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At least 109 records · Page 6Linked to original sources
PubMed2001

N-[3,4-dimethoxycinnamoyl]-anthranilic acid (tranilast) inhibits transforming growth factor-beta relesase and reduces migration and invasiveness of human malignant glioma cells.

Extensive infiltration of normal brain tissue and suppression of anti-tumor immune surveillance mediated by molecules such as transforming growth factor-beta (TGF-beta) are key biological features that contribute to the malignant phenotype of human gliomas. Tranilast (N-[3,4-dimethoxycinnamoyl]-anthranilic acid) is an anti-allergic compound used clinically to control atopic and fibrotic disorders. These effects are attributed to the suppression of TGF-beta1 synthesis and interference with growth factor-mediated proliferation and migration of fibroblasts and vascular smooth muscle cells. Here, we show that tranilast inhibits DNA synthesis and proliferation of human malignant glioma cells and promotes p21 accumulation in the absence of cytotoxicity. Further, tranilast reduces the release of TGF-beta1 and TGF-beta2 by glioma cells and inhibits migration, chemotactic responses and invasiveness. These effects are not associated with a reduction of alpha(v)beta(3) integrin expression at the cell surface but appear to involve inhibition of matrix metalloproteinase-2 expression and activity. Neither the tranilast-mediated inhibition of proliferation nor the inhibition of migration was counteracted by supplementation with exogenous TGF-beta. Finally, tranilast administered orally inhibited the growth of experimental 9L rat gliomas and reduced expression of TGF-beta2 in vivo. We conclude that tranilast might be a useful therapeutic agent for the treatment of human malignant glioma because of a TGF-beta-independent abrogation of the malignant phenotype of proliferation, migration and invasiveness and because of the antagonism of TGF-beta-associated immunosuppression.

3T3 Cells↗
PubMed1981

Adsorptive bonding to hydroxyapatite I: adsorption of anthranilic acid - the effect of solvents. Search for surface bonding groups for coupling agents to teeth.

A study was initiated to explore the nature of surface-active groups of model compounds that might cause chemisorption of comonomers used in the polymerization of dental resins on hydroxyapatite (the main constituent of bone) and thus effect a strong and durable bond between the resins and hard tooth tissues. In an effort to accomplish this objective, adsorption of anthranilic acid on hydroxyapatite was studied from three solvents: 95% aq. ethanol, dimethyl sulphoxide and methylene chloride. The adsorption is reversible from the first two solvents and the isotherms follow Langmuir plots. Adsorption is irreversible from methylene chloride; a constant amount of adsorbate is removed from different solutions above a certain threshold concentration but all adsorbate is removed from solutions below this threshold concentration. The saturation amounts obtained from the two Langmuir plots and the maximum irreversibly adsorbed amount in the above three solvents are 11.4, 6.0 and 17.2 mmol/100 g, respectively. These, together with the surface area (41.0 m2/g; BET, N2) of the hydroxyapatite, yield the effective molecular areas of 60, 114, and 40 A2, respectively. These areas can be matched, on geometrical considerations, with areas of 60, 110, and 40 A2 of the model adsorbate molecule rotating about; (i) its centre, lying flat on the surface, (ii) its carboxyl group at 45 degrees to the surface, and (iii) the carboxyl group in an upright position, respectively.

Adsorption↗
PubMed1978

[Experimental asthma in rats, and the effect of N (3', 4'-dimethoxycinnamoyl) anthranilic acid (N-5') (author's transl)].

Although guinea pigs have been frequently used as a model of asthma, antibodies produced in this species are generally gamma1 and gamma2 and belong to IgG. The antibody responsible for asthmatic attacks in humans is IgE, and such is quite different from gamma1 and gamma2, immunologically. Guinea pigs are not therefore an adequate model for investigating anti-asthmatic drugs which inhibit IgE-mediated mediator release, such as disodium cromoglycate. On the other hand, rats do produce an antibody similar to human IgE, the so-called homocytotropic antibody (HTA), by sensitization with dinitrophenylated ascaris extract (DNP-As) together with killed Bordetella pertussis as an adjuvant. To rats actively sensitized with DNP-As or passively sensitized with HTA serum against DNP-As, intravenous administration of antigen did not produce a transient increase in respiration (unlike that of guinea pigs) immediately after the antigen treatment, but a respiratory disorder similar to that seen during asthmatic attacks in humans did occur. The response to antigen was reproducible in passively sensitized rats compared with that of actively sensitized ones, though the symptom was moderate. The effect of N(3', 4'-dimethoxycinnamoyl) anthranilic acid (N-5'), a new anti-allergic drug, was determined in cases of experimental asthma in passively sensitized rats. Respiratory disorders as a result of antigen were clearly inhibited with oral administration of this agent.

Animals↗
PubMed2000

Metal complexes of salicylhydroxamic acid (H2Sha), anthranilic hydroxamic acid and benzohydroxamic acid. Crystal and molecular structure of [Cu(phen)2(Cl)]Cl x H2Sha, a model for a peroxidase-inhibitor complex.

Stability constants of iron(III), copper(II), nickel(II) and zinc(II) complexes of salicylhydroxamic acid (H2Sha), anthranilic hydroxamic acid (HAha) and benzohydroxamic acid (HBha) have been determined at 25.0 degrees C, I=0.2 mol dm(-3) KCl in aqueous solution. The complex stability order, iron(III) >> copper(II) > nickel(II) approximately = zinc(II) was observed whilst complexes of H2Sha were found to be more stable than those of the other two ligands. In the preparation of ternary metal ion complexes of these ligands and 1,10-phenanthroline (phen) the crystalline complex [Cu(phen)2(Cl)]Cl x H2Sha was obtained and its crystal structure determined. This complex is a model for hydroxamate-peroxidase inhibitor interactions.

Copper↗
PubMed1966

Biosynthesis and utilization of aromatic compounds by Mycobacterium smegmatis with particular reference to the origin of salicylic acid.

1. Although Mycobacterium smegmatis could utilize a number of aromatic compounds as sole sources of carbon for growth, it did not appear to be able to use salicylic acid for growth or to metabolize it to any great extent. 2. When M. smegmatis was grown on shikimic acid as sole source of carbon, salicylic acid, anthranilic acid and 3,4-dihydroxybenzoic acid were released into the medium. When it was grown on quinic acid these compounds, together with p-hydroxybenzoic acid, p-hydroxyphenylacetic acid and a number of unidentified compounds, were formed. When it was grown on glucose only small amounts of salicylic acid could be detected. 3. When a washed suspension of cells with a normal iron content was incubated with shikimic acid, only small amounts of aromatic compounds were formed in the medium. When the cells were iron-deficient, substantial amounts of salicylic acid, 3,4-dihydroxybenzoic acid and catechol were formed, together with several other compounds not definitely identified. 4. When washed suspensions of cells, whether iron-sufficient or iron-deficient, were incubated with tryptophan no evidence of formation of salicylic acid, anthranilic acid or phenolic compounds was obtained. Washed suspensions did not convert anthranilic acid into salicylic acid. 5. When cell-free extracts of M. smegmatis were incubated with shikimic acid, or shikimic acid 5-phosphate, traces of anthranilic acid were formed under certain conditions. No formation of salicylic acid or other phenolic compound was observed even when a number of combinations of cofactors and coenzymes were tried.

Benzoates↗