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PubMed1983

The use of 4-aminobenzoic acid as a marker to validate the completeness of 24 h urine collections in man.

1. At the present time there is no method whereby the completeness of 24 h urine collections can be accurately assessed when clinical studies are undertaken. The suitability of 4-aminobenzoic acid (PAB) given with meals as a marker for completeness of urine collections was therefore investigated. 2. When a single dose of 80 mg of PAB was given to four volunteers 93% was recovered in the urine in 5 h. 3. Eight volunteers living in a calorimeter, where complete urine collection could be guaranteed, were given various doses of PAB divided up throughout the day. 88 +/- 5% was excreted in the urine over a 24 h period. Urine excretion and oral dose were directly related. 4. Thirty-three reliable free-living volunteers eating their normal diet took 80 mg of PAB with meals (240 mg/day). Mean urine recovery over the 24 h period was 223 +/- 9 mg, or 93 +/- 4% of the administered dose. The range in individual recovery from maximum to minimum was 15%, compared with 75% for creatinine excretion per kg fat-free mass. 5. PAB is a safe marker of the completeness of 24 h urine collections. Any collection containing less than 205 out of 240 mg (85%) of PAB, given as 80 mg with each of three meals, is probably incomplete.

4-Aminobenzoic Acid↗
PubMed1991

Effects of dietary proteins on absorption and gastrointestinal movement of p-aminobenzoic acid in conscious rats.

We monitored the absorption and movement of dietary soluble components along the gastrointestinal tract of rats by using p-aminobenzoic acid (PABA) as a marker after feeding 8 and 16% casein or soybean protein isolate (SPI) diets containing 1% PABA. The portal concentration of PABA, as an index of absorption, increased rapidly and reached the same high level 10 min after the feeding of all four diets, and the increased level of portal PABA was maintained for 30-80 min in each group. The increased levels of the SPI-fed groups continued longer than those of the casein-fed groups. In contrast, the gastric emptying rate slowed after 20 min in all the groups, and the gastric emptying of PABA for the initial 60 min in the 8% casein group was significantly faster than that in the 8% SPI group. The PABA content of the first small intestinal segment, which may be influenced by small intestinal transit, was higher in the casein group. These results indicate that the absorptive rate of PABA is determined not only by gastric emptying but also by small intestinal transit. The gastric emptying and the content of PABA in the first segment of the small intestine was not correlated in 8% protein groups. This suggests that the effect of SPI on gastrointestinal movement is different from that of casein.

4-Aminobenzoic Acid↗
PubMed2001

[Quantitative assay of metabolic rate of para-aminobenzoic acid combining glycine for the assessment of rabbit liver function].

OBJECTIVE: To evaluate liver function by the assessment of the capacity of glycine combining para-aminobenzoic acid (PABA) to form hippuric acid in rabbits with acute liver injury. METHODS: Thirty rabbits were randomly divided into two groups: experiment group (n=20) received D-galactosamine to be subject to acute liver necrosis, and control group (n=10) received saline as placebo. Serum concentrations of PABA, para-aminohippuric acid (PAHA), para-acetamidobenzoic acid (PAABA), and para-acetamidohippuric acid (PAAHA) were measured by high pressure liquid chromatography (HPLC). RESULTS: Compared with control group, the serum concentrations of PAHA and PAAHA were significantly reduced in experimental group, which were correlated with the degree of liver injury. CONCLUSIONS: The metabolic rate of glycine combining PABA is a sensitive index for quantitative test of liver function and assessment of acute liver necrosis.

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PubMed2002

The pab1 gene of Coprinus cinereus encodes a bifunctional protein for para-aminobenzoic acid (PABA) synthesis: implications for the evolution of fused PABA synthases.

The pab1 gene of the basidiomycete Coprinus cinereus encodes PABA synthase, necessary for para-aminobenzoic acid production. The C. cinereus protein is bifunctional with an N-terminal glutamine amidotransferase domain and a C-terminal chorismate amination domain. In most bacteria, these two functions are encoded in separate genes (e.g., pabA and pabB of E. coli). Fused PABA synthases have so far been detected in actinomycetes, Plasmodium falciparum, fungi and Arabidopsis thaliana. Phylogenetic analysis shows that the fused PAB sequences form a tight group that also includes uncharacterized PabB homologues from several bacteria. Unfused bacterial PabA proteins group with the glutamine amidotransferase subunits of bacterial anthranilate synthases, independent of organismal systematics, indicating a complex and perhaps independent evolutionary origin. In contrast, unfused PabB group and fused PabA/B proteins form a monophyletic group on a branch separate from the chorismate amination subunits of anthranilate synthases, probably reflecting a need for recognition of different positions in the common substrate chorismate.

4-Aminobenzoic Acid↗
PubMed1977

P-Aminobenzoic acid derivatives. Mode of action and structure-activity relationships in a cell-free system (Escherichia coli).

