Lycorine

CAS# 476-28-8

Lycorine

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Quality Control of Lycorine

Number of papers citing our products

Chemical structure

Lycorine

3D structure

Chemical Properties of Lycorine

Cas No. 476-28-8 SDF Download SDF
PubChem ID 72378 Appearance Powder
Formula C16H17NO4 M.Wt 287.31
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES C1CN2CC3=CC4=C(C=C3C5C2C1=CC(C5O)O)OCO4
Standard InChIKey XGVJWXAYKUHDOO-DANNLKNASA-N
Standard InChI InChI=1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2/t11-,14-,15+,16+/m0/s1
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 Lycorine

The bulbus of Lycoris radiata (L. Herit.) Herb

Biological Activity of Lycorine

DescriptionLycorine is a toxic crystalline alkaloid found in various Amaryllidaceae species that weakly inhibits acetylcholinesterase (AChE) and ascorbic acid biosynthesis.Lycorine has antiviral, and anti-cancer effects, the mechanisms of Lycorine on the multiple myeloma cell line ARH-77 are associated with G1 phase cell cycle arrest, mitochondrial dysfunction, reactive oxygen species (ROS) generation, ATP depletion, and DNA damage.
TargetsROS | JAK | STAT | Histone Demethylase | p53 | p21 | AChE | ATP
In vitro

Lycorine induces programmed necrosis in the multiple myeloma cell line ARH-77.[Pubmed: 25487618]

Tumour Biol. 2015 Apr;36(4):2937-45.

Lycorine, a natural alkaloid, has been widely reported to possess potential efficacy against cancer. However, the anti-multiple myeloma mechanism of Lycorine is not fully understood.
METHODS AND RESULTS:
In this study, the results demonstrated that Lycorine is effective against multiple myeloma cell line ARH-77 via inducing programmed necrosis. The mechanisms of Lycorine on the multiple myeloma cell line ARH-77 are associated with G1 phase cell cycle arrest, mitochondrial dysfunction, reactive oxygen species (ROS) generation, ATP depletion, and DNA damage.
CONCLUSIONS:
Our results elucidate the new mechanism of Lycorine against multiple myeloma.

In vivo

Lycorine is a novel inhibitor of the growth and metastasis of hormone-refractory prostate cancer.[Pubmed: 25915156]

Oncotarget. 2015 Apr 12.

Lycorine, a natural alkaloid extracted from the Amaryllidaceae plant family, has been reported to exhibit a wide range of physiological effects, including the potential effect against cancer. However, the anti-prostate cancer (PCa) efficacy of Lycorine remains unrevealed. In this context, we figured out Lycorine's anti-proliferative and anti-migratory properties for PCa treatment. Lycorine inhibited proliferation of various PCa cell lines, induced cell apoptosis and cell death.
METHODS AND RESULTS:
Here we showed that Lycorine decreased proliferation, migration, invasion, survival and EMT of prostate cancer cell lines. Subcutaneous and orthotopic xenotransplantations by ectopic implantation of the human hormone-refractory PC-3M-luc cells were used to confirm in vivo anticancer effects of Lycorine. Lycorine inhibited both growth and metastasis in multiple organs (liver, lung, kidney, spleen and bone) in vivo and improved mice survival. Lycorine prevented EGF-induced JAK/STAT signaling. Importantly, anti-cancer effects of Lycorine were dependent on STAT expression.
CONCLUSIONS:
We suggest that Lycorine is a potential therapeutic in prostate cancer.

Protocol of Lycorine

Cell Research

Lycorine induces cell-cycle arrest in the G0/G1 phase in K562 cells via HDAC inhibition.[Pubmed: 23176676]

Cancer Cell Int. 2012 Nov 23;12(1):49.

