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PubMed1980

Comparative study of tumorigenicity in mice administered transplacentally or neonatally with metabolites of tryptophan and its related compounds.

Intermediate metabolites of tryptophan, 3-hydroxy-L-kynurenine (3-OHKY), 3-hydroxyanthranilic acid (3-OHAA) and anthranilic acid (AA), and an enzyme inhibitor from 3-OHKY to 3-OHAA, isonicotinic acid hydrazide (INH) with or without 3-OHKY at the maximum tolerated dose were injected s.c. to infant CDF1 mice. AA and 3-OHAA were tested transplacentally for tumorigenicity. Animals treated were observed for 1 year. Hepatocellular adenoma was developed at the incidence of 21.7% in male mice administered with 3-OHKY and INH as compared with 5.6% incidence in control males, but no leukemia was induced. Incidences of lung (3.4--15.0%) and liver tumors (4--5%) in other groups treated at infant stage were comparable to that in controls (lung: 11.1%; liver: 5.6%). Other tumors were one angiogenic sarcoma in a female treated with 3-OHAA, and one granulosa cell tumor of ovary in female treated with INH. Transplacentally the 10.3% incidence of liver tumor in male offspring, whose mothers were treated with AA, was slightly higher than that in male control (5.6%). However, the incidences of tumor were apparently in a critical level in these experimental conditions.

3-Hydroxyanthranilic Acid↗
PubMed1975

Biosynthesis of p-aminophenylalanine: part of a general scheme for the biosynthesis of chorisimic acid derivatives.

p-Aminophenylalanine is biosynthesized in Vigna vexillata (L.) A. Rich. from shikimic acid through a pathway different from that giving phenylalanine and tyrosine. Experiments with 1,6-14C-labelled shikimic acid demonstrate that the C3-side chain in p-aminophenylalanine is attached to the original C-1 in shikimic acid. The biosynthesis of p-aminophenylalanine in Vigna vexillata probably follows the same pathway as the biosynthesis of this amino acid in Streptomyces species where it is known to be an intermediate in the biosynthesis of chloramphenicol. It is proposed that the biosynthesis takes place through chorismic acid, 4-amino-3-enolpyruvylcyclohexa-1,5-dienecarboxylic acid, 3-(4-amino-1-carboxycyclohexa-2,5-dienyl) pyruvic acid, and 4'-aminophenyl-yruvic acid. It is proposed that chorismic acid can gave rise to 4-amino-3-enolpyruvylcyclohexa-1,5-dienecarboxylic acid, 2-amino-3-enolpyruvylcyclohexa-4,6-dienecarboxylic acid, and isochorismic acid, and that these three compounds and chorismic acid itself by simple rearrangements and elimination reactions can give rise to most known chorismic acid derivatives, i. e.p-hydroxybenzoic acid, 3,4-dihydroxy-3,4-dihydrobenzoic acid, phenylalanine, tyrosine, p-aminobenzoic acid, p-aminophenylalanine, anthranilic acid, 2-amino-3-hydroxy-2,3-dihydrobenzoic acid, 3-(3-carobxyphenyl) alanine, 3-(3-carbocy-4-hydrocyphenyl) alanine, salicylic acid, and 2,3-dihydroxy2,3-dihydrobenzoic acid.

Amines↗
PubMed2006

Search of antitubercular activities in tetrahydroacridines: synthesis and biological evaluation.

A series of 9-substituted tetrahydroacridines were synthesized by nucleophilic substitution of chloro group with different nucleophiles in 9-chlorotetrahydroacridine (2). The latter could be obtained by POCl(3) mediated cyclization of the intermediate enamine, which in turn, was prepared by acid catalyzed condensation of anthranilic acid and cyclohexanone. Most of the compounds on antitubercular evaluation against M. tuberculosis H37 Rv and H37 Ra strains exhibited potent activities with MIC 6.125-0.78 microg/mL comparable to the standard drugs.

Acridines↗
PubMed1971

Formation of bilirubin glucoside.

1. Rat liver microsomal preparation can effect the transglucosylation from UDP-glucose to bilirubin in the presence of Mg(2+). 2. Other nucleotides, namely CDP-glucose, ADP-glucose and GDP-glucose, were not active as glucosyl donors. 3. Only trace amounts of galactose, galacturonic acid and N-acetylglucosamine were conjugated to bilirubin when their respective UDP derivatives were used in the reaction mixture. 4. The azobilirubin glucosides produced by coupling with p-diazobenzenesulphonic acid and diazotized ethyl anthranilic acid were separable from the corresponding azobilirubin glucuronides by t.l.c. 5. The glucoside was, however, hydrolysed by both beta-glucosidase and various preparations of beta-glucuronidase; azobilirubin and glucose were liberated in the process. 6. Kinetic studies showed that the effects of pH and Mg(2+) on the two conjugating systems were similar. 7. The specific activities of hepatic bilirubin UDP-glucosyltransferase, expressed as mug of bilirubin ;equivalents' conjugated/h per mg of protein, are respectively 1.7 and 2.4 for male and female rats. 8. The K(m) values for bilirubin and UDP-glucose are 5.7x10(-5)m and 1.6x10(-3)m respectively. 9. The glucoside and glucuronide conjugations of bilirubin are discussed in relation to the availability of the conjugating agents and aglycone in the liver.

