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Chemical Compound Review

Aminobenzamide     2-aminobenzamide

Synonyms: Anthranilamide, PubChem13631, CHEMBL43175, SureCN38228, A89804_ALDRICH, ...
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Disease relevance of LS-25344

  • Furthermore, chronic administration of 0.2% ABA in the diet did not result in detectable toxicity and/or carcinogenic effects [1].
  • A single i.p. injection of ABA at greater than 150 mg/kg body weight (B.W.) enhanced dose-dependently the induction of gamma-GTP positive foci in rat liver initiated by 20 mg/kg B.W. of DEN [1].
  • In this study, a synthetic peptide (FRETN 89-98), containing residues 89-98 of lambda N protein and a fluorescence donor (anthranilamide) and quencher (3-nitrotyrosine), has been examined for ATP-dependent degradation by E. coli and human Lon proteases [2].
  • A series of novel unsymmetrical anthranilamide-containing HIV protease inhibitors was designed [3].
  • 2-Aminobenzamide, an inhibitor of ADP-ribosylation, antagonizes induced DNA hypomethylation during differentiation of murine Friend erythroleukemia cells by N'-methylnicotinamide [4].

High impact information on LS-25344

  • These most comprehensive CoMFA and CoMSIA models are useful in understanding the structure-activity relationships of anthranilamide derivatives as well as aid in the design of novel derivatives with enhanced modulation of P-gp activity [5].
  • Two readily synthesized anthranilamide, VEGF receptor tyrosine kinase inhibitors have been prepared and evaluated as angiogenesis inhibitors [6].
  • While several analogues had potent in vitro and in vivo activities indicative of potential atypical antipsychotic activity, anthranilamide 77 (1192U90) ddemonstrated a superior pharmacological profile [7].
  • Based on the above results, ABA was used as a representative ADPRT inhibitor for clarifying the mechanisms underlying the effects [1].
  • Liver cell necrosis was not detectable either by analysis of serum enzymes or histologically 1, 3, 5, 7 and 14 days after 20 mg/kg B.W. of DEN with or without administration of 600 mg/kg B.W. of ABA [1].

Chemical compound and disease context of LS-25344


Biological context of LS-25344


Anatomical context of LS-25344


Associations of LS-25344 with other chemical compounds


Gene context of LS-25344

  • O-glycans were released from CF and ND mucins and derivatized with 2-aminobenzamide (2-AB), separated by ion exchange chromatography, and quantified by fluorescence [20].
  • Aminobenzamide inhibited ADP-ribosylation of only HMG 2 in young but all HMGs except HMG 2 in the old [21].
  • In a similar fashion, the 2AB-labeled O-glycans derived from APP were determined to be mono- and disialylated core type 1 structures [22].
  • In short-term 51Cr-release assays with several mouse and human tumor cell lines, the inhibitors aminobenzamide (ABA) and nicotinamide (NA) of ADP-ribosylation sensitized HER-2/neu-nonoverexpressing cells (CaOV-3 and MCF-7) but not HER-2/neu-overexpressing cells (SKOV-3 and SKBR-3) to TNF [23].
  • Latencies of haloperidol-, cis-N-(1-benzyl-2-methyl-pyrrolidin-3-yl)-2-methoxy-5-chloro-4-met hyl- aminobenzamide (YM-09151-2)- and sulpiride-, dopamine D2 receptor antagonists, treated groups did not differ from that seen in the PCP-treated group [24].

Analytical, diagnostic and therapeutic context of LS-25344

  • To adequately resolve deficiencies affecting the first steps of lipid-linked oligosaccharide formation, we have used a non-radioactive procedure employing the fluorescence detection of 2-aminobenzamide-coupled oligosaccharides after HPLC separation [25].
  • The magnitude of the effect was similar to that observed when partial hepatectomy (PH) was performed instead of ABA administration [1].
  • Fluorescent labelled derivatives formed by reductive amination of neutral oligosaccharides with 2-aminobenzamide have been chromatographed on PGC-HPLC and by BioGel P4 gel filtration [26].
  • A sensitive and rapid bioassay of homogalacturonan synthase using 2-aminobenzamide-labeled oligogalacturonides [27].
  • MATERIALS AND METHODS: Cells (asynchronous, logarithmic phase) were pre-incubated with 2 mM aminobenzamide at 37 or 25 degrees C, X-irradiated with 10 Gy and allowed to repair DNA breaks for 15, 60 and 120 min at 37 or 25 degrees C. The remaining double-strand break were estimated by the neutral comet assay [28].


