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Galegine hydrochloride 2368870-39-5

Galegine hydrochloride 2368870-39-5

CAS No.: 2368870-39-5

GalegineHCl, a guanidine analogue, helps mice lose weight. Guanidines are compounds found in G. officinalis, producing b
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Galegine HCl, a guanidine analogue, helps mice lose weight. Guanidines are compounds found in G. officinalis, producing biguanides, metformin, and phenformin. Galegine HCl activates AMPK in 3T3-L1 adipocytes, L6 myotubes, H4IIE rat liver cancer, and HEK293 human kidney cell line. Galegine HCl has anti-bacterial effect with a minimum inhibitory concentration of 4 mg/L against Staphylococcus aureus strains.

Physicochemical Properties


Molecular Formula C6H14CLN3
Molecular Weight 163.648459911346
Exact Mass 163.087
CAS # 2368870-39-5
PubChem CID 139034173
Appearance White to off-white solid powder
Hydrogen Bond Donor Count 3
Hydrogen Bond Acceptor Count 1
Rotatable Bond Count 2
Heavy Atom Count 10
Complexity 127
Defined Atom Stereocenter Count 0
SMILES

Cl.N(=C(/N)\N)/C/C=C(\C)/C

InChi Key QORPDBRMGGUYRL-UHFFFAOYSA-N
InChi Code

InChI=1S/C6H13N3.ClH/c1-5(2)3-4-9-6(7)8;/h3H,4H2,1-2H3,(H4,7,8,9);1H
Chemical Name

2-(3-methylbut-2-enyl)guanidine;hydrochloride
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)

Biological Activity


ln Vitro Pre-treating 3T3-L1 adipocytes with galegine hydrochloride (10 μM-3 mM; 5 h) stimulates their insulin-independent glucose uptake in a concentration-dependent manner without affecting their viability. Without affecting the survival of the cells, a concentration-dependent stimulation of glucose absorption into L6 myotubes is produced after 5 hours of incubation with galegine hydrochloride (1 μM–1 mM)[1]. On 3T3-L1 adipocytes, galegine hydrochloride (0.3-300 μM; 24 hours) causes a reduction in basal glycerol release and a greater reduction in isoprenaline-stimulated glycerol release. H4IIE rat hepatoma cells exhibit a time-dependent activation of marked AMPK measured in cell lysates upon incubation with Galegine hydrochloride (10 or 300 μM) for up to 6 hours. The maximal activation occurs at 360 minutes, and the twofold activation remains visible at 24 hours in the presence of 300 μM Galegine hydrochloride. 300 MM of galegine hydrochloride has a notably bigger effect than 10 μM. After an hour of incubation with galegine hydrochloride, 3T3L-1 adipocytes and L-6 myotubes exhibit concentration-dependent activation of AMPK. Moreover, a human kidney cell line (HEK293) exposed to galegine hydrochloride exhibits concentration-dependent enzyme activation[1].
ln Vivo Body weight is significantly reduced when galegine hydrochloride (63 mg/kg; feed; daily for 11 days) is administered[1].
Animal Protocol Animal/Disease Models: Adult male BALB/ c mice[1]
Doses: 63 mg/kg
Route of Administration: feed; daily for 11 days
Experimental Results: Produced a significant reduction in body weight.
References

[1]. Mechanisms underlying the metabolic actions of galegine that contribute to weight loss in mice. Br J Pharmacol. 2008 Apr;153(8):1669-77.

[2]. In Vitro Antibacterial Activity of Prenylated Guanidine Alkaloids from Pterogyne nitens and Synthetic Analogues. J Nat Prod. 2014 Aug 22;77(8):1972-5.


Solubility Data


Solubility (In Vitro) H2O : 43.33 mg/mL (264.77 mM)
DMSO : 5.2 mg/mL (31.78 mM)
Solubility (In Vivo) Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)

Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.1106 mL 30.5530 mL 61.1060 mL
5 mM 1.2221 mL 6.1106 mL 12.2212 mL
10 mM 0.6111 mL 3.0553 mL 6.1106 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.