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Biacetyl monoxime

Cat No.:V49302 Purity: ≥98%
Biacetyl monoxime (Diacetyl monoxime) is a myosin ATPase inhibitor and an inhibitor (blocker/antagonist) of skeletal and cardiac muscle contraction.
Biacetyl monoxime
Biacetyl monoxime Chemical Structure CAS No.: 57-71-6
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
250mg
500mg
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Product Description
Biacetyl monoxime (Diacetyl monoxime) is a myosin ATPase inhibitor and an inhibitor (blocker/antagonist) of skeletal and cardiac muscle contraction. Biacetyl monoxime is also a well-characterized, noncompetitive inhibitor of the chemical and locomotor activity of skeletal muscle myosin II (myosin-II). Biacetyl monoxime induces Ca2+ release from the sarcoplasmic reticulum.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
In both 6 and 48 hours, Diacetone monoxime (50 mM) decreases C's cellulase secretion. cinerea [1]. Endoplasmic reticulum localization is not affected by diethyl monoxime (50 mM, 2 and 4 hours), although the Golgi apparatus is [1]. Without the use of efflux inhibitors, dialethylmonoxime (0–30 mM) causes the concentration-dependent release of SR Ca2+, which is maximally reduced by 72% at pCa 6.0 [2]. Diacetyl monoxime functions as a chemical phosphatase, which has led to theories that its contraction-inhibiting effect may be due to the dephosphorylation of important Ca2+ channel proteins [2]. Neither myosin-V nor myosin-VI, the two distinct myosin-I isoforms, had their ATPase activity inhibited by dialetyl monoxime [3]. In isolated single cardiomyocytes from SHR and WKY rats, diethyl monooxime (0–50 mM) suppresses L-type Ca2+ currents [4]. In cultured newborn rat cardiomyocytes, dialetyl monooxime dramatically shortens the length of both electrically triggered and spontaneous action potentials [4].
ln Vivo
Hypotensive effects can be caused by intravenous injection of dialetyl monoxime (0-200 mg/kg) once [4]. Picrotoxin-induced convulsions can be treated with diacetyl monoxime (0-205 mg/kg; intraperitoneal injection; once) to prevent convulsions [5].
Animal Protocol
Animal/Disease Models: Male SHR and age-matched WKY rats [4]
Doses: 5, 30, 100 and 200 mg/kg
Route of Administration: intravenous (iv) (iv)administration, 1 mL/kg, once
Experimental Results: Arterial blood pressure of both strains were the same By lowering the SHR, the response speed is Dramatically improved.

Animal/Disease Models: Male mice (20 to 25 g) [5] Doses: 51, 103 and 205 mg/kg combined with intraperitoneal (ip) injection of 3.0 mg/kg Picrotoxin
Route of Administration: one intraperitoneal (ip) injection
Experimental Results: demonstrated dose-dependent resistance Convulsions caused by picrotoxins.
References

[1]. 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.

[2]. 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.

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

[4]. 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.

[5]. 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.

Additional Infomation
2-oxime 2,3-butanedione is a cream-colored powder. (NTP, 1992)
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.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H7NO2
Molecular Weight
101.1039
Exact Mass
101.047
CAS #
57-71-6
PubChem CID
6409633
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
185.5±9.0 °C at 760 mmHg
Melting Point
75-78 °C(lit.)
Flash Point
66.0±18.7 °C
Vapour Pressure
0.3±0.7 mmHg at 25°C
Index of Refraction
1.452
LogP
-0.47
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Heavy Atom Count
7
Complexity
106
Defined Atom Stereocenter Count
0
SMILES
C/C(=N\O)/C(=O)C
InChi Key
FSEUPUDHEBLWJY-HWKANZROSA-N
InChi Code
InChI=1S/C4H7NO2/c1-3(5-7)4(2)6/h7H,1-2H3/b5-3+
Chemical Name
(3E)-3-hydroxyiminobutan-2-one
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~989.12 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (20.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (20.57 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (20.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 9.8912 mL 49.4560 mL 98.9120 mL
5 mM 1.9782 mL 9.8912 mL 19.7824 mL
10 mM 0.9891 mL 4.9456 mL 9.8912 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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