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Chemical Compound Review

Pamisyl     4-amino-2-hydroxy-benzoic acid

Synonyms: Aminopar, Deapasil, Ferrosan, Rezipas, Aminosalicylic acid, ...
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Disease relevance of Aminosalicylic acid


High impact information on Aminosalicylic acid

  • Here we examine the structure of TBHA2 with the electron microscope and compare it with the fusion pH structure of HA2 in virosomes, HA2 in aggregates formed at fusion pH by the soluble, bromelain-released ectodomain BHA and HA2 in liposomes with which BHA associates at fusion pH [5].
  • Since the synthetic antioxidant BHA was first found to exert carcinogenic potential in rat and hamster forestomach epithelium, many other synthetic and naturally occurring antioxidants have been examined for their ability to induce proliferative activity in the alimentary canal [6].
  • It is thus conceivable that BHA is oxidatively metabolized in the forestomach epithelium (possibly entering into redox cycling), and reactive metabolites including semiquinone radicals or active oxygen species are responsible for the carcinogenesis by a mechanism involving binding to macromolecules [6].
  • Aminosalicylic acid inhibits IkappaB kinase alpha phosphorylation of IkappaBalpha in mouse intestinal epithelial cells [7].
  • Other substituted benzoates with free amino and carboxyl groups in the ortho or para position (e.g. 4-aminosalicylate and anthranilate) serve as substrates for hydroxylation, but, in these cases, H2O2 is formed simultaneously with the hydroxylation [8].

Chemical compound and disease context of Aminosalicylic acid


Biological context of Aminosalicylic acid

  • 3. Hybridization of the 32P-labeled cDNA plasmid with total liver RNA indicates a 26-fold increase in homologous mRNA in response to the feeding of BHA [14].
  • These facts indicated that the acylation was not significant in membrane fusion by BHA but that pore formation and pore dilation were appreciably affected by the particular amino acid sequence of the CT and the existence of a single acylation site in CT residue 578 [4].
  • The present results indicate that metabolic activation of BHA yielding reactive oxygen species may induce a carcinogenic potential, since the BHA metabolite TBHQ, appeared to be a strong inducer of oxidative DNA damage [15].
  • A well-defined electron density for BHA is observed in the peroxidase active site, with a hydrophobic pocket surrounding the aromatic ring of the substrate [16].
  • Here, we report that incubation of Raw 264.7 cells with SSZ but not salicylates [acetylsalicylic acid (ASA), 4-aminosalicylic acid (4-ASA), and 5-ASA] causes a mixed apoptotic and necrotic form of cell death [17].

Anatomical context of Aminosalicylic acid


Associations of Aminosalicylic acid with other chemical compounds


Gene context of Aminosalicylic acid

  • Another limitation is that antioxidant concentrations high enough to block NK-kappa B activation were shown to have a suppressive effect on immune functions in vitro, because NAC and BHA blocked IL-2-induced PBMC proliferation [25].
  • Reducing H2O2 through overexpression of catalase or treatment of cells with NAC or BHA did not have an effect on TNF-induced chromosomal aberration [26].
  • BHA has significantly induced the activities of GR and GSH in the present study [27].
  • The cytoplasmic tail (CT) of hemagglutinin (HA) of influenza B virus (BHA) contains at positions 578 and 581 two highly conserved cysteine residues (Cys578 and Cys581) that are modified with palmitic acid (PA) through a thioester linkage [4].
  • In contrast, cytochrome P450 1A mRNA levels increase only slightly after BHA induction but are induced dramatically by beta-naphthoflavone [28].

