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PubMed2005

Synthesis, spectral and thermal studies of Co(II), Ni(II) and Cu(II) complexes 1-(4,6-dimethyl-pyrimidin-2-ylazo)-naphthalen-2-ol.

The electronic absorption spectra of 1-(4,6-dimethyl-pyrimidin-2-ylazo)-naphthalen-2-ol is studied in organic solvents of different polarity as well as in buffer solutions of varying pH values at different temperatures and different ratios of methanol. The probable structure of the azodye has been assigned on the basis of spectral studies (IR and (1)H NMR). The effect of Co(II), Ni(II) and Cu(II) ions on the emission spectrum of the free azodye is also assigned. The stoichiometry of the metal complexes is determined spectrophotometrically and conductometrically. Novel complexes of Co(II), Ni(II) and Cu(II) with the pyrimidine azodye have been synthesized and characterized on the basis of elemental analyses, molar conductance, magnetic susceptibility measurements, IR, electronic as well as ESR spectral studies The thermal decomposition of the metal complexes is studied by TGA and DTA techniques. The kinetic parameters like activation energy, pre-exponential factor and entropy of activation are estimated.

Azo Compounds↗
PubMed2005

Light-emitting conjugated molecule containing 1,3,4-oxadiazole, carbazole and naphthalene units.

A novel pi-conjugated small molecule VNCO, 2,5-bis{3'-[3''-vinyl-9''-(alpha-naphthyl)carbazolyl]phenyl}-1,3,4-oxadiazole, containing hole-transporting carbazole moieties, electron-injecting 1,3,4-oxadiazole moieties and chromophore naphthalene was designed and synthesized by Wittig reaction of 2,5-bis(3-tolylene-triphenylphosphonium bromide)-1,3,4-oxadiazole and 3-formyl-9-(alpha-naphthyl)carbazole. The UV-vis absorption, fluorescence excitation and emission spectra have been obtained in solution for VNCO. The photoluminescence (PL) of VNCO were examined in different solvents and the luminescence quantum yield was 0.746 in chloroform. It emitted blue and blue-green light, with the band gap of 3.30 eV estimated from the onset absorption. In addition, the light-emitting can be quenched by both electron donor (N,N-dimethylaniline) and electron acceptor (dimethylterephalate). Furthermore, the molecular interactions of VNCO with fullerene (C60) or carbon nanotubes (CNTs) were also carefully investigated.

Aniline Compounds↗
PubMed2006

Preconcentration of thallium(III) with 2,6-bis(N-phenyl carbamoyl) pyridine on microcrystalline naphthalene prior to its trace determination in human serum spectrophotometrically.

A novel, simple, sensitive and effective method has been developed for preconcentration of thallium on 2,6-bis(N-phenyl carbamoyl)pyridine-naphthalene adsorbent in the pH range 5.0-10.0, prior to its spectrophotometric determination, based on the oxidation of bromopyrogallol red at lambda = 518 nm. This method makes it possible to quantitize thallium in the range of 3.0 x 10(-9) to 1.0 x 10(-5) M, with a detection limit (S/N=3) of 1.2 x 10(-9) M. This procedure has been successfully applied to determine the ultra trace levels of thallium in the environmental and biological samples, free from the interference of some diverse ions. The precision, expressed as relative standard deviation of three measurements is better than 4.17%.

Adsorption↗
PubMed2004

Impaired recovery from naphthalene-induced bronchiolar epithelial injury in mice exposed to aged and diluted sidestream cigarette smoke.

The effect of sidestream tobacco smoke combined with other pollutants is largely unknown. Previously, we found that distal airway epithelial repair was inhibited in mice exposed to sidestream tobacco smoke (TS) for 5 days followed by single exposure to naphthalene (NA), a common polycyclic aromatic hydrocarbon found in cigarette smoke, diesel exhaust, and pesticide formulations. The main injury target of NA is the nonciliated (Clara) bronchiolar cell. NA injury normally resolves in two weeks. Repair in mice exposed to TS and NA was unresolved in the distal bronchioles 14 days post-NA injury. We hypothesized that repair inhibition persisted as a first step towards long-term airway remodeling and expanded the previous study by evaluating repair 21 days after acute NA injury. Repair was evaluated using high resolution histopathology, TEM, and quantitative morphometry. In animals exposed to TS and NA, repair was still impaired; re-differentiation of Clara cells at the bronchoalveolar duct junction was incomplete, indicating repair was continuing. Compared to 14 days post-NA-injury, repair at 21 days post-NA treatment was more extensive. Animals exposed only to TS had epithelium similar to controls. While TS exposure impairs bronchiolar epithelial repair after NA exposure, this effect appears to be slowly resolving over time.

