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PubMed1997

Novel naphthalene derivatives as inhibitors of human immunoglobulin E antibody production.

A series of naphthalene derivatives with a variety of substituents at the 2-position was prepared in order to evaluate their suppressive effect on immunoglobulin E (IgE) antibody production by human peripheral blood mononuclear cells provoked with anti-CD40 antibody (alpha-CD40), interleukin-4 (IL-4), and interleukin-10 (IL-10). Compounds having a 1,4-phenylene spacer moiety tethered between the 2-naphthyl nucleus and anthranilic acid suppressed IgE antibody production in vitro in preference to that of IgG antibody without affecting cell viability. Deletion of the anthranilic acid moiety diminished the inhibitory activities. Changing the 2-naphthyl to a 1-naphthyl or phenyl nucleus led to no change in the potency, indicating that the aromatic group at this position is indispensable for the inhibitory activities. On the other hand, changing the 1,4-phenylene spacer to a 1,3-phenylene one resulted in reduced potency. Similarly, inhibitory activities were lost when the CO2H moiety at the 2-position was moved to the 3- or 4-position on the terminal benzene. These observations suggest that the conformation around the anthranilic acid moiety affects the inhibitory activities toward IgE biosynthesis. 2-(4-(2-Naphthyloxy)benzamido)benzoic acid (29) seemed to be a more potent inhibitor of IgE production than of IgG production. Insertion of a methylene between the inter-phenylene and the amide moiety resulted in 2-((4-(2-naphthyloxy)phenyl)acetamido)benzoic acid (31), which provided a stronger inhibition of both IgE and IgG production, although the selectivity toward IgE was lower than that of 29. Introduction of a benzyl group at the 6-position on the naphthalene ring considerably increased the inhibitory activity toward IgE production with an IC50 of 8.3 nM (36). The potency of 31 and 36 was retained when hydrocortisone or lipopolysaccharide was used instead of alpha-CD40 and IL-10 as costimulatory factors with IL-4, implying that these compounds may interfere with signal transduction between IL-4/IL-4 receptor cognition and genetic transcription that induce class-switching of immunoglobulin in B cells. These novel naphthalene derivatives are thus excellent candidates for further investigation with a view toward a therapeutic remedy against IgE-mediated allergic diseases.

Antibody Formation↗
PubMed1963

Antagonism by mefenamic and flufenamic acids of the bronchoconstrictor action of kinins in the guinea-pig.

In the guinea-pig, N-(2,3-xylyl)anthranilic acid (mefenamic acid) and N-(alpha,alpha,alpha-trifluoro-m-tolyl)anthranilic acid (flufenamic acid), two new anti-inflammatory agents, antagonize bronchoconstriction, but not hypotension, produced by kinins. They do not reduce bronchoconstrictor responses to acetylcholine, histamine or 5-hydroxytryptamine. The antibradykinin potencies of mefenamic and flufenamic acids approximately equal that of acetylsalicylic acid when given intravenously and of phenylbutazone when given into the duodenum. After administration of mefenamic and flufenamic acids, the bronchoconstrictor response can be restored by higher doses of bradykinin. The quantitative relationship between the intravenous dose of sodium mefenamate or flufenamate and the dose of bradykinin needed to surmount either antagonist in bronchial muscle fulfils the requirements for competitive antagonism. Antagonism by calcium acetylsalicylate can also be surmounted with higher doses of bradykinin, but in this instance the relationship of antagonist to agonist fulfils requirements for competitive antagonism only at the lower part of the dose range.

Acetylcholine↗
PubMed2004

Neutral, acidic, and basic derivatives of anthranilamide that confer different formal charge to reducing oligosaccharides.

