| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
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| Other Sizes |
| Targets |
Quorum sensing (QS) systems in Gram-negative bacteria; also modulates drug resistance mechanisms in cancer cells. N-Acetyltyramine inhibits the QS of C. violaceum ATCC 12472 and reverses resistance to doxorubicin in drug-resistant leukemia P388 cells. It acts as both a quorum sensing inhibitor and a chemosensitizer.
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|---|---|
| ln Vitro |
In resistant P388 murine leukemia cells, N-acetyltyramine increases the cytotoxicity of doxorubicin with an IC50 value of 0.13 μg/ml as opposed to an IC50 value of 0.48 μg/ml for doxorubicin alone[2].
In vitro, N-Acetyltyramine inhibits quorum sensing in C. violaceum ATCC 12472. It reverses doxorubicin resistance in drug-resistant leukemia P388 cells. The compound shows weak activity in a diverse range of bioassays and serves as an important standard for analytical and bioassay dereplication of crude microbial extracts. It is produced by V. alginolyticus M3-10 as a natural quorum sensing inhibitor. |
| ln Vivo |
In vivo activity data for N-Acetyltyramine are limited in the available literature. Its quorum sensing inhibitory activity has been characterized primarily in vitro. Further studies in animal models would be needed to evaluate its potential as an anti-infective agent or chemosensitizer in vivo. The compound is primarily used as a research standard rather than as a therapeutic candidate.
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| Enzyme Assay |
Quorum sensing inhibition is assessed using C. violaceum ATCC 12472 as a reporter strain. The bacteria are cultured in the presence of varying concentrations of N-Acetyltyramine, and inhibition of violacein pigment production (a QS-regulated phenotype) is measured spectrophotometrically at 585 nm. The compound's ability to inhibit QS is quantified as the percentage reduction in pigment production compared to untreated controls.
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| Cell Assay |
Doxorubicin-resistant leukemia P388 cells are cultured and treated with N-Acetyltyramine alone or in combination with doxorubicin. Cell viability is assessed by MTT or CCK-8 assays to evaluate reversal of drug resistance. The compound's chemosensitizing effect is calculated as the fold-reduction in the IC50 of doxorubicin in the presence of a fixed concentration of N-Acetyltyramine.
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| Animal Protocol |
Specific in vivo protocols for N-Acetyltyramine are not well-documented. Potential studies could include infection models using quorum sensing-dependent pathogens or tumor xenograft models to evaluate chemosensitization. The compound would be administered at doses determined from preliminary pharmacokinetic and tolerability studies. Further research is needed to establish in vivo efficacy.
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| ADME/Pharmacokinetics |
N-Acetyltyramine has molecular formula C10H13NO2 and molecular weight 179.22. It is a member of the tyramine class with an acetyl group replacing one of the hydrogens of the amino group. CAS number is 1202-66-0. The compound is soluble in organic solvents. Its pharmacokinetic properties (oral bioavailability, half-life, tissue distribution) have not been extensively characterized.
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| Toxicity/Toxicokinetics |
No comprehensive toxicity data are currently available for N-Acetyltyramine. As a natural metabolite and quorum sensing inhibitor, it is generally considered to have a favorable safety profile, but systematic toxicological evaluation is lacking. Standard laboratory safety precautions should be followed when handling the compound. It is not intended for human or veterinary use.
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| References |
[1]. Reina JC, et al. A Quorum-Sensing Inhibitor Strain of Vibrio alginolyticus Blocks Qs-Controlled Phenotypes in Chromobacterium violaceum and Pseudomonas aeruginosa. Mar Drugs. 2019;17(9):494. Published 2019 Aug 24.
[2]. Kunimoto S, et al. Reversal of resistance by N-acetyltyramine or N-acetyl-2-phenylethylamine in doxorubicin-resistant leukemia P388 cells. J Antibiot (Tokyo). 1987;40(11):1651-1652. |
| Additional Infomation |
N-acetyltrolamine is a type of tyramine compound whose structure involves replacing a hydrogen atom on the amino group with an acetyl group. It is a marine metabolite, bacterial metabolite, Aspergillus metabolite, animal metabolite, and quorum sensing inhibitor. It belongs to the acetamide and tyramine classes and is functionally related to tyramine. N-acetyltrolamine has been reported to be found in soybeans, Streptomyces, and other organisms with relevant data.
N-Acetyltyramine is a natural quorum sensing inhibitor produced by Vibrio alginolyticus M3-10. It inhibits quorum sensing in C. violaceum ATCC 12472 and reverses doxorubicin resistance in leukemia P388 cells. The compound serves as a research tool for studying bacterial communication (quorum sensing), antimicrobial agents, and cancer therapeutics. It has not entered clinical trials or received FDA approval. Purity is typically >99%. |
| Molecular Formula |
C10H13NO2
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|---|---|
| Molecular Weight |
179.22
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| Exact Mass |
179.094
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| CAS # |
1202-66-0
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| PubChem CID |
121051
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| Appearance |
Light yellow to brown solid
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
424.1±28.0 °C at 760 mmHg
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| Melting Point |
134°C
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| Flash Point |
210.3±24.0 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.546
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| LogP |
0.39
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
13
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| Complexity |
162
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O([H])C1C([H])=C([H])C(=C([H])C=1[H])C([H])([H])C([H])([H])N([H])C(C([H])([H])[H])=O
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| InChi Key |
ATDWJOOPFDQZNK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H13NO2/c1-8(12)11-7-6-9-2-4-10(13)5-3-9/h2-5,13H,6-7H2,1H3,(H,11,12)
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| Chemical Name |
N-[2-(4-hydroxyphenyl)ethyl]acetamide
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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 (557.97 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 5 mg/mL (27.90 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 DMSO stock solution (50.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.5797 mL | 27.8987 mL | 55.7973 mL | |
| 5 mM | 1.1159 mL | 5.5797 mL | 11.1595 mL | |
| 10 mM | 0.5580 mL | 2.7899 mL | 5.5797 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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