Disease relevance of ethenoxyethene

• We have previously observed that the administration of the biological response modifier (BRM) maleic anhydride divinyl ether (MVE-2) strongly augmented NK activity in lung and liver, and the augmented NK activity coincided with increased resistance to the formation of experimental metastases in these organs [1].
• The P12/UV hypersensitivity of the plasmalogen-deficient mutants, together with the selective, P12/UV-induced decomposition of plasmalogens in wild-type cells, documented in the accompanying manuscript, suggest that the vinyl ether linkage of plasmalogens plays a direct role in protecting animal cell membranes against certain oxidative stresses [2].
• In contrast, hyporesponsiveness to augmentation by multiple injections of maleicanhydride divinyl ether (MVE-2) or Propionibacterium acnes was limited to the spleen and peripheral blood lymphocytes, with continued augmentation of NK cell activity in the peritoneum, lungs, and liver [3].
• Recombinant 0.19 expressed in Escherichia coli showed the same reactivity with IgE as native wheat 0.19 in Western blotting and ELISA using methyl vinyl ether maleic anhydride co-polymer as an immobilizing reagent, suggesting that the allergenic epitopes are located in the peptide portions [4].
• Restoration of plasmenylethanolamine, which contains the vinyl ether, resulted in wild-type-like resistance to chemical hypoxia and ROS generators, whereas increasing levels of its precursor, which bears the saturated ether, had no effect on cell survival [5].

High impact information on ethenoxyethene

• Plasmalogens (phospholipids with a vinyl-ether bond in the sn-1 position) account for more than 50% of total myocardial sarcolemmal and sarcoplasmic reticulum phospholipids [6].
• The agents tested, levan, lentinan, mannozym, maleic anhydride divinyl ether, polyriboinosinic-polycytidylic acid-poly-L-lysine, and highly purified L-cell interferon, gave significant increases in the DTH response above the sheep red blood cell control [7].
• Maleic vinyl ether activation of murine macrophages against lung-metastasizing tumors [8].
• Targeting of the LDL plasmalogen vinyl ether bond was dependent on the presence of MPO-derived RCS [9].
• Here we show that reactive brominating species produced by the eosinophil peroxidase system of activated eosinophils attack the vinyl ether bond of plasmalogens [10].

Chemical compound and disease context of ethenoxyethene

• Protection against murine cytomegalovirus infection in aged mice and mice with severe combined immunodeficiency disease with the biological response modifiers polyribosinic-polycytidylic acid stabilized with L-lysine and carboxymethylcellulose, maleic anhydride divinyl ether and colony stimulating factor 1 [11].
• Recombinant proteins of these cDNAs produced in Escherichia. coli cleaved both 9- and 13-hydroperoxide of linoleic and linolenic into aldehydes, while having only a trace level of AOS activity and no divinyl ether synthase activity [12].

Biological context of ethenoxyethene

• The vinyl ether hydrolysis catalyzed by PhzD represents yet another example of the catalytic diversity seen in the alpha/beta-hydrolase family, whose members are also known to hydrolyze amides, phosphates, phosphonates, epoxides, and C-X bonds [13].
• A mechanistic scheme for the reaction of clavulanate with TEM-2 beta-lactamase is proposed in which acylation at Ser-70 and subsequent decarboxylation is followed either by cross-linking with Ser-130 to form a vinyl ether or by reformation of unmodified enzyme via a Ser-70 linked (hydrated) aldehyde [14].
• A reaction route involving an initial internal Heck arylation of the hydroxyalkyl vinyl ether, iminium ion formation, and subsequent tandem cyclization is invoked to explain the selective formation of the isolated tertiary 3-aminoindan acetals [15].
• Here, the identification of a potato cDNA is described, whose predicted amino acid sequence corresponds to divinyl ether synthases, belonging to the recently identified new P450 subfamily CYP74D [16].
• Hydrogenation of the vinyl ether was required to desorb the alkyl, acyl-substituted species in fast-atom-bombardment mass spectrometry [17].