The agonistic and antagonistic effects of nuclearly substituted p-aminobenzoic acids (PABA) on the folate-synthesizing system of E. coli have been studied in whole cell and cell-free systems. All studied derivatives form dihydropteroic acid analogues in the presence of a cell-free folate-synthesizing enzyme system. A thin-layer chromatographic system has been elaborated to determine the rate of analogue formation in the cell-free system. Physicochemical parameters of the PABA derivatives, such as pKa, pi, and Rm values, have been determined. These values have been used in a structure-activity analysis which revealed that the rate of analogue formation in the absence of PABA is independent of the lipophilic properties. Ionization seems to be the decisive factor for the incorporation. As all studied PABA derivatives are totally ionized under the experimental conditions, the rates of analogue formation are very similar with the exception of compounds bearing bulky groups in the 2 position. The variance in inhibitory power may therefore either be due to differences in the ability of the analogues to serve as metabolites or to competition with PABA.

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PubMed2002

Drug evolution: p-aminobenzoic acid as a building block.

The core or the building block is an important component in drug development. In this article, we propose and review p-aminobenzoic acid (PABA) as a building block used in the design of drugs or drug candidates. PABA is frequently found as a structure moiety in drugs. For example, in a database of 12,111 commercial drugs, 1.5% (184 drugs) were found to contain the PABA moiety. These drugs have a wide range of therapeutic uses, such as: sun-screening, antibacterial, antineoplastic, local anesthetic, anticonvulsant, anti-arrhythmic, anti-emetic, gastrokinetic, antipsychotic, neuroleptic, and migraine prophylactic. This article reviews the molecular targets and the mechanisms of these activities. Drugs containing PABA also show a wide range of structural diversity. Of the 184 PABA containing drugs identified, 95 different substitutions were found at the carboxylic group and 61 were found at the amino group of the building block. Substitution on the aromatic ring was also diverse. 13, 3, and 13 different side chains were found to modify positions 2, 3 and 5 of the aromatic ring respectively. In some drugs, the amino group is further substituted to form tertiary amine (4 different side chains). Substitutions at the carboxyl and amino groups of PABA are particularly suitable for the generation of combinatorial libraries. Just by reshuffling the identified side chains of the 184 PABA containing drugs, 4.5 million compounds can be generated. Consequently, PABA fits well as a building block for a general chemical library of "drug-like" molecules with a wide range of functional and structural diversity.

4-Aminobenzoic Acid↗
PubMed1992

Photoaddition of p-aminobenzoic acid to thymine and thymidine.

Several studies in the literature have shown that DNA is damaged after UV irradiation in the presence of the sunscreen agent p-aminobenzoic acid (PABA), both in vivo and in vitro. One type of damage has been shown to be the result of increased yields of pyrimidine cyclobutane dimer formation. However, it has been suggested that other types of lesions are produced as well. We have studied the photochemistry of the thymine-PABA and thymidine-PABA systems and report here the isolation and characterization of thymine-PABA and thymidine-PABA photoadducts. These products have been identified, respectively, as 5-(2-amino-5-carboxyphenyl)-5,6-dihydrothymine and isomeric forms of 5-(2-amino-5-carboxyphenyl)-5,6-dihydrothymine. The quantum yields for the formation of these adducts in deaerated aqueous solutions at pH 7.0 have been determined to be 9.5 x 10(-4) and 4.3 x 10(-3) for the thymine and thymidine based adducts respectively. A pH profile for the thymine-PABA system indicated a maximum quantum yield for adduct formation at pH 6.5, although it could be detected over the whole pH range studied (pH 3.5-11.0).

4-Aminobenzoic Acid↗
PubMed1997

Pharmacokinetic examination of p-aminobenzoic acid passage through the placenta and the small intestine in rats.

In the present study the permeability of the rat small intestine and the placenta to p-aminobenzoic acid (PABA) and antipyrine (AP) was investigated. Perfusion of the rat term placenta was used to determine the materno-fetal transfer of both compounds. PABA appeared in the fetal compartment faster than AP (ktransfer = 0.064 and 0.046 min-1, respectively). The rate of equilibration between the maternal and fetal compartments and placental clearance were lower for PABA than for AP (kequilibration = 0.011 and 0.020 min-1; Clp = 0.22 and 0.33 ml/min, respectively); the feto-maternal concentration ratios at equilibrium (FMCReq) were, however, mutually comparable. Similarly, PABA proved to be absorbed from the small intestine significantly faster than AP (ka = 0.824 min-1 and 0.479 min-1; tmax = 3.1 min and 8.9 min, respectively). The apparent volume of distribution (Vd) of AP in non-pregnant animals showed that the drug is distributed into the whole body water as expected (Vd = 0.66 l/kg); however, Vd of AP in pregnant animals was estimated to be 1.81 l/kg. Vd of PABA in non-pregnant animals showed its partially limited distribution, which was only slightly increased in the pregnant animals. Our results confirmed a faster penetration of hydrophilic PABA across the placenta and the small intestine than that of lipophilic AP. The mechanism of transplacental passage of PABA, however, remains to be determined.

