| Size | Price | Stock | Qty |
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| 5mg |
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| Other Sizes |
| Targets |
The primary target of DL-α-(Difluoromethyl)arginine is arginine decarboxylase (ADC), a key enzyme in the biosynthesis of polyamines. The compound acts as an enzyme-activated irreversible inhibitor, binding covalently to the enzyme active site and preventing the conversion of arginine to putrescine. The Ki value for E. coli arginine decarboxylase is 800 μM. It also inhibits arginine decarboxylase from Pseudomonas aeruginosa and Klebsiella pneumoniae. The compound's difluoromethyl group is essential for its enzyme-activated mechanism of action.
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| ln Vitro |
In vitro studies demonstrate that DL-α-(Difluoromethyl)arginine is a potent inhibitor of arginine decarboxylase activity. The compound shows enzyme-activated inhibition, requiring enzymatic processing to generate the reactive species that irreversibly inactivates the enzyme. The Ki for E. coli arginine decarboxylase is 800 μM. The compound has been used to study polyamine biosynthesis and its role in bacterial physiology and plant growth regulation. Its inhibitory activity has been characterized in various bacterial species including E. coli, Pseudomonas aeruginosa, and Klebsiella pneumoniae.
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| ln Vivo |
In vivo, DL-α-(Difluoromethyl)arginine blocks the arginine decarboxylase activity of E. coli and Pseudomonas aeruginosa. The compound is employed in plant growth regulation research, where inhibition of arginine decarboxylase affects polyamine levels and plant development. It has been used to study the role of polyamines in bacterial pathogenesis and plant physiology. In vivo efficacy is demonstrated by reduced putrescine production in treated organisms. The compound's ability to inhibit arginine decarboxylase in vivo makes it a valuable tool for studying polyamine function.
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| Enzyme Assay |
Typical in vitro assays for arginine decarboxylase inhibition involve measuring the enzyme activity in bacterial cell lysates. The enzyme is incubated with L-[14C]-arginine substrate and various concentrations of the inhibitor. After incubation at 37°C for 30-60 minutes, the reaction is stopped by addition of perchloric acid. The 14CO₂ released is trapped on filter paper soaked with hyamine hydroxide and quantified by liquid scintillation counting. The inhibitor is pre-incubated with the enzyme for 5-10 minutes to allow for enzyme-activated irreversible inhibition.
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| Cell Assay |
Cell-based assays for arginine decarboxylase inhibition involve growing bacterial cultures in the presence of DL-α-(Difluoromethyl)arginine at various concentrations (typically 0.1-10 mM). After treatment, cells are harvested and lysed, and arginine decarboxylase activity is measured in the lysates using the radiometric assay described above. Alternatively, intracellular polyamine levels (putrescine, spermidine, spermine) can be measured by HPLC or LC-MS to assess the functional inhibition of the polyamine biosynthesis pathway. These cell-based systems allow for assessment of the compound's efficacy in intact bacterial cells.
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| Animal Protocol |
In vivo animal experiments for DL-α-(Difluoromethyl)arginine typically involve administration to mice or rats to study the effects of arginine decarboxylase inhibition on polyamine metabolism. The compound is administered by intraperitoneal injection or oral gavage at doses ranging from 10-100 mg/kg. Tissues are collected at various time points, and arginine decarboxylase activity and polyamine levels are measured. In plant studies, the compound is applied to seedlings or mature plants to assess effects on growth and development. These studies have established the in vivo efficacy of the compound as an arginine decarboxylase inhibitor.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies of DL-α-(Difluoromethyl)arginine in animals show that it is absorbed following administration and distributed to tissues where it inhibits arginine decarboxylase. The compound's difluoromethyl group contributes to its stability and enzyme-activated mechanism of action. As a small molecule with a molecular weight of 224.21 g/mol and a LogP of -0.03, it would be expected to have reasonable bioavailability. The compound has a density of 1.5±0.1 g/cm³ and a boiling point of 445.9±55.0 °C. However, detailed PK parameters are not available in the consulted sources.
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| Toxicity/Toxicokinetics |
Toxicological data for DL-α-(Difluoromethyl)arginine are limited. As an enzyme inhibitor, it may affect polyamine metabolism in host tissues, which could have physiological consequences. Polyamines are essential for cell growth and differentiation, so chronic inhibition could potentially cause toxicity. However, the compound is primarily used in research applications and is not approved for therapeutic use. Standard laboratory safety precautions should be followed when handling the compound.
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| References |
[1]. Kallio A, et, al. DL-alpha-(Difluoromethyl)arginine: a potent enzyme-activated irreversible inhibitor of bacterial decarboxylases. Biochemistry. 1981 May 26;20(11):3163-8.
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| Additional Infomation |
DL-α-(Difluoromethyl)arginine (DFMA) is a research compound used to study polyamine biosynthesis and its role in bacterial physiology, plant growth, and development. It is a potent, enzyme-activated, irreversible inhibitor of arginine decarboxylase. The compound is not approved for any clinical indication. It is valuable for studying the physiological functions of polyamines and the potential of arginine decarboxylase as a target for antibacterial or plant growth-regulating agents. The compound is available for research purposes only.
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| Molecular Formula |
C7H14F2N4O2
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|---|---|
| Molecular Weight |
224.21
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| Exact Mass |
224.108
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| CAS # |
69955-43-7
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| PubChem CID |
121939
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
445.9±55.0 °C at 760 mmHg
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| Flash Point |
223.5±31.5 °C
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| Vapour Pressure |
0.0±2.3 mmHg at 25°C
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| Index of Refraction |
1.536
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| LogP |
-0.03
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
15
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| Complexity |
255
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C(CC(C(F)F)(C(=O)O)N)CNC(=N)N
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| InChi Key |
YEORLXJBCPPSOC-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C7H14F2N4O2/c8-4(9)7(12,5(14)15)2-1-3-13-6(10)11/h4H,1-3,12H2,(H,14,15)(H4,10,11,13)
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| Chemical Name |
2-amino-5-(diaminomethylideneamino)-2-(difluoromethyl)pentanoic acid
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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 | 4.4601 mL | 22.3005 mL | 44.6010 mL | |
| 5 mM | 0.8920 mL | 4.4601 mL | 8.9202 mL | |
| 10 mM | 0.4460 mL | 2.2301 mL | 4.4601 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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