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Indole-3-pyruvic acid

Cat No.:V43322 Purity: ≥98%
Indole-3-pyruvic acid, a ketone analog of tryptophan, is an orally bioactive AHR agonist.
Indole-3-pyruvic acid
Indole-3-pyruvic acid Chemical Structure CAS No.: 392-12-1
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
100mg
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Product Description
Indole-3-pyruvic acid, a ketone analog of tryptophan, is an orally bioactive AHR agonist. Indole-3-pyruvic acid has antioxidant properties and may be utilized to treat inflammation and anxiety.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
In HepG2 cells, indole-3-pyruvic acid (50 and 250 μM, 24 h) activates AHR[1]. Triole-3-pyruvic acid (50 μM, 4 days) stimulates Tr1 cells but does not prevent Th1 cell elimination [1]. Indole-3-pyruvic acid (1 mM, 24 h) lessens the cytotoxicity of UVB-induced HaCaT [1]. In HaCaT cells, indole-3-pyruvic acid (25 mM, 6 hours) lowers COX-2 levels [2].
ln Vivo
Mice BALB/c are given indole-3-pyruvic acid (face, 0.1% chow; 5 d) to activate their AHR [1]. Indole-3-pyruvic acid (100 μM, dose at skin) protects HR-1 hairless shell from UVB-induced skin damage. Indole-3-pyruvic acid (face, fed MF food (0.1%) for 5 weeks) eliminates T cells [ 2]. mediated long-term inflammation in vaginitis models [1]. -In the elevated plus maze, mice can open their arms for a longer period of time when given pyruvate (ip, 100–200 mg/kg) [3].
Cell Assay
RT-PCR[2]
Cell Types: HaCaT cells
Tested Concentrations: 5-25mM
Incubation Duration: 6 hrs (hours)
Experimental Results: Inhibition of UVB-stimulated mRNA expression of IL-1β, IL-6 and cyclooxygenase 2 (Cox-2).
Animal Protocol
Animal/Disease Models: balb/c (Bagg ALBino) mouse [1]
Doses: Fed with MF feed. 0.1% for 5 days.
Route of Administration: Oral.
Experimental Results: Up-regulated the expression of Cyp1a1 (a biomarker of AHR activation) in the colon.

Animal/Disease Models: SCID mouse T cell-mediated colitis model [1]
Doses: fed with 0.1% MF feed for 5 consecutive weeks.
Route of Administration: oral.
Experimental Results: inhibited diarrhea and improved colon inflammation. Downregulates the expression of Th1 and pro-inflammatory cytokines and upregulates the expression of IL-10 in the colon.

Animal/Disease Models: HR-1 hairless mice [2]
Doses: 100 μM
Route of Administration: Skin Dose
Experimental Results: Increased epidermal thickness. Attenuation of UVB-induced necrosis was observed in the upper dermis.
References

[1]. Indole-3-Pyruvic Acid, an Aryl Hydrocarbon Receptor Activator, Suppresses Experimental Colitis in Mice. J Immunol. 2018 Dec 15;201(12):3683-3693.

[2]. Protective effect of indole-3-pyruvate against ultraviolet b-induced damage to cultured HaCaT keratinocytes and the skin of hairless mice. PLoS One. 2014 May 8;9(5):e96804.

[3]. Anxiolytic effect of indole-3-pyruvic acid (IPA) in mice. Pharmacol Res. 1993 Sep;28(2):129-34.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H9NO3
Molecular Weight
203.19406
Exact Mass
203.058
CAS #
392-12-1
Appearance
Light yellow to brown solid powder
Density
1.4±0.1 g/cm3
Boiling Point
445.2±28.0 °C at 760 mmHg
Melting Point
215 °C (dec.)(lit.)
Flash Point
223.0±24.0 °C
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.685
LogP
0.46
InChi Key
RSTKLPZEZYGQPY-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H9NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H,14,15)
Chemical Name
3-(1H-indol-3-yl)-2-oxopropanoic acid
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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 : ~166.67 mg/mL (~820.27 mM)
H2O : ~20 mg/mL (~98.43 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 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: ≥ 2.08 mg/mL (10.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 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 4.9215 mL 24.6075 mL 49.2150 mL
5 mM 0.9843 mL 4.9215 mL 9.8430 mL
10 mM 0.4922 mL 2.4608 mL 4.9215 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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