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Chemical Compound Review

biacetyl     butane-2,3-dione

Synonyms: diacetyl, Butanedione, Lopac-D-3634, Biacetyl; BDM, CCRIS 827, ...
 
 
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Disease relevance of biacetyl

  • Regional myocardium function was measured during a selective intracoronary infusion of 2,3-butanedione monoxime (BDM), a specific inhibitor of actin-myosin coupling, in the control state (10 pigs) and in a protocol of a 51-minute coronary occlusion followed by reperfusion (40 pigs) [1].
  • Five heart groups (cold) were perfused with AVP, D-ARG, L-ARG, L-NAME, or nothing (control), but after 2 hours they were perfused at low flow for 22 hours at 3.7 degrees C and again for 3 hours at 37.5 degrees C. ADE, butanedione monoxime, and NP were given for cardioprotection before, during, and after hypothermia [2].
  • The role of contracture in the manifestation of calcium paradox-induced damage was examined using 2,3-butanedione monoxime (BDM) to inhibit myofibrillar activity [3].
  • Cleaving Xenopus embryos and parthenogenetically activated eggs treated with 2,3-butanedione monoxime (BDM) undergo a dramatic large-scale torsion, with the cortex of the animal hemisphere shearing in an exclusively counterclockwise direction past the vegetal cortex [4].
  • Inactivation of Escherichia coli L-threonine dehydrogenase by 2,3-butanedione. Evidence for a catalytically essential arginine residue [5].
  • Exposure to an agent during diacetyl production appears to be responsible for causing bronchiolitis obliterans syndrome in chemical process operators, consistent with the suspected role of diacetyl in downstream food production [6].
 

Psychiatry related information on biacetyl

  • Controlled clinical evaluation of diacetyl morphine for treatment of intractable opiate dependence [7].
  • The determination of diacetyl permits the detection of microbial growth in the processing of citrus fruit before the appearance of other organoleptic, chemical or microbiological changes [8].
  • The biosensor could be used to determine diacetyl concentration within the range from 0.1 microgram/mL to 0.5 microgram/mL and the response time was less than two minutes, and its performance was stable within 9 days [9].
 

High impact information on biacetyl

  • Chemical modification with 2,3-butanedione in borate buffer indicates that nine of ten glycolytic enzymes studied contain arginyl residues at their active sites [10].
  • In apicomplexan parasites, actin-disrupting drugs and the inhibitor of myosin heavy chain ATPase, 2,3-butanedione monoxime, have been shown to interfere with host cell invasion by inhibiting parasite gliding motility [11].
  • Cells lacking MyoB (myoA(-)/B(-), and myoB(-) cells) and wild-type cells treated with the myosin inhibitor butanedione monoxime accumulated a plasma membrane marker and biotinylated surface proteins on intracellular endocytic vacuoles [12].
  • In addition, the involvement of myosin-based cytoskeleton in uropod formation and ICAM-3 redistribution in response to chemokines was suggested by the prevention of this phenomenon with the myosin-disrupting agent butanedione monoxime [13].
  • Maintenance of such cell-cell contact structures critically depended on the contractility of actin cytoskeleton, as inhibition of contractility with serum-free medium or 2,3-butanedione 2-monoxime (BDM) resulted in loss of strand formation [14].
 

Chemical compound and disease context of biacetyl

 

Biological context of biacetyl

  • Chemotaxis toward one such odorant, diacetyl (butanedione), requires the function of a seven-transmembrane receptor protein encoded by the odr-10 gene [20].
  • In separate hearts (n = 8), costs (basal metabolism and excitation-contraction coupling) were estimated by use of 2,3-butanedione monoxime [21].
  • Although their specific effects are difficult to quantitate, other LAB metabolic products such as hydrogen peroxide and diacetyl can also contribute to the overall antibiosis and preservative potential of these products [22].
  • The polarization and homotypic cell aggregation induced through CD43 was prevented by butanedione monoxime, indicating the involvement of myosin cytoskeleton in these phenomena [23].
  • Interestingly, the myosin-disrupting drug butanedione monoxime inhibited the redistribution of CD43 induced by the specific MoAb, whereas the stimulation of cell adhesion induced by engagement of CD43 was preserved in the presence of this drug [24].
 

Anatomical context of biacetyl

 

Associations of biacetyl with other chemical compounds

  • Conversely, treatment of cells on firm substrates with myosin inhibitors 2,3-butanedione monoxime or KT5926 caused the reduction of both vinculin and phosphotyrosine at adhesion sites [30].
  • We found that modification with butanedione of four arginine residues in the HMW kininogen molecule prevented bradykinin release, which results from cleavage of HMW kininogen [31].
  • Phytomonas iPDH and R. eutropha ADH are able to use a wide range of substrates with similar Km values such as primary and secondary alcohols, diols, and aldehydes, as well as ketones such as acetone, diacetyl, and acetoin [32].
  • When both NAD and NADP were present, the butanedione effect was completely abolished, thus suggesting the possible presence of arginyl residues at the nucleotide binding site of the NADPH leads to NAD transhydrogenase enzyme [33].
  • The results imply that P34H and diacetyl reductase (EC ) are identical to l-xylulose reductase (EC ), which is involved in the uronate cycle of glucose metabolism, and the unique localization of the enzyme in kidney suggests that it has a role other than in general carbohydrate metabolism [34].
 

Gene context of biacetyl

  • Yeast hexokinase PII is rapidly inactivated (assayed at pH 8.0) by either butanedione in borate buffer or phenylglyoxal, reagents which are highly selective for the modification of arginyl residues [35].
  • Cytochalasin B or butanedione monoxime blocked the contraction, which suggested that both actin filaments and myosin ATPase activity were required for the contraction [36].
  • Correspondingly elevated levels of ILV5 transcript in strain WM56 compared to the control (i.e. non-tandem) parental strain led to increased amounts of encoded acetohydroxyacid reductoisomerase as evidenced by significantly lower diacetyl production [37].
  • These findings suggest that one, or both, of the two arginyl residues which appear to be unique to the active sites of the mammalian CA III isozymes are modified by butanedione [38].
  • Towards diacetyl-less brewers' yeast. Influence of ilv2 and ilv5 mutations [39].
 

Analytical, diagnostic and therapeutic context of biacetyl

References

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