To facilitate the use of oligosaccharides as analytical tools in biological studies, we have designed, synthesized, and conjugated to maltosaccharides a novel series of homologous small fluorescent moieties that differ in formal charge. These moieties are amide derivatives of anthranilic acid: uncharged N-(2-aminobenzoyl)glycinamide (ABGlyAmide; 2), acidic N,N-dimethyl-N(')-(2-aminobenzoyl)ethylenediamine (ABGlyDIMED; 3), and basic N-(2-aminobenzoyl)glycine (ABGly; 1). Routes for synthesis and optimal reaction conditions for glycoconjugation by conventional reductive amination are presented, as is the compatibility of these adducts with common analytical and preparative chromatographic methods, including RP-HPLC and HPAEC-PAD. These novel anthranilic acid derivatives confer both fluorescence and defined charge to oligosaccharides, and so enhance the repertoire of chromatographic and analytical methods for which anthranilic acid can be used. Furthermore, because glucosaccharides have rigid solution structure, these small fluorescent adducts with different formal charge are ideal tools for molecular sizing studies of membrane pores.

Acids↗
PubMed1968

In vivo regulation of intermediate reactions in the pathway of tryptophan biosynthesis in Neurospora crassa.

The in vivo regulation of intermediate reactions in the pathway of tryptophan synthesis in Neurospora crassa was examined in a double mutant (tr-2, tr-3) which lacks the functions of the first and last enzymes in the pathway from chorismic acid to tryptophan. The double mutant can convert anthranilic acid to indole and indole-3-glycerol, and the production of these indolyl compounds by germinated conidia was used to estimate the activity of the intermediate enzymes in the pathway. Indole-synthesizing activity was maximal in germinated conidia obtained from cultures in which the levels of l-tryptophan were growth-limiting; the formation of this activity was markedly repressed when the levels of l-tryptophan exceeded those required for maximal growth. d-, 5-methyl-dl-, and 6-methyl-dl-tryptophan were less effective than l-tryptophan, and 4-methyl-dl-tryptophan, tryptamine, and indole-3-acetic acid were ineffective in repressing the formation of indole-synthesizing activity; anthranilic acid stimulated the formation of indole-synthesizing activity. Preformed indole-synthesizing activity was strongly and specifically inhibited by low levels of l-tryptophan; several related compounds were ineffective as inhibitors. These results suggest that, in addition to repression, an end product feedback inhibition mechanism is operative on an intermediate enzyme(s) in tryptophan biosynthesis. The relation of these results to other in vivo and in vitro studies and to general aspects of the regulation of tryptophan biosynthesis in N. crassa are discussed.

Enzyme Repression↗
PubMed1985

Cyclopeptine synthetase activity in surface cultures of Penicillium cyclopium.

Cyclopeptine synthetase, the key enzyme of benzodiazepine alkaloid biosynthesis in Penicillium cyclopium forms cyclo-(anthranoyl-phenylalanyl) from anthranilic acid, L-phenylalanine, the methyl group of L-methionine and ATP. The following in vitro measurable partial activities of the enzyme system were followed during the development of P. cyclopium: anthranilic acid and L-phenylalanine adenylyltransferase activities, and the ability for thioester-binding of L-phenylalanine to the enzyme protein. These activities became measurable at the beginning of the idiophase and reached a maximum 6 days after inoculation, i.e., the pattern of activity was similar to that of the other enzymes participating in the biosynthesis of the benzodiazepine alkaloids indicating that the activities of all enzymes of the pathway were coordinatedly expressed. Inhibitor experiments indicated that 48-55 h after inoculation a preprotein of anthranilic acid adenylyltransferase was formed, which later on became activated by a hitherto unknown mechanism.

Benzodiazepinones↗
PubMedDate not supplied

[Examination of the action of effectors after storing glutamine synthetase from the fodder yeast Candida tropicalis at room temperature].

