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PubMed1998

Phenolphthalein and 3',3"-dinitrophenolphthalein.

Phenolphthalein, C20H14O4, crystallized in the noncentrosymmetric space group Pna2(1) with two crystallographically inequivalent molecules. Each of these is linked to four others of its own type by four hydrogen bonds having Odonor...Oacceptor distances ranging from 2.631 (4) to 2.787 (4) A. While chains of hydrogen bonds propagate in a number of directions in this structure, cyclic hydrogen bonding is not observed. 3',3"-Dinitrophenolphthalein, C20H12N2O8, crystallized in the centrosymmetric space group Pbcn with a single molecule in the asymmetric unit. Each molecule is linked to three others by four hydrogen bonds having Odonor...Oacceptor distances ranging from 2.572 (4) to 3.274 (3) A. Although chains of hydrogen bonds are prominent in this structure, cyclic hydrogen bonding also occurs and forms dimers. As expected on the basis of the excess of potential acceptor O atoms over donors in both structures, significant C-H...O interactions are also abundant.

Cathartics↗
PubMed1986

Drug metabolism and metabolite transport in the small and large intestine: experiments with 1-naphthol and phenolphthalein by luminal and contraluminal administration in the isolated guinea pig mucosa.

The metabolism and metabolite transport of the monophenol 1-naphthol (I) and the diphenol phenolphthalein (II) have been studied in a symmetrical setup of the isolated jejunal and colonic mucosa from the guinea pig (Lauterbach 1977). In both tissues, the main metabolites of I were its sulphoconjugate and glucuronide, but the rate of metabolism, relative proportion of the metabolites and their distribution pattern varied with tissue and drug administration side in the following manner: By luminal administration (50 nmol/ml) in the jejunum, the metabolism was nearly complete within 45 min., more sulphate (1.5-3x) than glucuronide was formed, and both metabolites were predominantly transferred back to the lumen. By blood-side administration, the metabolism was less complete due to a significant decrease of the sulphated fraction. In consequence, more glucuronide (1.5-3x) than sulphate was formed. Moreover, the efflux pattern of the metabolites changed completely; the greater part of the glucuronide fraction now being conveyed to the blood side, whereas the sulphate tended to distribute in a 1:1 fashion on the lumen and blood side. The colonic mucosa behaved in a dissimilar way, since neither I metabolism nor metabolite efflux pattern in this tissue was influenced significantly by drug administration side. More sulphate (1.5-3x) than glucuronide was formed by both routes, and the metabolite distribution was similar to that observed by blood side administration in the jejunum. The changes described above were associated with changes in tissue accumulation of free I and metabolites; accumulation of I by luminal administration in jejunum was insignificant and that of the metabolites small. The main change caused by a higher concentration of I (130 nmol/ml) was a decrease in the sulphated fraction in the colon. II was metabolized at a slower rate than I, and a significant tissue accumulation of free II was observed in all instances. The monoglucuronide was the main metabolite. Only minor amounts of II monosulphate were formed, making its distribution pattern difficult to ascertain. The distribution of II monoglucuronide on the other hand was generally similar to that described for its I analogue.

Animals↗
PubMed1984

Acute pancreatitis complicating excessive intake of phenolphthalein.

A case is described in which a patient presented with acute pancreatitis following inadvertent ingestion of large quantities of phenolphthalein for the treatment of his chronic constipation. There was complete recovery and no sequelae from the acute attack of pancreatitis.

Acute Disease↗
PubMed1985

Contraluminal sulfate transport in the proximal tubule of the rat kidney. V. Specificity: phenolphthaleins, sulfonphthaleins, and other sulfo dyes, sulfamoyl-compounds and diphenylamine-2-carboxylates.

In order to evaluate the specificity for the contraluminal sulfate transport system the inhibitory potency of phenol- and sulfonphthaleins, of sulfamoyl-compounds (diuretics) as well as diphenylamine-2-carboxylates (Cl- channel blockers) on the 35SO4(2-) influx from the interstitium into cortical tubular cells in situ has been determined. The following was found: 1) Phenolsulfonphthalein (phenol-red) inhibited with an app. Ki-value of 1.7 mmol/l, while analogs which had additional Br-atoms in position 3 and/or 5, i.e. bromphenol-blue, bromcresol-purple and bromcresol-green, inhibited with an apparent Ki of 0.1 and 0.5 mmol/l respectively. 2) Phenolphthalein and tetrabromphenolphthalein did not inhibit, while the disulfonate dyes bromsulfalein, fuchsin acid and indigocarmine inhibited with a Ki between approximately equal to 1 and 3 mmol/l. The highest inhibitory potency in this class of compounds was seen with orange G (app. Ki 0.07 mmol/l). The monosulfonate dyes tested, fluorescein-sulfonate and orange I inhibited moderately with an app. Ki of approximately equal to mmol/l. 3) The 3-sulfamoyl compounds inhibited to a varying degree, when they had a neighbouring -NH-group (furylmethylamino-group), i.e. in position 6 to the COOH or SO3H-group, or when they had a phenoxy-group in position 4. 4) 4-sulfamoylbenzoate and the related compounds probenecid, acetazolamide and hydrochlorothiazide inhibited with an app. Ki between 4 and 7 mmol/l. 5) All diphenylamine-2-carboxylate analogs inhibited with an app. Ki between 3 and 5 mmol/l, even when the -NH-group was replaced by an = O-group or the benzene ring was replaced by a pyrimidine ring, but not when it was replaced by a thiophen ring.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1978

Effect of phenolphthalein on the function and structure of rodent and human intestine.