Analytical, diagnostic and therapeutic context of Aminosalicylic acid


  1. Disulphide bonds of haemagglutinin of Asian influenza virus. Waterfield, M., Scrace, G., Skehel, J. Nature (1981) [Pubmed]
  2. Oral 4-aminosalicylic acid therapy in ulcerative colitis. Gaffney, P., Doyle, C., Gaffney, A. Gastroenterology (1992) [Pubmed]
  3. Carcinogenicity and modification of the carcinogenic response by BHA, BHT, and other antioxidants. Ito, N., Fukushima, S., Tsuda, H. Crit. Rev. Toxicol. (1985) [Pubmed]
  4. Influence of acylation sites of influenza B virus hemagglutinin on fusion pore formation and dilation. Ujike, M., Nakajima, K., Nobusawa, E. J. Virol. (2004) [Pubmed]
  5. Electron microscopy of antibody complexes of influenza virus haemagglutinin in the fusion pH conformation. Wharton, S.A., Calder, L.J., Ruigrok, R.W., Skehel, J.J., Steinhauer, D.A., Wiley, D.C. EMBO J. (1995) [Pubmed]
  6. Antioxidants--carcinogenic and chemopreventive properties. Ito, N., Hirose, M. Adv. Cancer Res. (1989) [Pubmed]
  7. Aminosalicylic acid inhibits IkappaB kinase alpha phosphorylation of IkappaBalpha in mouse intestinal epithelial cells. Yan, F., Polk, D.B. J. Biol. Chem. (1999) [Pubmed]
  8. Purification and properties of 4-aminobenzoate hydroxylase, a new monooxygenase from Agaricus bisporus. Tsuji, H., Ogawa, T., Bando, N., Sasaoka, K. J. Biol. Chem. (1986) [Pubmed]
  9. Double blind, controlled trial of 4-aminosalicylic acid and prednisolone enemas in distal ulcerative colitis. O'Donnell, L.J., Arvind, A.S., Hoang, P., Cameron, D., Talbot, I.C., Jewell, D.P., Lennard-Jones, J.E., Farthing, M.J. Gut (1992) [Pubmed]
  10. Simultaneous assessments of exocrine pancreatic function by cholesteryl-[14C]octanoate breath test and measurement of plasma p-aminobenzoic acid. Bruno, M.J., Hoek, F.J., Delzenne, B., van Leeuwen, D.J., Schteingart, C.D., Hofmann, A.F., Tytgat, G.N. Clin. Chem. (1995) [Pubmed]
  11. Comparison of the effects of 13 phenolic compounds in induction of proliferative lesions of the forestomach and increase in the labelling indices of the glandular stomach and urinary bladder epithelium of Syrian golden hamsters. Hirose, M., Inoue, T., Asamoto, M., Tagawa, Y., Ito, N. Carcinogenesis (1986) [Pubmed]
  12. Febrile and acute hyperthermia enhance TNF-induced necrosis of murine L929 fibrosarcoma cells via caspase-regulated production of reactive oxygen intermediates. Leroux, E., Auzenne, E., Weidner, D., Wu, Z.Y., Donato, N.J., Klostergaard, J. J. Cell. Physiol. (2001) [Pubmed]
  13. Identification and functional characterization of arylamine N-acetyltransferases in eubacteria: evidence for highly selective acetylation of 5-aminosalicylic acid. Deloménie, C., Fouix, S., Longuemaux, S., Brahimi, N., Bizet, C., Picard, B., Denamur, E., Dupret, J.M. J. Bacteriol. (2001) [Pubmed]
  14. Increased synthesis of glutathione S-transferases in response to anticarcinogenic antioxidants. Cloning and measurement of messenger RNA. Pearson, W.R., Windle, J.J., Morrow, J.F., Benson, A.M., Talalay, P. J. Biol. Chem. (1983) [Pubmed]
  15. The role of prostaglandin H synthase-mediated metabolism in the induction of oxidative DNA damage by BHA metabolites. Schilderman, P.A., van Maanen, J.M., ten Vaarwerk, F.J., Lafleur, M.V., Westmijze, E.J., ten Hoor, F., Kleinjans, J.C. Carcinogenesis (1993) [Pubmed]
  16. Structural interactions between horseradish peroxidase C and the substrate benzhydroxamic acid determined by X-ray crystallography. Henriksen, A., Schuller, D.J., Meno, K., Welinder, K.G., Smith, A.T., Gajhede, M. Biochemistry (1998) [Pubmed]
