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PubMed1998

[A rapid determination of allantoin by high-performance liquid chromatography using tris(hydroxymethyl)aminomethane-HCl buffer as a mobile phase].

A rapid and simple method for the determination of allantoin in pharmaceuticals by reversed-phase ion-pair high-performance liquid chromatography using an ODS column was presented. In general, it is difficult to retain allantoin to the ODS column owing to its very low hydrophobicity. We solved these problems by the use of a Tris-HCl buffer (pH 7.5) containing tetra-n-hexyl-ammonium bromide (THAB) as an ion-pair reagent for the mobile phase. Comparatively low concentrations of Tris-HCl buffer (0.9 mM) and THAB (0.5 mM) gave a high capacity factor (k'). As a results of the examination of the chromatographic behavior, it is confirmed that the retention mechanism of allantoin to the ODS column on the present method was not the ion-pair mode, but the ion-exchange mode. Calibration curves for allantoin showed a good linearity in the range of 10 to 400 micrograms/ml (r = 0.9999). The reproducibility (R.S.D., n = 6) was invariably good (0.37%). The lowest concentration of allantoin for the determination was 200 ng per 20 microliters of injection. The present method was successfully applied to the determination of allantoin in commercial eyedrops with good recovery (99.4%). It was found that allantoin in pharmaceuticals could be determined by the present method in short time and without any complicated derivatization.

Allantoin↗
PubMed1992

[The effect of the energy intake of cows on the rumen metabolism studied using the excretion of allantoin in milk].

With two groups of dairy cows (A: 12 German Black and White- and 6 German Simmental Cows; B: 16 German Black and White- and 11 German Simmental Cows) allantoin concentrations of blood plasma (A) and milk (A and B) were analysed by HPLC. There exists a close correlation (r = 0.758) between allantoin concentration in blood plasma (370.6 +/- 79.1 mumol/l) and milk (474.1 +/- 78.9 mumol/l). The relation between milk yield and allantoin excretion with milk seems to be non-linear (r = 0.936). On the other hand there is a close correlation between energy intake with feed and allantoin excretion via milk (r = 0.885). In a further experiment the allantoin concentrations in blood plasma of 5 Angler steers were monitored for 24 h every second hour with feeding twice daily. There were remarkable fluctuations in the allantoin concentration from nearly 156 to 129 mumol/l. After that the rumen of the steers was emptied, while plasma concentrations were still monitored the same way as before. Concentrations of allantoin declined for about 55% to 65 mumol/l.

Allantoin↗
PubMed1992

Quantitative separation of uric acid and allantoin from rat liver tissue.

A simple procedure is described for the assay of liver uric acid and allantoin and their specific radioactivity after administration of a radioactive precursor. Uric acid was quantified by the uricase reaction in liver trichloroacetic acid (TCA) extracts. The 'true' allantoin content of the liver could be estimated only after precipitation with Hg-acetate, a step by which the standard allantoin was also quantitatively recovered. Crude extracts lead to the evaluation of 'apparent' allantoin. For the determination of specific radioactivity, the Hg-acetate precipitate was further purified by ion-exchange chromatography. The purity of the two metabolites was confirmed by ultraviolet absorbance spectra, HPLC, constancy of specific radioactivity and the absence of amino acids. The incorporation of [14C]formate into uric acid and allantoin in the liver was studied by this procedure. The radioactivity in allantoin was several-fold higher than that in uric acid up to 60 min after administration of the precursor. This quite unexpected result is not easily explained on the basis of current knowledge.

Allantoin↗
PubMed2002

Purine nucleotide catabolism in rat liver: labelling of uric acid and allantoin after administration of various labelled precursors.

Uric acid and allantoin are the key compounds of purine nucleotide catabolism formed in liver and many other organs of the rat. We observed that, after administration of 14C-formate, incorporation of radioactivity into uric acid and allantoin is not similar, as one would expect. The phenomenon was demonstrated to be specific to liver and perfused liver, and not to other organs such as heart, jejunal mucosa, lung, spleen, and kidney. To interpret these results, the specific radioactivity of uric acid and allantoin in rat liver were analysed comparatively, after administration of the following labelled precursors: 14C-glycine, 14C-formate, 14C-hypoxanthine, 14C-uric acid and 14C-adenine. After administration of 14C-formate the specific radioactivity of allantoin was higher than that of uric acid and the same behavior was observed after 14C-uric acid and 14C-hypoxanthine, but not after 14C-glycine and 14C-adenine administration. The results indicate that the rate of their incorporation into uric acid and allantoin, and the subsequent export of these compounds into serum, can only partially explain the observed phenomenon, while the presence of different pools of uric acid and allantoin may give a complete explanation.

