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Regulation of onset of development of UDP-glucuronosyltransferase activity towards o-aminophenol by glucocorticoids in late-foetal rat liver in utero.

1. A precocious development of UDP-glucuronosyltransferase activity (EC 2.4.1.17) towards o-aminophenol is demonstrated in 15-17 day foetal rat liver in utero after dexamethasone administration to the mother. 2. This stimulation of liver transferase activity in utero is directly proportional to the dose of dexamethasone infected. 3. Precocious development of transferase activity in utero can also be effected with the natural glucocorticoid cortisol by multiple injections of large amounts of this hormone into the mother. 4. Transferase activity towards o-aminophenolin foetal lung, kidney and upper alimentary tract can also be precociously stimulated by dexamethasone in 17-day foetuses in utero. 5. Natural development of hepatic transferase activity between days 18 and 20 of gestation is retarded after foetal hypophysectomy by decapitation in utero. 6. Overall glucuronidation of o-aminophenol, as observed in foetal rat liver, is also precociously stimulated by dexamethasone. 7. From this and from evidence previously presented we suggest that glucocorticoids, which are known to increase in rat foetuses between days 17 and 20 of gestation, trigger the normal development in utero of hepatic transferase activity towards o-aminophenol which occurs at that time. We also suggest that these hormones are responsible for the rise in activity of the enzyme in foetal lung, kidney and upper alimentary tract which occurs during the same gestational period.

Aniline Compounds↗

Final report on the safety assessment of 6-Amino-m-Cresol, 6-Amino-o-Cresol, 4-Amino-m-Cresol, 5-Amino-4-Chloro-o-Cresol, 5-Amino-6-Chloro-o-Cresol, and 4-Chloro-2-Aminophenol.

Each of these ingredients function as hair colorants. 5-Amino-4-Chloro-o-Cresol and 5-Amino-6-Chloro-o-Cresol are identified as oxidative hair dyes, that is, they are combined with an oxidizing agent before being applied to the hair. 6-Amino-m-Cresol, 6-Amino-o-Cresol, 4-Amino-m-Cresol, and 5-Amino-4-Chloro-o-Cresol are used in oxidative hair dyes, but it is not known if they are also used in nonoxidative (semipermanent) hair dyes. No toxicologically significant impurities are present with these two ingredients. To supplement the safety test data on these ingredients, available data on related ingredients (4-amino-2-hydroxytoluene and p-,m-, and o-aminophenol) previously found safe as used by the Cosmetic Ingredient Review (CIR) Expert Panel were summarized. 5-Amino-4-Chloro-o-Cresol and 5-Amino-6-Chloro-o-Cresol do not absorb significant ultraviolet radiation in the UVB region and none in the UVA region, although 4-Amino-m-Cresol had a symmetrical UV absorption peak at 300 nm. Percutaneous penetration of 5-Amino-4-Chloro-o-Cresol and 5-Amino-6-Chloro-o-Cresol alone was significant, but when combined with oxidative developer, skin absorption was extremely low. Both of these dyes are excreted rapidly via the urine. Repeated exposure of animal skin to 5-Amino-4-Chloro-o-Cresol and 5-Amino-6-Chloro-o-Cresol failed to produce any cumulative irritation and single exposures up to 10%were not irritating to animal skin. 5-Amino-4-Chloro-o-Cresol and 5-Amino-6-Chloro-o-Cresol combined with oxidizer were not sensitizers in guinea pig maximization tests. Ocular irritation resulted from exposure of animals to undiluted 5-Amino-4-Chloro-o-Cresol, but not to a 5%solution. Only minor irritation was observed with 5%5-Amino-6-Chloro-o-Cresol. Subchronic toxicity testing in animals using 5-Amino-4-Chloro-o-Cresol, 5-Amino-6-Chloro-o-Cresol, and 4-Amino-m-Cresol did not yield any adverse reactions. 6-Amino-m-Cresol and 4-Amino-m-Cresol were generally not mutagenic in in vitro and in vivo tests. Exposure to 5-Amino-4-Chloro-o-Cresol, 5-Amino-6-Chloro-o-Cresol, 6-Amino-m-Cresol and 4-Amino-m-Cresol from cosmetics were several orders of magnitude below developmental toxicity no-observed-adverse effect levels (NOAELs). Although irritation data on several ingredients are absent, products containing these ingredients must include a caution statement and patch test instructions for determining whether the product causes skin irritation. The Expert Panel expects that following this procedure would identify individuals who would have an adverse reaction and allow them to avoid significant exposures. These compounds, when tested alone, are moderate skin sensitizers, but when combined with the developer, these ingredients are not sensitizers in animal tests. This information, coupled with the available animal test data, supports the safety of these ingredients in oxidative hair dyes. In the absence of systemic toxicity data, however, the available data are insufficient to support the safety of 6-Amino-o-Cresol and 4-Chloro-2-Aminophenol in semipermanent hair dyes. The types of data required for these two ingredients for this use include (1) physical and chemical properties, including the octanol/water partition coefficient; (2) impurities data, especially regarding the presence of m-cresol, other organic molecules, and heavy metals; (3) data demonstrating that the metabolism is similar to that of 4-amino-2-hydroxytoluene and/or p-,m-, and o-aminophenol, or 28-day dermal toxicity with histopathology, dermal reproductive toxicity data, and an in vitro genotoxicity study for 6-Amino-o-Cresol and one genotoxicity study in a mammalian system; if positive, a 2-year dermal carcinogenicity study using National Toxicology Program methods may be needed.

