General Description
Cream-colored powder.
Reactivity Profile
2-OXIME 2,3-BUTANEDIONE(57-71-6) may react violently during vacuum distillation above 130 pascals.
Air & Water Reactions
Soluble in water.
Fire Hazard
Flash point data for this chemical are not available, but 2-OXIME 2,3-BUTANEDIONE is probably combustible.
Chemical Properties
white crystals
Uses
2,3-Butanedione monoxime is a reversible inhibitor of myosin ATPase. It is also used as a reagent for colorimetric determination of urea.
Definition
ChEBI: Diacetylmonoxime is a ketoxime obtained via formal condensation of butane-2,3-dione with hydroxylamine. It is a reversible myosin ATPase inhibitor. It has a role as a cholinesterase reactivator, a chromogenic compound and an EC 3.6.1.3 (adenosinetriphosphatase) inhibitor.
Biological Activity
2,3-butanedione-2-monoxime is a myosin atpase inhibitor.myosin, an atpase, can convert chemical energy into directed movement and is regarded as a molecular motor. myosin has various shapes and sizes. more than 11 myosin classes have been identified, and more will be found. the common feature of all of these molecules is a section close to the n terminus, which can be identified as a motor domain.
Biochem/physiol Actions
DRK1 is a delayed rectifier (Kv2.1) cloned K+ channel from rat brain with consensus sites for protein kinase-dependent phosphorylation that might be expected to be functionally regulated by phosphorylation. 2,3-Butanedione monoxime (BDM) chemically removes phosphate groups from many proteins, and its action on DRK1 channels was examined after expression of DRK1 cRNA in Xenopus oocytes. In two-microelectrode voltage-clamp experiments, the application of 2,3-Butanedione monoxime to the bath inhibited DRK1 current (ki = 16.6 mM, H = 0.96) rapidly and reversibly, with a time course similar to the time course of solution change within the bath. DRK1 current was inhibited at all potentials; the time course of current activation, deactivation and inactivation were unaffected by 2,3-Butanedione monoxime. In inside-out patch-clamp experiments, the application of 2,3-Butanedione monoxime to the cytoplasmic surface similarly inhibited channel activity rapidly and reversibly (ki = 10.7 mM, H = 1.01) in the absence of rephosphorylating substrates. These results are inconsistent with a phosphatase effect, because such an effect should be irreversible in cell-free, ATP-free patches. Instead, the results suggest that 2,3-Butanedione monoxime can inhibit DRK1 channels directly from inside or outside of the membrane.
Safety Profile
Poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.
in vitro
2,3-butanedione-2-monoxime (bdm), a general probe of myosin function, was widely used in muscle research as a low-affinity but specific chemical phosphatase that could reversibly inhibit the myosin cross-bridge cycle. it was found that wild-type cells treated with bdm at 20 mm for around two generation times were smaller than untreated controls and showed a septation index about twice that observed in the absence of the inhibitor. moreover, the organization of actin at the cell poles was disorganized in the presence of bdm, however, cells formed a cytokinetic actin ring. in addition, when nitrogen-starved stationary-phase cells were reinoculated into fresh medium in the presence of bdm, the time taken to repolarize the actin cytoskeleton and to resume the characteristic vegetative cell shape were both delayed substantially [1].
References
[1] may km, wheatley sp, amin v, hyams js. the myosin atpase inhibitor 2,3-butanedione-2-monoxime (bdm) inhibits tip growth and cytokinesis in the fission yeast, schizosaccharomyces pombe. cell motil cytoskeleton. 1998;41(2):117-25.