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| 10mg |
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| 25mg |
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| 50mg |
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| Targets |
Farnesyl pyrophosphate targets the transient receptor potential melastatin 2 (TRPM2) channel as an agonist, activating TRPM2 to open and allowing ion influx into cells. It also serves as a substrate for multiple enzymatic pathways, including cholesterol synthesis, ubiquinone synthesis, protein farnesylation, and geranyl-geranyl pyrophosphate (GGPP) synthesis. In stroke, farnesyl pyrophosphate functions as a danger signal that causes immediate cell death and subsequent loss of neurons. The cation channel TRPM2 and extracellular calcium influx are key mediators of the cell death caused by farnesyl pyrophosphate.
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| ln Vitro |
In stroke, farnesyl pyrophosphate functions as a well-known danger signal that causes immediate cell death and subsequent loss of neurons. With its highly charged pyrophosphate head group and hydrophobic 15-carbon isoprenyl chain, farnesyl pyrophosphate causes abrupt cell death without affecting the cell's downstream metabolic pathways. Mechanistically, the cation channel transient receptor potential melastatin 2 (TRPM2) and extracellular calcium influx are key players in the cell death caused by farnesyl pyrophosphate. TRPM2 is activated by farnesyl pyrophosphate acid, which opens ion inflow [1].
In vitro studies demonstrate that farnesyl pyrophosphate functions as a well-known danger signal that causes immediate cell death and subsequent loss of neurons in stroke models. With its highly charged pyrophosphate head group and hydrophobic 15-carbon isoprenyl chain, farnesyl pyrophosphate causes abrupt cell death without affecting the cell's downstream metabolic pathways. Mechanistically, the cation channel TRPM2 and extracellular calcium influx are key players in the cell death caused by farnesyl pyrophosphate. TRPM2 is activated by farnesyl pyrophosphate, which opens ion channels and allows ion inflow. It serves as a prenylation agonist in human osteogenic sarcoma cells in collagen-based cell invasion assays. |
| ln Vivo |
Farnesyl pyrophosphate builds up in the brain of a mouse model of middle cerebral artery occlusion (MCAO), suggesting a role for both Farnesyl pyrophosphate and the TRPM2 danger signal axis in ischemia damage. Important functions for the MVA pathway and the Farnesyl pyrophosphate/TRPM2 signaling axis are seen in brain ischemia and possible neurodegenerative disorders [1].
In vivo studies show that farnesyl pyrophosphate accumulates in the brain of mouse models of middle cerebral artery occlusion (MCAO), suggesting a role for both farnesyl pyrophosphate and the TRPM2 danger signal axis in ischemia damage. Important functions for the MVA pathway and the farnesyl pyrophosphate/TRPM2 signaling axis are seen in brain ischemia and possible neurodegenerative disorders. The compound is a key intermediate in the biosynthesis of more complex sesquiterpenoids, higher terpenoids, and steroids. Various biological functions have been discovered for farnesyl pyrophosphate and the corresponding alcohol farnesol. |
| Enzyme Assay |
For TRPM2 channel activation assays, cells expressing TRPM2 channels (e.g., HEK293 cells) are cultured and loaded with calcium-sensitive fluorescent dyes. Farnesyl pyrophosphate is dissolved in appropriate buffer and added to cells at varying concentrations. TRPM2 activation is measured by monitoring intracellular calcium flux using fluorescence plate readers. The compound's ability to open TRPM2 channels and allow ion influx is quantified. For enzyme assays, farnesyl pyrophosphate is used as a substrate for prenylation reactions or metabolic pathway studies. Reactions are carried out in appropriate buffers with purified enzymes (e.g., farnesyltransferase). Product formation is quantified by HPLC, LC-MS, or radiometric methods. Assays are performed in replicate with appropriate controls.
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| Cell Assay |
For in vitro cellular assays, cells expressing TRPM2 channels (e.g., HEK293 cells) or cell lines of interest are cultured in appropriate media under standard conditions (37°C, 5% CO2). Farnesyl pyrophosphate is dissolved in DMSO or appropriate buffer and diluted in culture medium to desired concentrations. Cells are treated with compound for specified durations. Cellular responses are assessed by measuring calcium influx using fluorescent indicators, cell viability assays (e.g., MTT), or apoptosis markers. For invasion assays, human osteogenic sarcoma cells are used in collagen-based cell invasion assays with farnesyl pyrophosphate as a prenylation agonist. Each concentration is tested in replicate wells with vehicle controls.
