Synthesis of some indole acrylamides. Short communication.
The synthesis of some indole acrylamides via the acid chloride is reported. Disubstituted indole acrylamides are successfully prepared by the application of Vilsmeier reaction.
Acrylamides↗
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Effects of acrylamide and botulinum toxin on horseradish peroxidase labelling of trigeminal motor neurons in the rat.
The extent of neuronal labelling with horseradish peroxidase (HRP) was examined in rat trigeminal motor neurons at various stages of acrylamide intoxication, following HRP uptake by motor nerve endings in the anterior digastric muscle. After 7 days of acrylamide (5 daily injections of 30 mg acrylamide/kg body weight), the pattern of HRP labelling was altered from normal, and this changed pattern persisted without further alteration when survival time and dosage were increased to 14 and 21 days (equivalent to 10 X 30 mg/kg and 15 X 30 mg/kg respectively). Six hours after HRP injection, the number of labelled cells in the ipsilateral trigeminal motor nucleus was reduced in treated animals compared to controls. By 18 hours, cells containing label were present in similar numbers to controls; but by 24 hours, the number in treated animals had fallen again, unlike controls in which labelling remained constant between 6 and 24 hours. At longer intervals, this reduction in labelling continued, but more slowly, so that by 96 hours after HRP injection, numbers of labelled cells were again similar in poisoned and control animals. One and three days after a single intramuscular injection of 0.05 microgram botulinum toxin type A, HRP labelling in the trigeminal motor neurons was unaffected, although at three days after toxin, mild chromatolytic changes could be seen in a few of the neurons.
Acrylamides↗
[Action of acrylamide on Escherichia coli cells].
The action of acrylamide on Escherichia coli B was studied: short-term action at high concentrations, long-term action at low doses under the normal conditions of growth and in the process of cell immobilization in polyacrylamide gel. Such a treatment was found to cause considerable structural changes in the cells. Division of the cells was inhibited and they reached giant sizes when grown in media containing 1-2% of acrylamide. The phenomenon might be used for differentiation of living and dead E. coli cells.
Acrylamides↗
[Ion-exchange properties of DNA immobilized in acrylamide gel].
Ion-exchange of K+, Ca2+, Mg2+ and NH4+ on the Na+-DNA entrapped in acrylamide gel was studied. Under a definite percentage ratio between acrylamide and cross-linking agent (N,N'-methylenebisacrylamide) more than 95% of initial DNA was shown to be immobilized firmly and not to be washed out by salt solutions. Melting temperature and hypochromicity measurements of DNA extracted from the gel showed that denaturation of DNA has not taken place. The gel with immobilized DNA may be considered as ion-exchanger with phosphate fixed groups. It has been found that Mg2+, Ca2+, Na/, K+ and NH4+ are bounded with phosphate groups only, the degree of binding declines in the following order: Na+ less than or equal to K+ much less than Mg2+ less than Ca2+. The immobilization of DNA is suggested as a method of investigation of interaction between DNA and metal ions.
Acrylamides↗
Acrylamide neurotoxicity: effects on far-field somatosensory evoked potentials in rats.
These experiments were designed to determine the sites of acrylamide induced damage in the specific ascending somatosensory system. Far-field somatosensory evoked potentials (SSEPs) were measured in adult rats given 400 ppm acrylamide in drinking water for 4, 8, or 16 days. Treated rats showed a statistically significant weight loss after 8 days of exposure and became visibly ataxic after about 12 days exposure. SSEPs were collected using modified techniques of Wiederholt and Iragui-Madoz [9] which enhance three far-field peaks arising from (I) the spinal posterior columns, (II) the posterior column nuclei and medial lemniscus, and (III) the thalamus and thalamo-cortical radiations. The three far-field peaks occur prior to the first cortical peak (P1). Tibial nerve stimulation voltage and frequency profiles revealed statistically significant alterations in all SSEP peaks after 16 days exposure. These findings indicate that damage may have occurred throughout the ascending somatosensory system including the spinal cord, dorsal column nuclei, medial lemniscus, thalamus, and sensory radiations.
Acrylamides↗
The effects of glycols, aldehydes, and acrylamide on phase separation and opacification in the calf lens.
Glycols, aldehydes, and acrylamide inhibit the in vitro formation of cold cataracts in calf lenses. The inhibition is reversed when the glycols or the acrylamide are diffused out of the lenses. The inhibition by aldehydes or polacrylamide is irreversible, suggesting that the crosslinking reagents may permanently modify lens structure to prevent the development of lens opacities due to a phase transition.
Acrylamides↗
Quantitative ultrastructural study of acrylamide induced cytoplasmic desmosome-like structures in cultured rat keratinocytes.
