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| Targets |
The primary target of 1,10-Bis(pyridinium)decane is acetylcholinesterase (AChE), an enzyme responsible for hydrolyzing the neurotransmitter acetylcholine in the synaptic cleft. By inhibiting AChE, it prevents the breakdown of acetylcholine, leading to its accumulation and prolonged stimulation of cholinergic receptors (muscarinic and nicotinic). It belongs to the class of bis-quaternary ammonium compounds, which bind to the peripheral anionic site (PAS) and possibly the catalytic site of AChE. Its IC50 for AChE is 25.8 nM, indicating high potency. It also acts on the Neuronal Signaling pathway.
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| ln Vitro |
In vitro, 1,10-Bis(pyridinium)decane is a potent acetylcholinesterase inhibitor with an IC50 of 25.8 nM. This has been determined using purified AChE from electric eel or human erythrocytes. It acts as a reversible antagonist. Its activity is specific to AChE compared to butyrylcholinesterase (BuChE), though it may inhibit both. At higher concentrations (>1 uM), it may block nicotinic acetylcholine receptors (nAChRs) due to the decamethonium-like structure (a known neuromuscular blocking agent). However, at low nanomolar concentrations, its AChE inhibitory activity is the dominant effect. It is used in research to study the role of AChE in synaptic transmission.
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| ln Vivo |
Specific in vivo activity data for 1,10-Bis(pyridinium)decane is limited, as it is a quaternary ammonium compound that does not cross the blood-brain barrier (BBB) efficiently. When administered peripherally, it may cause a transient increase in acetylcholine at neuromuscular junctions, but it is not used therapeutically. It can cause muscle fasciculations or weakness at high doses due to nicotinic receptor blockade (similar to decamethonium). Its inability to cross the BBB means it has minimal central nervous system effects. It is used strictly as an in vitro tool compound, not for in vivo efficacy studies in animal models of disease (e.g., Alzheimer's). It improves survival in L1210 leukemia mice? No, that is incorrect. It is a tool compound.
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| Enzyme Assay |
A standard non-cellular assay for 1,10-Bis(pyridinium)decane is the Ellman's colorimetric method for AChE inhibition. The assay buffer contains 100 mM phosphate buffer (pH 8.0), 0.5 mM 5,5'-dithiobis(2-nitrobenzoic acid) (DTNB), and 0.5 mM acetylthiocholine iodide as the substrate. Purified AChE (e.g., 0.1 U/mL) is pre-incubated with varying concentrations of the test compound (0.1-1000 nM) for 15 minutes. The reaction is started by adding the substrate. The formation of the yellow 5-thio-2-nitrobenzoate anion (TNB) is monitored continuously at 412 nm using a microplate reader for 5-10 minutes. The rate of the reaction is proportional to enzyme activity. The IC50 is calculated by fitting the dose-response curve.
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| Cell Assay |
A cell-based assay is not typically used for this compound due to its membrane impermeability. However, to measure its effect on intact cells, a standard protocol can be performed with erythrocytes (red blood cells) which contain AChE on their membrane. Human or rat red blood cells are washed and resuspended in PBS. The cells are incubated with various concentrations of 1,10-Bis(pyridinium)decane (0.1 nM to 10 uM) for 15 minutes. The AChE activity is measured on the intact cells using a modified Ellman's assay. The IC50 value should be similar to the purified enzyme. This confirms that the compound can access the enzyme on the cell surface. It is not used on nucleated cells like neurons because it cannot cross the plasma membrane.
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| Animal Protocol |
In vivo animal experiments using 1,10-Bis(pyridinium)decane are rare. A typical protocol to assess its potential toxicity or neuromuscular effects is performed in mice. The compound is dissolved in sterile saline and administered intraperitoneally (IP) at doses of 0.1, 0.3, 1.0, 3.0, and 10.0 mg/kg. Mice are observed for 30 minutes for signs of cholinergic excess (salivation, tremors, lacrimation) or neuromuscular blockade (muscle weakness, respiratory distress). The median lethal dose (LD50) is estimated. The results are used for safety classification. It is not a drug candidate, so efficacy studies in disease models are not performed. A significant increase in survival is not expected.
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| ADME/Pharmacokinetics |
1,10-Bis(pyridinium)decane has a molecular weight of 458.27 g/mol. It is a solid at room temperature (white to off-white powder). It is highly soluble in water (175 mg/mL) due to its ionic nature, as well as in DMSO and ethanol. It has a logP of 1.087. The structure features two positively charged nitrogen atoms, rendering it a bication, which prevents it from crossing the blood-brain barrier (BBB). It should be stored as a powder at -20degC (stable for 3 years) or at 4degC (2 years). In solution (water or DMSO), it should be stored at -80degC (6 months) or -20degC (1 month). It is stable at room temperature during shipping.
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| Toxicity/Toxicokinetics |
The toxicity of 1,10-Bis(pyridinium)decane is moderate. The LD50 in mice is likely in the range of 5-15 mg/kg (IP). The toxic effects are related to cholinergic crisis (due to AChE inhibition) and neuromuscular blockade. It is a severe eye and skin irritant. It is harmful if swallowed. Safety precautions include wearing gloves (nitrile), a lab coat, and safety goggles. Work should be performed in a fume hood to avoid inhalation of dust. It is not a drug and is not intended for human consumption. It is a research chemical for biochemical assays. It should be considered hazardous waste at the end of its use.
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| References | |
| Additional Infomation |
1,10-Bis(pyridinium)decane is a useful tool compound for studying the structure-activity relationship of cholinesterase inhibitors. The long decamethylene chain linking the two pyridinium rings allows it to span the active site gorge of AChE, interacting with both the catalytic anionic site (CAS) and the peripheral anionic site (PAS). This bivalent binding mode results in high potency (IC50 25.8 nM). It is often used as a control or reference inhibitor in AChE inhibition assays when screening for new potential drugs for Alzheimer's disease or myasthenia gravis. It is not a clinical drug. It is a high-purity (99.66%) research compound in the class of ChE inhibitors.
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| Molecular Formula |
C20H30BR2N2
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| Molecular Weight |
458.27
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| Exact Mass |
458.076
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| CAS # |
6266-40-6
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| PubChem CID |
201563
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| Appearance |
White to off-white solid powder
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| Density |
0.93g/cm3
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| Boiling Point |
422.2ºC at 760 mmHg
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| Flash Point |
186.8ºC
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| Index of Refraction |
1.503
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| LogP |
1.087
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
11
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| Heavy Atom Count |
24
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| Complexity |
216
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=[N+](C=C1)CCCCCCCCCC[N+]2=CC=CC=C2.[Br-].[Br-]
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| InChi Key |
XZZPVHYTBRRMNM-UHFFFAOYSA-L
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| InChi Code |
InChI=1S/C20H30N2.2BrH/c1(3-5-9-15-21-17-11-7-12-18-21)2-4-6-10-16-22-19-13-8-14-20-22;;/h7-8,11-14,17-20H,1-6,9-10,15-16H2;2*1H/q+2;;/p-2
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| Chemical Name |
1-(10-pyridin-1-ium-1-yldecyl)pyridin-1-ium dibromide
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| Synonyms |
Decamethylenebispyridinium dibromide
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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) |
H2O : ~175 mg/mL (~381.87 mM; with ultrasonication)
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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 | 2.1821 mL | 10.9106 mL | 21.8212 mL | |
| 5 mM | 0.4364 mL | 2.1821 mL | 4.3642 mL | |
| 10 mM | 0.2182 mL | 1.0911 mL | 2.1821 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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