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PubMed1975

Cycloalkanones V: synthesis, distribution, and effects on triglyceride metabolism.

The 14-C-labeled 2,8-dibenzylcyclooctanone was synthesized to study its absorption, distribution, and excretion in rats. Maximum drug absorption from the GI tract occurred between 12 and 14 hr after administration. The major organs possessed maximum amounts of the drug in 1 hr, with the liver concentrating the most with 6.56% 14-C and the muscle mass reaching a maximum of 41% 14-C after 14 hr. The drug remained in the GI tract over the first 6 hr and was associated with the lipid and glycogen fractions. Eighty-seven percent was eliminated in the feces after 72 hr. 2,8-Dibenzylcyclooctanone caused a significant reduction in vitro of dihydroxyacetone phosphatase acyltransferase and sn-glycerol-3-phosphate acyltransferase, which is the proposed mechanism for the observed in vivo reduction of hepatic, intestinal, and serum triglycerides and total glycerolipids. In vivo administration of the drug resulted in a depression of liver acid phosphatidyl phosphatase, acid phosphatase and lipase, and adipose lipase. The drug increased the rates of excretion of exogenous cholesterol, palmitic acid, and progesterone.

Acid Phosphatase↗
PubMed1975

Drug-biomolecule interactions: topographical study of active site of erythrocyte carbonic anhydrase using spin-labeled sulfanilamide drugs.

The topography of the active sites of human erythrocyte carbonic anhydrases B and C and bovine erythrocyte carbonic anhydrase B was studied using a series of spin-labeled sulfanilamide analogs. Results show that the active site of human carbonic anhydrase C is a narrow cleft approximately 14 A in depth. This observation is in good agreement with previously published X-ray diffraction data. While the active sites of human carbonic anhydrase B and bovine carbonic anhydrase B have the same general shape as the active site of human carbonic anhydrase C, they are slightly deeper.

Benzyl Compounds↗
PubMed1975

Electron-capture GLC determination of a new antiarrhythmic agent, alpha,alpha-dimethyl-4-(alpha,alpha,beta,beta-tetrafluorophenethyl) benzylamine, in biological fluids.

A highly specific and sensitive GLC method was developed for the analysis of alpha,alpha-dimethyl-4-(alpha,alpha,beta,beta-tetrafluorophenethyl) benzylamine, a new orally active antiarrhythmic drug, in biological fluids. The procedure involves the addition of an internal standard, 4-(alpha,alpha,beta,beta-tetrafluorophenethyl)benzylamine, to the plasma or urine samples followed by extraction of the drugs into benzene at pH 8. The extracted amines are converted to the trifluoroacetyl derivatives (characterized by GLG-mass spectrometry), chromatographed, and detected with a 63Ni electron-capture detector. The sensitivity of the method is such that 10 ng of alpha,alpha-dimethyl-4-(alpha,alpha,beta,beta-tetrafluorophenethyl)benzylamine/ml of plasma can be analyzed. These levels are suitable for the analysis of samples obtained following a therapeutic dose.

Animals↗
PubMed1975

High-pressure liquid chromatographic analysis of penicillin G potassium and its degradation products.

An anion-exchange high-pressure liquid chromatographic system capable of separating penicillin G potassium from five of its degradation products was developed. The retention times were: penicillin G potassium, 17.5 min; DL-penicillamine, 4.5 min; benzylpenilloic acid, 7.0 and 8.0 min; benzylpenamaldic acid, 13.0 min; benzylpenicilloic acid, 19.5 min; and benzylpenillic acid, 22.0 min. In addition, the system permits quantification using linear calibration curves.

Benzyl Compounds↗
PubMed1979

Metabolic fate of N6-benzyladenosine and N6-benzyladenosine-5'-phosphate in rats.

