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Oxindole

Cat No.:V29992 Purity: ≥98%
Oxindole (Indolin-2-one) is an aromatic heterocyclic building block/intermediate.
Oxindole
Oxindole Chemical Structure CAS No.: 59-48-3
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
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Product Description
Oxindole (Indolin-2-one) is an aromatic heterocyclic building block/intermediate. Oxindole analogues have become major compounds in kinase inhibitor research.
Oxindole (CAS#: 59-48-3), also known as 2-Indolinone, is an aromatic heterocycle and a versatile starting material in the synthesis of numerous biologically active compounds including anticancer, antibacterial, and antidiabetic agents, enzyme inhibitors, and channel blockers. It is an indole analogue that shows pharmacological activity. The compound exhibits biological activities such as anti-inflammatory, anticancer, and antimicrobial properties. Its molecular formula is C8H7NO with a molecular weight of 133.15 g/mol.
Biological Activity I Assay Protocols (From Reference)
Targets
Oxindole targets multiple biological pathways involved in inflammation, cancer, and microbial infection. The Oxindole structure has been used in receptor tyrosine kinases (RTKs) inhibitors such as SU4984 and intedanib. As a versatile heterocyclic compound, it serves as a scaffold for the development of enzyme inhibitors and channel blockers. Its mechanism involves modulation of kinase activity and other cellular targets.
ln Vitro
Oxindole (Indolin-2-one) is a bicyclic compound made up of 2-pyrrolidone and a fused benzene ring. Because of their great binding affinity for a wide variety of receptors and the abundance of licensed medications that incorporate this scaffold, substituted indolinones are sometimes referred to as "privileged structures" [1]. In addition to a variety of naturally occurring chemicals made by plants, microbes, and invertebrates, oxindole can be found in the tissues and bodily fluids of mammals. 2-A wide range of pharmacological activities are exhibited by indolinone derivatives, such as analgesic, spermicidal, vasopressin antagonist, progesterone antagonist, neuroprotective, NMDA blocker, anticancer, anti-HIV, antidiabetic, antibacterial, antioxidant, kinase inhibition, AChE inhibition, anti-leishmaniasis, and phosphatase inhibition[2].
In vitro, Oxindole exhibits anti-inflammatory, anticancer, and antimicrobial properties. It is a versatile heterocyclic compound featuring an indole framework with a ketone group at the 2-position. The Oxindole structure has been used in RTK inhibitors such as SU4984 and intedanib for anti-cancer drug development. It serves as a starting material for the synthesis of numerous biologically active compounds.
ln Vivo
In vivo, Oxindole has been studied for its pharmacological activities including anti-inflammatory, anticancer, and antimicrobial effects. The Oxindole scaffold is used in the development of RTK inhibitors for cancer treatment. Further in vivo studies are needed to fully characterize its pharmacokinetic and pharmacodynamic properties. The compound is typically administered orally or via injection in preclinical studies.
Enzyme Assay
In vitro enzyme assays for Oxindole involve measuring its effects on receptor tyrosine kinases (RTKs). RTK activity is assessed using kinase activity assays with appropriate substrates. The compound's inhibition of RTKs is evaluated. For anti-inflammatory studies, COX or LOX inhibition may be assessed. Antimicrobial activity is assessed by MIC determination against bacteria and fungi. Assays are performed in appropriate buffer systems with positive controls such as known RTK inhibitors.
Cell Assay
In vitro cell-based assays for Oxindole are conducted in cancer cell lines, immune cells, and bacterial cultures. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with the compound at varying concentrations. Cell viability is assessed by MTT or CCK-8 assays. RTK inhibition is confirmed by measuring phosphorylation of downstream targets. Anti-inflammatory activity is assessed by measuring cytokine production. Antimicrobial activity is assessed by measuring growth inhibition. Experiments are performed in triplicate with appropriate positive and negative controls.
Animal Protocol
Oxindole in vivo studies are conducted in animal models of cancer, inflammation, and infection. Tumor-bearing mice are treated with Oxindole or Oxindole-based compounds via oral administration or injection. Tumor growth is monitored by caliper measurements. For anti-inflammatory studies, animal models of inflammation are used. For antimicrobial studies, animal models of infection are used. Animals are monitored for clinical signs. Tissues and blood samples are collected for histopathological and biomarker analysis at study endpoints. Studies are conducted in accordance with institutional animal care guidelines.
ADME/Pharmacokinetics
Metabolism / Metabolites
Oxyindole is a known human indole metabolite.
Oxindole (MW 133.15 g/mol, C8H7NO) is an aromatic heterocycle. It is also known as 2-Indolinone and 2,3-dihydro-1H-indol-2-one. The compound appears as a beige to yellowish-orange or pinkish-brown powder with a melting point of 128°C and a boiling point of 227°C. It is soluble in organic solvents such as ethanol and DMSO. Oxindole is used in medicinal chemistry and drug discovery.
Toxicity/Toxicokinetics
Oxindole is generally well-tolerated in preclinical studies. The compound is a versatile heterocyclic scaffold with established safety profiles. Its anti-inflammatory, anticancer, and antimicrobial activities have been demonstrated with acceptable safety profiles. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard safety precautions should be followed when handling. Comprehensive toxicological evaluation would be required for therapeutic development.
References

[1]. 2-Indolinone a versatile scaffold for treatment of cancer: a patent review (2008-2014). Expert Opin Ther Pat. 2016;26(2):149-73.

[2]. Oxindole: A chemical prism carrying plethora of therapeutic benefits. Eur J Med Chem. 2016 Nov 10;123:858-894.

Additional Infomation
Indolin-2-one is an indolinone with an oxygen group at the 2-position. It is an indolinone and a γ-lactam. Oxindole has been reported in Penicillium and available data are available.
Oxindole (2-Indolinone) is an aromatic heterocycle and versatile starting material for the synthesis of anticancer, antibacterial, and antidiabetic agents, enzyme inhibitors, and channel blockers. It exhibits anti-inflammatory, anticancer, and antimicrobial properties. The Oxindole scaffold is used in RTK inhibitors such as SU4984 and intedanib. Its molecular formula is C8H7NO with a molecular weight of 133.15 g/mol. All applications are limited to non-human research use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H7NO
Molecular Weight
133.1473
Exact Mass
133.052
CAS #
59-48-3
PubChem CID
321710
Appearance
Off-white to light yellow solid powder
Density
1.3±0.1 g/cm3
Boiling Point
312.8±45.0 °C at 760 mmHg
Melting Point
123-128 °C(lit.)
Flash Point
190.0±18.0 °C
Vapour Pressure
0.0±0.7 mmHg at 25°C
Index of Refraction
1.640
LogP
0.61
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
0
Heavy Atom Count
10
Complexity
155
Defined Atom Stereocenter Count
0
InChi Key
JYGFTBXVXVMTGB-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H7NO/c10-8-5-6-3-1-2-4-7(6)9-8/h1-4H,5H2,(H,9,10)
Chemical Name
1,3-dihydroindol-2-one
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 : ~50 mg/mL (~375.52 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (18.78 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 25.0 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: ≥ 2.5 mg/mL (18.78 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 25.0 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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (18.78 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 7.5103 mL 37.5516 mL 75.1033 mL
5 mM 1.5021 mL 7.5103 mL 15.0207 mL
10 mM 0.7510 mL 3.7552 mL 7.5103 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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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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