  17. Dissociated ROS production and ceramide generation in sulfasalazine-induced cell death in Raw 264.7 cells. Salh, B., Assi, K., Huang, S., O'Brien, L., Steinbrecher, U., Gómez-Muñoz, A. J. Leukoc. Biol. (2002) [Pubmed]
  18. Hydrophobic photolabeling identifies BHA2 as the subunit mediating the interaction of bromelain-solubilized influenza virus hemagglutinin with liposomes at low pH. Harter, C., Bächi, T., Semenza, G., Brunner, J. Biochemistry (1988) [Pubmed]
  19. Killing of intracellular Mycobacterium tuberculosis by receptor-mediated drug delivery. Majumdar, S., Basu, S.K. Antimicrob. Agents Chemother. (1991) [Pubmed]
  20. Elevation of conjugation capacity in isolated hepatocytes from BHA-treated mice. Moldéus, P., Dock, L., Cha, Y.N., Berggren, M., Jernström, B. Biochem. Pharmacol. (1982) [Pubmed]
  21. The effects of aminosalicylic acid derivatives on nitric oxide in a cell-free system. Reynolds, P.D., Middleton, S.J., Shorthouse, M., Hunter, J.O. Aliment. Pharmacol. Ther. (1995) [Pubmed]
  22. Monomorphic and polymorphic human arylamine N-acetyltransferases: a comparison of liver isozymes and expressed products of two cloned genes. Grant, D.M., Blum, M., Beer, M., Meyer, U.A. Mol. Pharmacol. (1991) [Pubmed]
  23. Carbohydrates of influenza virus hemagglutinin: structures of the whole neutral sugar chains. Matsumoto, A., Yoshima, H., Kobata, A. Biochemistry (1983) [Pubmed]
  24. Inhibition of in vitro microsomal lipid peroxidation by isoflavonoids. Jha, H.C., von Recklinghausen, G., Zilliken, F. Biochem. Pharmacol. (1985) [Pubmed]
  25. Appraisal of potential therapeutic index of antioxidants on the basis of their in vitro effects on HIV replication in monocytes and interleukin 2-induced lymphocyte proliferation. Aillet, F., Gougerot-Pocidalo, M.A., Virelizier, J.L., Israël, N. AIDS Res. Hum. Retroviruses (1994) [Pubmed]
  26. TNFalpha induces chromosomal abnormalities independent of ROS through IKK, JNK, p38 and caspase pathways. Higashimoto, T., Panopoulos, A., Hsieh, C.L., Zandi, E. Cytokine (2006) [Pubmed]
  27. Modulatory influence of Adhatoda vesica (Justicia adhatoda) leaf extract on the enzymes of xenobiotic metabolism, antioxidant status and lipid peroxidation in mice. Singh, R.P., Padmavathi, B., Rao, A.R. Mol. Cell. Biochem. (2000) [Pubmed]
  28. Differences in induction by xenobiotics in murine tissues and the Hepa1c1c7 cell line of mRNAs encoding glutathione transferase, quinone reductase, and CYP1A P450s. Sisk, S.C., Pearson, W.R. Pharmacogenetics (1993) [Pubmed]
  29. Improved specificity of the PABA test with p-aminosalicylic acid (PAS). Hoek, F.J., van den Bergh, F.A., Klein Elhorst, J.T., Meijer, J.L., Timmer, E., Tytgat, G.N. Gut (1987) [Pubmed]
  30. Inheritance of acetylator genotype-dependent arylamine N-acetyltransferase in hamster bladder cytosol. Hein, D.W., Kirlin, W.G., Yerokun, T., Trinidad, A., Ogolla, F. Carcinogenesis (1987) [Pubmed]
  31. pH-induced conformational changes of membrane-bound influenza hemagglutinin and its effect on target lipid bilayers. Gray, C., Tamm, L.K. Protein Sci. (1998) [Pubmed]
  32. Colonic delivery of 4-aminosalicylic acid using amylose-ethylcellulose-coated hydroxypropylmethylcellulose capsules. Tuleu, C., Basit, A.W., Waddington, W.A., Ell, P.J., Newton, J.M. Aliment. Pharmacol. Ther. (2002) [Pubmed]
  33. Rectal aminosalicylate therapy for distal ulcerative colitis: a meta-analysis. Marshall, J.K., Irvine, E.J. Aliment. Pharmacol. Ther. (1995) [Pubmed]
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