Animals↗

Determination of aminophenol isomers by high-speed liquid chromatography.

The simultaneous quantitation of aminophenol isomers (p-, m- and o-aminophenol) and anilline, which with previously reported methods was difficult and/or complicated, has been performed using a high-speed liquid chromatographic method. The resolutions of chromatograms were appropriate for separation and quantitation, when analysis times were 20 minutes. Since the method is applicable in aqueous media, a successful quantitation of p- and o-aminophenol formed by cytochrome P-450 model systems was carried out.

Aniline Compounds↗

p-Aminophenol-induced liver toxicity: tentative evidence of a role for acetaminophen.

p-Aminophenol (PAP) is a widely used industrial chemical and a metabolite of analgesics, such as acetaminophen (APAP). It was found recently that PAP, a known nephrotoxicant, could cause acute hepatotoxicity in mice but not in rats. The mechanism of hepatotoxicity is not known. The aim of this study was to investigate the role of N-acetylation of PAP to APAP in PAP-induced toxicity. Male C57BL/6 mice injected intraperitoneally (i.p.) with various doses of PAP were sacrificed at 12 hours for measurement of serum glutamic-pyruvic transaminase (GPT) and sorbitol dehydrogenase (SDH) levels and determination of the extent of hepatic nonprotein sulfhydryl (NPSH) and glutathione (GSH) depletion. Plasma levels of APAP and its metabolites were measured by HPLC after PAP administration. p-Aminophenol depleted NPSH in a dose- and time-dependent manner. Depletion of NPSH in mouse liver occurred at PAP doses above 400 mg/kg. Buthionine sulfoximine (BSO), an inhibitor of GSH synthesis, potentiated the PAP-induced hepatotoxicity. Ascorbate, a reducing agent, did not affect PAP-induced hepatotoxicity and NPSH depletion. After PAP treatment, APAP and its sulfate and glucuronide conjugates as well as GSH conjugates (APAP-cysteine and APAP-mercapturate) were detected in the plasma. The results suggest the roles of GSH and N-acetylation of PAP to APAP in PAP-induced hepatotoxicity.

Acetaminophen↗

Studies on the effects of L(alpha S,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (AT-125) on 4-aminophenol-induced nephrotoxicity in the Fischer 344 rat.

4-Aminophenol (para-aminophenol; PAP) causes selective necrosis to the S3 segment of the proximal tubule in experimental animals. The mechanism of PAP nephrotoxicity has not been fully elucidated, although it has been suggested to involve glutathione (GSH)-dependent S-conjugation followed by processing by the enzyme gamma-glutamyl transpeptidase (gamma GT) to the corresponding cysteine S-conjugate. This proposed toxicity mechanism was probed further by administering L-(alpha S,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (AT-125), a potent gamma GT inhibitor, to Fischer 344 (F344) rats before treatment with PAP (100 mg/kg). AT-125 pretreatment did not appear to protect against PAP-induced nephrotoxicity as assessed by renal histopathology, clinical chemistry and proton nuclear magnetic resonance (1H NMR) spectroscopy of urine. These data suggest that renal gamma GT activity is not a prerequisite for PAP nephrotoxicity and that the generation of a cysteine S-conjugate is not a unique requirement for the induction of PAP nephrotoxicity.

Aminophenols↗

Inhibition of peroxidase-catalyzed oxidation of 3,3 ,5,5 -tetramethylbenzidine by aminophenols.

