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PubMed1996

Cosolvent-induced adsorption and desorption of serum proteins on an amphiphilic mercaptomethylene pyridine-derivatized agarose gel.

We studied the effects of the following cosolvents on the adsorption and desorption of serum proteins from an amphiphilic mercaptomethylene pyridine-derivatized agarose gel: glucose, sucrose, polyethylene glycol (PEG), 2-methyl-2,4-pentanediol (MFD), sorbitol, pentaerythritol, glycerol, and Na2SO4. The water-structuring salt 0.4 M Na2SO4 was the most potent promoter of protein adsorption, followed by 5 M sorbitol and, to a lesser extent, 0.2 M PEG 1000 and 2.25 M MPD. The other cosolvents (4 M glucose, 1.5 M sucrose, 0.3 M pentaerythritol, and 7.6 M glycerol) were unable to promote protein adsorption to the gel. Attempts to modulate the salt-promotion effect of Na2SO4 with different cosolvents demonstrated the occurrence of synergistic effects for pentaerythritol, sorbitol, and glucose and antagonistic effects for the other cosolvents. Sorbitol and glycerol were found to be the most interesting co-solvents studied, as the first promoted protein adsorption, whereas the other disrupted protein interaction. As a consequence of these novel findings we propose sorbitol and glycerol, both well-known protein stabilizers, as possible alternatives to water-structuring salts during the adsorption phase and to deleterious organic solvents during the desorption phase on amphiphilic gels.

Adsorption↗

PubMedDate not supplied

Synthesis and characterization of self-catalyzed poly(ortho ester).

Poly(ortho esters) are currently under investigation as a carrier system for an antiproliferative agent in glaucoma filtering surgery. The present investigation illustrates the development of a series of self-catalyzed poly(ortho ester). These polymers contain short dimer segments of alpha-hydroxy acids in their backbone and are prepared by the addition of different polyols to the diketene acetal 3,9-diethylidene-2,4,8,10-tetra-oxaspiro-[5.5]-undecane. The structures were confirmed by NMR- and FT-IR-spectroscopy. The polymers were characterized by determination of the molecular weight, the glass transition temperature and the rheological behavior. The amount of residual solvents was also analyzed. The characteristics of the polymer can be varied by the type of polyol incorporated in its backbone. Since poly(ortho ester) is susceptible to acid-catalyzed degradation, the polymer hydrolysis can be controlled by the amount of incorporated portion of alpha-hydroxy acid. Due to the high hydrophobicity of the polymer structure, the ester bonds are more susceptible to hydrolysis than the ortho ester bonds in the polymer backbone. The hydrolysis proceeds via initial protonation of the exocyclic alkoxy group to yield pentaerythritol dipropionate and the free diol. In a next step, the pentaerythritol dipropionate hydrolysis to pentaerythritol and propionic acid. The molecular weight decrease, weight loss and the pH profile of the polymer in aqueous medium were monitored during the degradation.

Antineoplastic Agents↗

PubMed1978

Activity of bepridil and other anti-anginals on cardiovascular modifications engendered by conditioned anxiety in the dog.

The action of bepridil (5 mg/kg), perhexilene (5 mg/kg) propranolol (0.5 mg/kg), dipyridamole (0.5 mg/kg), amiodarone (10 mg/kg), pentaerythritol tetranitrate (40 microgram/kg) and nitroglycerine (40 microgram/kg) on cardiovascular manifestations of auditory-inducted emotional stress has been investigated in the conscious dog. Bepridil, perhexilene and propranolol considerably reduce tachycardia provoked by the anxiogenic stimulus, with nitroglycerin exerting an attenuated effect and the others with no significant effect on this parameter. Beppridil, nitroglycerin, perhexilene, propranolol and pentaerythritol all significantly reduce the elevation of the Robinson index, the first four with the same intensity. Only amiodarone and dipyridamole are without effect on this parameter of cardiac workload. Finally, none of the products under investigation significantly reduces systolic hypertension, associated with the induction of conditioned anxiety.

Amines↗

PubMed1997

Properties of epsilon-caprolactone/DL-lactide (epsilon-CL/DL-LA) copolymers with a minor epsilon-CL content.

