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PubMed1999

Quantification of anthranilic acid and its related enzyme activity in several different species.

Anthranilic acid (AA) has been attracted considerable attention as one of the L-tryptophan-kynurenine pathway metabolites in the central nervous system. In this study, the concentration of L-kynurenine (L-KYN) and AA in serum and CSF, and its related enzyme activities were determined in several species. In rabbits, CSF AA concentrations were lower and serum AA concentrations were slightly higher than those in other species. However, the concentrations of L-KYN were substantially higher in rabbits in both serum and CSF compared with other species. Tissue enzyme activities varied among species. In rabbits, lung IDO activities were higher, but liver kynurenine 3-hydroxylase activities were lower than those of the other species tested. Furthermore, brain kynurenine 3-hydroxylase activities were higher in gerbils than those in other species. These results clearly demonstrated that kynurenine pathway enzyme activities and metabolite concentrations vary with species.

Animals↗
PubMed1995

Inhibition of iodide transport in rat thyroid cells using N-substituted anthranilic acid derivatives.

The purpose of this study was to test the effects of chloride channel blockers on iodide uptake in thyroid cells, in the hope of eventually using these blockers to identify and isolate a putative iodide transporter. The chloride channel blockers used in this report are derivatives of N-substituted anthranilic acid and were synthesized using published procedures. For these studies FRTL-5 cells, a line of continuous-growing rat thyroid cells, were used as a model system to study effects on iodide transport. In these cells, there are at least two ways for transmembrane iodide movements, a sodium-dependent influx step and a proposed channel that normally mediates iodide efflux. Two derivatives studied decreased iodide accumulation in FRTL-5 cells, but were found also to lower intracellular pH and ATP levels. To simplify interpretation of the effect of the drugs on iodide transport, we extended the studies using plasma membrane vesicles made from pig thyroid. Iodide entry in these vesicles depended on a sodium gradient and was independent of ATP levels. Iodide transport in plasma membrane vesicles and FRTL-5 cells was measured at 30 sec when the uptake was nearly linear and therefore likely to reflect iodide entry. The uptake was measured using three concentrations of iodide and three of drug. Kinetic analysis of the data described a competitive inhibition by the drugs with a Ki of approximately 250 microM. In summary, N-substituted anthranilic acid derivatives reversibly inhibit iodide entry in FRTL-5 cells and pig plasma membrane vesicles.(ABSTRACT TRUNCATED AT 250 WORDS)

Adenosine Triphosphate↗
PubMed1989

Enhancing activity of anthranilic acid on adjuvant arthritis in rats and antibody formation in mice.

Anthranilic acid (ANA), a metabolite of tryptophan, was examined for its immunopotentiating properties. Administration of ANA (12 mg/kg/day, p.o.) significantly enhanced the development of adjuvant arthritis in rats, although not in a dose-related manner. ANA tended to enhance adjuvant disease moderately suppressed by pretreatment with cyclophosphamide (CY), an immunosuppressive agent. ANA (3-30 mg/kg/day, p.o.) also caused a dose-related enhancement in the antibody formation to sheep erythrocytes (SRBC) in mice.

Animals↗
PubMedDate not supplied

[Pharmacological activity of the furfuryl amine salt of 4-chloro-N-(2-furylmethyl)-5-sulfamoyl anthranilic acid].

Furfuryl amine salt of 4-chloro-N-(2-furylmethyl)-5-sulfamoyl anthranilic acid was shown to exert more pronounced diuretic and saluretic action in rats, mice and dogs than that of furosemide. The previous administration of furfuryl amine salt of furosemide promoted normalization of the excretory processes of the kidney and increased survival rate of rats in ischemia of the single kidney. The antiedema activity of the drug was found to be much more pronounced than that of furosemide.

Acute Kidney Injury↗
PubMed1977

Determination of anthranilic acid in plasma.

