B0753

2,3-Butanedione monoxime

≥98% (GC), powder, ATP-sensitive K⁺ and Ca²⁺ channel inhibitor

• Synonyme(s) : BDM
• Formule linéaire : CH₃C(=NOH)COCH₃
• Numéro CAS: 57-71-6
• Poids moléculaire : 101.10
• Beilstein: 605582
• Numéro CE : 200-348-5
• Numéro MDL: MFCD00002116
• Code UNSPSC : 12352200
• ID de substance PubChem : 57653910
• Nomenclature NACRES : NA.77

Propriétés

• Nom du produit: 2,3-Butanedione monoxime, ≥98%
• Essai: ≥98%
• Forme: powder
• pb: 185-186 °C (lit.)
• Pf: 75-78 °C (lit.)
• Chaîne SMILES: CC(=O)\C(C)=N\O
• InChI: 1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3/b5-3+
• Clé InChI: FSEUPUDHEBLWJY-HWKANZROSA-N
• Informations sur le gène: human ... KCNB1(3745)

Description

Application

2,3-Butanedione monoxime has been used:

• in single-molecule myosin V motility assays[1]
• as an anesthetic in the approach of imaging transgenic animals[2]
• to reduce rigor tension in muscle fibres[3]
• as a media component for mice cardiomyocytes culture[4]

Actions biochimiques/physiologiques

2,3-Butanedione monoxime is inhibitor of ATP-sensitive K⁺ and Ca²⁺ channels.

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)