| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
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| Other Sizes |
| Targets |
N-Butanoyl-L-homoserine lactone targets the RhlR quorum sensing receptor in P. aeruginosa and other Gram-negative bacteria. RhlR is a LuxR-type transcriptional regulator that, upon binding to C4-HSL, activates the expression of target genes involved in virulence, biofilm formation, and other population-dependent behaviors. The compound's short acyl chain (4 carbons) confers specificity for RhlR over other quorum sensing receptors, such as LasR. N-Butanoyl-L-homoserine lactone is a key signaling molecule in the P. aeruginosa quorum sensing hierarchy.
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|---|---|
| ln Vitro |
The aptamer binding to n-butyrolyl-L-homose acid lactone (C4-HSL) has a dissociation constant (Kd value) of 28.47 nM [2].
In vitro, N-Butanoyl-L-homoserine lactone is used to activate quorum sensing in P. aeruginosa and other bacteria. The compound induces the expression of RhlR-regulated genes, including those encoding virulence factors such as rhamnolipid and pyocyanin. It also promotes biofilm formation and motility. In reporter strains, C4-HSL can be used to quantify RhlR activity and screen for quorum sensing inhibitors. |
| ln Vivo |
In vivo, N-Butanoyl-L-homoserine lactone plays a critical role in the pathogenesis of P. aeruginosa infections. The compound's production in vivo regulates the expression of virulence factors that contribute to tissue damage and immune evasion. C4-HSL has also been shown to have immunomodulatory effects, affecting host immune responses. The compound is a key target for the development of quorum sensing inhibitors as a novel approach to treating P. aeruginosa infections.
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| Enzyme Assay |
In vitro receptor binding assays for N-Butanoyl-L-homoserine lactone involve measuring its binding affinity to RhlR. The assay is typically performed using recombinant RhlR protein and a fluorescently labeled or radiolabeled ligand. The compound is incubated with the receptor and the labeled ligand, and the bound label is measured. The IC₅₀ and Ki values are calculated from the displacement curves. Functional activity is assessed using reporter gene assays.
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| Cell Assay |
In vitro cellular experiments for N-Butanoyl-L-homoserine lactone are performed using P. aeruginosa cultures. Bacteria are grown in the presence of varying concentrations of the compound, and the expression of RhlR-regulated genes is measured using reporter strains or qPCR. The effects of the compound on biofilm formation, motility, and virulence factor production are assessed using standard assays. These experiments are essential for characterizing the compound's biological activity.
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| Animal Protocol |
In vivo animal studies for N-Butanoyl-L-homoserine lactone are conducted using mouse or rat models of P. aeruginosa infection. The compound is administered via intraperitoneal or subcutaneous injection, or directly to the site of infection. The effects on bacterial virulence, biofilm formation, and disease progression are assessed by monitoring survival, bacterial burden, and clinical signs of infection.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of N-Butanoyl-L-homoserine lactone have not been extensively characterized. As a small, hydrophilic molecule, it is expected to be rapidly absorbed and distributed, but it may be susceptible to hydrolysis and degradation in biological fluids. The compound's stability and half-life in vivo are likely to be short, limiting its utility for in vivo studies.
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| Toxicity/Toxicokinetics |
The toxicity of N-Butanoyl-L-homoserine lactone has not been extensively characterized. As a bacterial signaling molecule, it is expected to have low toxicity in mammalian cells. However, high concentrations may have immunomodulatory effects. Standard safety precautions should be followed when handling this compound.
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| References |
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| Additional Infomation |
(+)-α(S)-butyramido-α-butyrolactone is an N-acyl amino acid. N-[(3S)-2-oxotetrahydrofuran-3-yl]butyramide has been reported in Lyngbya majuscula, and relevant data are available for reference.
N-Butanoyl-L-homoserine lactone is a naturally occurring quorum sensing signal molecule used by P. aeruginosa. It activates the RhlR receptor, regulating the expression of virulence factors, biofilm formation, and other population-dependent behaviors. C4-HSL is a key target for the development of quorum sensing inhibitors as a novel approach to treating P. aeruginosa infections. It is a valuable tool for studying bacterial cell-cell communication and pathogenesis. |
| Molecular Formula |
C8H13NO3
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|---|---|
| Molecular Weight |
171.19372
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| Exact Mass |
171.089
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| CAS # |
67605-85-0
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| Related CAS # |
N-Butanoyl-DL-homoserine lactone;98426-48-3;N-butyryl-L-Homoserine lactone-d5;2701379-46-4
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| PubChem CID |
10130163
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
428.1±34.0 °C at 760 mmHg
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| Flash Point |
212.7±25.7 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.476
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| LogP |
-1.1
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
12
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| Complexity |
191
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CCCC(=O)N[C@H]1CCOC1=O
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| InChi Key |
VFFNZZXXTGXBOG-LURJTMIESA-N
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| InChi Code |
InChI=1S/C8H13NO3/c1-2-3-7(10)9-6-4-5-12-8(6)11/h6H,2-5H2,1H3,(H,9,10)/t6-/m0/s1
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| Chemical Name |
N-[(3S)-2-oxooxolan-3-yl]butanamide
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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) |
DMSO : ~100 mg/mL (~584.15 mM)
H2O : ~20 mg/mL (~116.83 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (14.60 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL 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: ≥ 2.5 mg/mL (14.60 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 25.0 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: ≥ 2.5 mg/mL (14.60 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 | 5.8415 mL | 29.2073 mL | 58.4146 mL | |
| 5 mM | 1.1683 mL | 5.8415 mL | 11.6829 mL | |
| 10 mM | 0.5841 mL | 2.9207 mL | 5.8415 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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