The pattern of action of effectors (AMP, IMP, CMP, anthranilic acid, tryptophane, alanine, glutamine, glycine, histidine) and glutamine synthetase (GS) extracted from the fodder yeast Candida tropicalis and stored at room temperature for 1.5-2 hrs was examined. As regards the action of effectors on GS after its exposure at room temperature, they can be subdivided into four groups: 1) the effector loses completely its inhibitory effect (glutamine, CMP, anthranilic acid in the synthetase reaction); 2) the inhibitory effect on the enzyme increases (AMP, IMP, anthranilic acid in the transferase reaction); 3) at low concentrations of the effector the peak of activation appears (tryptophane, GMP, alanine, glycine); 4) at low concentrations of the enzyme two peaks of activation appear (histidine). Similar results were obtained with the purified preparation of GS.

Amino Acids↗
PubMed1975

Tryptophan metabolism in baboons: effect of riboflavin and pyridoxine deficiency.

Seven urinary metabolites of tryptophan-kynurenine pathway were measured in riboflavin-deficient, pyridoxine-deficient, pair-fed and natural diet baboons. The most significant changes in the pyridoxine-deficient baboons was a mean sevenfold increase in the excretion of xanthurenic acid and a threefold decrease in 3-hydroxy anthranilic acid. The riboflavin-deficient baboons showed a twelvefold increase in the excretion of anthranilic acid, and a tenfold decrease in 3-hydroxy kynurenine. Red blood-cell pyridine nucleotides decreased only in the pyridoxine-deficient baboons, while plasma 11-hydroxy corticosteroids increased only in the riboflavin-deficient baboons. These results are discussed in relation to enzymatic changes that may be expected during these deficiencies.

11-Hydroxycorticosteroids↗
PubMed2003

Kynurenine metabolism in central nervous system in experimental chronic renal failure.

Tryptophan metablolism via kynureninc pathway leads to the formation of several neuroactive substances including kynurenine, anthranilic acid and quinolinic acid, which are involved in numerous neurodegenerative diseases. Also chronic renal insufficiency is associated with neurological disturbances but it is still not clear which substances are responsible for those disorders. Thus, the aim of our study was to evaluate the concentration of tryptophan, kynurenine and anthranilic acid in plasma as well as in different brain regions in uremic rats. We have shown that tryptophan concentrations in plasma and in brain were decreased, whereas kynurenine and anthranilic acid levels were elevated, both in plasma and in central nervous system. Only in cerebellum and hippocampus were no difference in concentration of antranilic acid between control and uremic rats. Accumulation of tryptophan metabolites in nervous tissue may be involved in pathogenesis of several neurological disorders in uremia.

Animals↗
PubMed2006

Copper(II) interactions with non-steroidal anti-inflammatory agents. III--3-Methoxyanthranilic acid as a potential *OH-inactivating ligand: a quantitative investigation of its copper handling role in vivo.

Pharmacological activities of copper(II) complexes are a direct function of the nature of their ligands associated with the metal ion in vivo. Some of these, defined as *OH-inactivating ligands (G. Berthon, Agents Actions 39 (1993) 210-217), may act as specific "lures" for hydroxyl radicals at inflammatory sites and behave as pseudo-catalase-like agents. This property has been advanced for anthranilic acid (H. Miche, V. Brumas, G. Berthon, J. Inorg. Biochem. 68 (1997) 27-38). With a view to improve the chemical features required to render such inactive substances effective anti-inflammatory drugs through their association with copper(II), an in vitro investigation into copper(II) interactions with the anionic form of an anthranilic acid derivative, namely 3-methoxyanthranilate (Man), has been performed under experimental conditions pertaining in vivo. Copper(II)-Man complex equilibria have been determined using glass electrode potentiometry, then checked by UV-vis and mass spectrometries. Given the prime role of histidine as a copper(II) ligand in blood plasma, copper(II)-histidine-Man ternary equilibria have also been studied. Subsequent computer simulations of the distribution of copper(II) in the extracellular fluid revealed that Man can specifically mobilize Cu(II) ions under inflammatory conditions without affecting their distribution under normal physiological conditions. Thiobarbituric acid reactive substances (TBARS) tests conducted with respect to standardized copper-mediated Fenton-type reactions (P. Maestre, L. Lambs, J.P. Thouvenot, G. Berthon, Free Rad. Res. 20 (1994) 205-218) have shown that, like anthranilic acid, Man can effectively both increase the Fenton-like reactivity of copper and decrease the amount of TBARS detected in solution, i.e., act as a potential *OH-inactivating ligand.

