. Cell (1988) [Pubmed]
  7. Binding of antigen in the absence of histocompatibility proteins by arsonate-reactive T-cell clones. Rao, A., Ko, W.W., Faas, S.J., Cantor, H. Cell (1984) [Pubmed]
  8. The molecular genetics of the arsonate idiotypic system of A/J mice. Rathbun, G., Sanz, I., Meek, K., Tucker, P., Capra, J.D. Adv. Immunol. (1988) [Pubmed]
  9. Somatic mutation in genes for the variable portion of the immunoglobulin heavy chain. Sims, J., Rabbitts, T.H., Estess, P., Slaughter, C., Tucker, P.W., Capra, J.D. Science (1982) [Pubmed]
  10. Two murine natural polyreactive autoantibodies are encoded by nonmutated germ-line genes. Baccala, R., Quang, T.V., Gilbert, M., Ternynck, T., Avrameas, S. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  11. Activation specificity of arsonate-reactive T cell clones. Structural requirements for hapten recognition and comparison with monoclonal antibodies. Rao, A., Faas, S.J., Cantor, H. J. Exp. Med. (1984) [Pubmed]
  12. Complete heavy and light chain variable region sequence of anti-arsonate monoclonal antibodies from BALB/c and A/J mice sharing the 36-60 idiotype are highly homologous. Juszczak, E., Near, R.I., Gefter, M.L., Margolies, M.N. J. Immunol. (1984) [Pubmed]
  13. Antinuclear antigen B cells that down-regulate surface B cell receptor during development to mature, follicular phenotype do not display features of anergy in vitro. Liu, X., Manser, T. J. Immunol. (2005) [Pubmed]
  14. Arsonate-specific murine T cell clones. V. Antigen presentation by L cells transfected with normal and mutant class II genes. Norton, F.L., Davis, C.B., Jones, P.P., Goodman, J.W. J. Immunol. (1989) [Pubmed]
  15. Analogs that compete for antigen binding to an arsonate-reactive T-cell clone inhibit the functional response to arsonate. Rao, A., Faas, S.J., Cantor, H. Cell (1984) [Pubmed]
  16. Idiotype connectance in the immune system. I. Expression of a cross-reactive idiotype on induced anti-p-azophenylarsonate antibodies and on endogenous antibodies not specific for arsonate. Hornbeck, P.V., Lewis, G.K. J. Exp. Med. (1983) [Pubmed]
  17. Complete amino acid sequence of the heavy-chain variable region from an A/J mouse antigen-nonbinding monoclonal antibody bearing the predominant arsonate idiotype. Smith, J.A., Margolies, M.N. Biochemistry (1984) [Pubmed]
  18. Nature of the ligand recognized by a hapten- and carrier-specific, MHC-restricted T cell receptor. Nalefski, E.A., Rao, A. J. Immunol. (1993) [Pubmed]
  19. Protein modification by diazotized arsanilic acid: synthesis and characterization of the phenylthiohydantoin derivatives of azobenzene arsonate-coupled tyrosine, histidine, and lysine residues and their sequential allotment in labeled peptides. Schwaller, B., Sigrist, H. Anal. Biochem. (1989) [Pubmed]
  20. The anatomy of an antigen molecule: functional subregions of L-tyrosine-p-azobenzenearsonate. Godfrey, W.L., Lewis, G.K., Goodman, J.W. Mol. Immunol. (1984) [Pubmed]
  21. Effect of arsenite, arsenate, and the herbicide monosodium methyl arsonate (MSMA) on hepatic metallothionein expression and lipid peroxidation in channel catfish. Schlenk, D., Wolford, L., Chelius, M., Steevens, J., Chan, K.M. Comp. Biochem. Physiol. C, Pharmacol. Toxicol. Endocrinol. (1997) [Pubmed]
  22. Arsanilic acid-Sepharose chromatography of pyruvate kinase from KB cells. Huang, R.N., Yeh, H.Y., Cheng, S.C., Chow, L.P., Lee, T.C. J. Chromatogr. B Biomed. Sci. Appl. (2000) [Pubmed]
  23. VH families in the antibody response to p-azophenylarsonate: correlation between serology and amino acid sequence. Milner, E.C., Capra, J.D. J. Immunol. (1982) [Pubmed]
  24. T cell receptor-dependent, antigen-specific stimulation of a murine T cell clone induces a transient, VLA protein-mediated binding to extracellular matrix. Chan, B.M., Wong, J.G., Rao, A., Hemler, M.E. J. Immunol. (1991) [Pubmed]
  25. Fc{gamma}RIIB Regulates Autoreactive Primary Antibody-Forming Cell, but Not Germinal Center B Cell, Activity. Rahman, Z.S., Alabyev, B., Manser, T. J. Immunol. (2007) [Pubmed]
  26. Cells expressing an H chain Ig gene carrying a viral T cell epitope are lysed by specific cytolytic T cells. Zaghouani, H., Krystal, M., Kuzu, H., Moran, T., Shah, H., Kuzu, Y., Schulman, J., Bona, C. J. Immunol. (1992) [Pubmed]
  27. T cell hybrids with arsonate specificity. I. Initial characterization of antigen-specific T cell products that bear a cross-reactive idiotype and determinants encoded by the murine major histocompatibility complex. Pacifico, A., Capra, J.D. J. Exp. Med. (1980) [Pubmed]
  28. Evidence for low-molecular weight antibodies in the serum of a urodele amphibian, Ambystoma mexicanum. Warr, G.W., Ruben, L.N., Edwards, B.F. Immunol. Lett. (1982) [Pubmed]
  29. The influence of V kappa gene polymorphism on the induction of silent idiotypes in the arsonate system. Marvel, J., Tassignon, J., Brait, M., Meek, K., Milner, E.C., Moser, M., Capra, J.D., Urbain, J. Mol. Immunol. (1987) [Pubmed]
  30. Enhanced recovery of a secreted mammalian protein from suspension culture of genetically modified tobacco cells. Magnuson, N.S., Linzmaier, P.M., Gao, J.W., Reeves, R., An, G., Lee, J.M. Protein Expr. Purif. (1996) [Pubmed]
  31. Phosphonic and arsonic acids as inhibitors of human red cell acid phosphatase and their use in affinity chromatography. Dissing, J., Dahl, O., Svensmark, O. Biochim. Biophys. Acta (1979) [Pubmed]
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