In this study the properties of DL-lactide (DL-LA) copolymers with 5, 10, 15, 20, and 30 wt % (in feed) of epsilon-caprolactone (epsilon-CL) polymerized with stannous(II)octoate (SnOct) as catalyst and glycerol, laurylalcohol, or pentaerythritol as initiator were investigated. Thermal studies showed that the addition of 5 wt % (in feed) of epsilon-CL to the P(CL/DL-LA) copolymer decreased the Tg by about 5 degrees C. Hydrolysis tests were carried out for copolymers with 20 and 30 wt % (in feed) of epsilon-CL to study the degradation rate. Molecular weights decreased dramatically during the first week of hydrolysis, with mass losses occuring a few weeks later. The influence of glycerol and pentaerythritol as initiators, and the influence of epsilon-CL content on stress-strain behavior, tension set, and rheologic properties of the P(CL/DL-LA) copolymers were also investigated. The tensile testing of P(CL/DL-LA) copolymers containing 5, 10, 15, 20 wt % (in feed) of epsilon-CL showed that the properties of copolymers varied from hard and brittle to rubbery. The permanence of elastic properties was investigated with tension set measurements. These studies showed that copolymers crept remarkably under stress. The viscosity and elasticity of P(CL/DL-LA) copolymers at 120 degrees C were investigated using rheology studies.

Biocompatible Materials↗

PubMed2003

Water-borne, in situ crosslinked biomaterials from phase-segregated precursors.

A novel process for the preparation of water-borne biomaterials for hard tissue repair from injectable precursors is described, where the precursors form crosslinked materials in situ under physiological conditions. The precursors react by means of a Michael-type addition reaction that makes use of addition donors such as pentaerythritol tetrakis 3'-mercaptopropionate (QT) and addition acceptors such as poly(ethylene glycol) diacrylate 570 MW (PEGDA), pentaerythritol triacrylate (TA), and poly(propylene glycol) diacrylate 900 MW (PPODA). These crosslinked materials (at 75 wt% solid), prepared from water dispersions or reverse emulsions, showed ultimate strengths in compression of 1.8 +/- 0.2 and 6.7 +/- 0.5 MPa and ultimate deformations of 35 +/- 2+/- and 37 +/- 2%, respectively. Scanning electron microscopy (SEM) shows that the morphology of the precursors templated the morphology of the final materials. The current study indicates that it is possible to obtain injectable high-modulus materials that have appropriate mechanical properties and gelation kinetics for tissue augmentation and stabilization applications such as mechanical stabilization of the intervertebral disc annulus.

Acrylates↗

PubMed1983

Drug interactions I: detection of inorganic nitrite in organic nitrate esters under acidic conditions simulating the human stomach.

Both unformulated (bulk) and formulated (drugs) organic nitrate esters (isosorbide dinitrate, nitroglycerin, and pentaerythritol tetranitrate) were studied in the presence and absence of hydrochloric acid to determine if they could be sources of nitrite (and therefore lead to nitrosamine formation) under acidic conditions similar to those found in the stomach. The presence and generation of nitrite ion was detected by a modification of the Griess reaction. Bulk isosorbide dinitrate and nitroglycerin were found to be contaminated with 13.8-121.4 mumoles of inorganic nitrite per mole of nitrate ester. In addition, in the presence of hydrochloric acid, these preparations generated 0.52-1.18 mumoles of inorganic nitrite/mole of nitrate ester/min. Unformulated nitroglycerin generated nitrite at a rate roughly twice that of isosorbide dinitrate. In contrast, no evidence for nitrite contamination or generation by pentaerythritol tetranitrate was found. Tablets and capsules of isosorbide dinitrate contained approximately 27-216 mumoles of nitrite/mole of nitrate ester and, in the presence of hydrochloric acid, generated an average of 0.55 mumole nitrite/min. For isosorbide dinitrate, this rate was similar for bulk and formulated drug. In comparison to isosorbide dinitrate, the amount of nitrite initially present in tablets and capsules of nitroglycerin varied more widely (approximately 25-2290 mumoles nitrite/mole of nitrate ester), and in this case nitrite was generated at higher rates than unformulated drug averaging approximately 4.7 mumoles nitrite/mole of nitrate ester/min. Contrary to a literature report, we found that nitrate ion is not reduced to nitrite by hydrochloric acid (pH 1-3).(ABSTRACT TRUNCATED AT 250 WORDS)

Chemistry, Pharmaceutical↗

PubMed2003

Effect of nitric oxide releasing drugs on the intensity of infection during experimental trichinellosis in mice.

Nitric oxide (NO) has been shown to play a critical role in various physiological and pathological conditions. Apart from its physiological functions, NO indirectly participates in certain aspects of the pathology of infectious diseases. The aim of this work was to examine the influence of NO-releasing drugs on the intensity of infection in mice infected with Trichinella spiralis. The selected substances were nitroglycerin, isosorbide dinitrate, nitrendipine, sildenafil, and pentaerythritol. These were administered over a prolonged period of time: from the 3rd to the 28th day post-infection. Our study showed that NO administered during trichinellosis may enhance the infection in mice as compared to untreated controls. Thus, treatment with pentaerythritol caused a 44% increase in the intensity of infection relative to the untreated controls, sildenafil a 37% increase, and nitrendipine a 30% increase. This effect may be related to the action of NO on the host's defence mechanisms.