Peroxidase-catalyzed oxidation of 3,3 ,5,5 -tetramethylbenzidine (TMB) was inhibited by o-aminophenol (AP), 2-amino-4-tert-butylphenol (ATBP), 2-amino-4,6-di-tert-butylphenol (ADTBP), and 4-tert-butylpyrocatechol (TBP). Inhibitors were characterized by inhibition constant K(i) and stoichiometric coefficient f, the number of radicals terminated by one inhibitor molecule. The most efficient inhibitor is ADTBP characterized by K(i) = 36 microM in 0.015 M phosphate citrate buffer, pH 6.0, at 20 degrees C. According to their antiradical efficiency, the studied inhibitors can be arranged as follows: ADTBP > ATBP > AP > TBP. The role of the NH(2) group in the inhibitory capacity of aminophenols is discussed. Using gas-liquid chromatography, kinetics of consumption of the initial components and accumulation of the reaction products on peroxidase-catalyzed oxidation of the TMB-TBP pair was studied; the data clarify the stages of a complex process of co-oxidation of amines and phenols.

Aminophenols↗

Evaluation of the teratogenic potential of the oxidative dyes 6-chloro-4-nitro-2-aminophenol and o-chloro-p-phenylenediamine.

The oxidative dyes 6-chloro-4-nitro-2-aminophenol and o-chloro-p-phenylenediamine were administered by gavage to Sprague-Dawley rats on days 6-15 of gestation at dose levels of 87.5, 175 and 350 mg 6-chloro-4-nitro-2-aminophenol/kg body weight/day and 100, 200 and 400 mg o-chloro-p-phenylenediamine/kg/day. Maternal body-weight gain was significantly reduced by the high dose of each dye and the intermediate dose of o-chloro-p-phenylenediamine. Rats given the high dose of the latter dye showed a significant increase in resorptions and a significant decrease in foetal body weights. No embryotoxic or foetotoxic effects were observed with 6-chloro-4-nitro-2-aminophenol. Evaluation of foetuses for gross, visceral and skeletal anomalies revealed no statistically significant differences between dye-treated and vehicle-control groups but showed a significant increase (to 25-91%) in the incidence of abnormal foetuses in the group exposed to vitamin A, the positive control.

Aminophenols↗

Study on the enhancement of catalytic activity for hemoglobin by quinhydrone in poly(o-aminophenol) film.

Hemoglobin (Hb) and quinhydrone (QHQ) were incorporated in poly(o-aminophenol) [o-AP, POAP] film by electropolymerization of o-aminophenol in a weak acid solution containing Hb and QHQ. The nonconducting polymer film was found to be nearly rigid by piezoelectric quartz crystal (PQC) impedance. Therefore, the thickness of the Hb-QHQ-POAP film was estimated as about 104 +/- 10 nm by quartz crystal microbalance (QCM). The QHQ mediation effects on the biomacromolecule Hb entrapped in the POAP film were investigated by using cyclic voltammetry, amperometric technique and kinetic study. Cyclic voltammograms showed that the redox peaks in the Hb-QHQ-POAP film are much more reversible than those in the Hb-POAP film. The response current of the Hb-QHQ-POAP film to H(2)O(2) was almost twice than that of the Hb-POAP film. The Michaelis-Menten constant and the activation energy of Hb in the Hb-QHQ-POAP film are 7.47 mM and 13.91 kJ/mol, respectively, both are smaller than that in the Hb-POAP film. These results showed that the immobilized Hb in POAP film exhibited higher catalytic activity to H(2)O(2) due to the mediation of QHQ.

Aminophenols↗

Antioxidant and anticancer activities of novel p-alkylaminophenols and p-acylaminophenols (aminophenol analogues).

Novel compounds were designed based on fenretinide, N-(4-hydroxyphenyl)retinamide (2), which is a synthetic amide of all-trans-retinoic acid (1) that is a potent antioxidant and anticancer agent. Our recent findings indicated that antioxidant and anticancer activities were due to p-methylaminophenol moiety (8) in 2, and that p-octylaminophenol (7), which has an elongated alkyl chain, was more potent than 8. This finding lets us to investigate whether compounds containing alkyl or acyl chains linked to an aminophenol residue as long as 2 and 1, would show activities greater than 2. For this purpose, we prepared p-dodecanoylaminophenol (3), p-decanoylaminophenol (4), p-dodecylaminophenol (5), and p-decylaminophenol (6). The p-alkylaminophenols, 5 and 6, exhibited superoxide scavenging activities, but not p-acylaminophenols, 3 and 4. Elongation of the alkyl chain length reduced superoxide trapping capability (8>7>6>5). In contrast, lipid peroxidation in rat liver microsomes was reduced by 5 and 6 in dose-dependent manner. Compounds 3 and 4 were poor lipid peroxidation inhibitors, being approximately 400- to 1300-fold lower than 5 and 6. In addition, all compounds inhibited cell growth of human leukemia cell lines, HL60 and HL60R, in dose-dependent manners (5>6>3=4). The HL60R cell line is resistant against 1. Growth of both cell lines was suppressed by 5 and 6 in a fashion dependent on the length of the aminophenol alkyl chain, but not by 3 and 4. These results indicate that 5, a potent anticancer agent greater than 2, may potentially have clinical utility, and that its anticancer activity is correlated with inhibitory potency against lipid peroxidation, but not with superoxide scavenging activity.

