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PubMed2001

Fitting adsorption isotherms to the distribution data determined using packed micro-columns for high-performance liquid chromatography.

Knowing the adsorption isotherms of the components of a mixture on the chromatographic system used to separate them is necessary for a better understanding of the separation process and for the optimization of the production rate and costs in preparative high-performance liquid chromatography (HPLC). Currently, adsorption isotherms are usually measured by frontal analysis, using conventional analytical columns. Unfortunately, this approach requires relatively large quantities of pure compounds, and hence is expensive, especially in the case of pure enantiomers. In this work, we investigated the possible use of packed micro-bore and capillary HPLC columns for the determination of adsorption isotherms of benzophenone, o-cresol and phenol in reversed-phase systems and of the enantiomers of mandelic acid on a Teicoplanin chiral stationary phase. We found a reasonable agreement between the isotherm coefficients of the model compounds determined on micro-columns and on conventional analytical columns packed with the same material. Both frontal analysis and perturbation techniques could be used for this determination. The consumption of pure compounds needed to determine the isotherms decreases proportionally to the second power of the decrease in the column inner diameter, i.e. 10 times for a micro-bore column (1 mm I.D.) and 100 times for capillary columns (0.32 mm I.D.) with respect to 3.3 mm I.D. conventional columns.

Adsorption↗

PubMed1976

Electron capture and multiple ion detection of benzodiazepine esters in pharmacokinetic studies.

A sensitive and highly specific gas-liquid chromatographic method is described for the determination of benzodiazepine esters. The method involves the extraction of pivoxazepam and 2'-chloropivoxazepam from blood and urine samples and the hydrolysis of both drugs with strong acid to the corresponding 2-amino-5-chlorobenzophenone (ACB) and 2-amino-5,2'-dichlorobenzophenone (ACDB). Recoveries of 97-98% have been obtained and the trifluoroacetic (TFA) derivatives of both benzophenones (ACB-TFA and ACDB-TFA) can be chromatographed on OV-17, in a short time, with good electron-capture detector (ECD) responses. The mass spectra of these derivatives provide abundant molecular ions suitable for mass spectrometric detection by multiple ion detection (MID), with a considerable improvement in specificity compared with the ECD responses. The detection limits in blood specimens have been established at 5-10 ng/ml by ECD and 0.5-0.8 ng/ml by MID. The method has been applied to the study of blood levels attained after i.v. and oral doses in rats and in man.

Animals↗

PubMed2002

Determination of water-soluble UV-filters in sunscreen sprays by liquid chromatography.

Liquid chromatography was used for the determination of the three most used water-soluble UV filters, benzophenone-4 (BZ4), terephthalylidene dicamphor sulfonic acid (TDS), and phenylbenzimidazole sulphonic acid (PBS), in aqueous sunscreen sprays. A C18 stationary phase and an isocratic mobile phase of EtOH-20 mM sodium acetate buffer of pH 4.6 (30:70, v/v) were used at a flow-rate of 0.5 ml min(-1). Mobile phase was also used as solvent for samples and standards. UV detection was at 313 nm. The analytical run took 5.5 min. The limits of detection were 0.5, 0.9 and 2 microg ml(-1) for BZ4, TDS and PBS, respectively. The proposed method does not involve highly toxicsolvents.

Chromatography, Liquid↗

PubMed2001

Concentricol, a taxonomically significant triterpenoid from Daldinia concentrica.

In the course of a chemotaxonomic study of xylariaceous Ascomycetes, a major metabolite was isolated and identified from the ascostromata of Daldinia concentrica. The compound, for which the name concentricol is proposed, constitutes a highly oxidised squalene derivative. A survey of several Daldinia spp. from around the world (including several type materials), employing analytical HPLC-UV/Vis (with diode array detection) and positive electrospray HPLC-MS of stromatal MeOH extracts revealed that concentricol was omnipresent in the stromata of D. concentrica, as well as in those of several collections of the pantropical Daldinia eschscholzii. All other investigated Daldinia spp. were found devoid of concentricol but contained binaphthalenes, benzophenones and/or azaphilones as further taxonomically relevant main metabolites.