Phenolphthalein (PHE) is the active ingredient in at least 12 over-the-counter laxative preparations. It is alleged to have a minor effect in the small intestine compared with the colon where it is supposed to alter motor activity or water absorption or both. We measured water absorption from segments of rat intestine in vivo, and from the nearly intact small intestines of patients with established ileostomies. In rats, each intestinal segment served as its own control so that water absorption in a test period (PHE, 1--15 mg/100 ml) could be expressed as a percentage of the control period when buffer was infused. PHE inhibited water absorption, and the degree of inhibition was related linearly to log10 PHE concentration. The similarity of slopes of the regression lines suggested that all segments of the rat intestine were equally sensitive to PHE. In six patients, PHE, 100 mg four times a day, increased weight of ileostomy output by 30%, and Na+ output by 39%. These facts indicate that some of the laxative effects of PHE result from inhibition of water absorption in both large and small intestines.

Animals↗
PubMed1983

Glucuronidation and biliary excretion of phenolphthalein in temperature-acclimated steelhead trout (Salmo gairdneri).

Conjugative metabolism and biliary excretion of phenolphthalein (PP) were studied in steelhead trout (Salmo gairdneri) acclimated to 10, 14 or 18 degrees C. Significant seasonal effects were found on liver weight to body weight ratio and conjugative metabolism but not biliary excretion of free plus conjugate of PP. Temperature did not significantly interact with these relationships. PP was excreted in bile as parent compound and the glucuronide conjugate at all temperatures. Saturation of the excretory process was apparent at a dose of approximately 10 mumol/kg (i.p.) at 10 and 14, but not 18 degrees C.

Acclimatization↗
PubMed1987

Determination of cyclodextrins in biological fluids by high-performance liquid chromatography with negative colorimetric detection using post-column complexation with phenolphthalein.

A rapid and sensitive high-performance liquid chromatographic method for the analysis of beta- and gamma-cyclodextrin in aqueous biological fluids such as plasma, urine, or tissue homogenate is described. The chromatographic system consists of a microBondapak Phenyl column as stationary phase and a mobile phase of water with 10% methanol. After post-column addition of an alkaline solution of phenolphthalein, negative colorimetric detection is used. The elution solvent and post-column reagent were mixed in a capillary tubing of 1.5 m (1.0 mm I.D.). Two methods of sample treatment are given, one for large (1.0 ml) and one for small (0.1 ml) sample volumes. Both methods were shown to be linear and reproducible. The detection limit for beta-cyclodextrin was 1.0 microgram/ml (0.77 nmol/ml). The method was used in the determination of some pharmacokinetic parameters of beta-cyclodextrin in rats after intravenous injection.

Animals↗
PubMed2001

Molecular structure and vibrational spectra of phenolphthalein and its dianion.

Infrared (IR) and Raman spectra of phenolphthalein (PP) and its dianion form (sodium and potassium salts) were studied both in the solid state and in aqueous solution. Band assignments were carried out on the basis of the isotope shifts of the ring deuterated and 13C-substituted derivatives. Spectral analyses reveal that the PP dianion exists as mixtures of the benzenoid form (colorless) and the quinonoid form (colored) in the solid state and in aqueous solution, while the neutral PP solely takes the gamma-lactone form. This work provides the first vibrational spectroscopic evidence for the coexistence of the two species in the PP dianions.

Indicators and Reagents↗
PubMed2005

Phenolphthalein used to assess permeability of antibiotic-laden polymethylmethacrylate: a pilot study.

Elution of antibiotics from polymethylmethacrylate laden with antibiotics is dependent on the permeability of the polymethylmethacrylate. Increasing polymethylmethacrylate permeability by adding fillers has been suggested to increase antibiotic elution but the resulting increase in permeability has not been assessed directly. A simple method to assess polymethylmethacrylate permeability is proposed. Phenolphthalein was added to the polymethylmethacrylate to indicate the level of penetration of fluid with pH of 10.3. Glycine in three different amounts (0.45 g, 7 g, and 28 g) or a combination of antibiotics (13.6 g) was added as a filler to increase the permeability. Beads of each mixture were made and soaked in fluid with a pH of 10.3. An immediate intense magenta coloration occurred on contact of the beads with the fluid. A zone of magenta was seen to penetrate into the depths of polymethylmethacrylate beads. That penetration increased with the amount of the filler and with time in the fluid bath. The type of filler material also affected the rate of fluid penetration. Permeability of various antibiotic polymethylmethacrylate mixtures can be determined qualitatively using this method. The observations may be useful to determine which mixtures warrant more expensive antibiotic elution studies.