Animals↗

PubMed1995

Mono-, di- and tri-antennary D-galactose ligands as competitive inhibitors and photoaffinity labels of the hexose transporting system in erythrocytes. A model for the irreversible blocking of receptors in cell membranes.

Starting from pentaerythritol, photolabile mono-, di-, and tri-dentate galactose derivatives as well as their 3H-labelled isotopomers were synthesised. The hydrophilic chains linking the 6 position of D-galactose to pentaerythritol consist of 13 atoms in line. The mono-, di- and tri-dentate compounds, although themselves not transported, inhibit in increasing order 14C-D-galactose transport into erythrocytes. On irradiating whole cells in the presence of ligand with 350-nm UV light, these compounds also in increasing order, could irreversibly block the hexose transport system. Irradiation without ligand has no effect. By using the 3H-labelled tridentate galactose compound the hexose transporter (zone 4.5) is specifically radiolabelled, as could be shown in an SDS-PAGE of membrane proteins from erythrocytes previously photoaffinity labelled. Radiolabelling is significantly suppressed in the presence of D-glucose.

Affinity Labels↗

PubMed2004

Nucleosides and nucleotides. Part 226: alternate-strand triple-helix formation by 3'-3'-linked oligodeoxynucleotides composed of asymmetrical sequences.

In this paper, we describe the synthesis of the 3'-3'-linked oligonucleotides connected with pentaerythritol composed of asymmetrical sequences. Stability of the triplexes between these oligonucleotides and the DNA targets involving the adjacent oligopurine domains on alternate strands was investigated using the electrophoretic mobility shift assay (EMSA) and DNase I footprinting experiment. It was found that the 3'-3'-linked oligonucleotides composed of asymmetrical sequences formed the stable antiparallel triplexes with the DNA targets as compared with the unlinked oligonucleotides. Thus, oligonucleotides linked with pentaerythritol would be useful as antigene oligonucleotides for DNA targets consisting of the alternating oligopyrimidine-oligopurine sequences.

Base Composition↗

PubMed2001

Characterization of ageing products of ester-based synthetic lubricants by liquid chromatography with electrospray ionization mass spectrometry and by electrospray ionization (tandem) mass spectrometry.

Ageing products of a commercial jet engine oil based on pentaerythritol tetraesters which were formed upon operation in an aviation turbine were detected by electrospray ionization mass spectrometry (ESI-MS) and characterized by LC-ESI-MS. The fatty acid composition of these ageing products was investigated by ESI-MS-MS analysis. The ammonium adducts of the newly formed pentaerythritol tetraester degradation products were found to be suitable parent ions for further structure elucidation work. ESI-MS, LC-ESI-MS and ESI-MS-MS proved to be versatile tools to study the chemical composition (distribution of homologues) as well as the mechanism of ageing of ester based lubricants on a molecular level. Due to its high sensitivity, ESI-MS can also be used to characterize and identify trace levels of ester-based lubricants.

Chromatography, Liquid↗

PubMed2002

Stationary phase effects on the dynamic affinity of low-molecular-mass displacers.

In this paper, the selectivity of a variety of cation-exchange stationary phases was investigated using a homologous series of displacer molecules based on pentaerythritol. These displacers were derived from pentaerythritol and contained either four trimethyl ammonium groups [pentaerythrityl-(trimethylammonium chloride)4, PE(TMA)4], benzene rings [pentaerythrityl-(benzyl dimethylammonium chloride)4, PE(DMABzCl)4], heptyl groups [pentaerythrityl-(heptyl dimethylammonium iodide)4, PE(DMAHepI)4] or cyclohexyl groups [pentaerythrityl-(cyclohexyl dimethylammonium iodide)4, PE(DMACyI)4]. This series enabled us to probe the secondary interactions that can play a role in the affinity of low-molecular-mass displacers for different stationary phases. The relative affinities of these displacers were examined using a displacer ranking plot based on the steric mass action (SMA) isotherm model. While hydrophobicity and aromaticity played important roles in generating the affinity to the hydrophilized polystyrene-divinylbenzene (Source 15S) and polymethacrylate-based (Toyopearl 650M) resins, these secondary interactions had a minimal impact on the selectivity in agarose resins coated with dextran (SP Sepharose XL), "gel in a shell" (S Ceramic HyperD F), and monolithic (Bio-Rad Uno S6) cation-exchange materials. Further, the results with a tentacular stationary phase (Fractogel EMD) suggest that the alkyl chains on PE(DMAHepI)4 play an important role in increasing the affinity, possibly because of strong interactions between the alkyl moiety and the polymer matrix as well as between the charged groups and the polyelectrolyte tentacles. The results of this study provide insight into the design of high affinity, low-molecular-mass displacers for different cation-exchange stationary phase materials.