Ascomycota↗

PubMed1999

Cytotoxic constituents from the roots of Tovomita brevistaminea.

Two known xanthones, trapezifolixanthone and manglexanthone were isolated as cytotoxic constituents from the CHCl3 extract of the roots of Tovomita brevistaminea by bioassay-guided fractionation using the KB cell line. In addition, a new compound, tovophenone C, and two known compounds, tovophenones A and B which are benzophenones, were found to be inactive constituents in this investigation. The structure of the new isolate was determined by detailed analysis of spectroscopic parameters including its 1D and 2D NMR spectroscopy data.

Antineoplastic Agents, Phytogenic↗

PubMed2003

Molecular markers of anthropogenic activity in sediments of the Havel and Spree Rivers (Germany).

Detailed gas chromatographic/mass spectrometric analyses have been applied to sediment samples of the Havel and Spree River, tributaries to the Elbe River, in order to identify specific molecular markers of anthropogenic activities. Despite a wide variety of lipophilic organic compounds from diffuse anthropogenic contamination, a local emission of an industrial point source was reflected by specific markers including halogenated compounds and nitrogen containing substances (4-ethylnitrobenzene, formyl piperidine, acetyl piperidine). In addition to well-known anthropogenic markers various new molecular tracers were detected and are discussed, namely plasticizers (alkylsulfonic acid aryl esters, tributyl and tricresyl phosphates), synthetic fragrances (galaxolide, tonalide, 4-oxoisophorone), additives of personal care products (4-methoxycinnamic acid 2-ethylhexyl ester, benzyl benzoate, dibenzyl ether, benzophenone), occurring due to sewage treatment plant input.

Cosmetics↗

PubMed2001

Novel route for the resolution of both enantiomers of dropropizine by using oxime esters and supported lipases of Pseudomonas cepacia.

Resolution of (R)- and (S)-dropropizine which is an antitussive and central sedative therapeutic agent in high optical and chemical yields was achieved by lipases of Pseudomonas cepacia supported on ceramic particles (lipase PS-C) and on diatomite (lipase PS-D) with oxime esters in organic solvents. The influence of several factors (lipase source, structural variations in oxime esters, the amount of lipase and its recyclability) on the enantioselectivity have been investigated. Different properties were used to describe the solvents, namely the hydrophobicity (quantified by log P) and the dielectic constant (epsilon). This enzymatic acylation using oxime esters was significant as only (S)-dropropizine and (R)-dropropizine monoacetate was obtained. (R)-Dropropizine monoacetate was chemically hydrolyzed to obtain (R)-dropropizine. The highest enantioselectivity was observed when O-acetyl benzophenone oxime was used. This enzymatic resolution provides a versatile method for getting the pure enantiomers of dropropizine by effectively optimizing the various reaction parameters.

Journal Article↗

PubMed2000

Surface-modification of polystyrene-microtitre plates via grafting of glycidylmethacrylate and coating of poly-glycidylmethacrylate.

Photografting of glycidylmethacrylate (GMA) onto commercially available polystyrene-microtitre plates was carried out in methanol as well as butanol with benzophenone (BP) as photoinitiator. Alternatively, prepolymers of polyglycidylmethacrylate (PGMA) were synthesized in methanol with azo-iso-butyrodinitrile (AIBN) as initiator and dip-coated onto polystyrene-microtitre plates. Both modification methods were tested in order to reach a high binding capacity for proteins. Peroxidase was used as model protein. In addition, the immobilization of myelin basic protein (MBP) to epoxy-modified microtitre plates is shown and a MBP-based ELISA has been developed.

Biocompatible Materials↗

PubMed2005

[The prospective multicenter study on standard photopatch tests by the French Society of Photodermatology from 1991-2001].

