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| Other Sizes |
| Targets |
The molecular targets of 5-Methyl-DL-tryptophan include the bacterial trp repressor protein, for which it acts as a corepressor, binding to the repressor and enabling its interaction with operator DNA to inhibit transcription of the tryptophan biosynthesis operon. It also inhibits anthranilate synthesis in Neurospora crassa and serves as a substrate for tryptophanase.
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| ln Vitro |
In vitro, 5-Methyl-DL-tryptophan inhibits the synthesis of anthranilate compounds, which are the first steps in tryptophan biosynthesis in Neurospora crassa. As a corepressor of the E. coli trp repressor, it binds with high affinity to the repressor protein and promotes DNA binding, thereby repressing transcription of trp operon genes involved in tryptophan production.
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| ln Vivo |
In vivo studies show that 5-Methyl-DL-tryptophan may be used to select genetic mutants of the PS strain of Methanococcus voltae (archaebacteria). Recent research has identified that the metabolite 5-methyltryptophan, derived from Angelica sinensis polysaccharides, ameliorates colitis by modulating gut microbiota and the TLR4/MyD88/NF-kappaB signaling pathway, suggesting potential applications in inflammatory bowel disease research.
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| Enzyme Assay |
Cell-free binding assays for tryptophan analogs involve purified trp repressor protein. The compound (0.1-100 uM) is incubated with repressor in binding buffer containing L-tryptophan or analog, then operator DNA is added. Binding is measured by electrophoretic mobility shift assay (EMSA) or fluorescence anisotropy, with IC50 determined by competition with labeled tryptophan.
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| Cell Assay |
Cell-based assays for tryptophan derivatives use E. coli trp operon reporter strains containing lacZ or GFP under trp promoter control. Cells are grown in minimal medium with varying compound concentrations (0.1-1000 uM), then beta-galactosidase activity or fluorescence is measured. Repression of reporter expression indicates compound activity as a trp corepressor.
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| Animal Protocol |
Animal studies for colitis models using 5-methyltryptophan have been conducted in mice. Animals receive compound via oral gavage (10-100 mg/kg) in colitis models induced by dextran sulfate sodium (DSS). Endpoints include disease activity index scoring, colon length measurement, histological assessment of inflammation, and cytokine analysis (TNF-alpha, IL-6, IL-1beta) in colon tissues via ELISA.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of tryptophan derivatives generally include moderate oral bioavailability (30-60%), peak plasma concentration at 1-3 hours post-dose, plasma half-life 2-5 hours, volume of distribution 0.4-0.8 L/kg, plasma protein binding 70-90% due to albumin interaction, and elimination via urine as metabolites including kynurenine pathway products.
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| Toxicity/Toxicokinetics |
Toxicological studies of 5-methyltryptophan and related indole derivatives suggest low acute toxicity. However, tryptophan metabolites can influence serotonin synthesis and may affect mood, sleep, and appetite at high doses. The compound is not approved for human therapeutic use and is intended for laboratory research applications only.
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| Additional Infomation |
5-Methyltryptophan is a tryptophan derivative in which the 5-position of the indole ring is replaced by a methyl group. It is a non-protein α-amino acid and also a derivative of tryptophan. It has been reported that Aspergillus fumigatus contains 5-methyltryptophan, and relevant data are available for reference.
This compound appears as a white to faint yellow powder with molecular formula C12H14N2O2 and molecular weight 218.26. Melting point is 280-282degC. It is stable at 2-8degC and used in peptide synthesis, microbial genetics studies (trp operon repression), and gut microbiota research. For research use only, not for human consumption. |
| Molecular Formula |
C12H14N2O2
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|---|---|
| Molecular Weight |
218.25
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| Exact Mass |
218.105
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| CAS # |
951-55-3
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| PubChem CID |
92852
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
455.1±45.0 °C at 760 mmHg
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| Melting Point |
~275 °C (dec.)
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| Flash Point |
229.1±28.7 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.677
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| LogP |
1.5
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
16
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| Complexity |
270
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(C(CC1C2C(=CC=C(C)C=2)NC=1)N)O
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| InChi Key |
HUNCSWANZMJLPM-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H14N2O2/c1-7-2-3-11-9(4-7)8(6-14-11)5-10(13)12(15)16/h2-4,6,10,14H,5,13H2,1H3,(H,15,16)
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| Chemical Name |
2-amino-3-(5-methyl-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 |
| 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 | 4.5819 mL | 22.9095 mL | 45.8190 mL | |
| 5 mM | 0.9164 mL | 4.5819 mL | 9.1638 mL | |
| 10 mM | 0.4582 mL | 2.2910 mL | 4.5819 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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