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| Targets |
Acetylcholinesterase (AChE) – molecular docking simulations showed interactions with the catalytic and peripheral sites of mouse AChE (mAChE), including residues His447, Trp86, Glu334, Ser203, Tyr124, Trp286, and Tyr341. [1]
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| ln Vitro |
vincosamide (30 mg/kg, oral administration for 7 days) significantly decreased AChE activity in mouse brain structures: in the cerebral cortex by 36±1% (p<0.001); in the hippocampus by 28±3% (p<0.05); in the hypothalamus by 14±2% (p<0.05); no significant effect was observed in the striatum. [1]
Molecular docking simulations revealed that vincosamide interacts with both the catalytic anionic site (active center: His447, Trp86, Glu334, Ser203) and the peripheral anionic site (PAS: Tyr124, Trp286, Tyr341) of mouse AChE. Hydrogen bonds were formed with His447, Tyr124, and Arg296, anchoring the ligand in the active site. [1] |
| ln Vivo |
Oral administration of vincosamide (3, 30, and 100 mg/kg) dose-dependently reduced carrageenan-induced paw edema in mice. At 100 mg/kg, inhibition was 61.30±3% at 1 h, 73.21±2% at 2 h, and 67.94±2% at 4 h (p<0.001 at 2 and 4 h). [1]
In the carrageenan-induced pleurisy model, vincosamide at 3, 30, and 100 mg/kg inhibited leukocyte migration by 76.41±1%, 88.35±2%, and 88.51±1% respectively (p<0.001 for all doses) 4 h after carrageenan injection. [1] vincosamide (100 mg/kg) significantly reduced mechanical hyperalgesia in mice: 70.00±2% inhibition at 3 h (p<0.01) and 90.86±4% inhibition at 4 h (p<0.001) after carrageenan injection. [1] vincosamide (100 mg/kg) reduced cold sensitivity induced by acetone: 63.81±2% reduction at 3 h and 64.28±2% at 4 h after carrageenan injection (p<0.001 for both). [1] Oral administration of vincosamide (30 mg/kg) for 7 days significantly inhibited AChE activity in the cerebral cortex (36±1%, p<0.001), hippocampus (28±3%, p<0.05), and hypothalamus (14±2%, p<0.05) compared to control. [1] |
| Enzyme Assay |
Acetylcholinesterase (AChE) activity was measured in mouse brain structures (cerebral cortex, hippocampus, hypothalamus, striatum). Tissues were homogenized in 10 mM Tris-HCl buffer (pH 7.4, 1:10 w/v) and centrifuged at 3500 rpm for 10 min at 4°C. The supernatant was used for the assay. The reaction mixture contained DTNB (1.04 mmol), potassium phosphate buffer (24 mmol, pH 7.2), and 25 mL of sample, pre-incubated for 2 min at 30°C. The reaction was initiated by adding acetylthiocholine iodide (0.8 mM). The product was measured at 412 nm for 2 min. Enzyme activity was expressed as μmol ACSCh/h/mg protein. Protein concentration was determined by Coomassie blue method using bovine serum albumin as standard (cerebral cortex 0.7 mg/mL, hippocampus 0.8 mg/mL, hypothalamus 0.6 mg/mL, striatum 0.4 mg/mL). [1]
Molecular docking simulations were performed using Molegro Virtual Docker v6.0. The crystal structure of mouse AChE (mAChE) complexed with choline (PDB ID: 2HA3) was obtained from the Protein Data Bank. All water molecules and ions were removed. The docking protocol used Moldock Score as scoring function and Moldock Optimizer as search algorithm, with a search sphere radius of 11 Å around the catalytic site. The enzyme torsion angles were restricted, while the ligand was allowed flexibility. Redocking simulations were repeated five times, and results were reproducible. [1] |
| Animal Protocol |
For anti-inflammatory tests, male or female Swiss mice (50 days old, 20-30 g, n=6 per group) were used. vincosamide was dissolved in saline solution (0.9% NaCl) and administered orally (p.o.) at doses of 3, 30, or 100 mg/kg, 1 hour before carrageenan induction. Positive control was dexamethasone (DEX, 1 mg/kg, p.o.). [1]