A simple, specific GLC method was developed for the determination of anthranilic acid in plasma. This method is based on extraction from a carefully controlled buffer followed by removal of solvent, silyation, and detection in the gas chromatograph. The procedure is quantitative in the 2-10 microgram/ml range.

Animals↗
PubMed1976

Pharmacological properties of N-(3',4'-dimethoxycinnamoyl) anthranilic acid (N-5'), a new anti-atopic agent.

1 N-(3'-4'-dimethoxycinnamoyl) anthranilic acid (N-5') exhibited a dose-dependent, potent inhibition of the passive cutaneous anaphylaxis (PCA) mediated by homocytotropic antibodies (HTA), which was hardly affected by anti-inflammatory agents such as phenylbutazone, indomethacin and prednisolone at any dose used. The HTA-induced PCA was significantly inhibited by combined treatment with diphenydramine and cyproheptadine. 2 Doses of N-5' which potently inhibited HTA-induced PCA inhibited only slightly the heterologous PCA produced by anti-bovine serum albumin (BSA) rabbit serum. This heterologous PCA was clearly inhibited by phenylbutazone, indomethacin and prednisolone. Diphenydramine and cyproheptadine, singly or combined inhibited the heterologous PCA only slightly. 3 The increased vascular permeability caused by histamine and 5-hydroxytryptamine was significantly inhibited by diphenyldramine or cyproheptadine, but not by N-5' and the anti-inflammatory agents used. 4 N-5' 150 mg/kg orally inhibited rat paw oedema induced by carrageenin by about 26% while phenylbutazone, indomethacin and prednisolone produced significant inhibition. 5 N-5' at concentrations of 100 and 1000 muM significantly inhibited (by about 52% and 95%, respectively) the histamine release from rat peritoneal cells induced by HTA; 10 muM N-5' had little effect. Histamine release was inhibited by phenylbutazone or indomethacin at 1000 muM but not at 100 muM. Prednisolone had no effect on histamine release at any of the concentrations used. 6 These findings suggest that the inhibition of the HTA-induced PCA by N-5' may be due to inhibition of histamine release and is clearly different from the actions of anti-inflammatory agents such as phenylbutazone, indomethacin and prednisolone.

Animals↗
PubMed2004

Synthesis of new N-(2-(trifluoromethyl)pyridin-4-yl)anthranilic acid derivatives and their evaluation as anticancer agents.

The N-(2-(trifluoromethyl)pyridin-4-yl)anthranilic acid 6 and a series of its ester and amide derivatives were synthesized and evaluated for their in vitro cytotoxic activity against human cancer cells. Ester derivatives 13 and 18 exhibited potent growth inhibitory activity with GI(50) values at nanomolar concentrations. Among amide derivatives, N-anthraniloylglycinate 19 shown moderate inhibitory activity in the full panel cancer cell line screening.

Antineoplastic Agents↗
PubMed2001

Synthesis of N-terminal substituted anthranilic acid dimer derivatives for evaluation on CCK receptors.

A series of new N-substituted anthranilic acid dimer derivatives having a C-terminal Phe residue was synthesized and evaluated for their affinity for CCK receptors. These compounds resulted from a blended approach based firstly on the use of an alternative substructure embedded within asperlicin and secondly on the derivatization of this template with substituents chosen considering the C-terminal primary structure of the endogenous ligand. Although these compounds exhibited a regnylogical-type organization similar to that of CCK-4, they are characterized by about 1000-fold greater affinity for CCK-A receptor than the C-terminal tetrapeptide.

Animals↗
PubMed1987

Studies on the anti-allergic action of N-(3',4'-dimethoxycinnamoyl) anthranilic acid (N-5').