INTRODUCTION: To develop a standard panel of photopatch tests, the French Society of Photodermatology conducted a prospective study from 1991 to 2001 on the frequency of photoallergens encountered in France and on the relevance of the choice of the various photoallergens. PATIENTS AND METHODS: Thirteen photobiology centers participated in the study from 1991 to 1995, and ten centers from 1995 to 2001. A set of 3 samples of photopatch tests was applied on any patient suspected of photoallergy. On Day 2, two sets were irradiated with ultraviolet A (UVA) and total spectrum (DEM 0.75); with the third set being used as control. Readings were made on D3 and D4. RESULTS: Two thousand sixty-seven patients were tested. Eight hundred fifty-six, i.e., 41% exhibited one or several positive tests. In the majority of cases it was a photoallergy (39.7 to 60% of cases) and eczema (29.5 to 45.6%). Photoaggravation was infrequent (7.9 to 10.3%). Cases of phototoxicity were rare. Sesquiterpenic lactones constantly provoked photoallergy, with 12 cases in 10 years. Although phenothiazines were the most photosensitizing allergens up until 1995, they were then overridden by ketoprofen in 1996 with 107 cases of UVA photosensitive reactions (75 cases) and total spectrum (32 cases). These were followed closely by sun screens, benzophenone (notably Eusolex 4360 with 54 pertinent cases of photoallergy) and dibenzoylmethane (with 31 cases due to Eusolex 8020). UVB filters were all potentially photosensitizing but to a lesser degree from 1 to 5 cases). DISCUSSION: Our results differ from those of Anglo-Saxon teams in the appearance of a new photoallergen, ketoprofen, which provoked numerous photosensitivities in both UVA and UVB. This justifies the systematic addition of this substance in our prospective set. Photoallergy was relatively rare, with around 100 cases reported within 10 years. Total spectrum irradiation of the photopatch tests revealed photoallergies that would not have been found with UVA alone. CONCLUSION: Study of photopatch tests has permitted the uniformization of the methodology in France, an overview of the frequency of the photoallergens tested and the development of a new standard set.

France↗

PubMed2002

Development of a biologically active secretin analogue incorporating a radioiodinatable photolabile p-(4-hydroxybenzoyl)phenylalanine in position 10.

Photoaffinity labeling is a powerful approach for direct elucidation of residue-residue approximations as a ligand is bound to its receptor, providing important constraints for molecular modeling. Probes utilized for this need to incorporate photolabile sites of covalent attachment and an indicator, such as a radiolabel. Radioiodine provides a particularly useful high specific radioactivity label, but due to its size, can only be accommodated in limited positions within a peptide ligand. In this work, we attempted to develop a probe for the secretin receptor that would directly provide spatial approximation data for position 10 of secretin, its site of radiolabeling. This was achieved by incorporation into a secretin analogue of the radioiodinatable and photolabile benzophenone moiety, p-(4-hydroxybenzoyl)phenylalanine (OH-Bpa). An unintended additional modification of secretin in synthesizing this probe was the elimination of Gly(4). This probe was shown to bind to the secretin receptor specifically and saturably (K(i)=25.3+/-6.0 nM). It represented a full agonist, stimulating intracellular cAMP in a concentration-dependent manner (EC(50)=4.2+/-0.7 nM). It was also able to affinity label the secretin receptor in a specific and efficient manner. This probe should provide the opportunity to identify the region of the secretin receptor in spatial approximation with position 10, within the pharmacophore of secretin, leading to refinement of molecular conformational models of this agonist-bound receptor.

Amino Acid Sequence↗

PubMed1998

Identification of the creatine binding domain of creatine kinase by photoaffinity labeling.

A new photoaffinity probe with a benzophenone group, N-dibenzylphospho-N'-(4-benzoyl)-benzylguanidine (BzPG), has been synthesized on the basis on our previously described creatine kinase bisubstrate analog. BzPG is also a bisubstrate type analog whose photoinsertion is inhibited by the natural substrates of creatine kinase. When rabbit CK-MM is irradiated in the presence of BzPG then cleaved by CNBr, one labeled peptide can be purified by reverse phase HPLC and sequenced. This sequence of 31 amino acids (Ala30-Val60) contains a region which could be responsible for isoenzyme selectivity and another one just preceding the 11 amino acid peptide (Asp61-Thr70) very recently described as a putative creatine binding site. This second peptide was deduced from the comparison of 18 amino acid sequence alignments. We proposed the creatine binding site to be essentially a peptide from Lys39 to Val71.

Animals↗

PubMed2002

Comparison of reporter gene assay and immature rat uterotrophic assay of twenty-three chemicals.

