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PubMed1993

Determination of hyaluronic acid by high-performance liquid chromatography of the oligosaccharides derived therefrom as 1-(4-methoxy)phenyl-3-methyl-5-pyrazolone derivatives.

Hyaluronic acid (HA) was digested with various kinds of depolymerizing enzymes and the products were analysed by high-performance liquid chromatography (HPLC) after derivatization with 1-(4-methoxy)phenyl-3-methyl-5-pyrazolone (PMPMP). As hyaluronate 4-glycanohydrolase (EC 3.2.1.35) from sheep testis showed a high efficiency for depolymerization, giving the tetra- and hexasaccharides abundantly, and is inexpensive, a method for the specific determination of HA was established, based on digestion by this enzyme followed by determination of the tetra- or hexasaccharide derived therefrom as the PMPMP derivatives by HPLC with UV detection. This method allowed the determination of HA in the range 0.5-50 micrograms with high reproducibility.

Animals↗
PubMed2005

Synthesis and biological activity of N,N-dialkylaminoalkyl-substituted bisindolyl and diphenyl pyrazolone derivatives.

New compounds, structurally related to the potent protein kinase C inhibitor staurosporine, with a bisindolylpyrazolone framework and substituted on the pyrazolone nitrogens with N,N-dialkylaminoalkyl side chain, were synthesized and evaluated for growth-inhibitory properties in several human cell lines. Many showed inhibition of TNF-alpha production in response to the tumor promotor TPA on HL-60 cells. The apoptotic activity on HeLa cells has been examined for several of these compounds.

Chromatography, Thin Layer↗
PubMed2000

Occupational asthma caused by pyrazolone derivative used in silver halide photographic paper.

Occupational asthma has been documented in workers exposed to a wide variety of chemical compounds. Reactive dyes have been described as causing occupational asthma in textile industry workers. We report a case of occupational asthma resulting from exposure to pyrazolone dye used in silver halide photographic paper. There is a need for both further surveys of workers exposed to other reactive dyes and careful preventive measures in the handling of such compounds.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed2006

Anti-inflammatory and anti-oxidant activity of a new class of phenyl-pyrazolone derivatives.

The anti-inflammatory activity of a new class of phenyl-pyrazolone derivatives, structurally related to phenidone, has been evaluated using the Croton oil ear test in mice as model of acute inflammation. Derivative 5h reduces the percentage of oedema similarly to indomethacin and more efficiently than phenylbutazone. The anti-inflammatory activity of these two reference drugs depends on their COX inhibition, but for the synthesized derivatives it has not been demonstrated a significant COX or LOX inhibition, as previously reported. While the anti-inflammatory activity of phenidone is correlated to its anti-oxidant properties, the redox potential of these compounds appears not decisive in the inflammatory process inhibition. In order to investigate the mechanism of action for these compounds, we quantified their anti-oxidant activity and the lipophilicity, and a relationship between the calculated logP and the percentage of oedema reduction was found. We hypothesize that the anti-inflammatory activity, recorded in vivo, could be related to lipophilic parameter of these compounds.

Animals↗
PubMedDate not supplied

[The activation of specific type-III glucocorticoid receptors by pyrazolone series preparations].

Experiments were conducted on intact and adrenalectomized male Wistar rats (weighing 180-200 g) with labelled corticosterone of high specific activity to study the effect of analgin and aminopyrine on the level of type-III glucocorticoid receptors in the liver. Analgin and aminopyrine in doses of 10(-2) and 10(-3) increase the specific binding of labelled corticosterone by type-III glucocorticoid receptors of the hepatic cytosol and by blood plasma transcortin in modelled experiments. The effect of the agents depends on the dose. Intravenous administration of 140 mg/100 g of analgin to intact rats and intraperitoneal injection of an equal dose of analgin to adrenalectomized rats also increases the specific binding of labelled corticosterone by type-III glucocorticoid receptors of the hepatic cytosol. The importance of the revealed effect of agents of the pyrazolone series in stress regulation is discussed.

Adrenalectomy↗
PubMed1986

Pyrazolone drugs and agranulocytosis.

Ever since mass consumption of chemically pure drugs started at the beginning of this century, cases of agranulocytosis have been reported in the literature. These were very soon seen as being causally related to drug use. The present paper discusses the clinical symptoms of the disease, the possibilities of its treatment, and the obvious connections between the use of pyrazolone drugs and the occurrence of agranulocytosis.

