| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| Other Sizes |
| Targets |
Bacterial efflux pump (inhibition) [1]
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| ln Vitro |
At 500 µg/mL, 2-phenylacetophenone exhibits antibacterial activity against Mycobacterium aureus, Mycobacterium smegmatis, and Bacillus subtilis[1]. 2. Mycobacterium smegmatis biofilm formation is inhibited by phenylacetophenone (1000 µg/mL) [1].
Showed poor bacterial growth inhibitory properties against a panel of bacteria (E. coli K12, B. subtilis 168, M. smegmatis, M. aurum, M. bovis BCG), with MIC values >500 μg/mL for E. coli, 500 μg/mL for B. subtilis and M. smegmatis, 500 μg/mL for M. aurum, and 250 μg/mL for M. bovis BCG [1]. - Displayed low selectivity index (SI) when tested against RAW 264.7 and THP-1 cell lines. For RAW 264.7 cell line, SI values were 0.25 (E. coli), 1 (B. subtilis), 0.5 (M. bovis BCG). For THP-1 cell line, SI values were 0.5 (E. coli), 2 (B. subtilis), 1 (M. bovis BCG) [1]. - The GIC50 (50% growth inhibitory concentration) on RAW 264.7 macrophages was 125 μg/mL, and on THP-1 mammalian macrophages was 250 μg/mL [1]. - Demonstrated broad-spectrum efflux pump inhibition activity against Gram-negative (E. coli) and mycobacterium species (M. smegmatis, M. aurum, M. bovis BCG) at 1/4 MIC concentration, showing higher inhibitory activity compared to controls chlorpromazine and verapamil against mycobacterium species [1]. - Showed significant inhibition of M. smegmatis biofilm formation at 2× MIC of log phase cells (1000 μg/mL) [1]. - In drug-drug interaction studies, exhibited additive effects when combined with kanamycin (FIC index 1.00) and ampicillin (FIC index 0.99) against E. coli [1]. - Showed synergistic properties with anti-tubercular agents against M. smegmatis: synergistic with ethambutol (FIC index 0.38) and isoniazid (FIC index 0.26), and additive with rifampicin (FIC index 0.56) [1]. |
| Cell Assay |
Resazurin microtiter plate assay (REMA) for MIC determination: The compound was tested using a whole-cell phenotypic screen. Two-fold serial dilutions were prepared in a 96-well plate. A fluorescence reading step was included to eliminate any compound and dye interference. Fluorescence was read using a plate reader at excitation 544nm and emission 590nm, with gain 2200 and temperature 37°C. The MIC was determined as the lowest concentration of the drug at which no bacterial growth was observed. The experiment was performed in triplicate [1].
- Cytotoxicity assay: Performed in a 96-well plate. Two-fold serial dilutions of the compound were prepared by transferring 100 μl from the first row to the next row containing 100 μl of complete RPMI media. 100 μl of cell line (RAW264.7 or THP1) at a concentration of 5×10⁵ cells/ml was added to each well. The plate was incubated in a CO₂ incubator for 48h, then washed with 1×PBS, and fresh complete RPMI was added. 30 μl of freshly prepared 0.01% resazurin solution was added and incubated overnight in the CO₂ incubator. Fluorescence intensity was measured using a microplate reader at λexc=540nm, λemi=590nm. The 50% growth inhibitory concentration (GIC₅₀) was determined as the concentration giving fluorescence at the midpoint between the highest and lowest fluorescence detected [1]. - Biofilm inhibition analysis: M. smegmatis cells were passaged three times and grown until OD reached 2.0. The culture was diluted 1:100 in Sauton's media. 2 ml of diluted cell culture was added to Eppendorf tubes with specific volumes of the compound to achieve concentrations ranging from 1000–125 μg/ml. The tubes were incubated for 5 days at 35°C, then biofilm formation was examined for direct, visible phenotypic changes [1]. |
| Toxicity/Toxicokinetics |
Displayed higher toxicity results in the cytotoxicity assays, which was expected as many compounds in this chemical class are labeled as anti-cancer drugs [1].
- Low selectivity index (SI) values against both THP-1 and RAW 264.7 cell lines, indicating potential cytotoxicity concerns (see In Vitro section for specific SI values) [1]. |
| References | |
| Additional Infomation |
2-phenylacetophenone is a compound belonging to the flavonoid family (ketone class) that was identified as a novel efflux pump inhibitor [1].
- The compound displayed broad-spectrum efflux pump inhibition activity, matching the activity of known control chlorpromazine against E. coli in the first 30 minutes, and displaying significantly higher efflux inhibitory activity compared to controls chlorpromazine and verapamil when used against mycobacterium species [1]. - This compound has the potential to work additively with known antibacterial agents that affect cell-wall and DNA replication, and in combination therapy as an antibiotic adjuvant [1]. - The study highlights that this compound, along with other ketones, chalcones and stilbenes, has potential to help in the fight against antimicrobial resistance as a novel efflux pump and biofilm inhibitor [1]. |
| Molecular Formula |
C14H12O
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|---|---|
| Molecular Weight |
196.25
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| Exact Mass |
196.088
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| CAS # |
451-40-1
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| PubChem CID |
9948
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
320.6±11.0 °C at 760 mmHg
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| Melting Point |
54-55 °C(lit.)
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| Flash Point |
137.0±14.2 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.584
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| LogP |
3.18
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
15
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| Complexity |
197
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
OTKCEEWUXHVZQI-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H12O/c15-14(13-9-5-2-6-10-13)11-12-7-3-1-4-8-12/h1-10H,11H2
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| Chemical Name |
Acetophenone, 2-phenyl-
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| Synonyms |
Deoxybenzoin NSC-131456 NSC131456NSC 131456
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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 | 5.0955 mL | 25.4777 mL | 50.9554 mL | |
| 5 mM | 1.0191 mL | 5.0955 mL | 10.1911 mL | |
| 10 mM | 0.5096 mL | 2.5478 mL | 5.0955 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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