| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 25mg |
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| Targets |
α adrenergic receptor
Dicentrine targets multiple molecular targets. It acts as an alpha1-adrenoceptor antagonist, modulating vascular smooth muscle responses. The compound also inhibits topoisomerase II, displaying antitumor effects. Additionally, dicentrine modulates calcium channels and influences vascular smooth muscle responses. The compound's diverse pharmacological activities are mediated through these multiple targets, making it valuable in cardiovascular and oncology research. It has been shown to inhibit tumor cell proliferation through its effects on topoisomerase II. |
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| ln Vitro |
In vitro studies have demonstrated that dicentrine exhibits a wide range of pharmacological activities. It has been shown to inhibit tumor cell proliferation, modulate calcium channels, and influence vascular smooth muscle responses. The compound displays antitumor effects through inhibition of topoisomerase II. Dicentrine has anti-inflammatory, antioxidant, and vasorelaxant effects. As an alpha1-adrenoceptor antagonist, it modulates vascular smooth muscle tone. The compound's in vitro activities have been characterized in various cell-based and biochemical assays. Its diverse pharmacological profile makes it a valuable compound for cardiovascular and oncology research.
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| ln Vivo |
In vivo studies have demonstrated the antihypertensive effect of dicentrine. The compound's activity as an alpha1-adrenoceptor antagonist contributes to its vasorelaxant and antihypertensive effects in animal models. Dicentrine's antitumor effects through topoisomerase II inhibition have also been studied in vivo. The compound has been evaluated in various animal models for its cardiovascular and anticancer activities. Its diverse pharmacological activities, including anti-inflammatory and antioxidant effects, have been demonstrated in vivo. Dicentrine's effects on vascular smooth muscle and tumor growth have been documented in preclinical studies.
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| Enzyme Assay |
The in vitro enzyme/receptor binding assay for dicentrine typically involves studying its interactions with alpha1-adrenoceptors and topoisomerase II. For alpha1-adrenoceptor binding, membrane preparations from cells expressing the receptor are incubated with radiolabeled alpha1-adrenoceptor antagonist (e.g., 3H-prazosin) and varying concentrations of dicentrine (typically 0.001-100 uM) in binding buffer at room temperature for 1-2 hours. Bound and free ligand are separated by filtration, and radioactivity is measured by scintillation counting. For topoisomerase II inhibition, purified topoisomerase II is incubated with dicentrine and DNA substrates, and the extent of DNA relaxation or cleavage is assessed by gel electrophoresis. The inhibition constant (Ki) or IC50 is determined from dose-response data.
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| Cell Assay |
In vitro cellular assays for dicentrine are conducted using cancer cell lines and vascular smooth muscle cells. For antitumor studies, cancer cells are seeded in 96-well plates and treated with varying concentrations of dicentrine (typically 0.1-100 uM) for 24-72 hours. Cell viability is assessed using MTT, CellTiter-Glo, or crystal violet staining assays. Apoptosis is evaluated using Annexin V-FITC/PI double staining or by measuring caspase-3/7 activity. Topoisomerase II activity in cells is assessed by measuring DNA relaxation or cleavage in nuclear extracts. For vascular studies, vascular smooth muscle cells are treated with dicentrine and calcium mobilization is measured using fluorescent calcium indicators. Vasorelaxant effects are assessed using isolated aortic ring preparations.
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| Animal Protocol |
In vivo animal studies for dicentrine typically involve administration to rodent models to assess its antihypertensive and antitumor effects. For antihypertensive studies, spontaneously hypertensive rats or normotensive rats are administered dicentrine by intravenous injection or oral gavage at doses ranging from 0.1-10 mg/kg. Blood pressure is measured by tail-cuff plethysmography or radiotelemetry. For antitumor studies, mice bearing xenograft tumors are treated with dicentrine by intraperitoneal or intravenous injection at doses ranging from 1-50 mg/kg. Tumor volumes are measured with calipers, and tumor growth inhibition is calculated. Body weights and clinical observations are monitored for toxicity. At study termination, tissues are harvested for histological examination and biomarker analysis.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of dicentrine have been partially characterized. The compound has a molecular weight of 339.4 g/mol and a molecular formula of C20H21NO4. It is freely soluble in chloroform, ethyl acetate, acetone, benzene, and hot alcohol, and moderately soluble in ether and cold alcohol. It is also soluble in DMSO. The compound appears as white powder with a melting point of 178-179degC. The compound is a natural alkaloid with a defined chemical structure. Detailed ADME parameters such as half-life, bioavailability, and plasma protein binding are not extensively documented in the available literature.
