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Tryptanthrin

Alias: Tryptanthrin
Cat No.:V34547 Purity: ≥98%
Tryptanthrin is an indolequinazoline, which may be an alkaloid produced from the indigo plant.
Tryptanthrin
Tryptanthrin Chemical Structure CAS No.: 13220-57-0
Product category: Natural Products
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
Other Sizes
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Product Description
Tryptanthrin is an indolequinazoline, which may be an alkaloid produced from the indigo plant. Tryptanthrin is an orally bioactive inhibitor of cellular leukotriene (LT) biosynthesis. Tryptanthrin has anti-cancer effect. Tryptanthrin can inhibit the expression levels of NOS1, COX-2, and NF-κB, and regulate the expression levels of IL-2, IL-10, and TNF-α.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Tryptamine (0–60 μM; 24, 48, and 72 h) inhibits MCF-7 cell colony growth and proliferation [1]. EMT-associated E-calcium is restored by tryptophan (6.25–25 μM; 48 h; MCF-7 cells). With an IC50 value of 0.6 μM [Mucin, MMP-2, and Snail], tryptamine (0-30 μM; 15 min; MCF-7 cells) decreases leukotriene (LT)-formation in human neutrophils.
ln Vivo
Tryptamine (25-100 mg/kg; intraperitoneal; daily for 13 days; female Bal b/c mice with 4T1 xenografts) suppresses the formation of tumors and modifies IL-2, IL-6, IL-10, and IL-Tryptophan (10 mg/kg; powder; Vehicle Wistar Han Stent) to produce LTB4 in vivo [2].
Cell Assay
Cell viability assay [1]
Cell Types: MCF-7 cells
Tested Concentrations: 0-60 μM
Incubation Duration: 24, 48 and 72 hrs (hours)
Experimental Results: The inhibition rate of MCF-7 cells increased in a dose- and time-dependent manner. 2]. Way.

Western Blot Analysis[1]
Cell Types: MCF-7 Cell
Tested Concentrations: 6.25, 12.5 and 25 μM
Incubation Duration: 48 hrs (hours)
Experimental Results: E-cadherin protein levels increased, MMP-2 and Snail protein expression levels were Dramatically up-regulated TGF-β1 induction of MCF-7 cells.
Animal Protocol
Animal/Disease Models: α levels in female Bal b/c mice 12 and TNF-tumor-bearing mice [1]. 4T1 Xenograft[1]
Doses: 25, 50 and 100 mg/kg
Route of Administration: po (oral gavage); one time/day for 13 days
Experimental Results: Inhibition of tumor growth in a dose-dependent manner.

Animal/Disease Models: Male Wistar Han rat (220-230 g) [2]
Doses: 10 mg/kg
Route of Administration: Oral; primary
Experimental Results: LTB4 pleural levels were diminished by 46%. diminished PGE2 levels (42% reduction), exudate volume (80% reduction), and infiltrating cell number (41% reduction).
References
[1]. Zeng Q, et, al. Tryptanthrin exerts anti-breast cancer effects both in vitro and in vivo through modulating the inflammatory tumor microenvironment. Acta Pharm. 2021 Jun 1;71(2):245-266.
[2]. Pergola C, et, al. On the inhibition of 5-lipoxygenase product formation by tryptanthrin: mechanistic studies and efficacy in vivo. Br J Pharmacol. 2012 Feb;165(3):765-76.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H8N2O2
Molecular Weight
248.2362
Exact Mass
248.06
Elemental Analysis
C, 72.58; H, 3.25; N, 11.29; O, 12.89
CAS #
13220-57-0
Appearance
Solid powder
SMILES
C1=CC=C2C(=C1)C(=O)N3C4=CC=CC=C4C(=O)C3=N2
InChi Key
VQQVWGVXDIPORV-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H8N2O2/c18-13-10-6-2-4-8-12(10)17-14(13)16-11-7-3-1-5-9(11)15(17)19/h1-8H
Chemical Name
indolo[2,1-b]quinazoline-6,12-dione
Synonyms
Tryptanthrin
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~7.14 mg/mL (~28.76 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 0.71 mg/mL (2.86 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 7.1 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 0.67 mg/mL (2.70 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 6.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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 4.0284 mL 20.1418 mL 40.2836 mL
5 mM 0.8057 mL 4.0284 mL 8.0567 mL
10 mM 0.4028 mL 2.0142 mL 4.0284 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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