The radiolabeled antitumor nucleoside (14C-8)-N6-benzyladenosine and its (14C-8)-5'-phosphate were administered to rats intravenously, and their metabolic fate was studied. Twenty-nine percent of the radioactivity was recovered in the 48-hr urine collection after (14C-8)-N6-benzyladenosine administration. The following metabolites were isolated: unchanged N6-benzyladenosine (20%), adenine (12%), uric acid (5%), and N6-benzyladenine (0.3%). In the case of (14C-8)-N6-benzyladenosine-5'-phosphate, a total of 28% of the radioactivity was recovered in the 48-hr urine collection and the following metabolites were isolated: N6-benzyladenosine (40%), uric acid (12%), adenine (trace), and unidentified urea derivatives (30%). Metabolism of N6-benzyladenosine appears to involve N-debenzylation to some extent, followed by conversion to adenine and uric acid. N6-Benzyladenosine and its 5'-phosphate differ from other adenosine analogs in being retained in significant amounts by the animals.

Adenosine↗
PubMed1981

Simultaneous determination of hydroxyzine hydrochloride and benzyl alcohol in injection solutions by high-performance liquid chromatography.

A stability-indicating, high-performance liquid chromatographic method was developed for the simultaneous determination of hydroxyzine hydrochloride and benzyl alcohol in injection solutions. Separation was achieved using a mu Bondapak C18 column and the eluent [60% water, 25% acetonitrile, and 15% methanol containing 0.06% (v/v) sulfuric acid, 0.5% (w/v) sodium sulfate, and 0.02% (w/v) heptanesulfonic acid sodium salt] at a flow rate of 2 ml/min. Isobutyrophenone and p-nitroacetophenone were used as internal standards. The UV detector response at 257 nm was linear for hydroxyzine hydrochloride in the 3--10-mg/ml range and for benzyl alcohol in the 0.54--1.8 mg/ml range under analysis conditions. The method is accurate, simple, and precise.

Benzyl Alcohols↗
PubMed1982

Simultaneous determination of hydrocortisone and benzyl alcohol in pharmaceutical formulations by reversed-phase high-pressure liquid chromatography.

An accurate, reproducible, and specific reversed-phase high-pressure liquid chromatographic (HPLC) procedure that simultaneously determines hydrocortisone and benzyl alcohol in a variety of pharmaceutical formulations is presented. Cream, gel, ointment, and solution formulations containing varying hydrocortisone and benzyl alcohol concentrations can be analyzed with only minor modifications in sample preparation. To provide optimum accuracy and reproducibility, phenethyl alcohol is used as an internal standard. The specificity of the procedure allows for the quantitative determination of hydrocortisone and benzyl alcohol in the presence of their degradation products and without interference from the phenethyl alcohol. The determinations can be performed with an analysis time of 10-13 min/sample.

Benzyl Alcohol↗
PubMed1985

Stability-indicating liquid chromatographic determination of etoposide and benzyl alcohol in injectable formulations.

Simple and specific assays for etoposide, related impurities, and benzyl alcohol, as well as its degradation product, benzaldehyde, in injectable formulations were developed using high-performance liquid chromatography (HPLC). Etoposide, benzyl alcohol, benzaldehyde, and four etoposide impurities were determined with a mobile phase containing 26% acetonitrile in pH 4.0 acetate buffer with methyl p-aminobenzoate as the internal standard. Two etoposide precursors were additionally determined using 60% acetonitrile in the mobile phase with biphenyl as the internal standard. The assays were run sequentially. The etoposide assay had a total variability of less than 1% (RSD) and a recovery from placebo of 99.4%. Mean recovery of impurity standards spiked at the 2% level relative to the etoposide level was 98%. Recoveries for benzyl alcohol and benzaldehyde were 100.5% and 102.2%, respectively. Absorbance ratios generated from samples and compared with undegraded standards demonstrated specificity for etoposide. Similar response regression equations with correlation coefficients greater than 0.99 were obtained for etoposide and four impurities over the 2-8 micrograms/mL concentration range, indicating that an etoposide standard could be used to quantitate low impurity levels down to 0.2% relative to the etoposide injectable concentration. Benzaldehyde could be reliably detected at concentrations down to 0.5 micrograms/mL, equivalent to 0.16% of the benzyl alcohol level.