Adenosine Diphosphate↗
PubMed2000

[Non-opioid analgesics--irreplaceable in cancer pain therapy?

Sufficient therapy of pain is essential for the treatment of tumor patients. World Health Organisation (WHO)-guidelines recommend a combination of opioids with non-opioid-analgesics (NOA) for patients with medium to strong pain. Cancer pain is often a combination of pain caused by the tumor itself, tumor associated and pain caused by therapy. Various substances act by different mechanisms and therefore combinations may demonstrate superior effects. Opioids ("central analgesics") inhibit neuronal transduction within the spinal cord, enhance inhibiting function of midbrain nuclei on ascending pain transduction and influence pain perception via modulation of the limbic system. NOAs ("peripheral analgesics") inhibit cyclooxygenase hindering activation of the peripheral nociceptor-system. There are 2 different classes of NOAs: 1) non-acidic, antipyretic analgesics like pyrazolones (metamizol) and anilin-derivates (paracetamol) and 2) non-steroidal antirheumatics (NSAR) like salicylates (acetylsalicylic acid), derivates of propionic acid (ibuprofen, naproxen), acetate acid (indomethacin, diclofenac), enolic acid (piroxicam, meloxicam) and anthranil acid (mefenamin). Adjuvant therapy is necessary to control common NSAR-side-effects like dyspepsia, ulcer and gastrointestinal bleeding. Due to its exceptional analgesic, antipyretic and spasmolytic properties, metamizol is an essential substance in tumor therapy. As agranulocytosis-incidence of 1:1,000,000 is low, good gastrointestinal and renal tolerance makes metamizol an excellent alternative to NSAR. There is scientific evidence that adequate combinations of non-opioids, opioids and adjuvant drugs, considering adverse side effects, were effective and safe in the treatment of cancer pain.

Analgesia↗
PubMed1980

[Effect of kynurenine and its metabolites on the vascular effects of serotonin, noradrenaline, and acetylcholine].

In female albino rats anesthetized with urethane, the depressor effect of serotonin was basically diminished by kynurenine, 3-hydroxyanthranilic acid (3-HAA), and anthranilic acid and was potentiated by quinolinic and picolinic acids (PA). All kynurenines were injected in a dose of 200 micrograms. 3-Hydroxykynurenine and nicotinic acid (NA) had a dual action. The pressor effect of noradrenaline was largely diminished by 3-HAA, PA and NA. Each of the rest kynurenines exerted an opposite action in different experiments. The pressor effect of acetylcholine was not affected by kynurenines.

3-Hydroxyanthranilic Acid↗
PubMed1990

New quinoline derivatives: synthesis and evaluation for antiinflammatory and analgesic properties--Note I.

New 4-anilinoquinoline-3-carboxylic acids, N-[3-carboxyquinolyl (4)]anthranilic acids and their corresponding esters were synthetized by reacting 4-chloro-3-carbethoxyquinolines with substituted anilines and methyl anthranilate respectively. All the compounds were tested for antiinflammatory and analgesic activities. Some derivatives showed a significant antiinflammatory activity comparable to that of indomethacin.

Analgesics↗
PubMed1993

New quinoline derivatives: synthesis and evaluation for antiinflammatory and analgesic properties--Note II.

The synthesis of new halogenated series of 4-anilinoquinoline-3-carboxylic acids, N-[3-carboxyquinolyl(4)]anthranilic acids and their corresponding esters is reported. These have been obtained by reacting 4-chloro-3-carbethoxy-quinolines with variously substituted anilines and methyl anthranilate respectively. The synthesized compounds were tested for antiinflammatory and analgesic activities; some of them showed a good analgesic activity, sometimes higher than that of indomethacin, used as reference drug.

Aniline Compounds↗
PubMed1988

Gas chromatographic analysis of flunixin in equine urine after extractive methylation.