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| Toxicity/Toxicokinetics |
Toxicity Summary
Studies on the rat thoracic aorta revealed that dihydroflavonoids are potent α1-adrenergic receptor blockers, exhibiting competitive antagonism against norepinephrine (pA2 = 8.19 +/- 0.09) or phenylephrine (pA2 = 9.01 +/- 0.10)-induced vasoconstriction. These effects persisted even in aortas with endothelium removed. Dihydroflavonoids inhibited platelet aggregation and release responses by suppressing thromboxane production and increasing adenosine 3':S'-cyclic monophosphate (A15323) levels. d-Dihydroflavonoids significantly inhibited the growth of the human hepatocellular carcinoma cell line HuH-7, delaying its doubling time in tissue culture. In vitro colony formation assays showed that d-Dihydroflavonoids reduced the colony formation efficiency of both the HuH-7 and MS-G2 hepatocellular carcinoma cell lines. MTT assays conducted on 21 tumor cell lines also showed that d-dihydroflavonoids exhibited the strongest cytotoxicity against esophageal cancer HCE-6 cells, lymphoma cell lines Molt-4 and CESS, leukemia cell lines HL60 and K562, and liver cancer cell line MS-G2. (A15341) Dihydroflavonoids are also a selective α1-adrenergic receptor antagonist with potent antiarrhythmic and antihypertensive activity. (A15324) The toxicological profile of dicentrine is characteristic of a naturally occurring alkaloid. As an alpha1-adrenoceptor antagonist and topoisomerase II inhibitor, the compound may have effects on cardiovascular function and cell proliferation. The compound is for research use only and is not intended for human therapeutic use. Standard safety precautions should be followed when handling the compound in a laboratory setting. No specific LD50 values or detailed toxicity profiles have been reported. The compound's diverse pharmacological activities suggest that it should be handled with care, particularly given its effects on cell proliferation and vascular function. |
| References | |
| Additional Infomation |
Dicentrine alkaloids are apophene alkaloids. They have been reported in Illigera luzonensis, Lindera megaphylla, and other organisms with available data. Dicentrine alkaloids are also an anticancer compound isolated from the flowering plant Lindera.
Dicentrine (CAS 517-66-8) is a naturally occurring aporphine alkaloid found in several plant species, mainly from the family Lauraceae, including Lindera megaphylla. It is also known as (+)-Dicentrine, Eximine, and O,N-Dimethyllitseferine. The compound acts as an alpha1-adrenoceptor antagonist and displays antitumor effects through inhibition of topoisomerase II. It exhibits diverse pharmacological activities including anti-inflammatory, antioxidant, vasorelaxant, and anticancer effects. The compound modulates calcium channels and influences vascular smooth muscle responses, making it valuable in cardiovascular and oncology research. It is available for research purposes only. |
| Molecular Formula |
C20H21NO4
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|---|---|
| Molecular Weight |
339.38504
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| Exact Mass |
339.147
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| Elemental Analysis |
C, 70.78; H, 6.24; N, 4.13; O, 18.86
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| CAS # |
517-66-8
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| PubChem CID |
101300
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| Appearance |
Off-white to light brown solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
480.7±45.0 °C at 760 mmHg
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| Melting Point |
177-178ºC
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| Flash Point |
142.7±25.9 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.616
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| LogP |
3.98
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
25
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| Complexity |
502
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CN1CCC2=CC3=C(C4=C2[C@@H]1CC5=CC(=C(C=C54)OC)OC)OCO3
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| InChi Key |
YJWBWQWUHVXPNC-AWEZNQCLSA-N
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| InChi Code |
InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m0/s1
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| Chemical Name |
(12S)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene
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| Synonyms |
d-Dicentrine; Dicentrine; Eximine
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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: ~10 mg/mL (~29.5 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1 mg/mL (2.95 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 10.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of 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 mg/mL (2.95 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 10.0 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 mg/mL (2.95 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 | 2.9465 mL | 14.7323 mL | 29.4646 mL | |
| 5 mM | 0.5893 mL | 2.9465 mL | 5.8929 mL | |
| 10 mM | 0.2946 mL | 1.4732 mL | 2.9465 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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