Adenine↗
PubMed1990

Excretion of purine derivatives by ruminants: recycling of allantoin into the rumen via saliva and its fate in the gut.

The saliva of sheep was shown to contain significant concentrations of uric acid (16(SD 4.5) mumol/l) and allantoin (120(SD 16.4) mumol/l), sufficient to recycle purine derivatives equivalent to about 0.10 of the normal urinary excretion. When allantoin was incubated in vitro in rumen fluid, it was degraded at a rate sufficient to ensure complete destruction of recycled allantoin. In a series of experiments in which allantoin was infused into the rumen of sheep fed normally, or into the rumen or abomasum of sheep and the rumen of cattle completely nourished by intragastric infusion of volatile fatty acids and casein, no additional allantoin was recovered in the urine. These losses were probably due to the degradation of allantoin by micro-organisms associated with the digestive tract. It is concluded that all allantion and uric acid recycled to the rumen via saliva will be similarly degraded. Therefore, the use of urinary excretion of purine derivatives as an estimator of the rumen microbial biomass available to ruminants will need to be corrected for such losses.

Allantoin↗
PubMed1978

Enzymic racemization of allantoin.

Allantoin racemase was isolated from cells of Candida utilis, and purified by chromatography on columns of DEAE-cellulose and Sephadex G-100. Using this purified enzyme, the racemization of allantoin in deuterium oxide was investigated. Polarimetric and PMR spectroscopic analyses showed that racemization of allantoin by the enzyme proceeded in parrallel with release of the hydrogen atom (5-H) attached to the asymmetric carbon (C-5) of allantoin. Non-enzymic racemization of allantoin, which was examined for comparison, however, was accompanied by much less or almost no release of allantoin 5-H. This indicates that the mechanism of racemization by the enzyme differs from that of non-enzymic racemization.

Allantoin↗
PubMed2004

PvUPS1, an allantoin transporter in nodulated roots of French bean.

Nodulated legumes receive their nitrogen via nitrogen-fixing rhizobia, which exist in a symbiotic relationship with the root system. In tropical legumes like French bean (Phaseolus vulgaris) or soybean (Glycine max), most of the fixed nitrogen is used for synthesis of the ureides allantoin and allantoic acid, the major long-distance transport forms of organic nitrogen in these species. The purpose of this investigation was to identify a ureide transporter that would allow us to further characterize the mechanisms regulating ureide partitioning in legume roots. A putative allantoin transporter (PvUPS1) was isolated from nodulated roots of French bean and was functionally characterized in an allantoin transport-deficient yeast mutant showing that PvUPS1 transports allantoin but also binds its precursors xanthine and uric acid. In beans, PvUPS1 was expressed throughout the plant body, with strongest expression in nodulated roots, source leaves, pods, and seed coats. In roots, PvUPS1 expression was dependent on the status of nodulation, with highest expression in nodules and roots of nodulated plants compared with non-nodulated roots supplied with ammonium nitrate or allantoin. In situ RNA hybridization localized PvUPS1 to the nodule endodermis and the endodermis and phloem of the nodule vasculature. These results strengthen our prediction that in bean nodules, PvUPS1 is involved in delivery of allantoin to the vascular bundle and loading into the nodule phloem.

Allantoin↗
PubMed2002

A novel superfamily of transporters for allantoin and other oxo derivatives of nitrogen heterocyclic compounds in Arabidopsis.

A wide spectrum of soil heterocyclic nitrogen compounds are potential nutrients for plants. Here, it is shown that Arabidopsis plants are able to use allantoin as sole nitrogen source. By functional complementation of a yeast mutant defective in allantoin uptake, an Arabidopsis transporter, AtUPS1 (Arabidopsis thaliana ureide permease 1), was identified. AtUPS1 belongs to a novel superfamily of plant membrane proteins with five open reading frames in Arabidopsis (identity, 64 to 82%). UPS proteins have 10 putative transmembrane domains with a large cytosolic central domain containing a "Walker A" motif. Transport of (14)C-labeled allantoin by AtUPS1 in yeast exhibited saturation kinetics (K(m) approximately 52 microM), was dependent on Glc and a proton gradient, and was stimulated by acidic pH. AtUPS1 transports uric acid and xanthine, besides allantoin, but not adenine. Protons are cosubstrates in allantoin transport by AtUPS1, as demonstrated by expression in Xenopus laevis oocytes. In plants, AtUPS1 gene expression was dependent on the nitrogen source. Therefore, AtUPS1 presumably is involved in the uptake of allantoin and other purine degradation products when primary sources are limiting.