Benzaldehydes↗
PubMed1985

Simultaneous liquid chromatographic determination of glutaric acid, phenylephrine, and benzyl alcohol in a prototype nasal spray with application to di- and tricarboxylic acids.

A rapid reversed-phase high-performance liquid chromatographic method for the simultaneous determination of glutaric acid, phenylephrine, and benzyl alcohol in nasal spray has been developed. UV detection was utilized at 210 nm for the assay of glutaric acid and phenylephrine with an adjustment to 254 nm for the measurement of benzyl alcohol. Linearity and recovery data were obtained for each component in spiked placebo studies. An investigation of the retention mechanisms of the three components showed that phenylephrine was retained by ion-pairing with octanesulfonate anion while glutaric acid and benzyl alcohol partitioned as a suppressed ion and a neutral molecule, respectively. The method has been further extended to the reversed-phase separation of di- and tricarboxylic acids using a totally aqueous 0.0074 M phosphoric acid mobile phase. The retention of these acids was related to their octanol-water partition coefficients and structural variation.

Aerosols↗
PubMed1986

Toxicity of benzyl alcohol in adult and neonatal mice.

Benzyl alcohol, a bacteriostatic agent found in many parenteral preparations, has been implicated as the agent responsible for precipitating "the gasping syndrome" in premature neonates. To investigate this toxicity, benzyl alcohol was administered intraperitoneally to adult (23-28 g) and neonatal (2-7 g) CD-1 male mice. Gross behavioral changes were monitored. Low doses (less than 800 mg/kg) produced minimal toxic effects within an initial 4-h observation period. At the end of this time, the LD50 was determined to be 1000 mg/kg for both age groups. When mortality in the adult group was observed after 7 d following a single treatment with benzyl alcohol, the LD50 on day 7 was determined to be 650 mg/kg. Rapid absorption and conversion of benzyl alcohol to its primary metabolite, benzaldehyde, occurred within both experimental groups; the plasma levels of each were comparable in both neonatal and mature animals when determined by GC. In an attempt to alter the toxicity of benzyl alcohol, pyrazole and disulfiram were used to inhibit the activities of alcohol dehydrogenase and aldehyde dehydrogenase, respectively. Treatment with pyrazole, before benzyl alcohol exposure, resulted in an increase in benzyl alcohol levels to 203% of control values and a marked increase in toxicity. Although pretreatment with disulfiram led to benzaldehyde levels which were 368% of control values, toxicity was unchanged. These data imply that the acute toxicity of benzyl alcohol, which includes sedation, dyspnea, and loss of motor function, is due to the alcohol itself and not to its metabolite, benzaldehyde.

Aging↗
PubMed2005

Chromatographic determination of itopride hydrochloride in the presence of its degradation products.

Two sensitive and reproducible methods are described for the quantitative determination of itopride hydrochloride (IH) in the presence of its degradation products. The first method is based on HPLC separation on a reversed phase Kromasil column [C18 (5-microm, 25 cm x 4.6 mm, ID)] at ambient temperature using a mobile phase consisting of methanol and water (70:30, v/v) adjusted to pH 4.0 with orthophosphoric acid with UV detection at 258 nm. The flow rate was 1.0 mL per min with an average operating pressure of 180 kg/cm2. The second method is based on HPTLC separation on silica gel 60 F254 using toluene:methanol:chloroform:10% ammonia (5.0:3.0:6.0:0.1, v/v/v/v) as mobile phase at 270 nm. The analysis of variance (ANOVA) and Student's t-test were applied to correlate the results of IH determination in dosage form by means of HPLC and HPTLC methods. The drug was subjected to acid and alkali hydrolysis, oxidation, dry heat, wet heat treatment, UV, and photodegradation. The proposed HPLC method was utilized to investigate the kinetics of the acidic, alkaline, and oxidative degradation processes at different temperatures and the apparent pseudo-first-order rate constant, half-life, and activation energy were calculated. In addition the pH-rate profile of degradation of IH in constant ionic strength buffer solutions in the pH range 2-11 was studied.

