| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
This compound is classified as a phenylalanine derivative targeting halogen-recognizing domains in proteins. The bromine substituent can participate in halogen bonding (X-bond) interactions with electron-rich protein residues, potentially increasing binding affinity and selectivity for enzyme active sites or receptor binding pockets in therapeutic target studies.
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| ln Vitro |
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
In vitro studies on brominated phenylalanine derivatives demonstrate enhanced enzyme inhibition compared to unsubstituted phenylalanine. The bromine atom provides steric bulk and electronic effects that influence aromatic stacking interactions and hydrogen bonding. These compounds are used in the design of protease inhibitors and receptor antagonists for biochemical assays. |
| ln Vivo |
In vivo data for 3-Bromo-DL-phenylalanine are limited, as it is primarily a synthetic building block. Related bromophenylalanine analogs have been evaluated in animal models for aspartic proteinase inhibition, showing potential for therapeutic applications in diseases involving these enzymes, including certain cancers and infectious diseases.
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| Enzyme Assay |
Cell-free enzyme assays for bromophenylalanine derivatives typically involve testing as potential aspartic proteinase inhibitors. Purified enzyme (e.g., HIV-1 protease, renin, cathepsin D) is incubated with fluorogenic peptide substrate and varying compound concentrations (0.1-1000 uM) in acetate buffer (pH 4.5-5.5). Fluorescence increase is monitored to determine IC50 values.
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| Cell Assay |
Cell-based antiviral assays for bromophenylalanine-containing peptides use infected cell lines (e.g., HIV-1-infected MT-4 cells). Cells are treated with compound (0.01-100 uM) for 3-7 days, then viral replication measured by p24 antigen ELISA, reverse transcriptase activity, or cytopathic effect (CPE) reduction. Cytotoxicity is assessed in parallel using MTT assays on uninfected cells.
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| Animal Protocol |
Animal studies for bromophenylalanine derivatives typically use rodent models for pharmacokinetic evaluation. Compounds are administered intravenously (1-5 mg/kg) or orally (10-50 mg/kg) to male Sprague-Dawley rats. Serial blood samples (0-24 hours) are analyzed by LC-MS/MS. Tissue distribution studies collect organs (liver, kidney, brain) at 0.5-6 hours post-dose for compound quantification.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of brominated amino acids generally include moderate oral bioavailability (30-70%), peak plasma concentration at 0.5-2 hours, plasma half-life 2-5 hours, volume of distribution 0.3-0.6 L/kg, plasma protein binding 70-90% due to halogen affinity for albumin, and elimination via renal excretion of parent compound or dehalogenated metabolites.
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| Toxicity/Toxicokinetics |
Toxicological evaluation of brominated phenylalanine derivatives requires careful attention due to potential for metabolic dehalogenation releasing bromide ions. Bromine accumulation may cause bromism at high doses (nervous system depression). Acute toxicity is moderate (oral LD50 500-2000 mg/kg). No genotoxicity observed in standard assays. Not approved for human use.
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| References |
[1]. Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-923.
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| Additional Infomation |
This compound has molecular formula C9H10BrNO2 and molecular weight 244.09, with purity ≥95%. It appears as a solid and is used in synthetic preparation of hydroxyethylene sulfones as scaffolds for designing and structurally characterizing aspartic proteinase inhibitors. For research use only, not for human consumption.
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| Molecular Formula |
C9H10BRNO2
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|---|---|
| Molecular Weight |
244.09
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| Exact Mass |
242.989
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| CAS # |
30163-20-3
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| PubChem CID |
554078
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
368.4±32.0 °C at 760 mmHg
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| Melting Point |
226-231°C
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| Flash Point |
176.6±25.1 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.609
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| LogP |
1.88
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
13
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| Complexity |
187
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC(=CC(=C1)Br)CC(C(=O)O)N
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| InChi Key |
GDMOHOYNMWWBAU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H10BrNO2/c10-7-3-1-2-6(4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)
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| Chemical Name |
2-amino-3-(3-bromophenyl)propanoic acid
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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 | 4.0968 mL | 20.4842 mL | 40.9685 mL | |
| 5 mM | 0.8194 mL | 4.0968 mL | 8.1937 mL | |
| 10 mM | 0.4097 mL | 2.0484 mL | 4.0968 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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