Biacetyl monoxime

• CAT Number: M015047
• CAS Number: 57-71-6
• Molecular Formula: C4H7NO2
• Molecular Weight: 101.10
• Purity: ≥95%
• Synonyms: (3E)-3-hydroxyiminobutan-2-one
• InChI: InChI=1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3/b5-3+
• InChIKey: FSEUPUDHEBLWJY-HWKANZROSA-N
• SMILES: CC(=NO)C(=O)C

Biacetyl monoxime (Diacetyl monoxime), a myosin ATPase inhibitor, is a skeletal and cardiac muscle contraction inhibitor. Biacetyl monoxime is also a well-characterized non-competitive inhibitor of chemical and motile activity of skeletal muscle myosin-II. Biacetyl monoxime induces sarcoplasmic reticulum Ca2+ release[1][2][3].
Biacetyl monoxime (Diacetyl monoxime) (50 mM, 6 and 48 h) decreases cellulase secretion in C. cinerea[1].
Biacetyl monoxime (50 mM, 2 and 4 h) disrupts the localization of the Golgi apparatus, but not that of the endoplasmic reticulum[1].
Biacetyl monoxime (0-30 mM) induces SR Ca2+ release (no efflux inhibitors) in a concentration-dependent manner, with a maximal reduction of 72% of SR Ca2+ at pCa 6.0[2].
Biacetyl monoxime acts as a chemical phosphatase, which has led to speculation that dephosphorylation of key Ca2+ channel proteins may be involved in its inhibition of contraction[2].
Biacetyl monoxime does not inhibit the ATPase activity of two different myosin-I isoforms, myosin-V, or myosin-VI[3].
Biacetyl monoxime (0-50 mM) suppresses L-type Ca2+ current of single cardiac myocytes isolated from SHR and WKY rats[4].
Biacetyl monoxime significantly reduces the duration of both spontaneous and electrically stimulated action potentials of cultured neonatal rat cardiomyocytes[4].
Biacetyl monoxime (0-200 mg/kg; i.v.; once) shows hypotensive effect[4].
Biacetyl monoxime (0-205 mg/kg; i.p.; once) shows anticonvulsant effect against Picrotoxin (HY-101391)-induced convulsions[5].

Reference

[1]. Kohsuke Hashimoto, et al. The myosin ATPase inhibitor, 2,3-butanedione 2-monoxime, prevents protein secretion by the basidiomycete Coprinopsis cinerea. Biotechnol Lett. 2011 Apr;33(4):769-75.
 [Content Brief]

[2]. R M Phillips, et al. 2,3-Butanedione 2-monoxime (BDM) induces calcium release from canine cardiac sarcoplasmic reticulum. Biochem Biophys Res Commun. 1996 Dec 4;229(1):154-7.
 [Content Brief]

[3]. Ostap EM. 2,3-Butanedione monoxime (BDM) as a myosin inhibitor. J Muscle Res Cell Motil. 2002;23(4):305-8.
 [Content Brief]

[4]. Xiao YF, et al. Effects of 2,3-butanedione monoxime on blood pressure, myocardial Ca2+ currents, and action potentials of rats. Am J Hypertens. 1995 Dec;8(12 Pt 1):1232-40.
 [Content Brief]

[5]. Brightman T, et al. 2,3-Butanedione monoxime protects mice against the convulsant effect of picrotoxin by facilitating GABA-activated currents. Brain Res. 1995 Apr 24;678(1-2):110-6.
 [Content Brief]