A quantitative method for the analysis of flunixin, 2-(2-methyl-3-trifluoromethylanilino) nicotinic acid, in equine urine by gas chromatography with nitrogen-phosphorus detection has been developed. Flunixin and the internal standard, mefenamic acid, N-(2,3-xylyl) anthranilic acid, were analysed after extractive methylation of the carboxylic acid group using methyl iodide. The extraction and alkylation conditions of flunixin and mefenamic acid have been studied. The detection limit of the method was 0.25 mumol/l flunixin in urine (74 ng/ml). Flunixin was found to be conjugated to 96.5% in equine urine, and the conjugate was spontaneously hydrolysed to free flunixin. This approach can also be used to confirm the presence of flunixin or mefenamic acid in horse urine in the doping control of racehorses.

Alkylation↗
PubMed2006

In vitro evidence for an antioxidant role of 3-hydroxykynurenine and 3-hydroxyanthranilic acid in the brain.

We investigated the in vitro effect of 3-hydroxykynurenine (3HKyn), 3-hydroxyanthranilic acid (3HAA), kynurenine (Kyn) and anthranilic acid (AA) on various parameters of oxidative stress in rat cerebral cortex and in cultured C6 glioma cells. It was demonstrated that 3HKyn and 3HAA significantly reduced the thiobarbituric acid-reactive substances (TBA-RS) and chemiluminescence measurements in rat cerebral cortex, indicating that these metabolites prevent lipid peroxidation in the brain. In addition, GSH spontaneous oxidation was significantly prevented by 3HAA, but not by the other kynurenines in cerebral cortex. We also verified that 3HKyn and 3HAA significantly decreased the peroxyl radicals induced by the thermolysis of 2,2'-azo-bis-(2-amidinopropane)-derived peroxyl radicals, and to a higher degree than the classical peroxyl scavenger trolox. 2-Deoxy-d-ribose degradation was also significantly prevented by 3HKyn, implying that this metabolite was able to scavenge hydroxyl radicals. Furthermore, the total antioxidant reactivity of C6 glioma cells was significantly increased when these cells were exposed from 1 to 48h to 3HKyn, being the effect more prominent at shorter incubation times. TBA-RS values in C6 cells were significantly reduced by 3HKyn when exposed from 1 to 6h with this kynurenine. However, C6 cell morphology was not altered by 3HKyn. Finally, we tested whether 3HKyn could prevent the increased free radical production induced by glutaric acid (GA), the major metabolite accumulating in glutaric acidemia type I, by evaluating the isolated and combined effects of these compounds on TBA-RS levels and 2',7'-dihydrodichlorofluorescein (DCFH) oxidation in rat brain. GA provoked a significant increase of TBA-RS values and of DCFH oxidation, effects that were attenuated and fully prevented, respectively, by 3HKyn. The results strongly indicate that 3HKyn and 3HAA behave as antioxidants in cerebral cortex and C6 glioma cells from rats.

3-Hydroxyanthranilic Acid↗
PubMed1983

[A method for the fluorimetric determination of usnic acid in pharmaceutical preparations].

A new, rapid, sensitive and reproducible micromethod for the fluorometric determination of usnic acid in pharmaceutical formulations has been developed. The method makes use of the quenching of the fluorescence produced by usnic acid in the solution of anthranilic acid in TRIS. The possibility of extending the method to cosmetic finished products is demonstrated.

Benzofurans↗
PubMed2005

Studying the immunosuppressive role of indoleamine 2,3-dioxygenase: tryptophan metabolites suppress rat allogeneic T-cell responses in vitro and in vivo.

Pregnancy is a natural model of successful tolerance induction against allogeneic tissues. Recent studies pointed to a role of indoleamine 2,3-dioxygenase (IDO), a tryptophan-degrading enzyme expressed in the placenta, in mediation of T-cell suppression. We want to apply to organ transplantation what nature has developed for suppression of fetal rejection during pregnancy. Here we analyze whether IDO-induced tryptophan metabolites are able to suppress the allogeneic T-cell response and allograft rejection in rats. Rat lymphocytes were stimulated with allogeneic dendritic cells in vitro in the presence of increasing amounts of tryptophan metabolites (kynurenine, 3-hydroxykynurenine, anthranilic acid, 3-hydroxyanthranilic acid and quinolinic acid) and T-cell proliferation was determined. The findings showed that kynurenine, 3-hydroxykynurenine and 3-hydroxyanthranilic acid strongly suppress the T-cell response, whereas anthranilic and quinolinic acid are non-effective. Vital staining of cells with subsequent fluorescence-activated cell sorter analyses demonstrated that suppression is mediated by T-cell death. Thereafter, the action of metabolites was analyzed in a skin allograft model (BN-->LEW). Lewis recipients received daily s.c. injections of tryptophan metabolite mixture (kynurenine + 3-hydroxyanthranilic acid), cyclosporin A (positive control), or no treatment (negative control). The metabolites induced a significant prolongation (P = 0.0018) of graft survival. We conclude that IDO-induced tryptophan metabolites suppress the T-cell response and prolong allograft survival in rats.