The effects of the anti-allergic compound (N-(3',4'-dimethoxycinnamoyl) anthranilic acid (N-5' or Tranilast) have been investigated upon antigen-induced contractions of respiratory smooth muscle in vitro and bronchoconstriction in vivo. N-5' (3.1 X 10(-5) M) in vitro had no significant effect upon antigen-induced contractions of the guinea pig trachea. However, when tested at concentrations of 9.2 and 3.1 X 10(-5) M, but not 0.9 X 10(-5), N-5' significantly inhibited antigen-induced contractions of the human parenchyma. In vivo N-5' (5 and 10 mg/kg p.o.) failed to inhibit antigen-induced dyspnea in hyperreactive rats. N-5' (20 mg/kg p.o.) also failed to inhibit the immediate bronchoconstriction following ascaris challenge of conscious squirrel monkeys but significantly attenuated the reduction in dynamic compliance during the pulmonary late phase response observed between 4 and 10 h after antigen challenge. It is suggested that N-5' does not act as a "cromoglycate-like" compound but may have novel mechanisms of action in human bronchial asthma.

Airway Resistance↗
PubMed1987

Synthesis and enzymic hydrolysis of cyclic peptides containing an anthranilic acid residue.

Two cyclic peptides cyclo (Phe-MeAnt-Glyn) with MeAnt = 5-methyl-anthranilic acid residue, n = 4 (3b) and n = 6 (4b), have been synthesized in solution and their reaction with alpha-chymotrypsin analyzed. The polyglycyl chain was prepared by the phosphazo method; cyclization at the Gly-Phe site occurred in good yield using the azide method. Catalysis of the hydrolysis of peptides 3b and 4b by alpha-chymotrypsin was characterized at 37 degrees by the apparent second-order rate constants kcat/Km 0.12 and 1.15 M-1 S-1, respectively, in agreement with the usual acceleration observed upon enlargement of the size of the peptidic ring in cyclic peptides. alpha-Chymotrypsin specifically split the Phe-MeAnt amide bond in cyclopeptide 4b. This specific orientation suggests that analogous structures with a functionalized methylene group instead of the methyl substituent can be used in the design of suicide substrates for serine proteases.

Chromatography, High Pressure Liquid↗
PubMed1992

Inhibition of proliferative responses of lymphocytes to food antigens by an anti-allergic drug, N(3',4'-dimethoxycinnamoyl) anthranilic acid (Tranilast) in children with atopic dermatitis.

Experimental studies have shown that N(3',4'-dimethoxycinnamoyl) anthranilic acid (Tranilast) inhibits reaginic antibody-mediated hypersensitivity reactions, and it has been demonstrated to be an effective drug for patients with bronchial asthma. On the other hand, from the nature of the cellular infiltrate seen in eczematous lesions, it appears that some form of cell-mediated immunity may be involved in addition to IgE-mediated immunity in the pathogenesis of atopic dermatitis (AD). Moreover, we have previously reported that the proliferative responses of peripheral blood mononuclear cells (PBMCs) to ovalbumin (OA) or bovine serum albumin (BSA) in children with AD who are sensitive to hen's egg or cow's milk were significantly higher than those of healthy children and hen's egg or cow's milk sensitive children with immediate symptoms. In this study, we have showed that the proliferative responses of PBMCs to OA were dose-dependently inhibited by Tranilast on patients with AD. The responding cells to OA were shown, through separation experiments, to be T cells, and the proliferative responses of T cells to OA were also dose-dependently inhibited by Tranilast. Moreover, the inhibition was thought to occur at the initial stage of the proliferative reactions. These results suggest that Tranilast can be clinically applied to patients with AD.

Antigens↗
PubMed2002

Anti-tumor effect of N-[3,4-dimethoxycinnamoyl]-anthranilic acid (tranilast) on experimental pancreatic cancer.

