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PubMed1994

Antimutagenicity of three isomers of aminobenzoic acid in Salmonella typhimurium.

The m-, o- and p-isomers of aminobenzoic acid (ABA) repressed the mutagenicity of N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) in Salmonella typhimurium TA100. Their antimutagenic potency was in the order of o-ABA > m-ABA > p-ABA. The mechanism of this antimutagenicity is ascribed mainly to the decomposition of MNNG induced by the aminobenzoic acid isomers outside or within the bacterial cells. The inhibition of plant cell peroxidases and bacterial acetyltransferases that are required for the plant activation of 2-aminofluorene (2-AF) to mutagenic product(s) may participate in the repression of 2-AF mutagenesis by the aminobenzoic acids in S. typhimurium strain YG1024. The aminobenzoic acid isomers exhibited no inhibitory effects towards the direct-acting agent 2-acetoxy-2-acetylaminofluorene, the stable diacetylated metabolic product of 2-AF.

Acetoxyacetylaminofluorene↗
PubMed1993

Effects on cell morphology of growing Pseudomonas aeruginosa, Enterobacter cloacae and Staphylococcus aureus in subinhibitory concentrations of p-aminobenzoic acid.

Light microscopy and electron microscopy studies with Enterobacter cloacae, Pseudomonas aeruginosa and Staphylococcus aureus grown in the presence of subinhibitory concentrations of p-aminobenzoic acid indicate that p-aminobenzoic acid may have a direct or indirect effect on the cell walls. The morphological effects of p-aminobenzoic acid varied with different bacterial species. E. cloacae grown in the presence of p-aminobenzoic acid produced filaments while P. aeruginosa cells were elongated and had thicker peripheral cell walls. S. aureus had increased overall cell size and thicker transverse cell walls.

4-Aminobenzoic Acid↗
PubMed1993

Biotransformation of para-aminobenzoic acid and salicylic acid by PMN.

Para-aminobenzoic acid (PABA) is an essential cofactor for the production of folic acid in bacteria and has mild anti-inflammatory activity. We have recently reported that salicylic acid and benzoic acid are oxidized by stimulated granulocytes Polymorphonuclear Neutrophils (PMN). The oxidation of salicylate appears mediated by a potent oxygen metabolite generated during the respiratory burst which is dependent primarily on superoxide (O2-) for its production. These background studies with the salicylate group of drugs suggested that PABA might be similarly metabolized by PMN. In these studies, we demonstrate that PABA is metabolized by stimulated PMN. However, in contrast to the biochemical mechanism involved in the metabolism of salicylate, our scavenger studies indicate that PABA is metabolized primarily by the myeloperoxidase pathway. Our results may explain the mild anti-inflammatory actions of the drug and suggest that the degradation of PABA by PMN at an inflammatory site may limit the availability of PABA for bacterial growth.

4-Aminobenzoic Acid↗
PubMed2000

Paeonol promoted 2-aminofluorene and p-aminobenzoic acid acetylations by mononuclear leucocytes from Sprague-Dawley rats.

Following exposure of rats to the arylamine carcinogen 2-aminofluorene, DNA-carcinogen adducts were found in the target tissues of the liver and bladder, and also in circulating leucocytes. This work investigated how paeonol affects arylamine (2-aminofluorene and p-aminobenzoic acid) acetylations in rat leucocytes. Evidence is presented showing that rat mononuclear leucocytes are capable of acetylating 2-aminofluorene and p-aminobenzoic acid. Paeonol promoted 2-aminofluorene and p-aminobenzoic acid acetylation. Cultured lymphocytes produced about twice as much N-acetyl-2-aminofluorene from 2-aminofluorene and 2.2-fold as much N-acetyl-p-aminobenzoic acid from p-aminobenzoic acid as monocytes. After cotreatment with paeonol, the lymphocyte and monocyte cultures indicated that paeonol did increase 2-aminofluorene and p-aminobenzoic acid acetylations.

4-Aminobenzoic Acid↗
PubMedDate not supplied

[Aminobenzoic acid derivatives as specific inhibitors of cyclic nucleotide phosphodiesterase in the rat uterus].

It is shown, that p-aminobenzoic acid and its derivatives (p-acetylaminobenzoic acid and p-aminobenzoic acid hydrazide) in the concentration of 10(-6) M are the potent inhibitors (40% below the control specimens) of the phosphodiesterase activity of cyclic nucleotides in the soluble fraction of the adult rat uterus. These drugs exerted no action on the adenylate cyclase activity in membrane fractions. The inhibition is only specific to the uterus enzyme and is not revealed for other tissues. The inhibition is found to be of incompetitive character Ki for p-aminobenzoic acid hidrazide being equal to 3.2 microM.