Animals↗
PubMed1987

The effects of reversible freezing inactivation and inhibitor binding on redox properties of L-amino-acid oxidase.

We measured the redox potentials of frozen inactivated L-amino-acid oxidase (L-amino-acid:oxygen oxidoreductase (deaminating), EC 1.4.3.2) and inhibitor-bound (anthranilic acid) enzyme, and compared these redox properties to those of active L-amino-acid oxidase and benzoate-bound D-amino-acid oxidase (EC 1.4.3.3), respectively. The redox properties of the inactive enzyme are similar to the properties of free flavin; the potential is within 0.015 V of free flavin and no radical stabilization is seen. This corresponds to the loss of most interactions between apoprotein and flavin. In contrast, the anthranilic acid lowers the amount of radical stabilized from 85% to 35%. The potentials are still 0.150 V positive of free flavin, indicating that in the presence of inhibitor, many flavin-protein interactions remain intact. The difference between this behavior and that of D-amino-acid oxidase bound to benzoate, where the amount of radical declined from 95% to 5%, is explained on the basis of the relative tightness of binding of apoprotein to FAD. D-Amino-acid oxidase apoprotein has a relatively low Ka (10(6)) for FAD, and benzoate has a relatively high Ka (10(5)) for the enzyme. Therefore, the binding of benzoate increases the tightness of FAD binding to apo-D-amino-acid oxidase (10(11)), indicating significant changes in flavin-protein interactions. In contrast, apo-L-amino-acid oxidase binds flavin tightly (the Ka is greater than 10(7)) and the enzyme binds to anthranilate much less tightly, with a Ka of 10(3). The L-amino-acid oxidase apoprotein binding to FAD is tight initially, and the binding of anthranilate changes it only slightly.(ABSTRACT TRUNCATED AT 250 WORDS)

Amino Acid Oxidoreductases↗
PubMed1961

Repression and inhibition of indole-synthesizing activity in Neurospora crassa.

Lester, Gabriel (Worcester Foundation for Experimental Biology, Shrewsbury, Mass.). Repression and inhibition of indole-synthesizing activity in Neurospora crassa. J. Bacteriol. 82:215-223. 1961.-The possibility of repression and feedback inhibition as regulating mechanisms for the synthesis of tryptophan by Neurospora crassa has been examined in a tryptophan auxotroph which accumulates indole (and indole-glycerol). Indole-synthesizing activity was determined with germinated conidia suspended in medium lacking tryptophan. This activity was almost absent from cells cultured on germination medium containing more than 1.0 mumole l-tryptophan per ml, and increased with decreasing concentrations of l-tryptophan. A similar depression of the formation of indole synthesizing activity was caused by 6-methyl- and d-tryptophan, and less effectively by 5-methyltryptophan; 4-methyltryptophan was slightly stimulatory. Preformed indole synthesizing activity was inhibited by l-tryptophan, 4- and 6-methyltryptophan, and to a lesser extent by 5-methyltryptophan; d-tryptophan had no effect in this respect. The inhibition of preformed activity was partially reversed by anthranilic acid, which is a precursor of indole. However, anthranilic acid did not increase indole synthesis by cells wherein the formation of indole-synthesizing activity had been depressed by culture in the presence of high concentrations of l- or d-tryptophan. These observations indicate that regulation of tryptophan synthesis in N. crassa might result from the action of tryptophan as a repressor and as a feedback inhibitor. The relation of these results to other regulatory systems is discussed.

Indoles↗
PubMed2006

Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines.