Animals↗
PubMed2006

Effect of ultrasound pretreatment in mesophilic and thermophilic anaerobic digestion with emphasis on naphthalene and pyrene removal.

In many anaerobic digestion processes for the treatment of the sludge produced in wastewater treatment plants, the hydrolysis of the organic matter has been identified as the rate limiting step. This study is focused on the effect of ultrasonic pretreatment of raw sewage sludge before being fed to the mesophilic and the thermophilic anaerobic digestion. From particle size reduction, COD disintegration degree and biodegradability test, 11,000kJ/kg TS was estimated as the optimal specific energy in ultrasonic pretreatment. Moreover, the use of pretreated sludge improved significantly the COD removal efficiency and biogas production in lab-scale anaerobic digesters when compared with the performance without pretreatment, specially under mesophilic conditions. During ultrasonic pretreatment, the diffusion of polycyclic aromatic hydrocarbons (PAH) compounds to the aqueous phase was stated by a reduction in the pretreated sludge micropollutants content. With sonication, naphthalene was better removed than without this pretreatment, particularly in the mesophilic digester. However, pyrene removal remained at same efficiency level with and without ultrasonic pretreatment.

Anaerobiosis↗
PubMed2002

Induction of tolerance to naphthalene in Clara cells is dependent on a stable phenotypic adaptation favoring maintenance of the glutathione pool.

Repeated exposures to the Clara cell cytotoxicant naphthalene (NA) result in target cell populations that become refractory to further injury. To determine whether tolerance occurs from specific adaptations favoring glutathione (GSH) resynthesis without broad shifts in cellular phenotype, mice were administered NA for 21 days. We found that gamma-glutamylcysteine synthetase (gamma-GCS) was induced in tolerant Clara cells by repeated exposures to NA. Treating tolerant mice with buthionine sulfoximine, a gamma-GCS inhibitor, eliminates resistance acquired by repeated exposures to NA. Broad phenotypic shifts were not present. Marker proteins of differentiation declined over the first 3 days in the development of tolerance, but returned to control levels at 14 and 21 days. Epithelial organizational structure and internal organelle composition in Clara cells from tolerant mice were similar compared to corn oil-treated controls, while subtle shifts in organelle distribution were present. We conclude that induction of gamma-GCS expression is coordinated with the development of NA tolerance, but induction of NA tolerance does not markedly alter Clara cell differentiation, epithelial organization, or organelle composition in bronchiolar epithelium.

Adaptation, Physiological↗
PubMed2003

High-performance liquid chromatographic assay of asymmetric dimethylarginine, symmetric dimethylarginine, and arginine in human plasma by derivatization with naphthalene-2,3-dicarboxaldehyde.

Asymmetric dimethylarginine (ADMA) is an emerging cardiovascular risk factor. Its increased levels have been hypothesized to be a cause of endothelial dysfunction in pathological conditions such as hypertension, dyslipidemia, renal failure, hyperglycemia, and hyperhomocysteinemia. It acts as a potent competitive inhibitor of nitric oxide synthase. Methods using ortho-phthaldialdehyde (OPA) as derivatization reagent are widely performed in HPLC determination of ADMA, but they produce derivatives whose fluorescence rapidly decreases during time. Moreover, these methods do not allow a clear separation of ADMA from its stereoisomer symmetric dimethylarginine (SDMA). Our work describes a new method to determine ADMA, SDMA, and arginine that uses, as derivatizing reagent, naphthalene-2,3-dicarboxaldehyde (NDA). Chromatograms with low background, showing a complete separation of ADMA and SDMA, are obtained. NDA derivatives are considerably more stable than the OPA derivatives. The calibration curves of ADMA and SDMA are linear within the range of 0.01-16.0 microM. Coefficients of variation are less than 1.7% for within day and less then 2.3% for day to day. Absolute mean recoveries from supplemented samples are between 100 and 104%. These characteristics make this method reliable and easily manageable for large routine analyses.

