Allomatrine

CAS# 641-39-4

Allomatrine

Catalog No. BCN2368----Order now to get a substantial discount!

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Chemical structure

Allomatrine

3D structure

Chemical Properties of Allomatrine

Cas No. 641-39-4 SDF Download SDF
PubChem ID 7000681 Appearance Powder
Formula C15H24N2O M.Wt 248.36
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES C1CC2C3CCCN4C3C(CCC4)CN2C(=O)C1
Standard InChIKey ZSBXGIUJOOQZMP-KYEXWDHISA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Allomatrine

The herbs of Sophora alopecuroides L.

Biological Activity of Allomatrine

DescriptionAllomatrine can inhibit proliferation and invasion in vitro of human lung cancer A549 cell line by inducing ROS production,promoting apoptosis, arresting cell cycle, inhibiting ubiquitin proteasome and regulating tumor related gene expression. (+)-Allomatrine and (+)-matrine when given i.c.v. may stimulate the descending dynorphinergic neuron, resulting in the stimulation of KORs in the spinal cord, and this phenomenon in turn produces the antinociception in mice.
TargetsBcl-2/Bax | Caspase | Akt | ROS | NF-kB | CDK
In vitro

Effect and Mechanism of Allomatrine in Proliferation and Invasion in Vitro Inhibition of Human Lung Cancer A549 Cell Line[Reference: WebLink]

Chinese Pharmaceutical Journal, 2015 , 50 (13) :1111-6.

To investigate the effect and mechanism of Allomatrine in proliferation and invasion in vitro inhibition of human lung cancer A549 cell line.
METHODS AND RESULTS:
After treatment with Allomatrine, MTS assay was employed to determine the proliferation of cancer cells, flow cytometry to determine the apoptosis rate, cell cycle distribution and intracellular ROS production, transwell assay to determine the cell invasion potential in vitro, adhesion assay to determine the cell adhesion potential in vitro, realtime PCR and Western blotting assay to determine the expression of apoptosis related gene Survivin, Bcl-2 and caspase-3/8, the cell cycle related protein CDK-2, adhesion molecule CD44, matrix metalloproteinases MMP-2/9 and the phosphorylation of AKT, report gene assay to determine the transcription activity of NF-KB and the activity of ubiquitin proteasome. Allomatrine significantly inhibited the proliferation and invasion in vitro of A549 cells, flow cytometry showed that apoptosis rate and ROS production was increased and the cell cycle was halted by G2/M phase, the expression of pro-apoptosis gene caspase-3/8 was upregulated while the anti-apoptosis proteins Survivin and Bcl-2 was downregulated, the expression of CDK-2, CD44 and MMP-2/9 was downregulated, and the phosphorylation of AKT was downregulated, the transcription activity of NF-KB and the activity of ubiquitin proteasome were inhibited after Allomatrine treatment.
CONCLUSIONS:
Allomatrine was able to inhibit proliferation and invasion in vitro of human lung cancer A549 cell line by inducing ROS production, promoting apoptosis, arresting cell cycle, inhibiting ubiquitin proteasome and regulating tumor related gene expression.

In vivo

Implication of the descending dynorphinergic neuron projecting to the spinal cord in the (+)-matrine- and (+)-allomatrine-induced antinociceptive effects.[Pubmed: 15863891]

Biol Pharm Bull. 2005 May;28(5):845-8.

We previously reported that either (+)-matrine (matridin-15-one) or (+)-Allomatrine (the C-6 epimer of matrine)-induced antinociceptive effect was attenuated by s.c. pretreatment with a kappa-opioid receptor (KOR) antagonist nor-binaltorphimine (nor-BNI), indicating the critical role of KORs in antinociceptive effects induced by these alkaloids.
METHODS AND RESULTS:
In the present study, we found that i.c.v. administration of either (+)-matrine- or (+)-Allomatrine induced antinociceptive effects in the mouse tail-flick and warm-plate test, whereas these alkaloids when given spinally failed to induce antinociception. In the guanosine-5'-O-(3-[(35)S]thio)trisphosphate ([(35)S]GTPgammaS) binding assay, we demonstrated that neither (+)-matrine nor (+)-Allomatrine produced the stimulation of [(35)S]GTPgammaS binding in the membranes of the spinal cord, indicating that (+)-matrine- and (+)-Allomatrine-induced supraspinal antinociceptive actions was not due to a direct stimulation of KORs by these alkaloids. Therefore, we next investigated the involvement of dynorphin A (1-17) release at the spinal or supraspinal site in (+)-matrine- or (+)-Allomatrine-induced antinociception. The i.c.v. pretreatment with an antiserum against dynorphin A (1-17) could not affect the antinociceptive effect induced by s.c. treatment of (+)-matrine. In contrast, the s.c.-administered (+)-matrine- and (+)-Allomatrine-induced antinociceptive effect was significantly attenuated by i.t. pretreatment of an antiserum against dynorphin A (1-17).
CONCLUSIONS:
The present data suggest that either (+)-matrine or (+)-Allomatrine when given i.c.v. may stimulate the descending dynorphinergic neuron, resulting in the stimulation of KORs in the spinal cord, and this phenomenon in turn produces the antinociception in mice.