Analysis of Variance↗
PubMed2005

Effects of ethyl and benzyl groups on the miscibility and properties of castor oil-based polyurethane/starch derivative semi-interpenetrating polymer networks.

Cornstarch derivative (ES), prepared using diethyl sulfate as an etherifying reagent, was blended with castor oil-based polyurethane (PU) prepolymer to obtain a series of semi-interpenetrating polymer network (semi-IPN) materials, named as UES films. Simultaneously, other kinds of semi-IPN (UBS2) were prepared from PU and benzyl starch (BS2) to compare the effects of the substitute groups. The differences in the miscibility and properties of the two series of materials were investigated using attenuated total reflection Fourier transform infrared spectroscopy, atomic force microscopy, dynamic mechanical thermal analysis, ultraviolet-visible spectroscopy, water-sensitivity and tensile testing. The experimental results revealed that UBS2 films exhibit stronger interfacial attraction and better phase mixing than the UES films, as a result of specific interactions between the PU hard segments and BS2 phenyl groups. The optical transmittance, water-resistivity, tensile strength, and elongation at break of the UBS2 films were clearly higher than those of the UES films containing the same concentration of PU. In particular, the miscibility and properties of the UES film with 40 wt.-% ES, were very poor, whereas the semi-IPN films containing 70 wt.-% benzyl starch still had a certain miscibility and good properties. Therefore, the phenyl groups play an important role in the improvement of the miscibility and properties of the semi-IPN materials.

Benzyl Compounds↗
PubMed1997

Toxicological evaluation of myristicin.

Myristicin, or methoxysafrole, is the principal aromatic constituent of the volatile oil of nutmeg, the dried ripe seed of Myristica fragrans. Myristicin is also found in several members of the carrot family (Umbelliferae). Several intoxications have been reported after an ingestion of approximately 5 g of nutmeg, corresponding to 1-2 mg myristicin/kg body weight (b.w.). Although these intoxications may be ascribed to the actions of myristicin, it is likely that other components of nutmeg may also be involved. The metabolism of myristicin resembles that of safrole. No information is available, however, concerning the quantitative importance of the different metabolic pathways. The acute toxicity of myristicin appears to be low. No toxic effects were observed in rats administered myristicin perorally at a dose of 10 mg/kg b.w., while 6-7 mg/kg b.w. may be enough to cause psychopharmacological effects in man. A weak DNA-binding capacity has been demonstrated, but there are no indications that myristicin exerts carcinogenic activity in short-term assays using mice. Intake estimations indicate that nonalcoholic drinks may be the most important single source of myristicin intake. Based on available data, it seems unlikely that the intake of myristicin from essential oils and spices in food, estimated to a few mg per person and day in this report, would cause adverse effects in humans. It is, however, at present not possible to make a complete risk assessment, as studies regarding genotoxicity and chronic toxicity, including reproductive toxicity and carcinogenicity, are still lacking.

Allylbenzene Derivatives↗
PubMed2004

Novel 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2] benzopyran derivatives: synthesis of chiral glycol benzyl ether herbicides.

Novel tricyclic 3,3a,5,9b-tetrahydro-2H-furo[3,2-c][2]benzopyran (TFB) derivatives were synthesized, and their herbicidal activities were elucidated. They were synthesized from D-glucose as a natural chiral source. The formation of the TFB skeleton was achieved by a Friedel-Crafts type intramolecular cyclization of methyl 5-deoxy-2,3-O-dibenzyl-5-C-methyl-D-xylofranosides. The intramolecular cyclization was dependent upon the electronic effects of the substituents at the C-2 benzyloxy group of methyl xylofranosides. Some TFBs exhibited a remarkable herbicidal activity to annual paddy weeds, such as Echinochloa sp, without injury to the rice.

Benzopyrans↗
PubMed2005

Trapping 4-fluorobenzyl chloride in human plasma with chemical derivatization followed by quantitative bioanalysis using high-performance liquid chromatography/tandem mass spectrometry.