The anti-tumor effect of N- [3,4-dimethoxycinnamoyl] -anthranilic acid (tranilast) was examined in experimental pancreatic cancer. Proliferation of PGHAM-1 cells was inhibited by tranilast in a dose-dependent manner, showing a significant difference at a concentration of 25 microgram/ml (p<0.05). In colony formation, tranilast reduced the number of colonies at a concentration of 25 microgram/ml (p<0.01). DNA synthesis for 12 hours was attenuated dose-dependently and a significant difference was observed at concentrations of greater than 50 microgram/ml (p<0.05). From cell cycle analysis, a dose-dependent increase in the distribution of G0-G1 phase was observed. In the dorsal air sac model, the mean angiogenesis indices in PGHAM-1 chambers were 4.17 +/- 0.22 (control group) and 2.33 +/- 0.84 (treatment group), and in VEGF chambers they were 3.60 +/- 0.67 (control group) and 1.92 +/- 0.42 (treatment group), In the peritoneal dissemination model, the quantity of sanguineous ascites, the number and the size of diaphragmatic nodules and the microvessel density (MVD) of the metastatic site were reduced by tranilast significantly. In conclusion, the anti-tumor effect of tranilast on proliferation and on tumor-angiogenesis was confirmed in experimental pancreatic cancer.

Animals↗
PubMed1998

Spectrofluorimetric determination of anthranilic acid derivatives based on terbium sensitized fluorescence.

Terbium sensitized fluorescence was used to develop a sensitive and simple spectrofluorimetric method for the determination of the anthranilic acid derivatives furosemide and mefenamic and tolfenamic acids. The method makes use of radiative energy transfer from anthranilates to terbium ions in alkaline methanolic solutions. Optimum conditions for the formation of the anthranilate-Tb3+ complexes were investigated. Under optimized conditions, the detection limits are 6 x 10(-9), 1.4 x 10(-8) and 9.0 x 10(-9) mol l-1 for furosemide, mefenamic acids and tolfenamic acid, respectively. The range of application is 2.5 x 10(-8)-5.0 x 10(-5) mol l-1 for all three drugs. The method was successfully applied to the determination of furosemide and mefenamic and tolfenamic acids in serum after extraction of the samples with ethyl acetate, evaporation of the organic layer under a stream of nitrogen at 40 degrees C and reconstitution of the residue with alkaline methanolic terbium solution prior to instrumental measurement. The mean recoveries from serum samples spiked with furosemide (5.0 x 10(-7), 2.0 x 10(-6) and 8.0 x 10(-6) mol l-1), mefenamic acid (3.0 x 10(-6), 9.0 x 10(-6) and 3.0 x 10(-5) mol l-1) and tolfenamic acid (3.1 x 10(-6), 12.5 x 10(-6) and 2.5 x 10(-5) mol l-1) were 96 +/- 8, 101 +/- 5 and 98 +/- 7%, respectively. The within-run precision (RSD) for the method for two serum samples of each drug varied from 2 to 8% and the day-to-day precision for two concentration levels varied from 2 to 13%.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed1986

Inhibitory effect of N-(3,4-dimethoxycinnamoyl)anthranilic acid on release of SRS from alveolar macrophages in vitro.

The effects of N-(3,4-dimethoxycinnamoyl)anthranilic acid (N-5') on the release of the slow-reacting substance (SRS) by zymosan- or Ca ionophore-stimulated rat and human alveolar macrophages (AM) were examined in vitro. Disodium cromoglycate (DSCG) was used as a control. N-5' at concentrations of 10(-4)-10(-3) M significantly inhibited the release of SRS from both rat and human AM stimulated by zymosan. N-5' had almost the same inhibitory effect when added to the AM culture system at any time from 180 min before to 30 min after the addition of zymosan. N-5' (10(-4)-10(-3) M) also significantly inhibited the release of SRS by Ca ionophore-stimulated rat AM. N-5' (10(-6)-10(-3) M) had no significant effect on phagocytosis of yeast particles by rat AM. DSCG (10(-6)-10(-3) M) did not inhibit the release of SRS from the zymosan-stimulated rat AM. N-5' was concluded to have a relatively specific inhibitory effect on the non-immunological release of SRS from stimulated AM. It is postulated that N-5' inhibits the process of release of SRS from AM by acting after the initial stage.

Animals↗
PubMed1995

Nonselective and efficient fluorescent labeling of glycans using 2-amino benzamide and anthranilic acid.