4-Aminobenzoic Acid↗
PubMed1987

Use of p-aminobenzoic acid and tritiated cyanoborohydride for the detection of pyruvoyl residues in proteins.

A procedure for the detection of covalently bound pyruvic acid in purified proteins or in crude extracts is described. The dialyzed sample is first treated with sodium cyanoborohydride to reduce any Schiff bases present and then incubated with p-aminobenzoic acid and sodium [3H]cyanoborohydride. Derivatized proteins are visualized by fluorography following sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Gel slices containing the labeled proteins are hydrolyzed, and, after removal of polyacrylic acid, the hydrolysate is subjected to ion-exchange high-performance liquid chromatography. The presence of pyruvic acid is established by the detection of a tritiated, 280-nm absorbing compound with a retention time corresponding to that of synthetic N-(p-carboxyphenyl)alanine. The procedure is capable of detecting protein-bound pyruvic acid in the picomolar range and is easily modified to screen for other covalently bound keto acids.

4-Aminobenzoic Acid↗
PubMed1997

Aminobenzoic acid compounds as HOCl traps for activated neutrophils.

This study was designed to develop traps for hypochlorous acid (HOCl) which could be used to detect HOCl in the microenvironment of activated neutrophils. Reagent HOCl was found to react with para-aminobenzoic acid (PABA) in aqueous solution to produce a predominant metabolite detectable by high performance liquid chromatography (HPLC). Mass spectroscopy and nuclear magnetic resonance identified this metabolite as the ring addition product 3-chloro PABA. The related compound para-aminosalicylic acid (PAS) was also metabolized by HOCl to 3-chloro PAS. The formation of the 3-chloro metabolite was specific for reactions involving HOCl, since several other oxidants in chloride buffer failed to produce the metabolite. Human blood neutrophils activated by phorbol myristate acetate or zymosan in the presence of PABA (or PAS) used their HOCl to produce large amounts of the 3-chloro metabolite. The formation of 3-chloro PABA was inhibited by azide, catalase, and taurine, which is consistent with the production of the metabolite by the neutrophil myeloperoxidase (MPO) pathway. The reaction of HOCl with PABA and PAS was relatively slow as shown by competitive reactions with endogenous antioxidants like taurine, methionine, and glutathione. This was confirmed in reactions involving PABA/PAS and reagent HOCl or HOCl generated by the MPO enzyme system. In these in vitro systems, glutathione and serum completely inhibited the formation of the 3-chloro metabolite. In contrast, activated neutrophils metabolized PABA/PAS to the 3-chloro metabolite even in the presence of 1% serum. These findings demonstrate that PABA and PAS are specific trapping agents for HOCl produced by neutrophils in complex biological conditions.

4-Aminobenzoic Acid↗
PubMed2003

Para-aminobenzoic acid (PABA) used as a marker for completeness of 24 hour urine: effects of age and dosage scheduling.

OBJECTIVE: To examine the age dependency of the urinary para-aminobenzoic acid (PABA) excretion, and if a delayed PABA excretion can be overcome by advancing intake schedule; and to examine the recovery of PABA in fractionated urinary samples collected during 24 h after single and repeated doses of PABA. DESIGN: Cross-over study with subjects randomized to start with recommended schedule of PABA administration (80 mg at 08:00, 12:00 and 18:00; PABA18) and then an advanced schedule (80 mg at 08:00, 12:00 and 15:00; PABA15) or vice versa. One subgroup of eight subjects collected individual urine specimens for 24 h after a morning dose of 80 mg of PABA, and another subgroup of 10 subjects collected individual urine specimens for 24 h after ingestion of 80 mg of PABA three times at mealtimes. SUBJECTS: Employees and relatives from the Danish Food Administration. SETTING: Ninety-nine healthy volunteers (61 females and 38 males) aged 30-91 y. RESULTS: Linear regressions for PABA15 and PABA18 demonstrate significantly less recovery with age (PABA15: r(2)=0.1784, P=0.0002; PABA18: r(2)=0.1273, P=0.0019). Linear regression of DeltaPABA (PABA15-PABA18) with age showed the best fit line to be horizontal (slope -0.0066, P=0.89; 95% CI -0.1046, 0.0915) and with a Y-intercept not significantly different from 0 (1.575; 95% CI -4.176, 7.326). In this population the lower limit for complete 24 h urine collection was 79.2%. After a single dosage of 80 mg PABA 70-85% was recovered after 8 h. Within 16 h after ingestion of 240 mg PABA at recommended hours the lowest acceptable recovery (78.1%) was reached. CONCLUSION: There is a gradual decline of PABA recovery with age that cannot be overcome by advancing the dosage schedule. Because of a lower delimiting PABA recovery for the elderly, some 24 h collections in this age group will be rejected unjustly (false-negatives). Also, with the currently recommended dosage schedule (PABA taken with the main meals) the risk of false-positive 24 h urine collections prevails. With refinement of the PABA test procedure, ie employing a specific analytical method and age-dependent cut-off values, the test may achieve a higher specificity and sensitivity.

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