Agranulocytosis↗
PubMed1986

Pyrazolones and analgesic asthma syndrome.

Many peripherally acting analgesic and anti-inflammatory drugs, including pyrazolone derivatives, can precipitate idiosyncratic hypersensitivity reactions in intrinsic asthmatics. This contribution focuses on the symptomatology, diagnosis, and therapy ('desensitization') in childhood and adult analgesic asthma syndrome.

Adult↗
PubMed1986

Adverse dermatological reactions to pyrazolones.

All analgesics can occasionally induce adverse skin reactions. Especially in the early period of pyrazolone therapy, a large variety of cutaneous manifestations were attributed to the use of these drugs. An updated analysis is attempted.

Angioedema↗
PubMed1998

New thiazolidones-4 with pyrazolone-5 substituent as the potential NSAIDs.

The synthesis of a group of thiazolidine derivatives with pyrazolone-5 substituent is described. The structure of the new compounds is supported by 1H- and 13C-NMR spectra. Group of compounds was tested in vivo for their antiinflammatory activity. The obtained results gave the opportunity to separate the perspective groups of potential NSAIDs, which have got greater antiinflammatory activity than the best standard drugs.

Animals↗
PubMed1999

Electrospray ionization mass spectrometry of 1-phenyl-3-methyl-5-pyrazolone derivatives of neutral and N-acetylated oligosaccharides.

Derivatization using 1-phenyl-3-methyl-5-pyrazolone (PMP) was selected among a number of reported methods for labeling carbohydrates, since it gives a quantitative yield, proceeds through a rapid reaction and involves a simple clean-up procedure. Moreover, PMP derivatives provide an increase in sensitivity with ultraviolet and mass spectrometric detection relative to native neutral sugars. Sensitivity studies were carried out using a standard oligosaccharide, tetraglucose. One of the aims of these studies was to determine the minimum amounts of PMP-tetraglucose necessary to generate informative full-scan electrospray ionization (ESI) mass spectra and collision-induced dissociation tandem mass spectra. Another aim was to characterize the fragmentation pattern of PMP derivatives. Quantitative and qualitative studies were also carried out with a typical N-linked oligosaccharide obtained commercially. The PMP-labeled compound underwent directed cleavages which produced fragments containing the reducing end. The native N-linked sugar yielded fragments corresponding to cleavages from both ends of the molecule. Under the same ESI conditions, the N-linked oligosaccharide exhibited more lability, or tendency to fragment, than neutral tetraglucose, in both the derivatized and native forms. Also, PMP labeling was shown to enhance sensitivity in the case of a neutral oligosaccharide, i.e. tetraglucose, whereas the labeling of an N-acetylated oligosaccharide, NGA3, did not yield a noticeable improvement in sensitivity.

Acetylation↗
PubMed1999

Effect of 1-phenyl-3-methyl-5-pyrazolone labeling on the fragmentation behavior of asialo and sialylated N-linked glycans under electrospray ionization conditions.

The advantages of labeling free N-linked oligosaccharides with 1-phenyl-3-methyl-5-pyrazolone (PMP), for high performance liquid chromatography (HPLC) and electrospray ionization mass spectrometry (ESI-MS) are discussed. The study focuses on some asialo and sialylated sugars, and compares the HPLC and ESI-MS behaviors of the PMP-labeled substances vs. the native compounds. It is pointed out that native free N-linked carbohydrates have very low affinities for the C18 reversed phases commonly used in HPLC. Native asialo oligosaccharides yield good ESI-MS sensitivity, although they are very susceptible to in-source collision-induced dissociation (CID), and the fragments are produced from any of the branches of the molecules, i.e. do not give specific structural information. Native N-linked standards bearing one sialic acid residue yield a 10-fold loss of ESI-MS sensitivity vs. asialo compounds, and native sugars with two sialic acid moieties were not detectable. The PMP labeling of asialo and sialylated sugars yielded higher affinities for HPLC C18 columns and, even at the early stages of method development, it was possible to separate three PMP-labeled standards to a useful extent. In ESI-MS, PMP-asialo sugars did not yield a significant increase in sensitivity vs. the native species; however, fragmentation produced by in-source CID was more directed as all predominant fragment ions contained the bis-PMP label. This feature is particularly useful when structural determination of an unknown sugar is required. PMP-sialylated sugars gave rise to very clean and informative ESI mass spectra. The monosialo sugar yielded a 100-fold sensitivity improvement vs. its native analog and, in the case of the disialylated compound, a 100% improvement was obtained in the positive mode. Most fragment ions were informative and contained the reducing end on the molecules, thus facilitating spectral interpretation. The combination of PMP derivatization with on-line HPLC/ESI-MS is a promising method for the analysis of asialo and sialylated carbohydrate mixtures.