Cation Exchange Resins↗

PubMedDate not supplied

Nucleosides and nucleotides. 218. Alternate-strand triple-helix formation by the 3'-3'-linked oligodeoxynucleotides using a purine motif.

In this paper, we describe the synthesis of the 3'-3'-linked TFOs that can form the antiparallel triplexes with the duplex DNA target by reverse Hoogsteen hydrogen bonds. Stability of the alternate-strand triplexes between these TFOs and the target DNAs was investigated using the electrophoretic mobility shift assay (EMSA). It was found that the alternate-strand triplexes were significantly stabilized by linking the TFO fragments with the pentaerythritol linker. And, unlike the alternate-strand triplexes composed of the pyrimidine motif, the terminal ammonium ion of the aminobutyl-linker and the intercalator of the TFOs did not contribute to the stability of the alternate-strand triplex comprised of the purine motif. We also tested the ability of the 3'-3'-linked TFOs to inhibit cleavage of the duplex DNA target 17 by the restriction enzyme EcoT14I and found that the 3'-3'-linked TFOs 12 and 13 inhibited the cleavage by the enzyme more effectively than the unlinked decamer 8. Thus, the TFOs linked with pentaerythritol may be useful as the antigene oligonucleotide to the DNA targets, which have alternating oligopyrimidine-oligopurine sequences.

DNA↗

PubMedDate not supplied

Photocurable liquid biodegradable copolymers: in vitro hydrolytic degradation behaviors of photocured films of coumarin-endcapped poly(epsilon-caprolactone-co-trimethylene carbonate).

Coumarin-endcapped tetrabranched liquid copolymers composed of epsilon-caprolactone and trimethylene carbonate (TMC), prepared using pentaerythritol or four-branched poly(ethylene glycol) (PEG) as an initiator, were ultraviolet irradiated to produce photocured solid biodegradable copolymers. The hydrolytic degradation behaviors of photocured films were determined from the weight loss of the films. The initial hydrolysis rate (determined for up to 24 h using a quartz crystal microbalance) was enhanced with aqueous solutions of higher pH. The hydrolysis rate in the early period of immersion was increased with an increase in TMC content, whereas that in the later period (week order) decreased with a increase in TMC content. This inverse relation of composition dependence on the hydrolysis rate between the early and late periods was discussed. Topological measurements using scanning electron microscopy and atomic force microscopy as well as depth profiles of the fluorescein-stained hydrolyzed layer showed that for the pentaerythritol-initiated copolymer, irrespective of copolymer composition, hydrolysis occurred at surface regions and surface erosion proceeded with immersion time. For PEG-based copolymers, both surface erosion and bulk degradation occurred simultaneously. The hydrolyzed surfaces became highly wettable with water and exhibited noncell adhesivity.

Adhesives↗

PubMed2005

The structural and stereogenic properties of pentaerythritoxy-bridged cyclotriphosphazene derivatives: spiro-spiro, spiro-ansa and ansa-ansa isomers.

Reactions of pentaerythritol with hexachlorocyclotriphosphazene, N3P3Cl6, and gem-disubstituted cyclotriphosphazene derivatives, N3P3Cl4R2 [R = Ph, NHBu(t) or (OCH2CF2CF2CH2O)0.5] gave a series of pentaerythritol-bridged derivatives linked spiro-spiro, spiro-ansa and ansa-ansa. The structures and stereogenic properties of the products were characterised by X-ray crystallography and 31P NMR spectroscopy on addition of the chiral solvating agent, (S)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol. Molecules with spiro-spiro and spiro-ansa bridged gem-disubstituted cyclophosphazenes [R = Ph, NHBu(t) or (OCH2CF2CF2CH2O)0.5] are found to be chiral and exist as racemates. Molecules with ansa-ansa bridged cyclophosphazenes [R = Cl or (OCH2CF2CF2CH2O)0.5] have been characterised for the first time and are shown to have meso configurations. Analysis of crystal structure data shows that the six-membered chair form of the spiro rings and the eight-membered boat-chair form of the ansa rings in the bridged compounds are similar to analogous spiro and ansa exocyclic ring conformations of 1,3-propanedioxy-derivatives of cyclophosphazenes.