Allantoin↗
PubMed1977

Allantoin transport in Saccharomyces cerevisiae.

Allantoin uptake in both growing and resting cultures of Saccharomyces cerevisiae occurs by a low-Km (ca. 15 micrometer) transport system that uses energy that is likely generated in the cytoplasm. This conclusion was based on the observation that transport did not occur in the absence of glucose or the presence of dinitrophenol, carbonyl cyanide-m-chloro-phenyl hydrazine, fluoride, or arsenate ions. Normal uptake was observed, however, in the presence of cyanide. The rate of accumulation was maximal at pH 5.2. In contrast to the urea transport system, allantoin uptake appeared to be unidirectional. Preloaded, radioactive allantoin was not lost from cells suspended in allantoin-free buffer and did not exchange with exogenously added, nonradioactive allantoin. Treatment of preloaded cells with nystatin, however, released the accumulated radioactivity. Allantoin accumulated within cells was isolated and shown to be chemically unaltered.

Allantoin↗
PubMed1993

[Stability of allantoin and identification of its degradation compounds].

The stability of allantoin was studied in pH 3.0, 6.0, and 8.0 buffer solutions at 50 degrees C for 55 d. Allantoin was determined by high performance liquid chromatography (HPLC) with a cation exchange mode and colorimetry. The known degradation compounds, allantoic acid and glyoxylic acid, were simultaneously determined by ion chromatography. Urea was determined by HPLC with an ion pair mode. In the stability studies on pH 6.0 and 8.0 solutions, new degradation compounds of allantoin were identified as two growing unknown peaks in the HPLC chromatogram. Isolation of these compounds by preparative HPLC and 1H, 15N and 13C-NMR spectra revealed that they were condensates of allantoin and glyoxylic acid, which also reacted positively in phenylhydrazine colorimetry. The amounts of these compounds were calculated from the determination results of other allantoin related compounds in the buffer solutions and were estimated as the biggest amount among all other compound. As they were found to be stable in an alkaline solution, conditions for hydrolysis in the colorimetric determination of allantoin were further examined. It was found that the longer hydrolysis gave more than 90% recovery in the colorimetry.

Allantoin↗
PubMed1993

A high-performance liquid chromatographic method for the determination of hypoxanthine, xanthine, uric acid and allantoin in serum.

A method was developed for the simultaneous determination of hypoxanthine, xanthine, uric acid and allantoin based on isocratic reversed-phase chromatography. This HPLC-method additionally allows the direct determination with UV-detection of inosine-5'-phosphate, uridine, thymine, orotic acid, allopurinol and oxipurinol, besides hypoxanthine, xanthine and uric acid in the same chromatographic run. Allantoin elutes in this system near the void volume and a fraction is collected covering the retention time range for this substance. After hydrolysis allantoin is converted to glyoxylate-2,4-dinitrophenylhydrazone, rechromatographed and detected at 360 nm. The coefficient of variation for this method does not exceed 5.0% for a serum concentration of 0.3 mumol/l hypoxanthine and is not greater than 5.3% for a xanthine concentration of 0.3 mumol/l serum. Recoveries were 90-110% for both hypoxanthine and xanthine. The determination of uric acid had an imprecision and inaccuracy not exceeding 1.45% in the concentration range of 103-568 mumol/l. Due to the more complex procedure required for the determination of allantoin, the coefficient of variation between days was 13.6% for a sample containing 0.8 mumol/l allantoin and the recoveries for this analyte were in the range of 86-93%. Reference ranges (mean +/- SD) determined on 171 serum samples from healthy adults were 12.7 +/- 6.6 mumol/l for hypoxanthine, 3.3 +/- 1.4 mumol/l for xanthine, and 15.7 +/- 7.9 mumol/l for allantoin. No significant age or sex dependence was observed. Uric acid concentrations were 320 +/- 55 mumol/l serum for men and 206 +/- 55 mumol/l for women.

Adolescent↗
PubMed1993

Accumulation of allantoin and uric acid in plasma of exercising trotters.