Antipyrine↗
PubMedDate not supplied

Determination of nucleic acids based on the quenching effect on resonance light scattering of the Y(III)-1,6-bi(1'-phenyl-3'-methyl-5'-pyrazolone-4'-)hexane-dione system.

Nucleic acids can quench resonance light scattering (RLS) intensity of the Y(III)-1,6-bi(1'-phenyl-3'-methyl-5'-pyrazolone-4'-)hexane-dione(BPMPHD) complex in the pH range 5.0-5.8. Under optimal conditions, there are linear relationships between the quenching of RLS and the concentration of nucleic acids in the range 6.3 x 10(-8)-2.1 x 10(-5) g/mL for fish sperm DNA (fsDNA), 1.2 x 10(-8)-5.0 x 10(-5) g/mL for calf thymus DNA (ctDNA) and 6.0 x 10(-8)-2.0 x 10(-5) g/mL for yeast RNA (yRNA). The detection limits (3 s) of fsDNA, ctDNA and yRNA are 0.7 ng/mL, 3.8 ng/mL and 4.2 ng/mL, respectively.

Aldehydes↗
PubMed1998

Separation of 1-phenyl-3-methyl-5-pyrazolone derivatives of monosaccharides by capillary electrochromatography.

1-Phenyl-3-methyl-5-pyrazolone (PMP) derivatives of component monosaccharides in glycoproteins (fucose, galactose, mannose, N-acetylgalactosamine and N-acetylglucosamine) and epimeric aldopentoses (arabinose, lyxose, ribose and xylose) were well separated from each other by capillary electrochromatography on a Hypersil ODS column with a mixture of 50 mM N-(2-hydroxyethyl)piperazine-2'-(2-ethanesulfonic acid) buffer, pH 6.0 to approximately 6.3, and acetonitrile (2.2:1 v/v) as eluent. The elution of these compounds showed relatively strong dependence on the pH and concentration of the buffer salts contained in the eluent, as compared to the elution by pressure-driven high-performance liquid chromatography (HPLC) on the same stationary phase, but separation of PMP-monosaccharides was better than that by HPLC. Retention times of PMP-monosaccharides were highly reproducible with a relative standard deviation (RSD) of approximately 0.6%, and quantification with an RSD less than 5% could be achieved using 3-O-methylglucose as an internal standard.

Antipyrine↗
PubMed2003

High-speed electrophoretic analysis of 1-phenyl-3-methyl-5-pyrazolone derivatives of monosaccharides on a quartz microchip with whole-channel UV detection.

1-Phenyl-3-methyl-5-pyrazolone (PMP) derivatives of monosaccharides were analyzed by electrophoresis on a quartz microchip with whole-channel UV detection. Rapid separation of PMP derivatives of aldopentoses was achieved by plain-zone electrophoresis in a neutral phosphate buffer with the height equivalent to a theoretical plate at the micrometer level. Zone electrophoresis as borate complexes was also successful for the separation of PMP derivatives of a few aldoses, which were separated within 1 min. Separation by microchip electrophoresis was compared to that by capillary electrophoresis, and the difference was discussed in terms of column efficiency and sample column capacity.

Antipyrine↗
PubMed2006

Chiral resolution of monosaccharides as 1-phenyl-3-methyl-5-pyrazolone derivatives by ligand-exchange CE using borate anion as a central ion of the chiral selector.