Arginine↗
PubMed2000

Stability of sulfonated derivatives of benzene and naphthalene on disposable solid-phase extraction pre-columns and in an aqueous matrix.

The stability of 14 sulfonated benzene and naphthalene compounds was investigated using polymeric solid-phase extraction cartridges, based on the styrene-divinylbenzene polymer Isolute ENV+. Several different storage conditions were tested to carry out the stability study in polymeric cartridges, which included storage at room temperature, at 4 degrees C and at -20 degrees C, during a period of up to 3 months. An additional stability study was carried out, not with the polymeric solid matrix, but in an aqueous matrix. This study was performed storing the samples at 4 degrees C, during 2 months under three different conditions: acidifying the water sample to pH 2.5-3 with sulfuric acid, adding 1% of formaldehyde (additive used in waste water analyses), and storing the water sample at 4 degrees C without any additives. The extraction of the SPE process is analyzed by ion-pair chromatography-electrospray mass spectrometry, in the negative ion mode. This study showed that the stability of polar aromatic sulfonic acids on disposable polymeric cartridges and in the water matrix is related to temperature and pH, respectively. Target aromatic sulfonated compounds stored in polymeric solid-phase extraction cartridges, are more stable at lower temperatures. The target analytes showed also good stability when stored in water at acidic pH. From the different analytes studied, substituted naphthalenesulfonates suffered more degradation than mononaphthalenesulfonates or benzenesulfonates under the experimental conditions of this work.

Benzene↗
PubMed2002

Isolation and identification of diisopropylnaphthalene isomers in the alkylation products of naphthalene.

GC analysis of diisopropylnaphthalene (DIPN) isomers is presented. Naphthalene was repeatedly alkylated with propylene over an amorphous aluminosilicate catalyst under different preparation conditions, and then pure isomers or at least DIPN fractions enriched in individual isomers were isolated from the alkylates and analysed using GC-MS, IR and NMR techniques. Eight of the ten possible isomers appeared in the chromatograms; seven of them (1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 2,6- and 2,7-) were separated and identified, while the eighth one was indirectly proved to be 2,3-DIPN. The remaining two isomers (1,2- and 1,8-DIPN) were not found in the products.

Alkylation↗
PubMed1989

Determination of benzenes and naphthalenes in water by purge and trap isolation and capillary column chromatography.

A method for determination of volatile, aromatic hydrocarbons in the range from benzene to C2-naphthalenes has been adapted for monitoring the concentration of these components in water. The hydrocarbons are purged from the water by helium, trapped on an adsorbent, Tenax-GC, desorbed from this by rapid heating, transferred directly to a fused-silica gas chromatography column, which is cooled to -80 degrees C for initial cryotrapping, and finally chromatographed by programmed raising of the temperature of the column. The whole process is automated and takes 40 min, plus 10 min for temperature equilibration for the next experiment. With 5 ml water samples, concentrations of 0.1 microgram/l (ppb) of the individual components were determined. The method was applied to monitoring of a biotest system, and compared to the traditional liquid extraction method.

Benzene↗
PubMed1990

Naphthalene- and anthracene-2,3-dialdehyde as precolumn labelling reagents for primary amines using reversed- and normal-phase liquid chromatography with peroxyoxalate chemiluminescence detection.

Naphthalene-2,3-dialdehyde (NDA) and anthracene-2,3-dialdehyde (ADA) were applied as pre-column labelling reagents for the peroxyoxalate chemiluminescence detection of primary amines. The advantages of these labels are the selective derivatization reaction with primary amines and the good chemiluminescence properties. A serious disadvantage is the formation of cyanide-induced side-products which are major interferences in reversed-phase chromatography. For normal-phase chromatography, the excess of reagent was removed by adding a polar amine after derivatization, with subsequent extraction of the labelled analyte with an apolar solvent. The detection limit for NDA-labelled fluvoxamine, an anti-depressant, was in the low femtomole range in standard solutions and in urine samples. For ADA-labelled analytes difficulties were obtained with linearity in peroxyoxalate chemiluminescence detection, probably owing to oxidation of the derivative by hydrogen peroxide.