Plasma concentrations of hypoxanthine, uric acid, and allantoin, which are breakdown products of adenine nucleotides, were measured in Standardbred and Finnhorse trotters during and after an exercise test on a high-speed treadmill, after an incremental exercise test performed on a racetrack, and after a racing competition. Fiber-type composition of the middle gluteal muscle and the muscle concentrations of adenine nucleotides and inosine monophosphate were measured after the racetrack test. Changes in the concentration of hypoxanthine were not observed in any of the tests. Peak concentration of uric acid was measured between 5 and 30 minutes after exercise, and it was three- to tenfold higher than the value at rest. The variability can be explained by intensity of the exercise test and variation among horses. The concentration of allantoin after exercise was 2 to 3 times as high as that at rest, depending on the intensity of the exercise, although the absolute increase was about 10 times as high as the increase in the concentration of uric acid. Peak values of allantoin for the treadmill and the racetrack tests were obtained 4 to 6 minutes after exercise and < 30 minutes after the races. Peak concentration of allantoin correlated positively with the percentage of type-II (IIA+IIB) fibers in the middle gluteal muscle. Significant correlations were not observed between plasma concentration of uric acid or allantoin and muscle concentrations of adenosine triphosphate (ATP) or inosine monophosphate. It can be concluded that in horses, breakdown of ATP during and after exercise continues until allantoin is produced.(ABSTRACT TRUNCATED AT 250 WORDS)

Adenosine Triphosphate↗
PubMedDate not supplied

Preliminary electrochemiluminescence study of allantoin in the presence of tris(2,2'-bipyridine) ruthenium (II).

Electrochemiluminescence (ECL) based on allantoin and tris(2,2'-bipyridine)ruthenium (II) [Ru(bpy)3 (2+)] was studied in aqueous alkaline buffer solution (pH 11.0). In a flowing system, the eluted allantoin was mixed with 1.0 mmol/L Ru(bpy)3 (2+). When the solution passed through a thin layer flow electrolytic cell equipped with a glassy carbon disc electrode (22.1 mm2), both hydroxyl groups of allantoin and Ru(bpy)3 (2+) were oxidized at the potential of +1.50 V (vs. Ag/AgCl). The luminescence with lambdamax 610 nm caused by the reaction of electrolytically formed Ru(bpy)3 (2+) with alkoxide radical to generate the excited state of Ru(bpy)3 (2+*). A possible ECL process of allantoin in Ru(bpy)3 (2+) alkaline solution has been discussed. In addition, the factors affecting the ECL response of allantoin are also investigated.

2,2'-Dipyridyl↗
PubMed1987

Generation of allantoin from the oxidation of urate by cytochrome c and its possible role in Reye's syndrome.

Allantoin in the presence of calcium ions has been implicated as a potential toxic agent in Reye's syndrome. An investigation of possible alternative sources of allantoin in humans, which lack the enzyme uricase, has been initiated. Urate is a strong reducing agent which can reduce cytochrome c nonenzymatically, with the concomitant production of CO2 and H+. The stoichiometries measured for the various reactants and products were 1 urate:2 cytochrome c:1 H+:1 CO2. The initial reaction rate depended on the concentrations of both urate and cytochrome c, with reaction kinetics that were first order with respect to urate and second order with respect to cytochrome c. The participation of molecular oxygen in this reaction could not be detected. The pH and ionic strength optima for this reaction were determined to be 9.5-10.5 and 10(-5) M, respectively. Based on the results reported here, the following balanced equation can be written: urate-2 + 2 cytochrome c+3 + 2 H2O----allantoin + 2 cytochrome c+2 + H+ + HCO3-. We propose that allantoin can be generated from the oxidation of urate by cytochrome c+3, and that this is a potential source of allantoin in human tissues.

Allantoin↗
PubMed2002

Regulation of the Escherichia coli allantoin regulon: coordinated function of the repressor AllR and the activator AllS.