2',3'-Cyclic-Nucleotide Phosphodiesterases↗
PubMed1985

Practical assessment of the NBT-PABA pancreatic function test using high performance liquid chromatography determination of p-aminobenzoic acid in urine.

A practical method for determining p-aminobenzoic acid in urine by high-performance liquid chromatography has been assessed. The technique is quick, requires no extraction steps and has good precision. Using this method, healthy individuals had a p-aminobenzoic acid excretion index of 94% +/- 18 (mean +/- 1 SD). Patients with proven, severe chronic exocrine pancreatic dysfunction had index values of less than 5-25%. Unlike chemical methods available, there were no interferences in any of the urines tested, nor did 12 compounds tested interfere with the analysis.

4-Aminobenzoic Acid↗
PubMed1982

[Role of p-aminobenzoic acid in levorin biosynthesis].

The effect of p-aminobenzoic acid on the biosynthesis of levorin was studied. It was shown that in the presence of exogenic p-aminobenzoic acid the antibiotic activity increased by 11 per cent. The acid added was transformed into p-aminoacetophenone which was partially used for levorin synthesis and partially accumulated in the mycelium in a free state. In this case the synthesis of levorin was limited by the metabolites forming the macrolide ring. When the precursors of the macrolide ring and the aromatic group were simultaneously added to the medium, the content of free p-aminoacetophenone in the mycelium decreased while the antibiotic activity increased by 25 per cent.

4-Aminobenzoic Acid↗
PubMed1979

[Exocrine pancreatic function test by N-benzoyl-L-tyrosyl-p-aminobenzoic acid (author's transl)].

Urinary excretion of p-aminobenzoic acid (PABA) within 6 h after oral administration of N-benzoyl-L-tyrosyl-P-aminobenzoic acid (Peptide-PABA) was measured. In healthy subjects PABA-excretion rate was not different after 150 mg and 1 g Peptide-PABA. PABA-recovery was significantly lower in patients with chronic pancreatitis. Seperation between healthy persons and patients with chronic pancreatic insufficiency was better with 1 g Peptide-PABA.

4-Aminobenzoic Acid↗
PubMed1975

Kinetics of the oxidation of p-aminobenzoic acid catalyzed by horseradish peroxidase compounds I and II.

The kinetics of p-aminobenzoic acid oxidation catalyzed by horseradish peroxidase Compounds I and II was investigated intensively as a function of pH at 25 degrees in aqueous solutions of ionic strength 0.11. All of the rate data were collected from single turnover experiments involving reactions of a single enzyme compound. In reactions of both compounds, deviations from first order behavior with respect to the enzyme were observed at high pH values which were explained in terms of a free radical interaction of product with the enzyme. The effect could be eliminated with sufficient excess of substrate. Kinetic behavior which deviated from first order in substrate, observed at low pH, was explained by a mechanism involving an enzyme-substrate complex which reacted with an additional molecule of substrate but at a slower rate. The pH dependence of the second order rate constants for the reaction of p-aminobenzoic acid with free Compounds I and II is similar to results obtained for the comparable reactions of ferrocyanide, suggesting similar proton-transfer mechanisms for both reducing substrates. The reduction of Compound II by p-aminobenzoic acid appeared to be influenced by two ionizable groups on the enzyme which affect the electronic environment of the heme. The lack of influence of substrate ionizable groups on the rate of the Compound II reaction indicated that potential differences in reactivities of NH2C6H4COO- and NH2C6H4COOH were levelled by the diffusion-controlled limit in the acid region of pH. The reduction of Compound I by p-aminobenzoic acid was not diffusion-controlled and the rate-pH profile could be explained in terms of three acid ionizations, two on the substrate and one on Compound I.

Aminobenzoates↗
PubMed1991

Basic studies on ursodeoxycholyl-para-aminobenzoic acid for evaluation of intestinal microflora.