Aminophenols↗

Removal of p-aminophenol and p-nitrophenol from aqueous solution through adsorption on antimony, cadmium, and zirconium ferrocyanides.

Adsorptive interaction of p-aminophenol and p-nitrophenol in the concentration range 10(-4)-10(-5) M and at room temperature (30+/-1 degrees C) was studied with antimony, cadmium, and zirconium ferrocyanides. The interaction followed the Langmuir type of adsorption in general. The p-nitrophenol was found to have greater affinity for the antimony, cadmium, and zirconium ferrocyanides then the p-aminophenol.

Adsorption↗

Host-guest complexation in capillary isotachophoresis. II. Determination of aminophenol and diaminobenzene isomers in permanent hair colorants by using capillary isotachophoresis.

The separation of 2-, 3- and 4-aminophenol and 1,2-, 1,3- and 1,4-diaminobenzene is studied by using capillary isotachophoresis. In order to obtain complete resolution of the six cations beta-cyclodextrin was used. The analytical method was used for the determination of aminophenol and diaminobenzene isomers in permanent hair colorant creams.

Aminophenols↗

Migration behavior and separation of benzenediamines, aminophenols and benzenediols by capillary zone electrophoresis.

The migration behavior and separation of five benzendiamines, five aminophenols and three benzenediols were investigated in capillary zone electrophoresis. The results indicate that benzendiamines and aminophenols are optimally separated with a phosphate buffer at pH 5, whereas benzenediol isomers are best separated at pH about 12. The addition of surfactant monomers of tetradecyltrimethylammonium bromide to a phosphate buffer at pH 5 under the conditions of reversed electroosmotic flow is effective for separating these dye intermediates, except for the separation of 1,2-benzenediol from 1,3-benzenediol. The addition of sodium tetraborate as an electrolyte modifier is effective in the separation of 1,2-benzenediol from 1,3-benzenediol, but the latter comigrates with the 1,4-benzenediol isomer at pH 5.0. The electrophoretic mobility of ionized analytes can be described with Offord's equation, and the migration order depends on their ratios of charge to mass. In addition, the pKa values of these analytes in 50 mM phosphate buffer are reported.

Aminophenols↗

Iron(III) (hydr)oxide-mediated photooxidation of 2-aminophenol in aqueous solution: a kinetic study.

The photooxidation of 2-aminophenol in aqueous solution in the presence of an iron(III) (hydr)oxide (goethite, alpha-FeOOH), used as a heterogeneous catalyst, has been investigated at different pH (3.0-8.0) and catalyst loads (100-500 mg/l) aiming mainly at elucidating the reaction kinetics. A large experimental campaign allowed to rule out the intervention of HO radicals in the photodegradation of 2-aminophenol. The classic Langmuir-Hinshelwood equation has been used for the kinetic analysis, best estimated values of the kinetic parameters being derived by means of an optimization procedure. The dependence of reaction kinetics on the temperature in the range of 285-308K has also been investigated.

Aminophenols↗

Determination of 4-aminophenol impurities in multicomponent analgesic preparations by HPLC with amperometric detection.

A method for the determination of 4-aminophenol, the main impurity of paracetamol, by high-performance liquid chromatographic (HPLC) method with amperometric detection has been developed. The analysis was performed in an isocratic mode on a reversed phase Luna column 5 microm C-18 (100 x 4.6 mm). A mobile phase (0.05 mol l(-1) LiCl solution containing 18% methanol adjusted to pH 4.0 with orthophosphoric acid) was suitable for the separation and determination of 4-APh. Chromatograms were recorded for 250 s by means of an amperometric detector at a potential of +325 mV of the glassy carbon electrode versus the reference electrode Ag/AgCl. The proposed liquid chromatographic method was successfully applied to the analysis of commercially available multicomponent dosage forms. The sensitivity of the detection for 4-aminophenol was 1 ng ml(-1) for substance and 4 ng ml(-1) for tablets or capsules. The method developed in this study is sensitive and selective and can be applied for routine studies of pharmaceuticals in the form of tablets or capsules.

