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| Targets |
Amarogentin targets multiple cellular pathways and proteins. It acts as an agonist of the bitter taste receptor TAS2R1. It also interacts with AMP-activated protein kinase (AMPK), specifically the α2 subunit, activating the trimeric kinase with an EC₅₀ of 277 pM. Furthermore, Amarogentin inhibits topoisomerase I, preventing DNA replication and transcription. It promotes apoptosis, arrests the cell cycle at the G2/M phase, and downregulates the PI3K/Akt/mTOR signaling pathway. Molecular docking studies also suggest it inhibits cyclooxygenase-2 (COX-2).
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| ln Vitro |
Through transcription factors, amarogentin (0–20 μM, 24 hours) suppresses H2O2-induced oxidative damage in PC12 cells, reducing intracellular oxidative damage [3]. MDA content and ROS levels)[3].
In vitro, Amarogentin demonstrates significant antiproliferative activity. It inhibits the growth of human gastric cancer SNU-16 cells with an IC₅₀ of 12.4 µM after 48 hours of treatment. At a concentration of 50 µM, it increases apoptosis in these cells. Amarogentin also inhibits substance P-induced TNF-α production in LAD-2 cells. Its mechanism involves promoting apoptosis, arresting the cell cycle at G2/M, and downregulating the PI3K/Akt/mTOR signaling pathway. The compound's anti-tumor effects are linked to its ability to modulate cell cycle and apoptotic pathways. |
| ln Vivo |
Amarogentin (100 mg/kg, face) can ameliorate carbon tetrachloride-induced liver fibrosis and lower the expression of α-SMA and TGF-β1 in mice [1].
In vivo, Amarogentin has shown efficacy in mouse models. In a SNU-16 xenograft model, subcutaneous administration of Amarogentin (10-50 mg/kg) dose-dependently reduced tumor growth. It also helps inhibit skin carcinogenesis in mouse models by downregulating cyclooxygenase-2 (COX-2) activity. The compound exhibits various activities in different pathophysiological conditions, notably in leishmaniasis and carcinogenesis. These studies confirm its chemopreventive and therapeutic potential in vivo. |
| Enzyme Assay |
In vitro enzyme/receptor binding studies for Amarogentin involve several assays. Its activation of AMPK can be studied by measuring the phosphorylation of AMPK and its downstream target acetyl-CoA carboxylase (ACC) in cell lysates using Western blot. Its inhibition of topoisomerase I can be assessed using a DNA relaxation assay, where the compound's ability to prevent the enzyme from relaxing supercoiled DNA is measured. Molecular docking and dynamics simulations are used to study its binding and inhibitory mechanism on COX-2. These protocols are for reference only.
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| Cell Assay |
In vitro cell-based assays for Amarogentin are performed to evaluate its anti-cancer and anti-inflammatory activities. For cytotoxicity, cancer cell lines such as SNU-16 are cultured in appropriate media and treated with various concentrations of the compound for 48-72 hours. Cell viability is measured using MTT or CCK-8 assays. Apoptosis is assessed by flow cytometry using Annexin V/PI staining. Cell cycle analysis is performed using propidium iodide staining. For anti-inflammatory activity, LAD-2 cells can be stimulated with substance P, and TNF-α levels in the supernatant are measured by ELISA.
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| Animal Protocol |
Animal/Disease Models: Carbon tetrachloride-induced liver fibrosis mouse model [1] ]
Doses: 100 mg/kg Route of Administration: Oral Experimental Results:diminished expression of hepatic α-SMA and TGF-β1. Inhibits the phosphorylation of JNK, ERK and p38. In vivo animal studies for Amarogentin typically use xenograft mouse models. For example, nude mice bearing SNU-16 tumors are treated with Amarogentin via subcutaneous injection at doses of 10, 25, or 50 mg/kg. Tumor volumes are measured with calipers, and tumor weights are recorded at the end of the study. For skin cancer models, the compound is applied topically, and the number and size of tumors are monitored. Pharmacodynamic markers such as COX-2 expression in tumor tissues can be analyzed by immunohistochemistry. All procedures must comply with institutional animal care guidelines. |
| ADME/Pharmacokinetics |
The pharmacokinetic properties of Amarogentin are not fully characterized in the available literature. As a glycoside, its oral bioavailability may be limited. The compound has a molecular weight of 586.54 g/mol. It is typically administered via subcutaneous injection in animal studies. Further studies are needed to determine its absorption, distribution, metabolism, and excretion (ADME) profile. For research use, the compound is stored as a powder at -25 to -15°C for up to 3 years, and in solvent at -85 to -65°C for up to 2 years.
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| Toxicity/Toxicokinetics |
The toxicity profile of Amarogentin is not extensively detailed in public literature. It is classified for research use only and not for human consumption. As a natural product with multiple biological activities, its safety profile requires further investigation. In animal studies, it was administered at doses up to 50 mg/kg without reported overt toxicity. General safety precautions for handling bioactive compounds should be followed, including the use of personal protective equipment.
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| References |
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| Additional Infomation |
Amagargine is a secoiridinol glycoside with the structure (4aS,5R,6R)-5-vinyl-6-hydroxy-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one, with a 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-β-D-glucopyranosyl linked at position 6 via a glycosidic bond. It is an EC 5.99.1.2 (DNA topoisomerase) inhibitor and metabolite. It is a secoiridinol glycoside and monosaccharide derivative. Amagargine has been reported in Swertia japonica, Gentianella nitida, and several other organisms with relevant data.
Additional information: Amarogentin is also known as苦龙胆酯苷 and has the CAS number 21018-84-8. Its purity is typically ≥98%. The compound is soluble in DMSO. Its primary application is in research on cancer, diabetes, and inflammation, where it serves as a tool to study AMPK activation, apoptosis, and the PI3K/Akt/mTOR pathway. Amarogentin is not approved for clinical use and is intended for research purposes only. |
| Molecular Formula |
C29H30O13
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| Molecular Weight |
586.5407
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| Exact Mass |
586.168
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| CAS # |
21018-84-8
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| PubChem CID |
115149
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
928.5±65.0 °C at 760 mmHg
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| Melting Point |
229-230ºC
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| Flash Point |
306.9±27.8 °C
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| Vapour Pressure |
0.0±0.3 mmHg at 25°C
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| Index of Refraction |
1.693
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| LogP |
2.79
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
13
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
42
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| Complexity |
1020
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| Defined Atom Stereocenter Count |
8
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| SMILES |
C=C[C@@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)C4=C(C=C(C=C4O)O)C5=CC(=CC=C5)O
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| InChi Key |
DBOVHQOUSDWAPQ-WTONXPSSSA-N
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| InChi Code |
InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1
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| Chemical Name |
[(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate
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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 : ~100 mg/mL (~170.49 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.17 mg/mL (3.70 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 21.7 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: ≥ 2.17 mg/mL (3.70 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 21.7 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: ≥ 2.17 mg/mL (3.70 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 | 1.7049 mL | 8.5246 mL | 17.0491 mL | |
| 5 mM | 0.3410 mL | 1.7049 mL | 3.4098 mL | |
| 10 mM | 0.1705 mL | 0.8525 mL | 1.7049 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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