Amines↗
PubMed2002

Method of intracellular naphthalene-2,3-dicarboxaldehyde derivatization for analysis of amino acids in a single erythrocyte by capillary zone electrophoresis with electrochemical detection.

A novel method of intracellular derivatization was developed. In this method, the derivatization reagents [naphthalene-2,3-dicarboxaldehyde (NDA) and CN-] were introduced into living cells by electroporation for the derivatization reaction. After completion of derivatization reaction in cells, a single cell was drawn into the capillary tip by electroosmotic flow. Then the lysing solution was introduced into the capillary by diffusion. Once the individual cell was lysed, the derivatized amino acids in the individual cell were separated by capillary zone electrophoresis and detected by end-column amperometric detection at the outlet of the capillary. This method of intracellular NDA derivatization confined the analytes and the derivatization reagents to the volume of a single cell expanded. For an 8-microm erythrocyte, the contents were diluted by a factor of only ca. 1.6. The method was used to determination of amino acids in single erythrocytes. Six amino acids were identified and quantified.

Amino Acids↗
PubMed2002

Comparative study of naphthalene-2,3-dicarboxaldehyde and o-phthalaldehyde fluorogenic reagents for chromatographic detection of sphingoid bases.

Naphthalene-2,3-dialdehyde (NDA) was developed as a precolumn labeling reagent for the fluorescent determination in a HPLC system of bioactive sphingoid bases, including sphingosine, sphinganine, and C20-sphinganine. Cellular sphingoid bases generally exist in the range of 10 to approximately 100 pmol/10(6) cells in a wide variety of cell types and tissues. This study aimed to obtain stable fluorescent derivatives of sphingoid bases and to increase their detectability at low concentrations. Sphingoid bases were reacted with NDA in the presence of cyanide ion to readily make an intensely fluorescent structure, 1-cyano-2-alkyl-benz[f]isoindole (CBI) and were then eluted separately on a reversed-phase C18 column with a simple mobile phase of 90% acetonitrile. For evaluating the NDA method, we compared the fluorescent intensity, elution profile, stability, and detectability of NDA derivatives with those of corresponding o-phthalaldehyde (OPA) derivatives. By monitoring the fluorescent intensity at the excitation wavelength of 252 nm and emission wavelength of 483 nm, NDA derivatives were sensitively determined at concentrations below 1.0 pmol of sphingoid bases in 1 x 10(5) U937 cells and were more stable than OPA derivatives. Linear calibration plots were obtained in the range studied (0.5 to approximately 500 nM). The limit of detection for NDA derivatives of sphingoid bases was approximately 0.1 pmol (S/N=3). The method successfully measured the accumulation of sphingosine in U937 cells following N,N-dimethylsphingosine treatment, and of sphinganine following fumonisin B1 treatment.

Calibration↗
PubMed1997

Polychlorinated naphthalenes in groundwater samples from the Llobregat aquifer (Spain).

Polychlorinated naphthalenes (PCNs) have characteristics fairly similar to those of polychlorinated biphenyls and terphenyls (PCBs and PCTs) and although they have been used in numerous applications, very few reports on the occurrence of PCNs in water have been published. Both automated solid-phase extraction (SPE) and liquid-liquid extraction (LLE) procedures were evaluated to concentrate PCNs. High-resolution gas chromatography with electron-capture detection (HRGC-ECD) and mass spectrometric detection in the selected ion monitoring mode (SIM) were used to analyze PCNs in groundwater samples from the aquifer of the Llobregat river near Barcelona (NE Spain). The homologue distribution profiles of PCNs found in groundwater samples and the standard mixtures of Halowax (1099, 1013 and 1014) were compared. Quantification was achieved by HRGC-ECD. Total PCN concentrations expressed as Halowax 1099 equivalents ranged from < 0.5 ng/l to 79.1 micrograms/l in the water samples, with tetrachloronaphthalenes (TetraPCN) as the major group of congeners.

Gas Chromatography-Mass Spectrometry↗
PubMed1999

Quantitative structure-retention relationships of polychlorinated naphthalenes in gas chromatography.