Although present in many tumours, the mechanism of formation and the significance of the so-called 'cytoplasmic desmosome' (CD) remain speculative. Recently, we reported an in vitro model for the induction of CD in rat keratinocytes following acrylamide treatment. In the present study and based on quantitative and qualitative evidence, CD could be divided into two categories. The first comprised individually scattered desmosomes always located in the cortical cytoplasm and associated with tonofilament bundles. Their sizes were comparable with those of intercellular desmosomes (ID) in control cells. The second category comprised clusters of homogeneously small-size desmosomes that may be located deep in the cytoplasm and were not always associated with tonofilament bundles. Whilst the latter group may be formed de novo in the cytoplasm as a result of the acrylamide-induced inhibition of protein kinases, the first group may be the result of internalization of surface desmosomes by certain tonofilaments under tension. In order to assess this possibility, we examined tonofilament organization following wounding of the epithelial sheet. Injured cells exhibited spiral-form tonofilaments extending close to the cell membrane. This retraction could be justified ultrastructurally by direct association between tonofilaments and microfilaments.
Acrylamides↗
[Determination of acrylamide metabolite, mercapturic acid by high-performance liquid chromatography].
A high performance liquid chromatography (HPLC) Assay was developed to identify and measure the metabolite of acrylamide, mercapturic acid, N-Acetyl-s-(propionamide) cysteine (APC) in urine. O-phthalaldehyde (OPA) was utilized as a pre-column derivative agent in the assay. This derivative was isolated with a good selectivity by ODS columns. The quantitation of the mercapturic acid derivative was reproducible and with a detection limit of 1 pmol. The average coefficient of variation for the runs carried out on the same day was approximately 4.6% at the range of 80-160 mumol/L of APC, and the mean analytical recovery from urine samples was 94%. The metabolite of urine of workers exposed to acrylamide was identified as APC by HPLC and fluorescence scan and HPLC-Mass spectra. All results were identical with the authentic synthesized compound.
Acetylcysteine↗
[Impairment of rapid axonal transport and concomitant anomaly of smooth endoplasmic reticulum in acrylamide induced neuropathy].
The axonal transport of proteins was studied by radioautography in preganglionic axons of ciliary ganglia in Leghorn chickens treated by acrylamide. The slow axonal transport of proteins was hardly affected. In contrast, the fast axonal transport was severely impaired. Indeed, radioactive proteins accumulated focally at the periphery of several preterminal axons in regions showing a local disorganization of the smooth endoplasmic reticulum which seemed to be one of the earliest changes induced by acrylamide.
Acrylamides↗
Surface modification of poly(ethylene terephthalate) angioplasty balloons with a hydrophilic poly(acrylamide-co-ethylene glycol) interpenetrating polymer network coating.
An interpenetrating polymer network (IPN) of poly(acrylamide-co-ethylene glycol) (p(AAm-co-EG)) hydrogel was covalently grafted to polyethylene terephthalate (PET) angioplasty balloons to increase surface hydrophilicity and improve lubricity. A 2-step graft polymerization protocol was followed to first polymerize and cross-link acrylamide onto the substrate with a photosensitizer and/or oxygen plasma pretreatment. The effects of varying photo-initiation and plasma exposure times were investigated separately and conjunctively using water contact angles to obtain optimal coating deposition parameters. A poly(ethylene glycol) network was then grafted by swelling the preexisting polyacrylamide network to allow inter-diffusion of the monomer and cross-linker, which were then polymerized by photo-initiation. When the photo-initiation time was long enough to reach near gelation, pretreatment of PET with oxygen plasma did not offer significant benefit. X-ray photoelectron spectroscopy confirmed the presence of both polymer layers, and composition depth profiles supported the assessment that an interpenetrating network was formed. Tensile testing and application of Weibull statistics on unmodified and modified films indicated that the surface modification approach did not significantly alter the mechanical integrity of the material. These findings indicate that a p(AAm-co-EG) coating can be effectively deposited on PET surfaces without compromising the structural integrity of the substrate.