Reaction conditions for conjugation of two fluorescent ortho-substituted aniline derivatives, 2-amino benzamide (2-AB) and 2-anthranilic acid (2-AA), to N- and O-glycans have been investigated. Conjugation conditions for attaching 2-AB and 2-AA to core-fucosylated and non-fucosylated glycans were developed using complex N-glycans radiolabeled at the nonreducing terminus with [3H]C6-galactose. Optimal conditions for each of the following reaction parameters were experimentally defined: [glycans], [2-AB] or [2-AA], solvent and acid composition, temperature and time of Schiff's base formation, nature of reductant, and temperature and time of reduction. Using the optimized reaction conditions it has been shown with several standard glycans and glycoprotein-derived glycan libraries that (i) molar labeling efficiencies are high and essentially independent of the amount of glycans; (ii) negligible (< 2 mol%) desialylation occurs during conjugation; (iii) glycan labeling is nonselective, i.e., independent of glycan structure; and (iv) insignificant fluorescent or chemical "blank" is recovered during the glycan-labeling and purification protocol. Labeling glycan pools with 2-AB or 2-AA therefore allows representative glycan profiles to be obtained and also allows relative molar quantitation of individual glycans in a pool. The 2-AB label is compatible with several chromatographic means for separation of carbohydrates including Bio Gel P4 gel permeation, high-performance anion-exchange chromatography with fluorescence detection, and a variety of HPLC procedures, as well as with mass spectrometric methods including matrix-assisted laser desorption-mass spectrometry and electrospray-mass spectrometry. The 2-AA label is particularly well-suited for electrophoretic separations by polyacrylamide gel electrophoresis. These fluorophores show high intrinsic sensitivity and thus facilitate very sensitive analysis of protein glycosylation.

Chromatography, High Pressure Liquid↗
PubMed1979

A double blind controlled trial of N-(3',4'-dimethoxycinnamoyl) anthranilic acid on children with bronchial asthma. N-5' Study Group in Children.

A double blind controlled trial of N-(3',4'-dimethoxycinnamoyl) anthranilic acid (N-5') was carried out for treating children with bronchial asthma to determine its efficacy and safety. The results showed that the drug was significantly more effective in the N10 and N5 groups than in the N0 group. Adverse reactions appeared only in one patient in the N10 group who complained of slight anorexia while another patient in the N0 group reported moderate diarrhoea. Moreover there was no indication of abnormality in further laboratory investigations. It can be therefore concluded that this drug is useful for the treatment of children with bronchial asthma.

Asthma↗
PubMed1991

4-halo-3-hydroxyanthranilic acids: potent competitive inhibitors of 3-hydroxy-anthranilic acid oxygenase in vitro.

The mechanism of action of three potent inhibitors of 3-hydroxyanthranilic acid oxygenase (3HAO), the enzyme responsible for the production of the endogenous excitotoxin quinolinic acid, was examined in vitro. Using either liver homogenate or purified 3HAO, and following the rapid synthesis of the immediate enzymatic product alpha-amino-beta-carboxymuconic acid omega-semialdehyde spectrophotometrically, 4-halogenated (F, Cl, Br) 3-hydroxyanthranilic acids were found to inhibit enzymatic activity in a reversible fashion. Because of the very tight binding of the drugs to 3HAO, reversibility was detected only after warming the protein-inhibitor complexes at 37 degrees. Further studies showed that enzyme inhibition was competitive in nature (apparent Ki values: 190, 6 and 4 nM for the F-, Cl- and Br-compounds, respectively), and suggested that the drugs are metabolized by the enzyme. Specific, reversible, and tightly binding 3HAO inhibitors can be expected to become valuable tools for the study of quinolinate neurobiology. The drugs could also be of interest for the diagnostics and therapeutics of brain diseases which have been speculatively linked to a pathological overabundance of quinolinic acid.

3-Hydroxyanthranilic Acid↗