A quantitative structure-retention relationship (QSRR) model has been developed for the gas chromatographic relative retention indices (RRis) of 62 polychlorinated naphthalene (PCN) congeners in a non-polar column, DB-5 (5% phenyl, methylpolysiloxane). Chemical descriptors were calculated from the molecular structures of PCNs and related to their gas chromatographic RRis by multiple linear regression analysis. The proposed model had a multiple square correlation coefficient R2 = 0.995, and standard error SE = 16.7. A QSRR reveals that the gas chromatographic retention of PCNs is associated with the number of chlorine substitutions, influenced by electronic descriptors such as heat of formation, maximum value for atomic valence, and the minimum value for electronic orbital population.

Chromatography, Gas↗
PubMed2001

Five naphthalene glycosides from the roots of Rumex patientia.

Three novel and two known naphthalene glycosides were isolated from the roots of Rumex patientia L. (Polygonaceae). The structures of the new compounds were established, respectively as 2-acetyl-3-methyl-6-carboxy-1,8-dihydroxynaphthalene-8-O-beta-D-glucopyranoside, 4,4"-binaphthalene-8,8"-O,O-di-beta-D-glucopyranoside and 2-acetyl-3-methyl-1,8-dihydroxynaphthalene-8-O-beta-D-glucopyranosyl (1-->3) beta-D-glucopyranoside on the basis of spectral analysis. The other napthalene glycosides were determined as nepodin-8-O-beta-D-glucopyranoside and torachrysone-8-O-beta-D-glucopyranoside by comparison of their spectral data with those previously reported.

Glycosides↗
PubMed1998

Three naphthalenes from root bark of Hibiscus syriacus.

Three new naphthalenes, designated as syriacusins A-C, were isolated from the root bark of Hibiscus syriacus. These compounds were identified as 2,7-dihydroxy-6-methyl-8-methoxy-1-naphthalenecarbaldehyde, 2-hydroxy-6-hydroxymethyl-7,8-dimethoxy-1-naphthalenecarbaldehyde, 1-carboxy-2,8-dihydroxy-6-methyl-7-methoxynaphthalenecarbolactone (1-->8), respectively, on the basis of various spectral studies. The compounds inhibited lipid peroxidation with IC50s of 0.54, 5.90 and 1.02 micrograms ml-1, respectively. The first compound also showed cytotoxicity against some human cancer cell lines with an ED50 of 1.5-2.4 micrograms ml-1.

Animals↗
PubMed2000

Tissue distribution of polychlorinated naphthalenes (PCNs) and non-ortho chlorinated biphenyls (non-ortho CBs) in harbour porpoises (Phocoena phocoena) from Swedish waters.

Polychlorinated naphthalenes (PCNs) and non-ortho chlorinated biphenyls (non-ortho CBs) were analysed in blubber, nuchal fat, liver, muscle, kidney and brain of three male harbour porpoises (Phocoena phocoena) from the west coast of Sweden. To estimate spatial variation, PCNs and non-ortho CBs were analysed in six blubber samples collected at different anatomical sites of each animal. Highest wet weight concentrations of sigma PCNs were detected in the lipid rich tissues (blubber and nuchal fat) and liver (520-730 and 520 pg/g, respectively) and lowest in brain (22 pg/g). TetraCNs were most abundant in muscle, kidney and brain, while the hexaCNs were most abundant in the lipid rich tissues and liver. The highest lipid weight concentration recorded (11 ng/g) was for the hexaCN congeners no. 66/67 in liver. These coeluting hexaCN congeners accounted for 80-100% of total hexaCNs in all tissues examined. Concentrations of sigma non-ortho CBs were highest in lipid rich tissues (220-280 pg/g wet weight). Non-ortho CB no. 77 and 169 constituted between 62-86% and 4.9-9.3%, respectively, of total sigma non-ortho CBs. No major variation of sigma non-ortho CB concentrations was found between the six different blubber sites but higher sigma PCN concentrations (wet weight) were found dorsally at the peduncle. Toxic equivalent concentrations (TEQs) showed that non-ortho CB no. 126 was the main contributor to total TEQs in all tissues, except liver in which hexaCN congener nos. 66/67 contributed to about 50% of total TEQs.

Adipose Tissue↗