Oxymatrine (Matrine N-oxide)

Alias: Matrine N-oxide; Ammothamnine; Oxysophoridine; Matrine oxide; Matrine 1beta-oxide; Oxymatrine;
Cat No.:V2022 Purity: ≥98%
Oxymatrine (also known as Matrine N-oxide)is a naturally occuring quinolizidine alkaloid isolated from the root of Sophora flavescens, which is used for the treatment of viral hepatitis, cancer, viral myocarditis, gastrointestinal hemorrhage and skin diseases such as colpitis, psoriasis and eczema etc.
Oxymatrine (Matrine N-oxide) Chemical Structure CAS No.: 16837-52-8
Product category: TGF-beta(Smad)
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Oxymatrine (also known as Matrine N-oxide) is a naturally occuring quinolizidine alkaloid isolated from the root of Sophora flavescens, which is used for the treatment of viral hepatitis, cancer, viral myocarditis, gastrointestinal hemorrhage and skin diseases such as colpitis, psoriasis and eczema etc. Oxymatrine protects mice from fulminant hepatitis induced by GalN/LPS and may block hepatocyte apoptosis and subsequent necrosis through downregulating the production of serum tumor necrosis factor alpha and the expression of Fas and Fas ligand in liver tissue. Oxymatrine also shows anti-hepatitis B virus effect in vivo by reducing the contents of HBsAg and HBcAg in transgenic mice liver.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
An alkaloid called oxymatrine, which is taken from the roots of Sophora flavescens, has been demonstrated to have anti-inflammatory, anti-fibrotic, anti-tumor, and heart-protective properties. Potential signaling pathways for oxymatrine include the following: delta-opioid receptor-Bcl-2, CD40, nuclear factor erythroid-2-related factor 2/heme oxygenase-1 signaling pathway, dimethyl arginine dimethylaminohydrolase/asymmetric dimethylarginine metabolic pathway, Janus kinase/signal transducer and activator of transcription, toll-like receptor 9/TRAF6, delta-opioid receptor-activated B cell nuclear factor kappa light chain enhancer, and delta-opioid receptor-Bcl-2 [1]. The growth of PC-3 and DU145 cell lines was dramatically suppressed by oxymatrine in a time- and dose-dependent manner. On the other hand, oxymatrine therapy did not suppress the proliferation of PNT1B healthy human prostate cells [2].
ln Vivo
The dose-dependent reduction in the volume and weight of the mouse tumors was substantial. Oxymatrine induces apoptosis in vivo, which slows the proliferation of prostate cancer cells [2]. The formation and deposition of collagen in the liver tissue of experimental rats is significantly reduced by oxymatrine. When CCl4 induces liver fibrosis in SD rats, oxymatrine can regulate the TGFβ-Smad pathway's fibrosis signal transduction by upregulating the expression of Smad 7 and downregulating the expression of Smad 3 and CBP [3].
Animal Protocol
Mice: 50 mg/kg and 100 mg/kg; i.p.
Mice: BALB/c homozygous (nu/nu) nude mice are used in the study. 24 tumor-bearing mice are randomLy divided into three groups: The control group is treated with PBS, and two groups are treated with different concentrations of oxymatrine (50 mg/kg and 100 mg/kg body weight). Oxymatrine is administered to the mice, using daily intraperitoneal injections.


Rats: One hundred healthy male SD rats (weight 140-160 g) are used in the study. All 100 rats are randomLy divided into three groups: Control (n=20), Treatment (n=40) and Model group (n=40). For the model group, 300 g/L CCl4 soluted in liquid paraffin is injected subcutaneously at a dosage of 3 mL/kg twice per week. The treated rats receive Oxymatrine celiac injections at 10 mg/kg twice a week besides the injection of CCl4

References
[1]. Lu ML, et al. Potential Signaling Pathways Involved in the Clinical Application of Oxymatrine. Phytother Res. 2016 Jul;30(7):1104-12.
[2]. Wu C, et al. Oxymatrine inhibits the proliferation of prostate cancer cells in vitro and in vivo. Mol Med Rep. 2015 Jun;11(6):4129-34.
[3]. Wu XL, et al. Effect of Oxymatrine on the TGFbeta-Smad signaling pathway in rats with CCl4-induced hepatic fibrosis. World J Gastroenterol. 2008 Apr 7;14(13):2100-5.
[4]. Ding Y, et al. Oxymatrine Inhibits Bocavirus MVC Replication, Reduces Viral Gene Expression and Decreases Apoptosis Induced by Viral Infection. Virol Sin. 2019 Feb;34(1):78-87
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H24N2O2
Molecular Weight
264.36
CAS #
16837-52-8
Related CAS #
16837-52-8
SMILES
[O-][N+]12C([H])([H])C([H])([H])C([H])([H])C3([H])C([H])([H])N4C(C([H])([H])C([H])([H])C([H])([H])C4([H])C([H])(C([H])([H])C([H])([H])C1([H])[H])C23[H])=O
InChi Key
XVPBINOPNYFXID-VNSSVHEPSA-N
InChi Code
InChI=1S/C15H24N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h11-13,15H,1-10H2/t11-,12+,13+,15+,17+/m0/s1
Chemical Name
(4R,41R,7aS,13aR,13bR)-10-oxododecahydro-1H,5H-dipyrido[2,1-f:3,2,1-ij][1,6]naphthyridine 4(41H)-oxide
Synonyms
Matrine N-oxide; Ammothamnine; Oxysophoridine; Matrine oxide; Matrine 1beta-oxide; Oxymatrine;
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

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:53 mg/mL (200.5 mM)
Water:53 mg/mL (200.5 mM)
Ethanol:53 mg/mL (200.5 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.87 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 (7.87 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 (7.87 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.


Solubility in Formulation 4: 100 mg/mL (378.27 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.7827 mL 18.9136 mL 37.8272 mL
5 mM 0.7565 mL 3.7827 mL 7.5654 mL
10 mM 0.3783 mL 1.8914 mL 3.7827 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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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.
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