The allantoin regulon of Escherichia coli, formed by three operons expressed from promoters allA(P), gcl(P) and allD(P), is involved in the anaerobic utilization of allantoin as nitrogen source. The expression of these operons is under the control of the repressor AllR. The hyperinduction of one of these promoters (allD(P)) by allantoin in an AllR defective mutant suggested the action of another regulator, presumably of activator type. In this work we have identified ybbS (proposed gene name allS), divergently transcribed from allA, as the gene encoding this activator. Analysis of the expression of the three structural operons in DeltaallS mutant showed that the expression from allD(P) was abolished, suggesting that AllS is essential for the expression of the corresponding operon. In a wild-type strain expression of allS takes place mainly anaerobically and is hyperinduced when the nitrogen source limits growth. However, expression of allS is independent of regulators of the Ntr response, NtrC or Nac. Band shift experiments showed that AllR binds to DNA containing the allS-allA intergenic region and the gcl(P) promoter and its binding is abolished by glyoxylate. Both DNA fragments contain a highly conserved inverted repeat, which after site-directed mutagenesis, has been proven to be the AllR-binding site. This site displays similarity with the IclR family recognized consensus. Interaction of AllR with the single operator present in the allS-allA intergenic region prevented binding of RNA polymerase to either of the two divergent promoters. The regulator AllS interacts only with allD(P) even in the absence of allantoin. Analysis of this promoter allowed us to identify an inverted repeat as a motif for AllS binding. We propose a model for the coordinate control of the allantoin regulon by AllR and AllS.

Allantoin↗
PubMed1977

The use of silver-zinc-allantoin powder for the prehospital treatment of burns.

We describe our experimental studies of a powder formulated to treat serious burn wounds on-the-scene. The wound powder comprises two parts silver-citro-allantoinate, two parts zinc allantoinate and 96 parts pure allantoin. The back skin of 62 rats was shaved and exposed to actively boiling water for ten seconds, resulting in third degree burns of 20% of the total body surface. Immediately, 1 ml of a culture containing 2 X 10(8) Pseudomonas aeruginosa was applied to the burn. The animals were isolated. Of the 30 control rats, six were powdered with allantoin only. Thirty-two rats were dusted with the silver-zinc-allantoin powder within 15 minutes of burning. Cultures were taken at 48 hour intervals. Eighty-seven percent of the control animals died an average of six days postburn. In the treated animals, the mortality was 15%. A mean of 27% of the applied silver (0.35 gm) became incorporated in the eschar. In all control rats, sepsis was detected under the eschar. In treated animals, bacterial concentration fell from an initial average of 5 X 10(4) at 4 hours postburn to 6 X 10(2) at 96 hours.

Allantoin↗
PubMed1997

Simultaneous measurement of allantoin, uric acid, xanthine and hypoxanthine in blood by high-performance liquid chromatography.

A high-performance liquid chromatographic method for determining catabolism products of nucleic acids and purines, such as oxypurines (i.e. uric acid, xanthine and hypoxanthine) and allantoin in the blood plasma of ruminants was developed. The plasma was deproteinized with 10% trichloroacetic acid. The method enabled determination of oxypurines without derivatization. Allantoin was determined after conversion with 2,4-dinitrophenylhydrazine to a hydrazone (GLX-DNPH). Separation of converted allantoin, uric acid, xanthine and hypoxanthine derivatives was carried out using two reversed-phase C18 columns. The combination of pre-column derivatization and gradient elution with monitoring of the effluent at 205, 254 and 360 nm provides a simple and selective analytical tool for studying oxypurines and allantoin in plasma. The total run time of the HPLC analysis was 60 min. The recovery of the purine derivatives (i.e. oxypurines and allantoin) added to the plasma was between 95 and 106%. Purine derivatives were stable when the processed samples were stored for 7 days at -10 degrees C. The low values of the intra-assay coefficient of variations (2.5-4.6%) and the low values of the detection limits (0.187-0.004 nmol) point to the satisfactory precision and sensitivity of the method.

Allantoin↗
PubMed1999

Quantitative determination of an extremely polar compound allantoin in human urine by LC-MS/MS based on the separation on a polymeric amino column.

Quantitative determination of allantoin in biological matrix poses a challenge to bioanalysis due to the extreme polarity of allantoin. The molecule exhibits virtually no retention on any of the available hydrophobic HPLC packing materials. In this study, an assay was developed for the LC-MS/MS quantitation of allantoin in human urine using a polymeric amino column to achieve the necessary separation. The urine samples were prepared by a single-step solid phase extraction (SPE) procedure. The extracted samples were analyzed on a jordi-gel DVB polyamine column (operated under an acetonitrile/water gradient with water as the stronger mobile phase) interfaced with a Finnigan TSQ 7,000 mass spectrometer. Negative electrospray ionization (ESI) was employed as the ionization source. Allantoin and its internal standard (13C1, 15N1-allantoin) were detected by use of single reaction monitoring (SRM) mode. The method was validated in the concentration range of 14.6-213 microg/ml(-1), with within and between run accuracy and precision both < 7%. The method has been successfully applied to clinical sample analysis.

Acetonitriles↗