  1. Enhancement of DEN initiation of liver carcinogenesis by inhibitors of NAD+ ADP ribosyl transferase in rats. Takahashi, S., Nakae, D., Yokose, Y., Emi, Y., Denda, A., Mikami, S., Ohnishi, T., Konishi, Y. Carcinogenesis (1984) [Pubmed]
  2. Adenosine triphosphate-dependent degradation of a fluorescent lambda N substrate mimic by Lon protease. Lee, I., Berdis, A.J. Anal. Biochem. (2001) [Pubmed]
  3. Unsymmetric nonpeptidic HIV protease inhibitors containing anthranilamide as a P2' ligand. Randad, R.S., Lubkowska, L., Eissenstat, M.A., Gulnik, S.V., Yu, B., Bhat, T.N., Clanton, D.J., House, T., Stinson, S.F., Erickson, J.W. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
  4. 2-Aminobenzamide, an inhibitor of ADP-ribosylation, antagonizes induced DNA hypomethylation during differentiation of murine Friend erythroleukemia cells by N'-methylnicotinamide. Kuykendall, J.R., Cox, R. Differentiation (1990) [Pubmed]
  5. A comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) of anthranilamide derivatives that are multidrug resistance modulators. Labrie, P., Maddaford, S.P., Fortin, S., Rakhit, S., Kotra, L.P., Gaudreault, R.C. J. Med. Chem. (2006) [Pubmed]
  6. Anthranilic acid amides: a novel class of antiangiogenic VEGF receptor kinase inhibitors. Manley, P.W., Furet, P., Bold, G., Brüggen, J., Mestan, J., Meyer, T., Schnell, C.R., Wood, J., Haberey, M., Huth, A., Krüger, M., Menrad, A., Ottow, E., Seidelmann, D., Siemeister, G., Thierauch, K.H. J. Med. Chem. (2002) [Pubmed]
  7. Structure-activity relationships of a series of substituted benzamides: potent D2/5-HT2 antagonists and 5-HT1a agonists as neuroleptic agents. Norman, M.H., Rigdon, G.C., Hall, W.R., Navas, F. J. Med. Chem. (1996) [Pubmed]
  8. Synthesis and cancer antiproliferative activity of new histone deacetylase inhibitors: hydrophilic hydroxamates and 2-aminobenzamide-containing derivatives. Nagaoka, Y., Maeda, T., Kawai, Y., Nakashima, D., Oikawa, T., Shimoke, K., Ikeuchi, T., Kuwajima, H., Uesato, S. European journal of medicinal chemistry. (2006) [Pubmed]
  9. Subchronic toxicity, metabolism, and pharmacokinetics of the aminobenzamide anticonvulsant ameltolide (LY201116) in rhesus monkeys. Engelhardt, J.A., Parli, C.J., Kovach, P.M., Shoufler, J.R., Emmerson, J.L., Leander, J.D. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1992) [Pubmed]
  10. Some new routes for the preparation of 3-amino-2-phenyl-4(1H)-quinolinones from anthranilamides. Hradil, P., Grepl, M., Hlavác, J., Soural, M., Malon, M., Bertolasi, V. J. Org. Chem. (2006) [Pubmed]
  11. Effect of the reducing-terminal substituents on the high energy collision-induced dissociation matrix-assisted laser desorption/ionization mass spectra of oligosaccharides. Küster, B., Naven, T.J., Harvey, D.J. Rapid Commun. Mass Spectrom. (1996) [Pubmed]
  12. Role of cytosolic superoxide dismutase as a stimulator in anthranilamide hydroxylation by a microsomal monooxygenase system in rat liver. Ohta, Y., Ishiguro, I., Naito, J., Shinohara, R. J. Biochem. (1984) [Pubmed]
  13. Muscarinic M2 antagonists: anthranilamide derivatives with exceptional selectivity and in vivo activity. Clader, J.W., Billard, W., Binch, H., Chen, L.Y., Crosby, G., Duffy, R.A., Ford, J., Kozlowski, J.A., Lachowicz, J.E., Li, S., Liu, C., McCombie, S.W., Vice, S., Zhou, G., Greenlee, W.J. Bioorg. Med. Chem. (2004) [Pubmed]