Lycorine, a natural alkaloid extracted from Amaryllidaceae, has shown various pharmacological effects. Recent studies have focused on the potential antitumor activity of Lycorine. In our previous study, we found that Lycorine decrease the cell viability of leukemia HL-60 cells and multiple myeloma KM3 cells and induces cell apoptosis. However, the effect and molecular mechanism of Lycorine on human chronic myelocytic leukemia cells has yet to be determined.
METHODS AND RESULTS:
Human chronic myelocytic leukemia cells K562 were treated with Lycorine. Cell viability was monitored using the method of CCK-8. The histone deacetylase (HDAC) enzymatic activity was detected by HDAC colorimetric assay, and the cell cycle was analyzed by flow cytometry. The expression of cell-cycle related proteins were identified using Western blot. In the present study, we further revealed that Lycorine can inhibit the proliferation of K562 cells. Analysis of HDAC activity showed that lycroine decreases HDAC enzymatic activities in K562 cells in a dose-dependent manner. Inhibition of HDAC activity has been associated with cell-cycle arrest and growth inhibition. We evaluated the cell cycle distribution after Lycorine treatment and found that Lycorine causes cell-cycle arrest in the G0/G1 phase. To investigate the mechanism behind this cell cycle arrest, G1-related proteins were assayed by Western blot. After Lycorine treatment, cyclin D1 and cyclin-dependent kinase 4 expressions were inhibited and retinoblastoma protein phosphorylation was reduced. Lycorine treatment also significantly upregulated the expression of p53 and its target gene product, p21.
CONCLUSIONS:
These results suggest that inhibition of HDAC activity is responsible for at least part of the induction of cell-cycle arrest in the G0/G1 phase by Lycorine and provide a mechanistic framework for further exploring the use of Lycorine as a novel antitumor agent.

Structure Identification
ChemMedChem. 2014 Jul;9(7):1522-33.

Anti-dengue-virus activity and structure-activity relationship studies of lycorine derivatives.[Pubmed: 24574246]

Dengue is a systemic viral infection that is transmitted to humans by Aedes mosquitoes. No vaccines or specific therapeutics are currently available for dengue. Lycorine, which is a natural plant alkaloid, has been shown to possess antiviral activities against flaviviruses.
METHODS AND RESULTS:
In this study, a series of novel Lycorine derivatives were synthesized and assayed for their inhibition of dengue virus (DENV) in cell cultures. Among the Lycorine analogues, 1-acetylLycorine exhibited the most potent anti-DENV activity (EC50 =0.4 μM) with a reduced cytotoxicity (CC50 >300 μM), which resulted in a selectivity index (CC50 /EC50 ) of more than 750. The ketones 1-acetyl-2-oxoLycorine (EC50 =1.8 μM) and 2-oxoLycorine (EC50 =0.5 μM) also exhibited excellent antiviral activities with low cytotoxicity. Structure-activity relationships for the Lycorine derivatives against DENV are discussed. A three-dimensional quantitative structure-activity relationship model was established by using a comparative molecular-field analysis protocol in order to rationalize the experimental results.
CONCLUSIONS:
Further modifications of the hydroxy group at the C1 position with retention of a ketone at the C2 position could potentially lead to inhibitors with improved overall properties.

Lycorine Dilution Calculator

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Lycorine Molarity Calculator

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Preparing Stock Solutions of Lycorine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.4806 mL 17.4028 mL 34.8056 mL 69.6112 mL 87.014 mL
5 mM 0.6961 mL 3.4806 mL 6.9611 mL 13.9222 mL 17.4028 mL
10 mM 0.3481 mL 1.7403 mL 3.4806 mL 6.9611 mL 8.7014 mL
50 mM 0.0696 mL 0.3481 mL 0.6961 mL 1.3922 mL 1.7403 mL
100 mM 0.0348 mL 0.174 mL 0.3481 mL 0.6961 mL 0.8701 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 Lycorine

Lycorine is a novel inhibitor of the growth and metastasis of hormone-refractory prostate cancer.[Pubmed:25915156]

Oncotarget. 2015 Jun 20;6(17):15348-61.

Lycorine, a natural alkaloid extracted from the Amaryllidaceae plant family, has been reported to exhibit a wide range of physiological effects, including the potential effect against cancer. However, the anti-prostate cancer (PCa) efficacy of Lycorine remains unrevealed. In this context, we figured out Lycorine's anti-proliferative and anti-migratory properties for PCa treatment. Lycorine inhibited proliferation of various PCa cell lines, induced cell apoptosis and cell death. Here we showed that Lycorine decreased proliferation, migration, invasion, survival and EMT of prostate cancer cell lines. Subcutaneous and orthotopic xenotransplantations by ectopic implantation of the human hormone-refractory PC-3M-luc cells were used to confirm in vivo anticancer effects of Lycorine. Lycorine inhibited both growth and metastasis in multiple organs (liver, lung, kidney, spleen and bone) in vivo and improved mice survival. Lycorine prevented EGF-induced JAK/STAT signaling. Importantly, anti-cancer effects of Lycorine were dependent on STAT expression. We suggest that Lycorine is a potential therapeutic in prostate cancer.