Paw edema: Carrageenan (300 μg/paw, 50 μL in sterile 0.9% saline) was injected into the paw. Edema was measured at 1, 2, and 4 h using a paw plethysmometer. [1] Pleurisy: Carrageenan (300 μg, 0.1 mL in PBS, pH 7.4) was injected into the pleural cavity. After 4 h, exudate was collected and total leukocytes were counted using a Neubauer chamber after dilution in Turk solution (1:20). [1] Mechanical hyperalgesia: An electronic von Frey test (analgesymeter) was used. Carrageenan (300 μg/paw) was injected intrapulnarly into the right hind paw, and saline into the left. Withdrawal thresholds were measured at 3 and 4 h post-carrageenan. [1] Cold thermal stimulation (acetone test): Acetone (20 μL) was applied to the plantar surface of the right hind paw. Paw licking, shaking, or rubbing was recorded over 30 s at 3 and 4 h post-carrageenan. [1] For AChE assay, mice were treated orally for 7 days with vincosamide (30 mg/kg), and on the last day, 1 h after the last dose, animals were decapitated. Brains were collected and dissected into cerebral cortex, hippocampus, hypothalamus, and striatum. [1] Acute toxicity study followed protocol 425. A single oral dose of vincosamide was not tested; the methanolic extract (ME-PL) was tested up to 2000 mg/kg. No deaths or clinical signs of toxicity were observed over 14 days. [1] |
| Toxicity/Toxicokinetics |
Acute toxicity of the methanolic extract of P. leiocarpa (ME-PL) was evaluated, but vincosamide itself was not tested for toxicity. In the ME-PL acute toxicity study (doses up to 2000 mg/kg, oral), no clinical signs of toxicity or deaths were observed over 14 days. The LD50 could not be determined. [1]
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| References | |
| Additional Infomation |
Vincristine is a monoterpenoid indole alkaloid. It has been reported to exist in Uncaria rhynchophylla, Ceratophyllum demersum, and other organisms with relevant data.
vincosamide was isolated from Psychotria leiocarpa leaves collected in Dourados, Mato Grosso do Sul, Brazil. This is the first report of vincosamide in this species. The compound was quantified by HPLC, yielding 138.9 ± 0.3 mg/g of the methanolic extract (retention time 24.10 min). The structure was confirmed by 1H and 13C NMR spectroscopy. The alkaloid may be responsible, at least in part, for the anti-inflammatory and anticholinesterase effects observed. The study supports the traditional use of Psychotria genus for inflammatory diseases. [1] |
| Molecular Formula |
C26H30N2O8
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|---|---|
| Molecular Weight |
498.5250
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| Exact Mass |
498.2
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| CAS # |
23141-27-7
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| PubChem CID |
10163855
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| Appearance |
Off-white to light yellow solid
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
816.2±65.0 °C at 760 mmHg
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| Flash Point |
447.4±34.3 °C
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| Vapour Pressure |
0.0±3.1 mmHg at 25°C
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| Index of Refraction |
1.716
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| LogP |
-0.55
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
36
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| Complexity |
899
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| Defined Atom Stereocenter Count |
9
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| SMILES |
O1C([H])=C2C(N3C([H])([H])C([H])([H])C4C5=C([H])C([H])=C([H])C([H])=C5N([H])C=4[C@@]3([H])C([H])([H])[C@@]2([H])[C@@]([H])(C([H])=C([H])[H])[C@]1([H])O[C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)O[H])O[H])O[H])=O
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| InChi Key |
LBRPLJCNRZUXLS-AZVRXDBZSA-N
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| InChi Code |
InChI=1S/C26H30N2O8/c1-2-12-15-9-18-20-14(13-5-3-4-6-17(13)27-20)7-8-28(18)24(33)16(15)11-34-25(12)36-26-23(32)22(31)21(30)19(10-29)35-26/h2-6,11-12,15,18-19,21-23,25-27,29-32H,1,7-10H2/t12-,15+,18-,19-,21-,22+,23-,25+,26+/m1/s1
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| Chemical Name |
(1R,18S,19R,20S)-19-ethenyl-18-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,15-pentaen-14-one
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0059 mL | 10.0295 mL | 20.0590 mL | |
| 5 mM | 0.4012 mL | 2.0059 mL | 4.0118 mL | |
| 10 mM | 0.2006 mL | 1.0029 mL | 2.0059 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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