Aminophenols↗

An approach to metal-assisted DNA base pairing: novel beta-C-nucleosides with a 2-aminophenol or a catechol as the nucleobase.

The metal-chelating beta-C-nucleoside having a phenylenediamine moiety as the nucleobase was previously found to form a stable 2:1 complex with a Pd(2+) ion in aqueous media, where hydrogen bonding is replaced by metal coordination in the base pairing, thereby creating a novel hybridization motif in duplex DNA. In this regard, we have further designed two types of artificial beta-C-nucleosides possessing a metal-chelating site (a 2-aminophenol or a catechol) as the nucleobase moiety. These artificial nucleosides are directed toward controlling the net charges of the metal-assisted base pairs. This paper describes convenient syntheses of the artificial nucleosides bearing a 2-aminophenol or a catechol moiety. Each nucleoside was directly synthesized through 2'-deoxy derivative via a Friedel-Crafts coupling reaction as the key step between the aromatic ring and ribose moiety, whereas the nucleoside having a phenylenediamine moiety was prepared in rather longer steps through an RNA type intermediate followed by the removal of 2'-hydroxyl group.

Aminophenols↗

Lipolytic activities of p-aminophenol and n-decylamine in endogenous lipid droplets from rat adipocytes.

Lipolytic agents such as adrenaline (epinephrine), dibutyryl cyclic AMP (DBcAMP) and theophylline possess common structural characteristics, the existence of a positive charge and a hydrophobic area. p-Aminophenol, which has the same structural characteristics, was found to induce lipolysis in the endogenous lipid droplets from rat adipocytes. It was demonstrated that the positive group and the hydrophobic area of p-aminophenol are essential requirements for its lipolytic activity. Among various amine derivatives, only n-decylamine was found to induce lipolysis in the endogenous lipid droplets. Although the lipolytic action of n-decylamine is fairly low, it possesses remarkable inhibitory effects on both adrenaline- and DBcAMP-induced lipolytic activities. Furthermore, n-decylamine is found to inhibit competitively the DBcAMP-induced lipolysis.

Adipose Tissue↗

Early functional and morphological changes in renal tubular necrosis due to p-aminophenol.

Functional and morphological changes developed rapidly in rats after the intravenous administration of the organic nephrotoxin p-aminophenol. Proximal intratubular pressure remained close to its mean control value of 14.9 +/- 0.9 mm Hg up to 40 min after injection of the nephrotoxin then rose rapidly over the following 50 min to a maximum of 38.7 +/- 7.4 mm Hg. Distal tubular pressure also rose in the same manner. Renal blood flow remained constant, but GFR fell to 11% of control values while fractional excretion of sodium and water rose 12 and five times, respectively. Morphological changes developed in parallel with the functional changes. They were widespread, varied in intensity from cell to cell, were more severe in the distal third of the proximal convoluted tubule and consisted of cytoplasmic swelling, reduced organelle concentration, reduction or loss of basal infoldings, widening of lateral intercellular spaces, extrusion of bubbles of cell sap into the tubular lumen; brush borders were preserved. No casts were present up to 90 min. Similar results were seen when p-aminophenol was added to the perfusate of the isolated perfused kidney. It is proposed that metabolic and morphological damage leads rapidly to both impairment of proximal tubular sodium reabsorption and increased flow resistance in the cortical collecting system. Both effects contribute to a rise in tubular pressures which oppose glomerular filtration.

Acute Kidney Injury↗

Simultaneous determination of dihydroxybenzenes, aminophenols and phenylenediamines in hair dyes by high-performance liquid chromatography on hypercross-linked polystyrene.

The retention of polar organic molecules such as dihydroxybenzenes, aminophenols and phenylenediamines on a 250 x 4.6 mm id column packed with 5 microns hypercross-linked polystyrene Chromalite 5HGN (Purolite) was studied. The influence of separation parameters such as concentration of acetonitrile, buffer (citrate, phosphate) concentration, ionic strength and pH of the eluent on their retention was investigated. Under optimum conditions [acetonitrile-0.3 mol l-1 ammonium phosphate, pH 5.15 (30:70 v/v)], eight substances generally used as dye intermediates in hair colouring compositions could be separated within 20 min. An HPLC method with spectrophotometric detection is proposed for the simultaneous determination of pyrocatechol, resorcinol, hydroquinone, o-, m- and p-aminophenols and p-phenylenediamine in commercial haircolour products. The detection limits of these compounds are in the range 0.05-0.16 microgram ml-1. The suitability of the method is demonstrated by the analysis of three different permanent hair dyes.

Aminophenols↗