We performed a reporter gene assay for ERalpha-mediated transcriptional activation and an immature rat uterotrophic assay of 23 chemicals, to study the relationship between these two assays and to examine the usefulness of the reporter gene assay. The chemicals analyzed in the study were as follows: benzophenone, bisphenol A, bisphenol B, bisphenol F, p-cumyl phenol, dibutyl phthalate, dicyclohexylphthalate, dihydrotestosterone, equilin, 17alpha-estradiol, estrone, ethynyl estradiol, genistein, hematoxylin, nonylphenol mixture, 4-n-nonylphenol, norethindrone, norgestrel, octachlorostyrene, 4-n-octylphenol, 4-tert-octylphenol, tributyltin-chloride and zearalenone. To perform the reporter gene assay, HeLa cells were transfected with a rat ERalpha expression construct and an estrogen-regulated luciferase reporter construct. The transcriptional activities of each chemical were tested over concentrations ranging from 10 pM to 10 microM and the EC50, PC50 and PC10 values were calculated. In the immature rat uterotrophic assay, the doses of 21 chemicals, with the exception of dibutyl phthalate and ethynyl estradiol, were 0, 2, 20 and 200 mg/kg; each group consisted of six rats. The doses of dibutyl phthalate and ethynyl estradiol were 0, 40, 200 and 1000 mg/kg per day and 0, 0.2, 2 and 20 microg/kg per day, respectively. In the reporter gene assay, the PC10 values were calculated for 15 chemicals: bisphenol A, bisphenol B, bisphenol F, p-cumyl phenol, dihydrotestosterone, equilin, 17alpha-estradiol, estrone, ethynyl estradiol, genistein, nonylphenol mixture, norethindrone, norgestrel, 4-tert-octylphenol and zearalenone. These chemicals corresponded to the chemicals that tested positive in the uterotrophic assay. The other chemicals were negative in the reporter and uterotrophic assays. Although the EC50 and PC50 values could only be calculated for five and six chemicals, respectively, the PC10 values were shown to be well correlated with the EC50 values by a correlation analysis (R(2)=0.9202). These findings demonstrate that PC10 values are preferable to EC50 and PC50 values for predicting the estrogenic activities of chemicals.

Animals↗

PubMed1984

Separation, isolation and identification of optical isomers of 1,4-benzodiazepine glucuronides from biological fluids by reversed-phase high-performance liquid chromatography.

A reversed-phase high-performance liquid chromatographic (HPLC) method for the determination of four separate 1,4-benzodiazepine glucuronides in urine, plasma and bile is presented. We succeeded not only in determining the single glucuronides but also in separating the enantiomers (optical isomers) of the 1,4-benzodiazepine glucuronides. The optical isomers of the glucuronides of oxazepam and cinolazepam and of two other glucuronides of benzodiazepine metabolites could be well separated. The ratio of the isomers could be evaluated. An octadecyl reversed phase was used with a mobile phase of acetonitrile and 0.01 M orthophosphoric acid. After the initial separation, the isomers were fractionated by HPLC. After treatment with beta-glucuronidase to yield the aglycone, the separated fractions were hydrolysed to the corresponding benzophenones whose identity was confirmed by HPLC. Gas chromatography and gas chromatography-mass spectrometry demonstrated that the separated glucuronides corresponded to the enantiomeric benzodiazepines. Human urine and plasma as well as rabbit urine, plasma and bile were examined.

Benzodiazepines↗

PubMed1981

Determination of 1,4- and 1,5-benzodiazepines in urine using a computerized gas chromatographic-mass spectrometric technique.

A method for the determination of benzodiazepines and their main metabolites in urine after acid hydrolysis is described. The extract is analyzed by computerized gas chromatography-mass spectrometry. An on-line computer allows rapid detection using mass fragmentography with the masses m/e 211, 230, 241, 244, 249, 262, 276, and 285. The mass fragmentogram and the underlying mass spectra of the hydrolysis products (benzophenones and analogues) are documented.

Benzodiazepines↗

PubMed2001

Solid-phase microextraction and gas chromatography-mass spectrometry analysis of p,p' -DDE in biological samples.