Anti-Bacterial Agents↗
PubMed1997

Expression cloning of different bacterial phosphatase-encoding genes by histochemical screening of genomic libraries onto an indicator medium containing phenolphthalein diphosphate and methyl green.

A system for expression cloning of bacterial phosphatase-encoding genes has been developed, and its potential has been investigated. The system is based on histochemical screening of bacterial genomic libraries, constructed in an Escherichia coli multicopy plasmid vector, for phosphatase-producing clones using an indicator medium (named TPMG) made of Tryptose-Phosphate agar supplemented with the phosphatase substrate phenolphthalein diphosphate and the stain methyl green. To test the performance of this system, three genomic libraries were constructed from bacterial strains of different species which showed different patterns of phosphatase activity, and were screened using the TPMG medium. Following a partial screening, three different phosphatase-encoding genes (respectively encoding a class A non-specific acid phosphatase, an acid-hexose phosphatase and a non-specific alkaline phosphatase) were shotgun-cloned from the above libraries, indicating that the TPMG-based expression cloning system can be useful for rapid isolation of different bacterial phosphatase-encoding genes.

Acid Phosphatase↗
PubMed2002

Tumor promoting effect of phenolphthalein on development of lung tumors induced by N-ethyl-N-nitrosourea in transgenic mice carrying human prototype c-Ha-ras gene.

In order to examine tumor modifying effects of phenolphthalein (PhP), female transgenic mice carrying human prototype c-Ha-ras gene (rasH2 mice) were given a single intraperitoneal injection of 60 mg/kg body weight of N-ethyl-N-nitrosourea (ENU), followed by the diet containing 12,000 ppm PhP for 26-week. Histopathologically, alveolar hyperplasias, adenomas and adenocarcinomas were observed in the ENU + PhP group, but only hyperplasias and adenomas were observed in the ENU alone group. The incidence and multiplicity of adenocarcinomas in the ENU + PhP group was significantly increased as compared to that in the ENU alone group. The combined multiplicity of adenomas and adenocarcinomas in this group was also significantly higher than that of the ENU alone group. In addition, the ratio of area of adenomas in the ENU + PhP group was significantly higher than that in the ENU alone group. The result of our study suggests that PhP has a clear tumor promoting effect in the lung of rasH2 mice.

Adenocarcinoma↗
PubMedDate not supplied

Effect of nafenopin (SU-13437) on liver function. Influence on the hepatic transport of phenolphthalein glucuronide and chlorothiazide.

In rats treated with the hypolipidemic drug, nafenopin (NP), for 2 days the biliary excretion of phenolphthalein glucuronide (PPG) was markedly decreased, while in contrast that of chlorothiazide (CTZ) was enhanced. This suggests the existence of independent hepatic transport mechanisms for these two anions. For both PPG and CTZ blood disappearance curves showed an initial, rapid phase followed by a second, slow phase. The rapid phase for both compounds is affected only slightly by pretreatment with NP. Therefore, it is inferred that suppression of biliary excretion was attributable mainly to impairment of the liver-to-bile transport process. The increased bile flow induced by NP treatment was previously shown to be related to the biliary excretion of NP and its metabolites. Inhibition of NP choleresis by PPG may involve competition for biliary transport of these compounds. The marked hepatomegaly and choleresis seen after NP pretreatment was more evident in male rats than in females.

Animals↗
PubMed2006

Surface modification of phenolphthalein poly(ether sulfone) ultrafiltration membranes by blending with acrylonitrile-based copolymer containing ionic groups for imparting surface electrical properties.

Asymmetric ultrafiltration membranes were fabricated from the blends of phenolphthalein polyethersulfone (PES-C) and acrylonitrile copolymers containing charged groups, poly(acrylonitrile-co-acrylamido methylpropane sulfonic acid) (PAN-co-AMPS). From the surface analysis by XPS and ATR-FTIR, it was found that the charged groups tend to accumulate onto the membrane surface. This result indicated that membrane surface modification for imparting surface electrical properties could be carried out by blending charged polymer. Furthermore, with the help of a relatively novel method to measure membrane conduction, the true zeta potentials calculated on the basis of the streaming potential measurements were used to reflect the charge state of membrane surface. In addition, it was noteworthy that, from the profiles of zeta potential versus pH curves and the magnitude of zeta potentials, the determination of zeta potential was dependent not only on the electrical properties of membrane surface but also on its hydrophilicity. At last, based on a relatively elaborate study on the electrostatic interaction between the membrane surface and protein, it was found that these charged membranes could meet different demands of membrane applications, such as resisting protein fouling or protein separation, through adjusting solution pH value.

Journal Article↗
PubMed2001

Visual enantiomeric recognition using chiral phenolphthalein derivatives.

[structure: see text] Optically active artificial host molecules 2-5 based on a phenolphthalein skeleton have been prepared for visual enantiomeric recognition of alanine derivatives 8 and 9. The receptor 3 discriminates (R)-8 and (R)-9 from (S)-8 and (S)-9, respectively, to develop a purple color.

Journal Article↗