Journal Article↗

PubMed1968

Rapid starch synthesis associated with increased respiration in germinating lily pollen.

In vitro studies of germinating Lilium longiflorum pollen showed that starch increased more rapidly during the first 30 minutes of incubation than during the next several hours. The period of rapid starch formation coincided with the first period of high respiration. An estimate was made of the extra ATP utilized to form extra starch during the first 30 minutes, and this estimate indicates that starch synthesis accounts for a significant portion of the initial high rate of respiration. This pattern of respiration and starch synthesis was not altered when pollen germinated in a pentaerythritol medium that could not be metabolized instead of the standard sucrose medium.Sucrose was the predominant sugar in mature lily pollen. This sugar decreased 50% during several hours incubation in pentaerythritol culture medium. Reducing sugars remained low during incubation which may indicate that sucrose breakdown is regulated by the rate of utilization of hexose units.

Journal Article↗

PubMed1978

Evidence for a Functional myo-Inositol Oxidation Pathway in Lilium longiflorum Pollen.

Addition of myo-inositol to pentaerythritol-based germination media repressed the conversion of d-[1-(14)C]glucose to labeled uronosyl and pentosyl units of tube wall pectic substance in lily pollen (Lilium longiflorum Thunb.). Conversion of d-[1-(14)C]glucose to labeled glucosyl, galactosyl, and rhamnosyl units was unaffected. The reverse experiment, addition of d-glucose to pentaerythritol-based media, failed to affect the conversion of myo-[2-(3)H]inositol to uronosyl and pentosyl units although the flow of label into products of myo-inositol-linked glucogenesis was blocked. Results of these experiments are discussed in terms of a functional myo-inositol oxidation pathway.d-[1-(14)C]Glucose-labeled pollen tubes contain a labeled, 70% ethyl alcohol-soluble, acidic compound whose formation is blocked by the myo-inositol antagonist, 2-O,C-methylene-myo-inositol (Chen et al. 1977 Plant Physiol. 59: 658). This compound has been identified as l-malic acid.

Journal Article↗

PubMed1978

Skin problems associated with multifunctional acrylic monomers in ultraviolet curing inks.

Fifteen cases of contact dermatitis and three of irritant contact conjunctivitis due to multifunctional acrylic monomers in printing inks are described. Seven with dermatitis were sensitized to pentaerythritol triacrylate but evidenced no cross-reactivity to methyl methacrylate. The other eight cases of dermatitis were irritant. Pentaerythritol triacrylate has been shown experimentally to be a cutaneous sensitizer for guinea-pigs and man. Multi-functional acrylates should be handled with minimal skin contact, to avoid cutaneous problems.

Acrylates↗

PubMed1984

The sensitizing capacity of multifunctional acrylates in the guinea pig.

The multifunctional acrylates used in ultraviolet (UV) curable resins act as cross-linkers and "diluents". They are usually based on di(meth)acrylate esters of dialcohols or tri- and tetra-acrylate esters of polyalcohols. In UV-curable coatings, the most commonly used are pentaerythritol triacrylate (PETA), trimethylolpropane triacrylate (TMPTA) and 1,6-hexanediol diacrylate (HDDA). In other uses, such as dental composite resin materials, the dimethacrylic monomers based on n-ethylene glycol are the most useful. The sensitizing capacity of various multifunctional acrylates and their cross-reactivity pattern have been investigated with the guinea pig maximization test. The tests show that BUDA (1,4-butanediol diacrylate) and HDDA are moderate to strong sensitizers and that they probably cross-react with each other. The n-ethylene glycol diacrylates and methacrylates tested are weak or non-sensitizers. Tripropylene glycol diacrylate (TPGDA) is a moderate and neopentyl glycol diacrylate (NPGDA) a strong sensitizer, whereas neopentyl glycol dimethacrylate is a non-sensitizer. The commercial PETA is a mixture of pentaerythritol tri- and tetra-acrylate (PETA-3 and PETA-4). PETA-3 is a much stronger sensitizer than PETA-4. Simultaneous reactions were seen between PETA-3, PETA-4 and TMPTA. The oligotriacrylate OTA 480 is a moderate sensitizer, but no concomitant reactions were seen with PETA-3, PETA-4 or TMPTA. Of the multifunctional acrylates tested, the di- and triacrylic compounds should be regarded as potent sensitizers. The methacrylated multifunctional acrylic compounds are weak or non-sensitizers.

Acrylates↗