A simple and rapid extraction method for the analysis of p,p'-DDE from rat whole blood and tissues was developed using headspace solid-phase microextraction (SPME). A vial containing a sample of p,p'-DDE, sodium hydroxide, and benzophenone as internal standard was heated at 120 degrees C. A polydimethylsiloxane-coated SPME fiber was exposed for 15 min in the headspace of the vial. The fiber needle was then injected and desorbed by exposing the fiber in the injection port of a capillary gas chromatography-mass spectrometry system. The calibration curve demonstrated good linearity throughout the concentration range from 0.02 to 50 microg/g for rat whole blood and liver samples. The limit of detection for p,p'-DDE was 0.020 microg/g using 0.5 g rat whole blood and liver samples. Coefficients of variation ranged from 7.0 to 7.9%. This method was used to analyze a rat whole blood sample after administration of p,p'-DDE.

Animals↗

PubMed2002

Stability indicating methods for the determination of loratadine in the presence of its degradation product.

Four stability-indicating procedures have been suggested for determination of the non sedating antihistaminic agent loratadine. Loratadine being an ester undergoes alkaline hydrolysis and the corresponding acid derivative is produced as a degradation product. Its identity was confirmed using IR and MS. The first procedure is based on determination of loratadine by HPLC with detection at wavelength, 250 nm. Mobile phase is acetonitrile:orthophosphoric acid (35:65) using benzophenone as an internal standard. Sensitivity range is 5.00-50.00 microg/ml. Second determination is a densitometric procedure based on determination of loratadine in the presence of its degradate at lambda 246 nm using the mobile phase; methanol:ammonia (10:0.15). Sensitivity range is 1.25-7.50 microg per spot. The third procedure is a spectrophotometric one where a mixture of loratadine and its degradate are resolved by first derivative ratio spectra. Sensitivity range is found to be 3.00-22.00 microg/ml, upon carrying out the measurements at wavelengths 236, 262.4 and 293.2 nm. The fourth procedure is based on second derivative spectrophotometry, where D(2) measurements are carried out at lambda 266 nm. The sensitivity range is 3.00-22.00 microg/ml. The validity of the described procedures was assessed by applying the standard addition technique. Statistical analysis of the results have been carried out revealing high accuracy and good precision. The suggested procedures could be used for determination of loratadine both in pure and dosage forms, as well as in the presence of its degradate.

Chromatography, High Pressure Liquid↗

PubMed1998

Kinetic study on the degradation of prazepam in acidic aqueous solutions by high-performance liquid chromatography and fourth-order derivative ultraviolet spectrophotometry.

A reversed-phase HPLC method was developed for the kinetic investigation of the acidic hydrolysis of prazepam which was carried out in hydrochloric acid solutions of 0.01, 0.1 and 1.0 M. In addition, a fourth-order derivative method for monitoring the parent compound itself was proposed and evaluated. One intermediate was observed by HPLC, which should be formed from breakage of the azomethine linkage. Further slow hydrolysis of the amide bond led to the benzophenone product that was isolated and identified. The mechanism of hydrolysis was biphasic, showing a consecutive reaction with a reversible step. Relative standard deviation was less than 2% for HPLC and less than 5% for the derivative method. Detection limits were 1.2 x 10(-7) M for the former method and 6.7 x 10(-7)M for the latter. Accelerated studies at higher temperatures were employed. Results of HPLC and fourth-order derivative methods were statistically the same.

Anti-Anxiety Agents↗

PubMed2000

Preparation and use of a photoactivatable glucose-6-phosphate analogue.

A benzophenone-containing derivative of glucose-6-phosphate, 6-[(3-([2,3-3H2]-p-benzoyl dihydrocinnamidoylpropyl-1-oxy)phosphoryl]-D-glucopyranose ([3H]BZDC-Glc-6-P) was synthesized and employed to photoaffinity label proteins on intact rat liver microsomes. The use of a non-photoactivatable, UV-transparent desoxy analogue of BZDC, named p-benzyldihydrocinnamoyl (BnDC), is introduced as a general method to achieve competition when hydrophilic ligands are modified with hydrophobic photophores.

Animals↗