Six reducing monosaccharides (mannose, galactose, fucose, glucose, xylose, and arabinose) were derivatized with 1-phenyl-3-methyl-5-pyrazolone (PMP) and chiral resolution of these racemic PMP-monosaccharides was studied by ligand-exchange CE using borate anion as a central ion of the chiral selector and (S)-3-amino-1,2-propanediol (SAP) as a chiral selector ligand. PMP-mannose, PMP-galactose and PMP-fucose were successfully enantioseparated. Lowering the capillary temperature increased the resolution of PMP-mannose system, but decreased that of PMP-galactose and PMP-fucose systems. Whereas the maximum resolution was obtained at pH 8.9 in the PMP-mannose system, resolution increased gradually with pH in the PMP-galactose and PMP-fucose systems. Expecting the formation of the ternary borate complexes with SAP and PMP-monosaccharide in the CE experiments, the optimized structures of the borate diastereomers were obtained by semiempirical molecular orbital calculations to discuss the structural difference of the diastereomers in connection with the enantioseparation behaviors.

Anions↗
PubMed1997

Oligosaccharide characterization and quantitation using 1-phenyl-3-methyl-5-pyrazolone derivatization and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.

The 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatives of monosaccharides, maltooligosaccharides, and oligosaccharides enzymatically released from asparagine-linked sites in ribonuclease B and fetuin have been investigated using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS). Use of the matrix 2,6-dihydroxyacetophenone containing diammonium hydrogen citrate (DHAP/DAHC) resulted in predominance of protonated over sodiated pseudomolecular ions of PMP-derivatized oligosaccharides. By comparison, the matrices alpha-cyano-4-hydroxycinnamic acid and 2,5-dihydroxybenzoic acid resulted in predominantly sodiated pseudomolecular ions. In addition, tendencies for fragmentation of PMP-oligosaccharide derivatives were significantly lower with DHAP/DAHC which enabled meaningful data to be obtained in reflector mode, even for samples with high excipient levels. The relative magnitude of the ion signals for PMP-derivatized maltooligosaccharides and ribonuclease B oligosaccharides correlated well with the oligomer distribution apparent by HPLC. PMP-maltohexose was used as an internal standard to quantitate PMP-oligosaccharides from ribonuclease B and asialofetuin in crude derivatization mixtures. A linear relationship was observed between the ratio of the intensities of pseudomolecualr ions and the amount of glycoprotein derivatized. The limit of detection for the major oligosaccharide of each protein was reached with ca. 3 micrograms of glycoprotein but may be further enhanced by optimization of sample handling. PMP derivatives of sialylated fetuin oligosaccharides were readily detected as protonated pseudomolecular ions by linear mode analyses. By comparison, reflector mode analyses revealed substantially reduced magnitudes of protonated pseudomolecular ions and considerable post-source fragmentation of sialic acid residues. The PMP derivatives of fetuin oligosaccharides were also amenable to exoglycosidase treatment as shown by the mass shifts found upon treatment with sialidase.

Antipyrine↗
PubMed1987

The role of descending inhibition in the antinociceptive effects of the pyrazolone derivatives, metamizol (dipyrone) and aminophenazone ("Pyramidon").

The study was carried out to provide further evidence that the two pyrazolone derivatives, metamizol and aminophenazone, produce central antinociceptive effects by stimulating inhibition descending from the periaqueductal grey (PAG) to the spinal cord. Experiments were carried out on rats in which the tail-flick response to radiant heat, nociceptive activity in ascending axons of the spinal cord, and activity of neurones in the PAG and the substantia nigra were studied. Microinjection of procaine (10 micrograms) into the PAG reduced the tail-flick latency and abolished the increase in latency caused by i.p. injection of metamizol (40 mg/kg) and aminophenazone (150 mg/kg); it did not significantly reduce the antinociceptive effect of i.p. injection of morphine (2 mg/kg). Threshold doses of morphine (1 and 2 micrograms) administered by intrathecal (i.t.) injection potentiated the effect of threshold doses of metamizol injected i.p. (10 mg/kg) or into the PAG (10 micrograms) in the tail-flick test. Morphine (2 micrograms) injected i.t. potentiated the effect of i.v. injection of metamizol (80 mg/kg) on nociceptive activity in ascending axons by eliminating the stimulant effect of metamizol on about one third of the axons. Threshold doses of morphine injected i.t. failed to potentiate the antinociceptive effect of aminophenazone (50 mg/kg) injected i.p. in the tail-flick test. The results support the view that metamizol and aminophenazone activate pathways descending from the PAG and exerting an inhibitory effect on nociceptive impulse transmission at the spinal level.

Aminopyrine↗