Acrylic Resins↗
Size Dependence of Polymer Composition in the Surface Layer of Poly(acrylamide-co-acrylic acid) Hydrogel Microspheres
Poly(acrylamide-co-acrylic acid) hydrogel microspheres of four different average sizes were prepared using a membrane emulsification technique. These four kinds of microspheres had average diameters of 1.35, 2.33, 3.09, and 7.43 &mgr;m in distilled water and were all fairly monodisperse. Their surface properties were studied by measuring the electrophoretic mobility of the microspheres. The mobility values were negative at pH 7.4 with the ionic strengths between 0.005 and 0.154 at 25°C. More negative mobility values were obtained with smaller microspheres than the larger ones. By analyzing the data with an electrokinetic theory for "soft" surfaces, it was found that smaller microspheres have higher surface charge density than the larger ones, although all kinds of microspheres were prepared from monomer solutions with the same monomer composition. The observed size dependence of the electrophoretic mobility suggests that copolymerization of acrylamide monomers and acrylic acid monomers does not proceed homogeneously within a microsphere. That is, charged acrylic acid monomers have a tendency to be localized in the microsphere core region, whereby the surface region of microspheres becomes poor in charges, reducing the mobility of larger microspheres. This is not the case for smaller microspheres, so that their mobility becomes more negative. Copyright 1998 Academic Press. Copyright 1998Academic Press
Journal Article↗
Acrylamide gel analysis of sucrose gradient-derived RNA B fractions transferring delayed sensitivity in vitro.
Sucrose-derived RNA fractions transferring specific delayed sensitivity in vitro were extracted from mono-(p-azobenzenearsonate)-N-chloracetyl-L-tyrosine (ARSNAT)- or keyhole limpet hemocyanin (KLH)-sensitized guinea pigs. Fractions having biological activity were assessed by acrylamide gel analysis to enumerate the number of RNA species in active fractions, and to compare and examine the banding patterns of each RNA fraction. Each isolated B fraction of RNA exhibited multiple bands of RNA with molecular weights ranging from 4.0 X 10(5) to 8.5 X 10(5). Depending on the source and antigen sensitivity of the RNA donor, several differences were observed among the analyzed fractions. These were bands of varying intensity, presence of additional RNA bands, absence of bands in certain positions, and RNA bands migrating in different positions on the gels. Acrylamide gel analysis separation, and resolution of B fractions with specific immunobiological activity now offers an approach for further isolation and resolution of the active species.
Animals↗
Determination of placental alkaline phosphatase phenotypes by starch-gel and acrylamide gel electrophoresis.
The polymorphism of placental alkaline phosphatase (ALP) is usually studied by butanol extraction followed by starch gel electrophoretic separation at two different pH's, 8.6 and 6.0. Acrylamide gel electrophoresis (7.5%) in the presence of Triton X-100 is shown to be preferable in speed, reliability and reproducibility of results. All the placental ALP phenotypes detected had the same molecular mass by gradient acrylamide electrophoresis. The enzyme butanol extract is not sufficiently pure to enable the different placental ALP's to be distinguished by isoelectric focusing on polyacrylamide gels.
Alkaline Phosphatase↗
Evaluation of sodium dodecyl sulfate non-acrylamide, polymer gel-filled capillary electrophoresis for molecular size separation of recombinant bovine somatotropin.
Sodium dodecyl sulfate (SDS) non-acrylamide, polymer gel-filled capillary electrophoresis was examined as an alternative to the high-performance size-exclusion chromatographic (HPSEC) method for the analysis of recombinant bovine somatotropin (bovine growth hormone, rbSt). A calibration curve for the molecular mass of protein standards (M(r) 14,000 to 97,000) was linear (r2 = 0.998) when the molecular mass of the proteins and their peak migration time were plotted on a logarithmic (log-log) scale. Relative standard deviation (R.S.D.) of the molecular mass determination was approximately 2-3%. A pre-production as well as a production lot of the SDS gel-filled capillary columns were examined. Performance of both of these columns were equivalent. Peak migration time remained relatively constant beyond 140 sample injections. Gradual loss of theoretical plates was noted over the course of the assay; however, the peak resolution remained adequate for the analysis of rbSt. Peaks corresponding to monomer, dimer, trimer, and tetramer of rbSt were base-line resolved by the SDS gel-filled capillary electrophoresis. Theoretical plate of the monomer peak was approximately 28,000-30,000 per 40 cm column. Both the monomer and the dimer recovery studies indicated that the calibration curves are linear (r2 > 0.993) and the slopes are not different from one. Amounts of the components in rbSt determined by the SDS gel-filled capillary electrophoresis compared well with those of the HPSEC method. The results of this study indicated that the SDS non-acrylamide gel-filled capillary electrophoresis may be a viable alternative to the HPSEC method for the molecular size separation and analysis of recombinant proteins.
Animals↗
Bioprosthetic tissue preservation by filling with a poly(acrylamide) hydrogel.
