Disease relevance of vinyl acetate

• At extremely high and toxic doses, vinyl acetate is carcinogenic in rats and mice and causes chromosomal aberrations [1].
• Sarcomas were induced in CBA/H mice by sc implantation of 15 X 22 X 0.2-mm polyvinyl chloride vinyl acetate copolymer films [2].
• A remarkably increased enantioselectivity was obtained when the salt was added at 3-10 mol % versus substrate in the Burkholderia cepacia lipase (lipase PS-C)-catalyzed transesterification of 1-phenylethanol by using vinyl acetate in diisopropyl ether or a hexane solvent system [3].
• Model predictions of these dosimeters in rats corresponded well with observations of vinyl acetate toxicity [4].
• Vinyl acetate casting may offer a new and useful tool in evaluating experimental induction of emphysema in rats [5].

Psychiatry related information on vinyl acetate

• Low catalyst loadings of aryl- or alkyl-substituted NHC catalysts mediate the acylation of alcohols with vinyl acetate in convenient reaction times at room temperature [6].

High impact information on vinyl acetate

• The results indicate that vinyl acetate induces chromosome damage in cell cultures through enzyme-mediated hydrolysis to acetaldehyde [7].
• Acetaldehyde induced SCEs in human whole-blood lymphocyte cultures at concentrations (0.125-2 mM) comparable to those used for vinyl acetate [7].
• Gas chromatographic analysis of human whole-blood lymphocyte cultures treated for 10 s-20 min with vinyl acetate (5.4 mM) revealed a rapid degradation of vinyl acetate and formation of acetaldehyde [7].
• A 48-h treatment with vinyl acetate (0.05-1 mM) induced a drastic increase in sister chromatid exchanges (SCEs) and (in first division cells) structural chromosome aberrations in cultured human lymphocytes [7].
• A carboxylesterase inhibitor, bis-(p-nitrophenyl) phosphate, was able to block DPXL formation by vinyl acetate and microsomes [8].

Chemical compound and disease context of vinyl acetate

• METHODS: Paclitaxel-loaded ethylene vinyl acetate wraps were placed around the graft-vein anastomosis on one side, with control polymers being placed on the contralateral side in our pig model of arteriovenous graft stenosis [9].
• The thermal inactivation of mesophilic Bacillus subtilis alpha-amylase modified by maleic anhydride/vinyl acetate copolymer has been studied at different polymer/enzyme ratios in the pH range of relevance to enzymatic catalysis [10].

Biological context of vinyl acetate

• DPXL accumulation followed S-phase enzymatic kinetics, with a rate of formation of 1.1 DPXLs/plasmid molecule/mmol vinyl acetate/microgram microsomal protein/microgram DNA [8].
• This is consistent with investigations on metabolism and pharmacokinetics of vinyl acetate which show that this compound, after entering the organism, is immediately split by blood esterases and thus may not be available for epoxidation to an ultimately carcinogenic metabolite [11].
• PdCl(2) can catalyze the acetylation of primary and secondary alcohols with vinyl acetate [12].
• Three microbial lipases have been used to deracemize trans-2-fluorocycloalkanols 2 both by hydrolysis of the corresponding acetates 3 or chloroacetates 4 and by esterification of the fluorohydrins 2 using vinyl acetate and vinyl chloroacetate, respectively [13].
• [reaction: see text] Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary and secondary carbohydrate acceptors, followed by intramolecular aglycon delivery (IAD) [14].

Anatomical context of vinyl acetate

• Vinyl acetate was unable to cause formation of DPXLs in the absence of microsomes [8].
• 5. Induction of DPXL formation by 1-100 mM vinyl acetate in the presence of rat liver microsomes was observed at 37 degrees C over 3 h [8].
• Of lesser adsorptive capacity were vinyl acetate, nylon, acrylic, and Teflon membranes [15].
• The stereoselective acylation of meso polyol 2 by vinyl acetate (solvent and acyl donor) in the presence of porcine pancreas lipase gave the corresponding monoester 5 in good yield (76%) and high enantiomeric purity (ee > 98%) [16].
• Individual cellular analysis demonstrated that both respiratory and olfactory epithelial cells responded to vinyl acetate exposures with a dose-dependent decrease in pHi [17].

Associations of vinyl acetate with other chemical compounds

• Palladium(II) chloride catalyzed selective acetylation of alcohols with vinyl acetate [12].
• The ethyl ester produced by esterification of the sophorolipid mixture with sodium ethoxide was subjected to acylation catalyzed by Novozym 435 in dry tetrahedrofuran (THF) with vinyl acetate and vinyl methacrylate to produce 6'-monoacylated derivatives [18].
• The mixture was also sorbed to hydrogels made of ethylene vinyl acetate co-polymer and poly(2-hydroxyethyl methacrylate), and to cell culture insert membranes as control [19].
• These data support a hypothesis that carboxylesterase-mediated hydrolysis of vinyl acetate is necessary to generate the active intracellular cross-linking agent, acetaldehyde, and the cytotoxic metabolite, acetic acid [20].
• Several antinucleants were screened using differential scanning calorimetry (DSC) and two candidates showed particular promise: a cyclodextrin derivative (RAMEB) and a vinylpyrrolidone/vinyl acetate copolymer (Kollidon(R) VA64) [21].

Gene context of vinyl acetate

• Kinetics of nasal carboxylesterase-mediated metabolism of vinyl acetate [22].
• The purpose of this study was to define the kinetics of hydrolysis of vinyl acetate in nasal respiratory and olfactory mucosa of male and female rats and mice [22].
• Pretreatment of the nasal turbinates with 1 mM BNPP reduced 25 mM vinyl acetate-induced DPXL formation by over 75% in both tissues [20].
• PURPOSE: To investigate the influence of the extrusion parameters on the polymeric structure and release properties of polyethylene vinyl acetate (EVA) coaxial fibers, used for controlled release of steroids [23].
• Previous studies from our laboratory suggest that rat liver microsome-activated vinyl acetate induces plasmid DNA-histone crosslinks, in vitro, through esterase-mediated metabolism [20].

Analytical, diagnostic and therapeutic context of vinyl acetate

• Vinyl acetate has been shown to induce nasal lesions in rodents in inhalation bioassays [24].
• This study suggests a new hemodialysis membrane, which is prepared by plasma depositing vinylacetate (VAc) onto annealled nylon 4 membrane, followed by hydrolysis treatment [25].
• A chronic toxicity test was carried out in groups of 20 male and female F344 rats with vinyl acetate dissolved in drinking water at two concentrations, 2500 and 1000 mg/liter [26].
• A dose-dependent increase in micronucleated polychromatic erythrocytes was observed in the bone marrow of male C57B1/6 mice 30 h after a single intraperitoneal injection of vinyl acetate (250, 500, 1000 or 2000 mg/kg b.wt.; (9-14 animals per group) [27].
• Determination of vinyl acetate in air by gas chromatography [28].

References