A chemo- and regioselective copper-catalyzed cross-coupling procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection and produces N-aryl and N-alkyl anthranilic acid derivatives in up to 99% yield. N-(1-Pyrene)anthranilic acid has been employed in metal ion-selective fluorosensing. Titration experiments showed that this pyrene-derived amino acid forms an equimolar complex with Hg(II) in water resulting in selective fluorescence quenching even in the presence of other metal ions such as Zn(II) and Cd(II).

Amination↗
PubMed1994

Quantitative determination of monosaccharides in glycoproteins by high-performance liquid chromatography with highly sensitive fluorescence detection.

For specific determination of monosaccharides with high sensitivity, glycoprotein acid hydrolysates were derivatized in a simple step with excess anthranilic acid (2-aminobenzoic acid) in the presence of sodium cyanoborohydride to give highly fluorescent stable derivatives. The monosaccharide derivatives were completely separated from the excess reagent and from each other by HPLC on a C-18 reversed-phase column using a 1-butylamine-phosphoric acid-tetrahydrofuran mobile phase. Reductive amination of the monosaccharides in the methanol-acetate-borate medium was complete within 20 min at 80 degrees C. Derivatization of glucosamine with the anthranilic acid was accompanied by epimerization to mannosamine (> 15%) in methanol-acetic acid reaction medium, but it was reduced to < 3% in methanol-acetate-borate reaction medium. Fluorescence intensity of the hexosamines was greater than twice the intensity of the neutral monosaccharides. The fluorescent derivatives had excitation maxima at 230, 245, and 360 nm and an emission maximum at 425 nm. Fluorescence intensity at 230 nm excitation was about 10 times greater than that obtained with excitation at 360 nm for all the monosaccharides. Release and concomitant destruction of the monosaccharides during hydrolysis in 20% TFA at 100 degrees C for 7-8 h resulted in 83-85% recovery of all the monosaccharides from glycoproteins. The monosaccharide compositions determined by this method were in excellent agreement with the expected values for a recombinant immunoglobulin and fetuin and were highly reproducible. Relative standard deviation for the composition determinations and precision was less than 3%.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1976

The in-vitro adsorption of some antirheumatics on antacids.

The adsorption of sodium salicylate, salicylamide, acetylsalicylic acid, paracetamol, mefenamic acid, flufenamic acid, phenylbutazone, oxyphenbutazone, phenazone, aminophenazone, indometacin and methiazinic acid on some antacids was studied. The antacids used were magnesium trisilicate, magnesium oxide, aluminium hydroxide, bismuth oxycarbonate, calcium carbonate and kaolin. Magnesium oxide, followed by aluminium hydroxide and bismuth oxycarbonate showed a fairly high adsorptive capacity for salicylates, mefenamic acid, flufenamic acid, methiazinic acid, indometacin and to a lesser extent for phenylbutazone and oxyphenbutazone. On the other hand, magnesium trisilicate exhibited a tendency to adsorb phenazone, aminophenazone, indometacin and methiazinic acid. Kaolin was found to be a good adsorbent for anthranilic acid derivatives, indometacin and methiazinic acid. Calcium carbonate showed a weak adsorptive capacity for all drugs tested. The adsorption of phenylbutazone and salicylates on magnesium oxide, aluminium hydroxide and/or bismuth oxycarbonate obeyed the Freundlich adsorption isotherm. Elution study showed that salicylates and anthranilic acid derivatives were tenaciously held by magnesium oxide while magnesium trisilicate showed an intermediate retention power for phenazone and aminophenazone. Sodium hydrogen carbonate solution gave, in general, a higher eluting power than hydrochloric acid solution. A marked reduction in the apparent partition coefficients of all drugs tested was observed in the presence of magnesium trisilicate or aluminium hydroxide. Careful in vitro and in vivo testing of drug availability is advisable prior to the concomitant administration of antirheumatics with antacids or other adsorbents.

Adsorption↗
PubMed1979

Differences between the anthranilate-5-phosphoribosylpyrophosphate phosphoribosyltransferases of Salmonella typhimurium strains LT2 and LT7.

