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| Other Sizes |
| Targets |
2'-Hydroxy-1'-acetonaphthone targets cellular proteins and enzymes through its ability to form Schiff bases. It can inhibit or activate enzymes by forming Schiff bases that alter the enzyme's active site and affect its catalytic activity. In cancer cells, the compound targets the active methylene group of proteins. Its derivatives have been shown to upregulate p21 and downregulate cyclin D1 protein expression. The compound also exhibits selective binding properties with cancer cells, suggesting interactions with tumor-specific targets. Its antibacterial properties indicate interactions with bacterial cellular components. The compound's ability to bind copper(II) ions suggests metal-chelating properties.
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| ln Vitro |
In vitro studies have demonstrated that 2'-Hydroxy-1'-acetonaphthone exhibits significant antibacterial properties against various bacterial strains. Chalcones derived from this compound have shown anti-cancer activity in cell-based assays by upregulating p21 and downregulating cyclin D1 protein expression. The compound also shows selective binding and fluorescence properties with cancer cells. Its ability to form Schiff bases allows it to interact with cellular proteins and enzymes, potentially altering their function and activity. The compound can inhibit or activate enzymes, which can alter the enzyme's active site and affect its catalytic activity. These in vitro findings support its potential applications in antibacterial therapy, cancer treatment, and as a fluorescent probe.
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| ln Vivo |
In vivo studies of 2'-Hydroxy-1'-acetonaphthone are limited, as the compound is primarily used as a research chemical and pharmaceutical intermediate. Its antibacterial properties against various bacterial strains suggest potential for in vivo evaluation in animal models of infection. The anti-cancer activity of its chalcone derivatives indicates potential for in vivo evaluation in cancer models. The compound's selective binding properties with cancer cells could be exploited for in vivo imaging applications. However, comprehensive in vivo pharmacological studies specifically targeting this compound are not well documented in the available literature. Further research is needed to fully characterize its in vivo efficacy and safety.
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| Enzyme Assay |
In vitro enzyme inhibition and receptor binding assays for 2'-Hydroxy-1'-acetonaphthone typically involve testing its ability to form Schiff bases with enzymes and proteins. Enzyme activity is measured by monitoring substrate conversion in the presence of varying concentrations of the compound, using spectrophotometric or fluorometric methods. The compound's ability to bind copper(II) ions can be assessed using fluorescence spectroscopy. For antibacterial activity, standard disc diffusion or broth microdilution methods are employed to determine minimum inhibitory concentrations (MICs) against various bacterial strains. All assays are performed with appropriate controls and standardized protocols to ensure reproducibility of results.
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| Cell Assay |
In vitro cell-based assays for 2'-Hydroxy-1'-acetonaphthone involve culturing cancer cell lines to evaluate its anti-cancer activity. Cells are treated with varying concentrations of the compound or its derivatives, and cell viability is assessed using MTT or similar colorimetric assays. Apoptosis is quantified using flow cytometry with Annexin V/PI staining. Protein expression (p21 and cyclin D1) is measured by Western blotting. For fluorescence studies, cancer cells are incubated with the compound and fluorescence is measured using flow cytometry or fluorescence microscopy. For antibacterial activity, bacterial cultures are treated and cell viability is monitored. All experiments are performed in triplicate with appropriate controls.
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| Animal Protocol |
In vivo animal experiments for 2'-Hydroxy-1'-acetonaphthone would be conducted to evaluate its antibacterial and anti-cancer activities. For antibacterial studies, infected animals (typically mice) would be treated with the compound and bacterial load assessed. For anticancer studies, tumor-bearing animals would be treated with the compound or its derivatives and tumor growth monitored. For fluorescence imaging studies, animals would be administered the compound and fluorescence signals measured using in vivo imaging systems. Parameters assessed would include body weight, tumor size, survival, and general health. Control groups receiving vehicle alone would be included for comparison. All procedures would comply with institutional animal care and use committee guidelines.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of 2'-Hydroxy-1'-acetonaphthone reflect its nature as a small aromatic compound. It has a molecular weight of 186.21 and the molecular formula C12H10O2. The compound appears as a solid and has a purity of 99.69%. Its LogP and other physicochemical properties suggest moderate lipophilicity, which may facilitate absorption and distribution. The compound's ability to form Schiff bases suggests it may be metabolized through standard xenobiotic pathways in the liver. Complete pharmacokinetic profiling including half-life, clearance, volume of distribution, and bioavailability would require further systematic studies using appropriate analytical methods such as high-performance liquid chromatography-mass spectrometry.
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| Toxicity/Toxicokinetics |
The toxicity profile of 2'-Hydroxy-1'-acetonaphthone has been partially characterized. The compound is classified as a research chemical intended for laboratory use only. Its antibacterial properties suggest potential for biological effects that should be carefully evaluated. The compound's ability to interact with cellular proteins and enzymes could potentially lead to off-target effects. Proper handling procedures including use of personal protective equipment are recommended when working with the compound. The compound is not approved for human therapeutic use. Long-term toxicity studies would be needed to fully establish its safety profile for pharmaceutical applications. The compound should be handled with caution in laboratory settings.
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| References |
[1]. Wojciech Schilf, et al.Intramolecular hydrogen bond investigations in Schiff bases derivatives of 2-hydroxy-1-naphthaldehyde and 2-hydroxy-1-acetonaphthone in CDCl3 solution and in the solid state by NMR methods. Journal of Molecular Structure, Volumes 602–603, 9 January 2002, Pages 41-47.
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| Additional Infomation |
2'-Hydroxy-1'-acetonaphthone (CAS# 574-19-6) is also known as 1-(2-hydroxynaphthalen-1-yl)ethan-1-one. It has a purity of 99.69% and is used as a pharmaceutical intermediate. The compound is a Schiff base that can be used as a fluorescent probe for the determination of copper(II) ions. It exhibits selective binding properties and fluorescence properties with cancer cells. Chalcones derived from this compound have shown anti-cancer activity by upregulating p21 and downregulating cyclin D1 protein expression. The compound also exhibits significant antibacterial properties against various bacterial strains. It serves as an important scaffold for drug discovery and synthesis. The compound is intended for research use only.
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| Molecular Formula |
C12H10O2
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| Molecular Weight |
186.21
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| Exact Mass |
186.068
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| CAS # |
574-19-6
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| PubChem CID |
68455
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| Appearance |
White to yellow solid powder
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| Density |
1.213 g/cm3
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| Boiling Point |
334.9ºC at 760 mmHg
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| Melting Point |
61ºC to 66ºC
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| Flash Point |
130-132°C/2mm
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| Index of Refraction |
1.65
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| LogP |
2.748
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
14
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| Complexity |
224
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C1C([H])=C([H])C2=C([H])C([H])=C([H])C([H])=C2C=1C(C([H])([H])[H])=O
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| InChi Key |
VUIOUIWZVKVFCI-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H10O2/c1-8(13)12-10-5-3-2-4-9(10)6-7-11(12)14/h2-7,14H,1H3
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| Chemical Name |
1-(2-hydroxynaphthalen-1-yl)ethanone
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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 | 5.3703 mL | 26.8514 mL | 53.7028 mL | |
| 5 mM | 1.0741 mL | 5.3703 mL | 10.7406 mL | |
| 10 mM | 0.5370 mL | 2.6851 mL | 5.3703 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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