A newly synthesized conjugate of ursodeoxycholic acid with para-aminobenzoic acid (PABA) was investigated to determine its suitability for evaluation of enteric bacteria. This compound, PABA-UDCA, was deconjugated by cholylglycine hydrolase to release free PABA, whereas it was completely resistant to deconjugation by pancreatic and intestinal mucosal enzymes. In bacteriologic experiments almost all the microorganisms that split glycocholic acid deconjugated PABA-UDCA. In rat experiments urinary excretions of PABA were measured during 6 h after oral administration of 10 mg PABA-UDCA (PABA-UDCA administration test). Ten control rats excreted 338.5 +/- 13.8 micrograms (mean +/- SE) of PABA; 10 rats with intestinal stagnant loop excreted more (673.6 +/- 70.2 micrograms; P less than 0.01); whereas 10 rats in each of 7 groups pretreated with oral administration of various antibiotics excreted less (P less than 0.001; polymixin B + tinidazole, 14.0 +/- 2.5 micrograms; polymixin B, 224.9 +/- 23.5 micrograms; tinidazole, 42.7 +/- 8.6 micrograms; kanamycin, 50.3 +/- 5.8 micrograms; clindamycin, 57.4 +/- 7.4 micrograms; vancomycin, 70.4 +/- 8.5 micrograms; and paromomycin, 160.4 +/- 16.4 micrograms). This result was reflected by the bacterial mean count of feces. In the PABA-UDCA administration test, after 2 months of feeding with different diets, rats with high-fiber diet (n = 10) excreted less PABA in urine (70.9 +/- 15.9 micrograms; P less than 0.001) than rats on a control diet (n = 10) and a high-protein-high-fat diet (n = 10) (288.9 +/- 34.5 micrograms and 386.7 +/- 61.2 micrograms, respectively). Fecal bacteriologic status was consistently altered. In human volunteers 250 mg PABA-UDCA was tested. Amounts of PABA excreted in urine during 6 h after dosing were 21.11 +/- 2.02 mg in controls (n = 5) and 12.20 +/- 1.01 mg in the group treated with polymixin B plus tinidazole (n = 5; P less than 0.01). No adverse effect was observed. These basic studies indicate that this compound is likely to offer a simple and rapid method for evaluation of the intestinal microorganisms without use of radioisotopes or expensive, special equipment.

4-Aminobenzoic Acid↗
PubMed2003

A prospective, comparative study of the para-aminobenzoic acid test and faecal elastase 1 in the assessment of exocrine pancreatic function.

BACKGROUND: The assessment of exocrine pancreatic insufficiency is part of the routine work-up of patients with persistent diarrhoea or suspected steatorrhoea. Direct and indirect tests for the diagnosis of exocrine pancreatic insufficiency have their drawbacks. Measurement of faecal elastase 1 by enzyme-linked immunoabsorbent assay is a simple, non-invasive, robust test for exocrine pancreatic insufficiency. METHODS: We performed a prospective comparison of the para-aminobenzoic acid test and faecal elastase 1 test in 45 patients being investigated for diarrhoea or suspected steatorrhoea. Details of clinical suspicion, imaging and response to treatment were recorded. RESULTS: Exocrine pancreatic function was normal in 20 patients with normal para-aminobenzoic acid and faecal elastase 1 levels. Eight patients had exocrine pancreatic insufficiency with low para-aminobenzoic acid and faecal elastase 1 levels, which improved with enzyme supplementation. In 14 of the 15 patients with low or borderline low para-aminobenzoic acid and normal faecal elastase 1 levels, a non-pancreatic cause was found; one patient had a false positive para-aminobenzoic acid test. Two had normal para-aminobenzoic acid but low faecal elastase 1 levels. One improved with pancreatic supplementation, and imaging revealed chronic pancreatitis. The other had a false positive faecal elastase 1 test related to profuse diarrhoea. CONCLUSIONS: Faecal elastase 1 estimation is a simple, non-invasive, robust test of exocrine pancreatic insufficiency, performed on an out-patient stool sample. Its diagnostic performance is superior to that of the para-aminobenzoic acid test in investigating patients with diarrhoea or suspected steatorrhoea.

4-Aminobenzoic Acid↗
PubMed2005

A theoretical and experimental study of water complexes of m-aminobenzoic acid MABA.(H2O)n (n = 1 and 2).

We report studies of supersonically cooled water complexes of m-aminobenzoic acid MABA.(H(2)O)n (n = 1 and 2) using two-color resonantly enhanced multiphoton ionization (REMPI) and UV-UV hole-burning spectroscopy. Density functional theory calculations are also carried out to identify structural minima of water complexes in the ground state. For the most stable isomers of both complexes, water molecules bind to the pocket of the carboxyl group in a cyclic hydrogen bond network. Vibrational frequency calculations for the first electronically excited state (S(1)) of these isomers agree well with the experimental observation. The addition of water molecules has a major impact on the normal mode that involves local motion of the carboxyl group, while negligible effects are observed for other normal modes. On the basis of the hole-burning experiment, two major isomers for each complex are identified, corresponding to the two conformers of the bare compound. Compared with the other two isomers of aminobenzoic acid, the red shifts of the origin bands due to water complexation in MABA are considerably larger. Similar to p-aminobenzoic acid and different from o-aminobenzoic acid, the existence of the intermolecular stretching mode is ambiguous in the REMPI spectrum of MABA.(H(2)O)n.