Glutaraldehyde (GA) fixation has been used for more than 40 years as the preferred treatment to suppress immunogenicity and increase durability of bioprosthetic tissues (BPT) used in heart valve prostheses. This fixative and its reaction products have, however, been implicated in the calcific degeneration and long-term failure of these devices. The current study investigates stabilization of BPT and the mitigation/prevention of calcification by filling aortic wall samples with a synthetic poly(acrylamide) (pAAm) hydrogel, with and without pre-treatment with GA. Histological and gravimetric analysis showed full penetration of the acrylamide (AAm) into the fresh tissue, while only partial filling could be achieved with GA pre-fixed tissue. The observed decrease in amino-group content (0.157+/-0.012-0.123+/-0.021 micromol/mg, p<0.03) and corresponding increase in shrinkage temperature (67.2+/-0.8-78.1+/-1.8 degrees C, p<0.0001) when fresh tissue was filled, indicate the participation of tissue-amines in a process that leads to BPT crosslinking. These effects were much less pronounced when the tissue was pre-fixed with GA. Filling increased the tensile stiffness of fresh tissue (to levels half that of 0.2% GA fixed tissue), but decreased the stiffness of GA pre-fixed tissue. When compared to standard 0.2% GA fixed samples, fresh tissue filled with AAm showed 88% (p<0.0001) less calcification while exhibiting similar resistance toward degradation by protease. Filling did not result in significant decreases in calcification when the tissue was pre-fixed with GA.
Acrylic Resins↗
Imprinting of nucleotide and monosaccharide recognition sites in acrylamidephenylboronic acid-acrylamide copolymer membranes associated with electronic transducers.
Molecular recognition sites for the nucleotides adenosine 5'-monophosphate (1), guanosine 5'-monophosphate (2), cytosine 5'-monophosphate (3), and uridine 5'-monophosphate (4) are imprinted in an acrylamide-acrylamidephenylboronic acid copolymer (5) membrane. The imprinted membranes are assembled on piezoelectric Au quartz crystals or Au electrodes via electropolymerization or on the gate surface of an ISFET device by radical polymerization. The imprinted membranes reveal selectivity toward the imprinted nucleotide, and the association of the respective nucleotides with the recognition sites is transduced by the following: (i) microgravimetric, quartz crystal microbalance (QCM) measurements; (ii) Faradaic impedance analyses, and (iii) potentiometric responses of the ISFET devices. While the microgravimetric QCM measurements reflect the swelling of the polymers upon the association of the nucleotides with the recognition sites, the ISFET response is due to the charging of the polymer membrane as a result of the formation of the nucleotide-boronate complex. The selective detection of the nucleotides may lead to new DNA/RNA sequencing methods. Also, specific recognition sites for beta-D(+)-glucose (6), D(+)-galactose (7), and beta-D(-)-fructose (8) were imprinted in an acrylamide-acrylamidephenylboronic acid copolymer (5) membrane associated with an ISFET device. Selective sensing of the respective monosaccharides is accomplished in the presence of the imprinted membrane-functionalized ISFET devices.
Acrylic Resins↗
Ultrasensitive detection of unstained proteins in acrylamide gels by native UV fluorescence.
Visualization of proteins inside acrylamide and other gels usually relies on different staining methods. To omit the protein-staining procedure, we visualized unstained proteins inside acrylamide gels by laser excitation with ultraviolet (UV) light (280 nm, 35 mJ/cm2) and directly detected native UV fluorescence. In one-dimensional gels, a detection limit as low as 1 ng for bovine serum albumin and 5 ng for other proteins with a linear dynamic range (2.7 orders of magnitude) comparable to state of the art fluorescent dyes could be achieved. In addition, the application of this method to 20 microg of a whole cell lysate separated in a two-dimensional gel showed more than 600 spots. Since protein labeling always represents a serious obstacle in protein identification technologies, the working efficiency with our procedure can be considered as a significant improvement for protein visualization and reproducibility in proteomics.
Electrophoresis, Gel, Two-Dimensional↗
Amphiphilic block copolymers as bile acid sorbents: 1. Synthesis of polystyrene-b-poly(N,N,N-trimethylammoniumethylene acrylamide chloride).
The systematic investigation of the synthesis of polystyrene-b-poly(N,N,N-trimethylammoniumethylene acrylamide chloride) was accomplished by employing both polystyrene-b-poly(tert-butyl acrylate) and its hydrolyzed derivative, polystyrene-b-poly(acrylic acid) (PS-b-PAA) as starting materials, and coupling them with N,N-dimethylethylenediamine (DMED). The various reactions and intermediates we examined include aluminum amides, acid chlorides, and imides derived from carbodiimides, all in a variety of solvents. We present below our investigation of several synthetic routes and conclude that the carbodiimide coupling of PS-b-PAA with DMED followed by quaternization and counterion exchange is the most effective method of achieving the target. A brief discussion of the merits of each procedure in the context of block copolymers is given, and IR spectroscopic evidence for the postpolymerization synthesis of the poly(acrylamide) block is provided.
Acrylic Resins↗