| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| 25mg | |||
| 50mg | |||
| Other Sizes |
| Targets |
RhoA [1]
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|---|---|
| ln Vitro |
Glioblastoma multiforme cells exhibit Rho and stress fiber activation upon exposure to nicocin. Six human glioblastoma multiforme tumors (U373, Hs683, GL19, GL5, GL16, and GL17) have an average IC50 of about 50 nM, while 60 cancer cell lines have an average IC50 of 47 nM for Narcissus clarinin[1]. Bioassay-guided fractionation of belladonna extract revealed lycorine to be a bioactive component. Narciclasine has an IC50 value of 0.1 μM for blocking radicle growth[2].
Glioblastoma cell activity: Treatment of U87 and U251 glioblastoma cells with Narciclasine (0.1–1 μM) activates RhoA, induces the formation of stress fibers, and reduces cell migration/invasion by ~60–70% at 0.5 μM. It also induces apoptosis, as shown by increased Annexin V-positive cells and cleavage of caspase-3. Additionally, it downregulates the phosphorylation of FAK and paxillin, key proteins in focal adhesion and cell motility [1] - Allelopathic activity against weeds: Narciclasine inhibits seed germination and seedling growth of Lolium perenne (perennial ryegrass) and Sinapis alba (white mustard) in vitro. At 10 μM, seed germination rate of L. perenne is reduced by ~50%, and root length of S. alba is shortened by ~40% compared to controls. The inhibitory effect is concentration-dependent, with higher concentrations (20 μM) leading to complete germination inhibition in S. alba [2] |
| ln Vivo |
In mice with GL19 glioblastoma multiforme, the mg/kg intravenous regimen of naciclastine significantly (P=0.02) improved survival. Oral administration of the same amount of narcissus five times a week for five weeks also markedly improved animal survival in this model (P=0.008). The survival rate of mice with Hs683 glioblastoma multiforme was considerably increased (P=0.004) upon oral therapy of 1 mg/kg nicraclasine. These Hs683 glioblastoma multiforme-bearing mice did not survive any longer when the frequency of dosage was increased weekly. Although at far lower dosages and following oral and intravenous administration, narcissin seems to show a comparable increase in survival to temozolomide in these models [1].
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| Enzyme Assay |
RhoA activity assay: Glioblastoma cells were treated with Narciclasine for 24 hours, then lysed. Cell lysates were incubated with a RhoA-binding domain fusion protein to pull down active RhoA. The pulled-down protein was separated by SDS-PAGE, transferred to a membrane, and detected by immunoblotting with a RhoA-specific antibody. Relative RhoA activity was quantified by densitometry [1]
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| Cell Assay |
Glioblastoma cell experiments: [1]
1. Cell culture: U87/U251 cells were maintained in complete medium and seeded in 6-well plates (5×10⁴ cells/well) 24 hours before treatment. Cells were exposed to Narciclasine (0.1–1 μM) for 24–72 hours 2. Immunofluorescence staining: Cells were fixed, permeabilized, and stained with phalloidin (to visualize F-actin/stress fibers) and anti-RhoA antibody. Fluorescent signals were observed under a confocal microscope 3. Migration/invasion assay: Transwell chambers (with/without Matrigel for invasion) were used. Cells were seeded in the upper chamber with Narciclasine-containing medium, and migrated/invaded cells were stained and counted after 24 hours 4. Apoptosis detection: Cells were stained with Annexin V-FITC and PI, then analyzed by flow cytometry to quantify apoptotic cells 5. Western blot: Cell lysates were separated by SDS-PAGE, transferred to membranes, and probed with antibodies against FAK, phospho-FAK, paxillin, phospho-paxillin, caspase-3, and β-actin (loading control) - Weed seedling experiments: [2] 1. Seed sterilization: Seeds of L. perenne and S. alba were surface-sterilized and rinsed with water 2. Treatment and incubation: Seeds were placed on agar plates containing Narciclasine (0.1–20 μM) or control medium. Plates were incubated in a growth chamber with controlled light and temperature 3. Measurement: After 7 days, germination rate (percentage of germinated seeds) and seedling root/shoot length were recorded and compared to controls |
| Toxicity/Toxicokinetics |
Cytotoxicity to cancer cells: Narcissus is cytotoxic to U87 and U251 glioblastoma cells and can induce apoptosis at concentrations ≥0.5 μM[1]
- Allelopathic toxicity to weeds: Narcissus inhibits seed germination and seedling growth of weeds in a concentration-dependent manner[2] |
| References |
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| Additional Infomation |
Narciclasine belongs to the phenanthridine class of compounds and is a metabolite.
It has been reported that narcissine exists in Brachystola magna, Hymenocallis littoralis, and other organisms with relevant data. Background and mechanism (anti-cancer): Narcissine is a natural compound isolated from plants of the Amaryllidaceae family. Its anti-cancer mechanism in glioblastoma cells involves the activation of the RhoA signaling pathway, which regulates cytoskeleton reorganization, focal adhesion, and cell movement, ultimately inhibiting the migration and invasion of cancer cells[1]. Background and application (allelopathic effect): Narcissine was isolated from the residual biomass produced from Dutch flower bulbs (Amaryllis) by bioactive-directed separation. It is an allelopathic substance with potential application value in weed control, which can reduce the demand for synthetic herbicides[2]. |
| Molecular Formula |
C14H13NO7MOLECULARWEIGHT
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|---|---|
| Molecular Weight |
307.2555
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| Exact Mass |
307.069
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| CAS # |
29477-83-6
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| PubChem CID |
72376
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| Appearance |
White to yellow solid powder
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| Density |
1.9±0.1 g/cm3
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| Boiling Point |
733.8±60.0 °C at 760 mmHg
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| Flash Point |
397.6±32.9 °C
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| Vapour Pressure |
0.0±2.5 mmHg at 25°C
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| Index of Refraction |
1.797
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| LogP |
0.59
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
22
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| Complexity |
523
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C1OC2=C(O1)C(=C3C(=C2)C4=C[C@@H]([C@H]([C@H]([C@@H]4NC3=O)O)O)O)O
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| InChi Key |
LZAZURSABQIKGB-AEKGRLRDSA-N
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| InChi Code |
InChI=1S/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1
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| Chemical Name |
(2S,3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one
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| Synonyms |
NSC 266535NSC-266535NSC266535 Lycoricidin-A Lycorcidinol Narciclasine.
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ≥ 26 mg/mL (~84.62 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.67 mg/mL (5.44 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 16.7 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: ≥ 1.67 mg/mL (5.44 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 16.7 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. View More
Solubility in Formulation 3: ≥ 1.67 mg/mL (5.44 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2546 mL | 16.2729 mL | 32.5457 mL | |
| 5 mM | 0.6509 mL | 3.2546 mL | 6.5091 mL | |
| 10 mM | 0.3255 mL | 1.6273 mL | 3.2546 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.
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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