4-Aminobenzoic Acid↗
PubMed2004

Lysyl 4-aminobenzoic acid derivatives as potent small molecule mimetics of plasminogen kringle 5.

Kringle 5, a proteolytic fragment of human plasminogen has been shown to potently inhibit angiogenesis. The tetrapeptide KLYD derived from kringle 5 has been shown to capture many activities of kringle 5 in vitro. Further simplification has been achieved by replacement of the two central amino acids with a 4-aminobenzoic acid spacer group. Molecules displaying the required recognition groups on this core show similar in vitro properties to kringle 5, and are able to displace radiolabeled protein from a high affinity binding site on endothelial cells.

4-Aminobenzoic Acid↗
PubMed2006

The vitamin-like dietary supplement para-aminobenzoic acid enhances the antitumor activity of ionizing radiation.

PURPOSE: To determine whether para-aminobenzoic acid (PABA) alters the sensitivity of tumor cells to ionizing radiation in vitro and in vivo. METHODS AND MATERIALS: Cellular proliferation was assessed by WST-1 assays. The effects of PABA and radiation on tumor growth were examined with chick embryo and murine models. Real-time reverse transcriptase-polymerase chain reaction and Western blotting were used to quantify p21CIP1 and CDC25A levels. RESULTS: Para-aminobenzoic acid enhanced (by 50%) the growth inhibitory activity of radiation on B16F10 cells, whereas it had no effect on melanocytes. Para-aminobenzoic acid enhanced (50-80%) the antitumor activity of radiation on B16F10 and 4T1 tumors in vivo. The combination of PABA and radiation therapy increased tumor apoptosis. Treatment of tumor cells with PABA increased expression of CDC25A and decreased levels of p21CIP1. CONCLUSIONS: Our findings suggest that PABA might represent a compound capable of enhancing the antitumor activity of ionizing radiation by a mechanism involving altered expression of proteins known to regulate cell cycle arrest.

4-Aminobenzoic Acid↗
PubMed1999

[Para-aminobenzoic acid--an interferon inducer].

Para-aminobenzoic acid (PABA) was shown to be an early type interferon inductor. PABA (10 micrograms/ml) induced interferon production in vitro in the cells of human peripheral blood and in vivo in albino mice (10 mg/kg). The results of the study suggested that PABA was able to induce production of interferon-alpha/beta in various immunocyte populations. By its interferonogenic activity PABA was comparable with the known interferon inductors. One of the mechanisms of the previously described in vivo antiherpes action of PABA can be attributed to its interferon inducing activity.

4-Aminobenzoic Acid↗
PubMed1989

Photocarcinogenesis is retarded by a partly photodegraded solution of para-aminobenzoic acid.

A solution of para-aminobenzoic acid (PABA) was exposed to ultraviolet (UV) radiation emitted from a Philips TL 40 W/12 sunlamp and the degree of photodegradation following an exposure of 27 J/cm2 was estimated to be approximately 40%. The formation of the photoproducts was confirmed by mass spectroscopy and UV spectroscopy. The solution was painted on the backs of hairless light-pigmented mice prior to daily UV irradiation by the above sunlamp, and this procedure was continued for 30 weeks. The preirradiated solution of PABA significantly retarded the tumor induction time and reduced significantly the number of squamous cell carcinomas compared with nonprotected controls. This tumor-retarding ability did not differ significantly from the effect achieved when using nonirradiated PABA.

4-Aminobenzoic Acid↗
PubMed1979

Metabolism of p-aminobenzoic acid in the perfused livers of chronically uraemic rats.

1. Chronic renal failure was induced in rats by surgical removal of thirteen-sixteenths of renal tissue. 2. The metabolism of p-amino[14C]benzoic acid was studied in the isolated perfused livers of control and chronically uraemic rats. There was a slower rate of clearance and decreased overall metabolism of the compounds in the uraemic rats. 3. Conjugation of p-amino[14C]benzoic acid with glycine and the formation of p-aminobenzoic acid glucuronide were both significantly decreased in the uraemic rats, but there was a significant increase in acetylation of both p-aminobenzoic acid and its glycine conjugate.

4-Aminobenzoic Acid↗