Anatomical context of ethenoxyethene

• Taken together, these studies demonstrate for the first time a novel biochemical mechanism that targets the vinyl ether bond of plasmalogens during neutrophil activation resulting in the production of alpha-chloro fatty aldehydes that may enhance the recruitment of neutrophils to areas of active inflammation [18].
• Taken together, these results show that thyroid 2-IHDA is derived from plasmenylethanolamine via an attack of reactive iodine on the vinyl ether group [19].
• Recently alpha-chloro fatty aldehydes have been shown to be products of reactive chlorinating species targeting the vinyl ether bond of plasmalogens utilizing a cell-free system [18].
• Thus, the sensitivity of the vinyl ether bond of plasmalogens was investigated in a cerebral cortex homogenate under UV irradiation- or Fe2+/ascorbate-induced peroxidation [20].
• Although the predominance of plasmalogens in electrically-active membranes (e.g., sarcolemma) is well-known, identification of the molecular mechanisms through which the vinyl ether linkage facilitates electrophysiologic function has remained elusive [21].

Associations of ethenoxyethene with other chemical compounds

• Macrophages elicited in the primed state of activity in vivo with methyl vinyl ether co-polymer II (MVE-II) did not express p120, but could be induced to do so when treated with low doses of LPS [22].
• Eosinophil peroxidase-derived reactive brominating species target the vinyl ether bond of plasmalogens generating a novel chemoattractant, alpha-bromo fatty aldehyde [10].
• Reactive brominating species produced by myeloperoxidase target the vinyl ether bond of plasmalogens, resulting in the production of a neutral lipid and lysophosphatidylcholine [23].
• The vinyl ether bond of LDL plasmalogens was targeted by MPO-derived RCS, resulting in the release of the 16- and 18-carbon-containing alpha-chloro fatty aldehydes, 2-chlorohexadecanal and 2-chlorooctadecanal, respectively, from the plasmalogen glycerol backbone [9].
• Both the vinyl ether bond of phosphatidylethanolamine plasmalogen and polyunsaturated fatty acids are major targets in oxidative stress; thus, these specific lipid modifications strongly support the involvement of free radicals in the pathogenesis of AD [24].

Gene context of ethenoxyethene

• Other drugs tested (diethyldithiocarbamate, maleic anhydride divinyl ether, azimexone) failed to stimulate the in vitro secretion of significant amounts of CSF and PGE [25].
• These results indicate that developmental expression of the divinyl ether synthase gene is an important determinant of the tissue specific synthesis of divinyl ether oxylipins [26].
• Reactive brominating species produced by myeloperoxidase target the vinyl ether bond of plasmalogens: disparate utilization of sodium halides in the production of alpha-halo fatty aldehydes [23].
• On the other hand, similar reactions with tert-butyl vinyl ether at 30 degrees C gave diastereomeric mixtures of cis-(4S,6S)-, cis-(4R,6R)-, trans-(4S,6R)-, and trans-(4R,6S)-6-(tert-butoxy)-4-halo-5,6-dihydro-4H-1,2-oxazines 12 [27].
• We have previously reported a direct triggering approach [Thompson, D. H., et al. (1996) Biochim. Biophys. Acta 1279, 25-34; Gerasimov, O. V., et al. (1997) Biochim. Biophys. Acta 1324, 200-214] based on the facile degradation of plasmenylcholine and diplasmenylcholine vinyl ether linkages by either photooxidation or low-pH environments [28].

Analytical, diagnostic and therapeutic context of ethenoxyethene

• Analysis by thin layer chromatography revealed that reactive chlorinating species produced by myeloperoxidase target the vinyl ether bond of the plasmalogen, lysoplasmenylcholine (1-O-hexadec-1'-enyl-sn-glycero-3-phosphorylcholine), resulting in the production of a neutral lipid [29].
• A micellar electrokinetic chromatography (MEKC) method has been developed for the direct resolution of divinyl ether type of hydrophobic fatty acid isomers [30].
• Electrostatically driven immobilization of peptides onto (Maleic anhydride-alt-methyl vinyl ether) copolymers in aqueous media [31].
• Thermo-sensitive copolymer consists of poly(2-ethoxyethyl vinyl ether) and poly(hydroxyethyl vinyl ether) (EOVE200-HOVE400), whose sol-gel transition temperature was 20.5 degrees C, was synthesized and its applicability to a drug delivery system was examined [32].
• They were compared with a commercially available PFA (tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer) nebulizer and with two new prototypes called the polymeric pneumatic concentric nebulizer (PMN) and the high-solids micronebulizer (HSM) [33].

References