Animals↗
PubMed1990

Determination of urinary tryptophan and its metabolites along the nicotinic acid pathway by high performance liquid chromatography with ultraviolet detection.

A fast and sensitive method is given for analysing urinary tryptophan and six of its metabolites on the nicotinic acid pathway. Kynurenine, tryptophan, 3-hydroxykynurenine, anthranilic acid, 3-hydroxyanthranilic acid, kynurenic acid and xanthurenic acid were isocratically eluted and completely resolved with a mobile phase of acetonitrile + sodium acetate buffer, pH 4.76 (4:96, v/v). The flow rate was 0.8 mL/min at the beginning and was then linearly increased to 1.2 after 6 min; after 14 min the flow was augmented from 1.2 to 2 mL/min. The effluent was monitored with a variable UV detector set at 254 nm for the first five peaks and at 280 and 325 nm for the penultimate peak and final peak. Analytical recoveries of the compounds after deproteinization varied between 64% and 98%. The reported method should enable one to examine easily, extensively, quantitatively and routinely urinary tryptophan and the most important metabolites of the nicotinic acid pathway.

Chromatography, High Pressure Liquid↗
PubMed1987

Synthesis and biocidal activity of Zn(II) complexes of some 2,2'-substituted diphenylamines.

Binary as well as ternary complexes of Zn(II) with diphenylamine-2,2'-dicarboxylic acid (dpdc), diphenylamine-2-amino-2'-carboxylic acid (dpac), diphenylamine-2-hydroxy-2'-carboxylic acid (dphc), diphenylamine-2-mercapto-2'-carboxylic acid (dpmc), and N-(2-pyridino) anthranilic acid (npa) have been synthesized and characterized by their elemental analysis, IR spectral data, and molar conductance measurements. Antimicrobial activity of these ligands and their respective Zn(II) complexes have been determined on gram positive (Staphylococcus aureus) and gram negative (Escherichia coli) bacteria and on Aspergillus niger and Aspergillus nidulense, two common fungi by the serial dilution method. A considerable increase in the biocidal activity of these ligands on being coordinated with the metal ion has been reported in terms of their minimum inhibitory concentration (MIC) values.

Aniline Compounds↗
PubMed1985

Characterization and regulation of p-aminobenzoic acid synthase from Streptomyces griseus.

p-Aminobenzoic acid synthase (PABA synthase) of Streptomyces griseus catalyses the conversion of chorismic acid to p-aminobenzoic acid (PABA), a precursor of the aromatic p-aminoacetophenone moiety of candicidin, a polyene macrolide antibiotic. This enzyme uses glutamine or ammonia as amino donors for PABA formation. Enzyme extracts converted [14C]chorismic acid to labelled PABA. PABA synthase was present in S. griseus IMRU 3570 only during the antibiotic producing phase. No detectable levels of the enzyme were found in cell-free extracts of nonproducing mutants of S. griseus obtained after UV mutagenesis. PABA synthase activity was found also in Streptomyces coelicolor var. aminophilus, producer of the polyene macrolide antibiotic fungimycin, but it was not present in extracts of several other streptomycetes that do not produce aromatic polyene macrolide antibiotics. PABA synthase (amidotransferase) activity was partially purified by DEAE-Bio-gel and Sephacryl S-200 filtrations. The estimated molecular weight was 50000. PABA synthase was repressed by aromatic amino acids and PABA but not by anthranilic acid. Inorganic phosphate strongly repressed but did not inhibit PABA synthase activity.

Amino Acids↗
PubMed1965

Microbiological method for the determination of L-tryptophan.

Sebek, Oldrich K. (The Upjohn Company, Kalamazoo, Mich.). Microbiological method for the determination of l-tryptophan. J. Bacteriol. 90:1026-1031. 1965.-The ability of Chrombacterium violaceum to utilize l-tryptophan for the synthesis of a purple pigment, violacein, served as a basis for the development of a quantitative estimation of this amino acid. The method consists of suspending washed colorless cells of the organism in an agar layer, placing a paper disc impregnated with a tryptophan solution on top of the layer, and allowing the system to incubate. As tryptophan diffuses into the agar, it is converted into violacein, and appears as a zone of striking purple color. Since the diameter of the zone is a function of the amount of tryptophan applied, the amino acid can be quantitatively estimated within the range of 10 to 320 mug per sample with 5.6% standard deviation. The method is fairly specific for free tryptophan, since only indole, indole-3-pyruvic acid, and, to a small degree, anthranilic acid interfere. Other amino acids, tissue homogenates, tryptophan in peptide linkage, or compounds related to this amino acid do not affect its determination. The bacterium does not utilize tryptophan for the synthesis of cellular material unless its growth has been initiated by another substrate.

Amino Acids↗