| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Targets |
6-Fluorotryptophan functions through two primary mechanisms. Firstly, as a competitive inhibitor of tryptophan hydroxylase, it interferes with the conversion of tryptophan to 5-hydroxytryptophan, thereby inhibiting the synthesis of serotonin. Secondly, as a fluorinated amino acid, it serves as a site-specific probe for ¹⁹F NMR spectroscopy. When incorporated into proteins, the fluorine atom provides a sensitive, non-perturbing probe that can be detected with high sensitivity due to the lack of background signal from the protein itself.
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| ln Vitro |
In vitro, 6-fluorotryptophan is used in a variety of biochemical applications. It serves as a competitive inhibitor of tryptophan hydroxylase in enzymatic assays. As a fluorinated amino acid, it can be incorporated into proteins during synthesis, either uniformly or site-specifically. This allows for the study of protein structure, dynamics, and interactions using ¹⁹F NMR spectroscopy, as the fluorine atom provides a sensitive reporter of the local environment. It has also been used to create monoclonal antibodies.
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| ln Vivo |
In vivo, 6-fluorotryptophan can temporarily interrupt sleep in rats with long-term implantation of electroencephalogram recording electrodes by inhibiting serotonin synthesis. It can also be used as a probe to measure changes in tryptophan metabolism ex vivo, for instance, resulting from antibiotic-induced changes in gut microbiota composition. These applications highlight its utility in studying the physiological roles of serotonin and tryptophan metabolism.
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| Enzyme Assay |
Cell-free assays for 6-fluorotryptophan are used to study its interaction with enzymes like tryptophan hydroxylase. In these assays, the enzyme is incubated with its substrate (tryptophan) and varying concentrations of the inhibitor. The rate of product formation (5-hydroxytryptophan) is measured, and the inhibition constant (Ki) is determined. As a fluorinated probe, its properties are characterized by ¹⁹F NMR spectroscopy, where its chemical shift and relaxation parameters are measured in solution to assess its utility as a probe.
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| Cell Assay |
Cellular experiments with 6-fluorotryptophan involve incorporating it into proteins to study their structure and function. Cells, such as E. coli or yeast, are grown in media where tryptophan is replaced by 6-fluorotryptophan. This leads to the production of proteins containing the fluorinated analog. These labeled proteins can then be studied by ¹⁹F NMR to gain insights into their conformational dynamics and interactions.
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| Animal Protocol |
In vivo animal experiments have demonstrated that 6-fluorotryptophan can temporarily interrupt sleep in rats with long-term implantation of EEG recording electrodes. This effect is due to the compound's inhibition of serotonin synthesis. The compound can also be used as a probe to study tryptophan metabolism in ex vivo tissue samples from animals, for example, to measure changes resulting from antibiotic treatment.
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| ADME/Pharmacokinetics |
6-Fluorotryptophan (CAS: 7730-20-3) has a molecular formula of C11H11FN2O2 and a molecular weight of 222.22. It appears as an off-white to pink solid powder with a melting point of 280-285 °C (dec.). The compound requires protection from light during transportation and storage. It is soluble in water. For storage, the powder should be kept at -20°C for up to 3 years.
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| Toxicity/Toxicokinetics |
Specific toxicity data for 6-fluorotryptophan are not provided in the available sources. As a research compound, it is intended for research use only and is not for human use. Standard laboratory safety precautions should be observed when handling this compound.
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| References | |
| Additional Infomation |
6-Fluoro-DL-tryptophan is an indole carboxylic acid. It has been reported that 6-fluorotryptophan exists in Aspergillus fumigatus, and relevant data are available for reference.
6-Fluorotryptophan (CAS: 7730-20-3) is a fluorinated analog of tryptophan. It is also known as 6-Fluoro-DL-tryptophan. The compound functions as a competitive inhibitor of tryptophan hydroxylase and serotonin synthesis and as a ¹⁹F NMR probe for studying protein structure and dynamics. It has been reported to exist in Aspergillus fumigatus. It is not an approved drug and is strictly for research purposes. |
| Molecular Formula |
C11H11FN2O2
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|---|---|
| Molecular Weight |
222.2156
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| Exact Mass |
222.08
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| CAS # |
7730-20-3
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| PubChem CID |
94937
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| Appearance |
Off-white to pink solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
450.7±45.0 °C at 760 mmHg
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| Melting Point |
280-285 °C (dec.)(lit.)
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| Flash Point |
226.4±28.7 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.673
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| LogP |
1.09
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
16
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| Complexity |
275
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
YMEXGEAJNZRQEH-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C11H11FN2O2/c12-7-1-2-8-6(3-9(13)11(15)16)5-14-10(8)4-7/h1-2,4-5,9,14H,3,13H2,(H,15,16)
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| Chemical Name |
2-amino-3-(6-fluoro-1H-indol-3-yl)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 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) |
H2O : ~4.85 mg/mL (~21.83 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 | 4.5000 mL | 22.5002 mL | 45.0005 mL | |
| 5 mM | 0.9000 mL | 4.5000 mL | 9.0001 mL | |
| 10 mM | 0.4500 mL | 2.2500 mL | 4.5000 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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