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| Animal Protocol |
For in vivo animal studies, farnesyl pyrophosphate has been studied in mouse models of middle cerebral artery occlusion (MCAO) to investigate ischemia damage. Mice are subjected to MCAO surgery to induce brain ischemia. Brain tissue is collected and analyzed for farnesyl pyrophosphate accumulation. The compound is typically administered via appropriate routes (e.g., intravenous or intraperitoneal injection) in suitable formulations. Dosage regimens vary by study objective. Tissue samples are collected at predetermined time points for analysis of farnesyl pyrophosphate levels and downstream signaling markers. Behavioral assessments and histopathological examination may be performed. All procedures follow institutional animal care and use committee guidelines.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of farnesyl pyrophosphate are characteristic of an endogenous isoprenoid metabolite. The compound has a molecular weight of 382.33 and formula C15H28O7P2. It is typically stored as powder at -20°C for up to 3 years or at 4°C for up to 2 years; in solvent at -80°C for up to 6 months or at -20°C for up to 1 month. The compound is stable at ambient temperature for several days during ordinary shipping. Solubility: may dissolve in DMSO in most cases; if not, other solvents such as H2O, ethanol, or DMF may be tried. It exists as a solid at room temperature. The compound has a CAS number of 13058-04-3.
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| Toxicity/Toxicokinetics |
Toxicity information for farnesyl pyrophosphate is characteristic of an endogenous metabolite and research chemical. In stroke models, farnesyl pyrophosphate functions as a danger signal that causes acute cell death and subsequent loss of neurons. The compound causes abrupt cell death via TRPM2 activation and calcium influx. Standard laboratory safety precautions should be followed when handling this compound, including the use of appropriate personal protective equipment (gloves, lab coat, safety goggles). The compound should be handled in a well-ventilated area. Avoid dust formation and inhalation. The compound is for research use only and not for human therapeutic applications. No clinical toxicity data are available.
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| References | |
| Additional Infomation |
2-trans,6-trans-farnesyl diphosphate is the trans, trans stereoisomer of farnesyl diphosphate. It is a metabolite in both E. coli and mice. It is the conjugate acid of 2-trans,6-trans-farnesyl diphosphate (3-). Farnesyl pyrophosphate is a metabolite found or produced in E. coli (K12 strain, MG1655 strain). Farnesyl diphosphate has also been reported in Tripterygium wilfordii, Myxococcus, and other organisms with relevant data. Farnesyl pyrophosphate is a metabolite found or produced in Saccharomyces cerevisiae. 2-trans,6-trans-farnesyl diphosphate is a metabolite found or produced in Saccharomyces cerevisiae.
Farnesyl pyrophosphate (Farnesyl diphosphate) is a 15-carbon isoprenoid and a key metabolic intermediate in the mevalonate (MVA) pathway. It is a TRPM2 agonist that activates TRPM2 to open and allow ion influx. The compound serves as a key branch substrate for cholesterol synthesis, ubiquinone synthesis, protein farnesylation modification, and geranyl-geranyl pyrophosphate (GGPP) synthesis. In stroke, it functions as a danger signal causing acute cell death. The farnesyl pyrophosphate/TRPM2 signaling axis plays important roles in brain ischemia and neurodegenerative disorders. The compound is for research use only with no clinical development or regulatory approvals reported. |
| Molecular Formula |
C15H28O7P2
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|---|---|
| Molecular Weight |
382.33
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| Exact Mass |
433.21
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| CAS # |
13058-04-3
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| Related CAS # |
Farnesyl Pyrophosphate ammonium
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| PubChem CID |
445713
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| Appearance |
Typically exists as solid at room temperature
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| Flash Point |
16 °C - closed cup (lit.)
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| LogP |
5.603
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
11
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| Heavy Atom Count |
24
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| Complexity |
568
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C/C(=C/CC/C(=C/CC/C(=C/COP(OP(=O)(O)O)(O)=O)/C)/C)/C
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| InChi Key |
VWFJDQUYCIWHTN-YFVJMOTDSA-N
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| InChi Code |
InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
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| Chemical Name |
phosphono [(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl] hydrogen phosphate
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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) |
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 | 2.6155 mL | 13.0777 mL | 26.1554 mL | |
| 5 mM | 0.5231 mL | 2.6155 mL | 5.2311 mL | |
| 10 mM | 0.2616 mL | 1.3078 mL | 2.6155 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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