Protocol of Allomatrine

Structure Identification
Org Lett. 2013 Sep 6;15(17):4596-9.

Total synthesis of the tetracyclic lupin alkaloid (+)-allomatrine.[Pubmed: 23980915 ]

(+)-Allomatrine (1) has been synthesized using an imino-aldol reaction and N-acyliminium cyclization as key steps. Strategically, use of the tert-butylsulfinimine derivative of (E)-4-(trimethylsilyl)but-2-enal enabled the staged formation of three C-C bonds, a C-N bond, and the four stereogenic centers within the target.

Allomatrine Dilution Calculator

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Preparing Stock Solutions of Allomatrine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.0264 mL 20.1321 mL 40.2641 mL 80.5283 mL 100.6603 mL
5 mM 0.8053 mL 4.0264 mL 8.0528 mL 16.1057 mL 20.1321 mL
10 mM 0.4026 mL 2.0132 mL 4.0264 mL 8.0528 mL 10.066 mL
50 mM 0.0805 mL 0.4026 mL 0.8053 mL 1.6106 mL 2.0132 mL
100 mM 0.0403 mL 0.2013 mL 0.4026 mL 0.8053 mL 1.0066 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Allomatrine

Implication of the descending dynorphinergic neuron projecting to the spinal cord in the (+)-matrine- and (+)-allomatrine-induced antinociceptive effects.[Pubmed:15863891]

Biol Pharm Bull. 2005 May;28(5):845-8.

We previously reported that either (+)-matrine (matridin-15-one) or (+)-Allomatrine (the C-6 epimer of matrine)-induced antinociceptive effect was attenuated by s.c. pretreatment with a kappa-opioid receptor (KOR) antagonist nor-binaltorphimine (nor-BNI), indicating the critical role of KORs in antinociceptive effects induced by these alkaloids. In the present study, we found that i.c.v. administration of either (+)-matrine- or (+)-Allomatrine induced antinociceptive effects in the mouse tail-flick and warm-plate test, whereas these alkaloids when given spinally failed to induce antinociception. In the guanosine-5'-O-(3-[(35)S]thio)trisphosphate ([(35)S]GTPgammaS) binding assay, we demonstrated that neither (+)-matrine nor (+)-Allomatrine produced the stimulation of [(35)S]GTPgammaS binding in the membranes of the spinal cord, indicating that (+)-matrine- and (+)-Allomatrine-induced supraspinal antinociceptive actions was not due to a direct stimulation of KORs by these alkaloids. Therefore, we next investigated the involvement of dynorphin A (1-17) release at the spinal or supraspinal site in (+)-matrine- or (+)-Allomatrine-induced antinociception. The i.c.v. pretreatment with an antiserum against dynorphin A (1-17) could not affect the antinociceptive effect induced by s.c. treatment of (+)-matrine. In contrast, the s.c.-administered (+)-matrine- and (+)-Allomatrine-induced antinociceptive effect was significantly attenuated by i.t. pretreatment of an antiserum against dynorphin A (1-17). The present data suggest that either (+)-matrine or (+)-Allomatrine when given i.c.v. may stimulate the descending dynorphinergic neuron, resulting in the stimulation of KORs in the spinal cord, and this phenomenon in turn produces the antinociception in mice.

Total synthesis of the tetracyclic lupin alkaloid (+)-allomatrine.[Pubmed:23980915]

Org Lett. 2013 Sep 6;15(17):4596-9.

(+)-Allomatrine (1) has been synthesized using an imino-aldol reaction and N-acyliminium cyclization as key steps. Strategically, use of the tert-butylsulfinimine derivative of (E)-4-(trimethylsilyl)but-2-enal enabled the staged formation of three C-C bonds, a C-N bond, and the four stereogenic centers within the target.

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