Lycorine induces cell-cycle arrest in the G0/G1 phase in K562 cells via HDAC inhibition.[Pubmed:23176676]

Cancer Cell Int. 2012 Nov 23;12(1):49.

UNLABELLED: BACKGROUND: Lycorine, a natural alkaloid extracted from Amaryllidaceae, has shown various pharmacological effects. Recent studies have focused on the potential antitumor activity of Lycorine. In our previous study, we found that Lycorine decrease the cell viability of leukemia HL-60 cells and multiple myeloma KM3 cells and induces cell apoptosis. However, the effect and molecular mechanism of Lycorine on human chronic myelocytic leukemia cells has yet to be determined. METHODS: Human chronic myelocytic leukemia cells K562 were treated with Lycorine. Cell viability was monitored using the method of CCK-8. The histone deacetylase (HDAC) enzymatic activity was detected by HDAC colorimetric assay, and the cell cycle was analyzed by flow cytometry. The expression of cell-cycle related proteins were identified using Western blot. RESULTS: In the present study, we further revealed that Lycorine can inhibit the proliferation of K562 cells. Analysis of HDAC activity showed that lycroine decreases HDAC enzymatic activities in K562 cells in a dose-dependent manner. Inhibition of HDAC activity has been associated with cell-cycle arrest and growth inhibition. We evaluated the cell cycle distribution after Lycorine treatment and found that Lycorine causes cell-cycle arrest in the G0/G1 phase. To investigate the mechanism behind this cell cycle arrest, G1-related proteins were assayed by Western blot. After Lycorine treatment, cyclin D1 and cyclin-dependent kinase 4 expressions were inhibited and retinoblastoma protein phosphorylation was reduced. Lycorine treatment also significantly upregulated the expression of p53 and its target gene product, p21. CONCLUSIONS: These results suggest that inhibition of HDAC activity is responsible for at least part of the induction of cell-cycle arrest in the G0/G1 phase by Lycorine and provide a mechanistic framework for further exploring the use of Lycorine as a novel antitumor agent.

Anti-dengue-virus activity and structure-activity relationship studies of lycorine derivatives.[Pubmed:24574246]

ChemMedChem. 2014 Jul;9(7):1522-33.

Dengue is a systemic viral infection that is transmitted to humans by Aedes mosquitoes. No vaccines or specific therapeutics are currently available for dengue. Lycorine, which is a natural plant alkaloid, has been shown to possess antiviral activities against flaviviruses. In this study, a series of novel Lycorine derivatives were synthesized and assayed for their inhibition of dengue virus (DENV) in cell cultures. Among the Lycorine analogues, 1-acetylLycorine exhibited the most potent anti-DENV activity (EC50 =0.4 muM) with a reduced cytotoxicity (CC50 >300 muM), which resulted in a selectivity index (CC50 /EC50 ) of more than 750. The ketones 1-acetyl-2-oxoLycorine (EC50 =1.8 muM) and 2-oxoLycorine (EC50 =0.5 muM) also exhibited excellent antiviral activities with low cytotoxicity. Structure-activity relationships for the Lycorine derivatives against DENV are discussed. A three-dimensional quantitative structure-activity relationship model was established by using a comparative molecular-field analysis protocol in order to rationalize the experimental results. Further modifications of the hydroxy group at the C1 position with retention of a ketone at the C2 position could potentially lead to inhibitors with improved overall properties.

Lycorine induces programmed necrosis in the multiple myeloma cell line ARH-77.[Pubmed:25487618]

Tumour Biol. 2015 Apr;36(4):2937-45.

Lycorine, a natural alkaloid, has been widely reported to possess potential efficacy against cancer. However, the anti-multiple myeloma mechanism of Lycorine is not fully understood. In this study, the results demonstrated that Lycorine is effective against multiple myeloma cell line ARH-77 via inducing programmed necrosis. The mechanisms of Lycorine on the multiple myeloma cell line ARH-77 are associated with G1 phase cell cycle arrest, mitochondrial dysfunction, reactive oxygen species (ROS) generation, ATP depletion, and DNA damage. Our results elucidate the new mechanism of Lycorine against multiple myeloma.

Description

Lycorine is a natural alkaloid extracted from the Amaryllidaceae plant family with antiviral, antimalarial and antiinflammation activities. Lycorine inhibits the growth and metastasis of hormone-refractory anti-prostate cancer (PCa) and induces cell apoptosis.

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