  14. Identification of elongating beta-1,4-galactosyltransferase activity in mung bean (Vigna radiata) hypocotyls using 2-aminobenzaminated 1,4-linked beta- D-galactooligosaccharides as acceptor substrates. Ishii, T., Ohnishi-Kameyama, M., Ono, H. Planta (2004) [Pubmed]
  15. Asn-linked sugar chain structures of recombinant human thrombopoietin produced in Chinese hamster ovary cells. Inoue, N., Watanabe, T., Kutsukake, T., Saitoh, H., Tsumura, H., Arai, H., Takeuchi, M. Glycoconj. J. (1999) [Pubmed]
  16. Studies on the metabolic pathway of anthranilic acid in rats. Ishiguro, I., Naito, J., Shinohara, R. Acta Vitaminol. Enzymol. (1975) [Pubmed]
  17. Influence of the labeling group on ionization and fragmentation of carbohydrates in mass spectrometry. Lattová, E., Snovida, S., Perreault, H., Krokhin, O. J. Am. Soc. Mass Spectrom. (2005) [Pubmed]
  18. Microanalysis of glycosaminoglycan-derived oligosaccharides labeled with a fluorophore 2-aminobenzamide by high-performance liquid chromatography: application to disaccharide composition analysis and exosequencing of oligosaccharides. Kinoshita, A., Sugahara, K. Anal. Biochem. (1999) [Pubmed]
  19. Electrospray ionization ion trap mass spectrometry for structural characterization of oligosaccharides derivatized with 2-aminobenzamide. Morelle, W., Page, A., Michalski, J.C. Rapid Commun. Mass Spectrom. (2005) [Pubmed]
  20. Altered O-glycosylation and sulfation of airway mucins associated with cystic fibrosis. Xia, B., Royall, J.A., Damera, G., Sachdev, G.P., Cummings, R.D. Glycobiology (2005) [Pubmed]
  21. ADP-ribosylation of HMG proteins and its modulation by different effectors in the liver of aging rats. Thakur, M.K., Prasad, S. Mech. Ageing Dev. (1990) [Pubmed]
  22. Study of the sugar chains of recombinant human amyloid precursor protein produced by Chinese hamster ovary cells. Sato, Y., Liu, C., Wojczyk, B.S., Kobata, A., Spitalnik, S.L., Endo, T. Biochim. Biophys. Acta (1999) [Pubmed]
  23. TNF cytotoxicity: effects of HER-2/neu expression and inhibitors of ADP-ribosylation. Tang, P., Hung, M.C., Klostergaard, J. Lymphokine Cytokine Res. (1994) [Pubmed]
  24. Effect of NE-100, a novel sigma receptor ligand, on phencyclidine-induced cognitive dysfunction. Ogawa, S., Okuyama, S., Araki, H., Otomo, S. Eur. J. Pharmacol. (1994) [Pubmed]
  25. Deficiency of the first mannosylation step in the N-glycosylation pathway causes congenital disorder of glycosylation type Ik. Grubenmann, C.E., Frank, C.G., Hülsmeier, A.J., Schollen, E., Matthijs, G., Mayatepek, E., Berger, E.G., Aebi, M., Hennet, T. Hum. Mol. Genet. (2004) [Pubmed]
  26. Comparison of separation modes of high-performance liquid chromatography for the analysis of glycoprotein- and proteoglycan-derived oligosaccharides. Davies, M.J., Hounsell, E.F. Journal of chromatography. A. (1996) [Pubmed]
  27. A sensitive and rapid bioassay of homogalacturonan synthase using 2-aminobenzamide-labeled oligogalacturonides. Ishii, T. Plant Cell Physiol. (2002) [Pubmed]
  28. Differential DNA double strand break fixation dependence on poly(ADP-ribosylation) in L5178Y and CHO cells. Wojewódzka, M., Kruszewski, M., Sochanowicz, B., Szumiel, I. Int. J. Radiat. Biol. (2004) [Pubmed]
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