1-800-457-3801

2,3-Butanedione 2-Monoxime (CAS 57-71-6)

5.0(1)
Write a reviewAsk a question

Alternate Names:
BDM; Biacetyl monoxime
Application:
2,3-Butanedione 2-Monoxime is a reversible inhibitor of myosin ATPase
CAS Number:
57-71-6
Purity:
≥98%
Molecular Weight:
101.10
Molecular Formula:
C4H7NO2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

QUICK LINKS

loader
2,3-Butanedione 2-Monoxime is a skeletal and cardiac muscle contraction inhibitor. Broad reversible inhibitor of myosin ATPase in eukaryotes. Shown to induce Ca2+ release from canine cardiac SR. KV2.1 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 KV2.1 channels directly from inside or outside of the membrane.

References:

  1. Effects of 2,3-butanedione 2-monoxime on Ca2+ release channels (ryanodine receptors) of cardiac and skeletal muscle.  |  Tripathy, A., et al. 1999. J Membr Biol. 169: 189-98. PMID: 10354465
  2. Effects of myosin ATPase inhibitor 2,3-butanedione 2-monoxime on distributions of myosins, F-actin, microtubules, and cortical endoplasmic reticulum in maize root apices.  |  Samaj, J., et al. 2000. Plant Cell Physiol. 41: 571-82. PMID: 10929940
  3. Improved right heart function after myocardial preservation with 2,3-butanedione 2-monoxime in a porcine model of allogenic heart transplantation.  |  Warnecke, G., et al. 2002. J Thorac Cardiovasc Surg. 123: 81-8. PMID: 11782759
  4. The myosin ATPase inhibitor 2,3-butanedione-2-monoxime disorganizes microtubules as well as F-actin in Saccharomyces cerevisiae.  |  Chon, K., et al. 2001. Cell Biol Toxicol. 17: 383-93. PMID: 11787860
  5. Neurofilament transport is dependent on actin and myosin.  |  Jung, C., et al. 2004. J Neurosci. 24: 9486-96. PMID: 15509735
  6. Mechanical and spatial determinants of cytoskeletal geodesic dome formation in cardiac fibroblasts.  |  Entcheva, E. and Bien, H. 2009. Integr Biol (Camb). 1: 212-9. PMID: 20023805
  7. The myosin ATPase inhibitor, 2,3-butanedione 2-monoxime, prevents protein secretion by the basidiomycete Coprinopsis cinerea.  |  Hashimoto, K., et al. 2011. Biotechnol Lett. 33: 769-75. PMID: 21165671
  8. Impact of tropomyosin isoform composition on fast skeletal muscle thin filament regulation and force development.  |  Scellini, B., et al. 2015. J Muscle Res Cell Motil. 36: 11-23. PMID: 25380572
  9. Cardiac tissue slices: preparation, handling, and successful optical mapping.  |  Wang, K., et al. 2015. Am J Physiol Heart Circ Physiol. 308: H1112-25. PMID: 25595366
  10. Eliminating contraction during culture maintains global and local Ca2+ dynamics in cultured rabbit pacemaker cells.  |  Segal, S., et al. 2019. Cell Calcium. 78: 35-47. PMID: 30594820
  11. Multiple effects of 2,3-butanedione monoxime.  |  Sellin, LC. and McArdle, JJ. 1994. Pharmacol Toxicol. 74: 305-13. PMID: 7937562
  12. Effect of 2,3-butanedione monoxime on smooth-muscle contraction of guinea-pig portal vein.  |  Watanabe, M. 1993. Pflugers Arch. 425: 462-8. PMID: 8134262
  13. 2,3-butanedione monoxime blockade of Ca2+ currents in adult rat sympathetic neurons does not involve ′chemical phosphatase′ activity.  |  Zhu, Y. and Ikeda, SR. 1993. Neurosci Lett. 155: 24-8. PMID: 8395671
  14. 2,3-Butanedione 2-monoxime (BDM) induces calcium release from canine cardiac sarcoplasmic reticulum.  |  Phillips, RM. and Altschuld, RA. 1996. Biochem Biophys Res Commun. 229: 154-7. PMID: 8954098
  15. The myosin ATPase inhibitor 2,3-butanedione-2-monoxime (BDM) inhibits tip growth and cytokinesis in the fission yeast, Schizosaccharomyces pombe.  |  May, KM., et al. 1998. Cell Motil Cytoskeleton. 41: 117-25. PMID: 9786087