8-Nitrotryptanthrin

Alias: O=C1N2C(C(C3=C2C=CC([N+]([O-])=O)=C3)=O)=NC4=CC=CC=C41

Cat No.:V2811 Purity: ≥98%

COA Product Data Instructions for use SDS

8-Nitrotryptanthrin is a potent selective inhibitor of the human indoleamine 2,3-dioxygenase 2 (hIDO2) which dramatically reduces IDO2 activity with Kivalue of 0.97 μM.

8-Nitrotryptanthrin Chemical Structure CAS No.: 77603-42-0
Product category: IDO

This product is for research use only, not for human use. We do not sell to patients.

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Citations by Top Journals: Nature, Cell, Science, etc.

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Biological Data

Product Description

8-Nitrotryptanthrin is a potent selective inhibitor of the human indoleamine 2,3-dioxygenase 2 (hIDO2) which dramatically reduces IDO2 activity with Ki value of 0.97 μM. As an analogue of IDO1 (indoleamine 2, 3-dioxygenase 1), the well-known new therapeutic target, IDO2 is receiving increased attention for its potential therapeutic applications. The typtanthrin derivative 8-Nitrotryptanthrin is found to be a potent hIDO2 inhibitor with superior efficiency much better than that of the most frequently-used inhibitor L-1-MT. 8-Nitrotryptanthrin has a microplate Alamar Blue assay (MABA) minimum inhibitory concentration (MIC) value of 0.032 μg/mL. 8-Nitrotryptanthrin also has a LORA MIC value of 2.4 μg/mL, while the majority of analogues lack LORA activity.

Biological Activity I Assay Protocols (From Reference)

ln Vitro

It has been discovered that the tytanthrin derivative GNF-PF-3777 (8-Nitrotryptanthrin; compound 5i) is a strong hIDO2 inhibitor with exceptional efficiency, far more effective than the most widely used inhibitor L-1-MT. All nine tryptophan compounds exhibited hIDO2 inhibitory activity, as indicated by IC50 values. GNF-PF-3777 demonstrated a stronger inhibitory effect than D-1-MT (262.75 μM) and L-1-MT (82.53 μM) (1.87 μM). GNF-PF-3777 has an EC50 of 0.82 μM and demonstrates strong anti-trypanosome activity[2]. The minimum inhibitory concentration (MIC) of GNF-PF-3777 (8-nitrotryptamine) in the microplate Alamar Blue assay (MABA) is 0.032 μg/mL. GNF-PF-3777 has a LORA MIC of 2.4 μg/mL, whereas the majority of its analogues don't exhibit any LORA activity [3].

ln Vivo

Animal Protocol

References

[1]. Establishment of a human indoleamine 2, 3-dioxygenase 2 (hIDO2) bioassay system and discovery of tryptanthrin derivatives as potent hIDO2 inhibitors. Eur J Med Chem. 2016 Nov 10;123:171-9.

[2]. Antitrypanosomal activities of tryptanthrins. Antimicrob Agents Chemother. 2002 Mar;46(3):882-3.

[3]. Design, synthesis, and structure-activity relationship studies of tryptanthrins as antitubercular agents. J Nat Prod. 2013 Mar 22;76(3):354-67.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C15H7N3O4

Molecular Weight

293.234

Exact Mass

293.04

Elemental Analysis

C, 61.44; H, 2.41; N, 14.33; O, 21.82

CAS #

77603-42-0

Related CAS #

77603-42-0

PubChem CID

478573

Appearance

White to off-white solid powder

LogP

1.9

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

Rotatable Bond Count

Heavy Atom Count

Complexity

582

Defined Atom Stereocenter Count

InChi Key

UFMQJYHLIUACCG-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H7N3O4/c19-13-10-7-8(18(21)22)5-6-12(10)17-14(13)16-11-4-2-1-3-9(11)15(17)20/h1-7H

Chemical Name

8-nitroindolo[2,1-b]quinazoline-6,12-dione

Synonyms

O=C1N2C(C(C3=C2C=CC([N+]([O-])=O)=C3)=O)=NC4=CC=CC=C41

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:6.4 mg/mL (Need warming)

Water:

Ethanol:

Solubility (In Vivo)

8-Nitrotryptanthrin;8-Nitro tryptanthrin

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.4103 mL	17.0515 mL	34.1029 mL
	5 mM	0.6821 mL	3.4103 mL	6.8206 mL
	10 mM	0.3410 mL	1.7051 mL	3.4103 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

Mass

Concentration

Volume

Molecular Weight*

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

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

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.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

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)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

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:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

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.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
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)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

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.)

% DMSO

% Tween 80

% ddH₂O

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.

Note： (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.

Biological Data

Eur J Med Chem.2016 Nov 10;123:171-179.