The anthranilate-5-phosphoribosylpyrophosphate phosphoribosyltransferases (PRT), coded by the second structural gene (trpB) of the tryptophan (trp) operon in strains LT2 and LT7 of Salmonella typhimurium, differ from each other in a number of parameters. These include the apparent Km values for their substrates anthranilic acid and 5-phosphoribosylpyrophosphate, thermostability, sensitivity to substrate inhibition by anthranilic acid, as well as end-product inhibition by tryptophan and specific activity. The PRT of strain LT7 further differs from that of strain LT2 in that its apparent Km for 5-phosphoribosylpyrophosphate is three to seven times higher when associated with anthranilate synthase in the enzyme complex which catalyses the first two steps of tryptophan biosynthesis than in its free uncomplexed form, which the PRT of strain LT2 shows the same apparent Km for this substrate in both its free and complexed forms. These results confirm and extend the finding of Stuttard (1975) that strains LT2 and LT7 differ genetically form each other at a single site within region II of the trpB gene.

Anthranilate Phosphoribosyltransferase↗
PubMed1993

Technetium-aspirin molecule complexes.

Technetium-aspirin and technetium-aspirin-like molecule complexes were prepared. The structure of N-acetyl-anthranilic acid (NAA) has been decided through CNDO calculations. The ionization potential and electron affinity of the NAA molecule as well as the charge densities were calculated. Comparative studies of the electronic absorption spectra of acetylthio-salicylic acid (ATS) and aspirin (Asp) reveal the structure resemblance in which the acetyl carbonyl group is perpendicular to the plane of the corresponding organic acid. The studies of the electronic absorption spectra of NAA and anthranilic acid reveal the planarity of the NAA molecule. The electronic absorption spectra of Tc(V)-Asp and Tc(V)-ATS complexes have two characteristic absorption bands at 450 and 600 nm, but the Tc(V)-NAA spectrum has one characteristic band at 450 nm. As a comparative study, Mo-ATS complex was prepared and its electronic absorption spectrum is comparable with the Tc-ATS complex spectrum.

Aspirin↗
PubMed1983

Structure activity correlation for diuretic furosemide congeners.

The structure activity correlation of several groups of anthranilic acid derivatives was studied. 59 compounds, most of them possessing the anthranilic acid moiety, were synthesized and tested for diuretic and saluretic activities. Equations correlating the biological activities of these compounds with their physicochemical constants suggest positive dependence of the diuretic activity on log P (octanol:water partition coefficient). It is concluded that, within limits, the variation in biological activity is primarily governed by the lipophilicity of the molecule, and further increase in log P value will not enhance this activity.

Animals↗
PubMed2001

Photochemical oxygen consumption, oxygen evolution and spectral changes during UVA irradiation of EMT6 spheroids.

Remarkable rates of oxygen consumption are observed via microelectrode measurements immediately upon the onset of 325 nm irradiation of multicell tumor spheroids. Consumption is irradiance dependent over the range 20-200 mW cm-2, and its magnitude is comparable to that observed previously in the same system using exogenous photosensitizers. Oscillations in the oxygen concentrations suggest that oxygen is also being evolved during irradiation. Oxygen evolution is likely the result of enzymatic dissociation of hydrogen peroxide, which is formed through UV-induced photochemistry. Irradiation of spheroids at 442 and at 514 nm produces a much more modest but detectable oxygen consumption. The dynamics of oxygen concentration changes are quite different at these wavelengths, suggesting a different photochemical mechanism. In these cases, initial oxygen depletion is followed immediately by a more gradual, monotonic increase in the oxygen concentration, consistent with irreversible photobleaching. No oscillations in the oxygen concentration are detectable. At 662 nm, no oxygen consumption was observed over the range of irradiances studied. Fluorescence spectra of cells prior to irradiation include contributions from anthranilic acid and reduced nicotinamide adenine dinucleotide (NADH). During 325 nm irradiation, anthranilic acid is rapidly and irreversibly bleached, while NADH emission undergoes only modest reduction.

Animals↗