A quantitative bioanalytical method involving chemical derivatization, solid phase extraction (SPE) and high-performance liquid chromatography/tandem mass spectrometry (HPLC/MS/MS) was developed for the determination of 4-fluorobenzyl chloride (4FBCl) in human plasma. 4FBCl is a volatile and reactive molecule that is very unstable in human plasma. In order to stabilize 4FBCl in plasma samples prior to storage, 4-dimethylaminopyridine (DMAP) was added, forming a stable quaternary amine salt derivative. A three-step weak cation-exchange SPE procedure was then employed to remove excess DMAP. The plasma extracts were analyzed by HPLC/MS/MS using a TurboIonspray interface and multiple reaction monitoring. Unlike 4FBCl, the quaternary amine derivative shows excellent sensitivity in electrospray mass spectrometry. The method was validated over a concentration range of 0.5-500 ng/mL using 45 microL of plasma. The maximum within-run and between-run precision observed in a three-run validation for quality control (QC) samples was 12.5 and 7.6%, respectively. The maximum percentage bias observed at all QC sample concentrations was 11.9%. The method has proven to be robust and compatible with high-throughput bioanalysis.

Benzyl Compounds↗
PubMed1993

Cultured Ehrlich ascites tumor cells show increased N-linked alpha 2,6-sialyltransferase activity.

Ehrlich ascites tumor cells (EAT cells) are routinely grown in the peritoneal cavity of mice. These cells, EAT-wt, grow in suspension and exhibit a high level of alpha-2,3-O-linked sialyltransferase activity with benzyl-T-antigen (Gal beta 1,3Ga1NAc-alpha-O-CH2C6H5) as acceptor. These cells also contain a very low level of alpha-2,6-O-linked and alpha-2,6-N-linked sialyltransferase activity. A variant of these cells, EAT-c, has been selected to grow in cell culture, attached to the surface of culture flasks. EAT-c cells exhibit a selective increase of two- to fivefold in the activity of alpha-2,6-N-linked sialyltransferase activity, using asialo-alpha 1-acid glycoprotein as acceptor. Since a similar selective increase has been previously observed in metastatic human colorectal cancer tissues, the EAT-wt/EAT-c cell system may serve as a good experimental model for the investigation of sialyltransferases and their cell surface sialylated products in relation to cancer, metastasis, and cell-cell interaction.

Animals↗
PubMed1995

Chloroperoxidase-catalyzed benzylic hydroxylation.

Chloroperoxidase oxidizes p-methylanisole and p-ethylanisole to 4-methoxybenzyl alcohol and 1-(4'-methoxyphenyl)ethanol, respectively. It ineffectively oxidizes toluene to benzyl alcohol but does not appear to oxidize toluene substituted with strong electron-withdrawing groups. O-Demethylation is also observed. The enzyme is sensitive to substituents at other than the para position and does not detectably catalyze benzylic hydroxylation of p-methylanisole if it bears additional methyl or methoxy groups. An exception is 1,2-(methylenedioxy)-4-methylbenzene, which is oxidized to both 3,4-(methylenedioxy)benzyl alcohol and 2-hydroxy-4-methylphenol. Studies with H2(18)O2 indicate that all the oxygen incorporated into the product in the oxidation of p-methylanisole to 4-methoxybenzyl alcohol derives from the peroxide. The mono- and dideuterated methyl analogues of p-methylanisole are oxidized with apparent intramolecular isotope effects of 3.51 and 3.34, respectively. Abstraction of a hydrogen from a carbon bearing a hydroxyl group competes effectively with benzylic oxidation because 2-[1,1-2H2]phenylethanol is oxidized to 2-[1-2H]- rather than 2-[1,2-2H2]phenylacetaldehyde. Aldehyde formation therefore involves abstraction of the carbinol hydrogen rather than hydrogen migration to a benzylic carbocation intermediate. Chloroperoxidase resembles cytochrome P450 in that it catalyzes benzylic hydroxylation reactions but it has a more limited substrate specificity.

Anisoles↗