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| Other Sizes |
| Targets |
Methyl 2-amino-5-bromobenzoate targets PqsD, an enzyme involved in the biosynthesis of Pseudomonas aeruginosa quorum sensing signal molecules. Inhibition of PqsD disrupts quorum sensing, which is a key virulence mechanism in P. aeruginosa. The compound is also used to synthesize FabH inhibitors and hepatitis C virus NS5b RNA polymerase inhibitors.
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| ln Vitro |
Methyl 2-amino-5-bromobenzoate demonstrates in vitro activity as a potential PqsD inhibitor against Pseudomonas aeruginosa infections. Its derivatives exhibit FabH inhibitory activity, suggesting potential as antibacterial agents. The compound's utility as a synthetic intermediate enables the preparation of various bioactive molecules.
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| ln Vivo |
In vivo activity of methyl 2-amino-5-bromobenzoate is not extensively documented. Its potential as a PqsD inhibitor suggests possible in vivo efficacy against Pseudomonas aeruginosa infections, but further studies are needed to evaluate its pharmacokinetic properties and therapeutic potential.
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| Enzyme Assay |
In vitro enzyme assays for methyl 2-amino-5-bromobenzoate include measuring its inhibition of PqsD activity. The assay typically uses recombinant PqsD and measures the enzymatic conversion of substrates in the presence of the compound. FabH inhibition can also be assessed using similar enzymatic assays. IC50 values are determined from dose-response curves.
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| Cell Assay |
In vitro cellular assays for methyl 2-amino-5-bromobenzoate involve treating Pseudomonas aeruginosa cultures with the compound and measuring inhibition of bacterial growth or quorum sensing. The compound's ability to inhibit PqsD activity can be assessed by measuring the production of quorum sensing signal molecules. MIC values can be determined from growth inhibition assays.
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| Animal Protocol |
In vivo animal experiments for methyl 2-amino-5-bromobenzoate are not extensively documented. If used in animal models of Pseudomonas aeruginosa infection, typical protocols would involve administering the compound to infected animals and evaluating efficacy by measuring bacterial load in tissues or survival rates. Further studies are needed to characterize its in vivo activity.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for methyl 2-amino-5-bromobenzoate are limited. As a small aromatic ester, its absorption, distribution, metabolism, and excretion properties would influence its bioavailability. Further pharmacokinetic studies are needed to determine its systemic exposure and elimination pathways.
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| Toxicity/Toxicokinetics |
Toxicological data for methyl 2-amino-5-bromobenzoate are limited. As a chemical intermediate, it should be handled with appropriate safety precautions. The compound is intended for research use only and is not for human therapeutic application.
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| References |
[1]. Weidel E, et al. Structure optimization of 2-benzamidobenzoic acids as PqsD inhibitors for Pseudomonas aeruginosa infections and elucidation of binding mode by SPR, STD NMR, and molecular docking. J Med Chem. 2013 Aug 8;56(15):6146-55.
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| Additional Infomation |
Methyl 2-amino-5-bromobenzoate (CAS#: 52727-57-8) has the molecular formula C8H8BrNO2 and a molecular weight of 230.06 g/mol. It is also known as 4-Bromo-2-(methoxycarbonyl)aniline or Methyl 5-bromoanthranilate. The compound is used as a chemical intermediate and potential PqsD inhibitor.
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| Molecular Formula |
C8H8BRNO2
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|---|---|
| Molecular Weight |
230.06
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| Exact Mass |
228.973
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| CAS # |
52727-57-8
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| PubChem CID |
736224
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
286.3±20.0 °C at 760 mmHg
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| Melting Point |
72-74 °C(lit.)
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| Flash Point |
126.9±21.8 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.601
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| LogP |
3.06
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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 |
2
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| Heavy Atom Count |
12
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| Complexity |
174
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| Defined Atom Stereocenter Count |
0
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| SMILES |
BrC1C([H])=C([H])C(=C(C(=O)OC([H])([H])[H])C=1[H])N([H])[H]
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| InChi Key |
QVNYNHCNNGKULA-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H8BrNO2/c1-12-8(11)6-4-5(9)2-3-7(6)10/h2-4H,10H2,1H3
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| Chemical Name |
methyl 2-amino-5-bromobenzoate
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 : ≥ 300 mg/mL (1304.01 mM)
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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 | 4.3467 mL | 21.7335 mL | 43.4669 mL | |
| 5 mM | 0.8693 mL | 4.3467 mL | 8.6934 mL | |
| 10 mM | 0.4347 mL | 2.1733 mL | 4.3467 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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