| Size | Price | Stock | Qty |
|---|---|---|---|
| 10g |
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| 25g | |||
| 50g | |||
| Other Sizes |
Purity: ≥98%
Isatin (also named 2,3-Indolinedione) is an endogenous MAO inhibitor. Isatin induces apoptosis of MCF-7 cells. Bcl-2 expression is decreased and the ratio of Bcl-2 to Bax is significantly decreased by isatin. The mitochondrial transmembrane potential is markedly decreased and the release of cytochrome c into the cytosol is elevated following treatment with isatin. At the same time, caspase-9 and -3 are stimulated, followed by the degradation of ICAD, a caspase-3 substrate.
| Targets |
Monoamine Oxidase A (MAO-A) (Ki = 3.4 μM) [1]
Monoamine Oxidase B (MAO-B) (Ki = 2.8 μM) [1] |
|---|---|
| ln Vitro |
Isatin (1–400 μM) causes dose- and time-dependent cell death in dopaminergic SH-SY5Y cells. A continuum of necrosis, apoptosis, and survival led to this death[2].
Isatin (Indoline-2,3-dione) inhibited purified rat brain MAO-A and MAO-B with Ki values of 3.4 μM and 2.8 μM, respectively, showing similar affinity for both isoforms [1] In human neuroblastoma cells (SH-SY5Y), Isatin (Indoline-2,3-dione) triggered a dose- and time-dependent switch from apoptosis to necrosis: 100-200 μM for 6-12 hours induced apoptosis (25-40% apoptotic cells) via mitochondrial membrane potential loss and caspase-3 activation; 300-500 μM for 24 hours induced necrosis (55-70% necrotic cells) with ATP depletion and plasma membrane rupture [2] At concentrations of 50-200 μM, Isatin (Indoline-2,3-dione) reduced cell viability of SH-SY5Y cells by 20-65% in a dose-dependent manner [2] In rat brain synaptosomes, Isatin (Indoline-2,3-dione) (10-100 μM) inhibited serotonin (5-HT) degradation by MAO, increasing extracellular 5-HT levels by 1.5-3.2-fold [3] |
| ln Vivo |
Isatin, at a single dose of 80 mg/kg, acts quickly on the hypothalamic serotonergic system. While it did not significantly change 5-HIAA concentrations, isatin dramatically raises 5-HT concentrations in the cortex and hypothalamus[3].
In male Wistar rats, intraperitoneal injection of Isatin (Indoline-2,3-dione) (50 mg/kg) increased brain serotonin (5-HT) and noradrenaline (NA) levels by 45% and 38%, respectively, within 2 hours, due to MAO inhibition [3] Rats treated with Isatin (Indoline-2,3-dione) (25-100 mg/kg ip) showed dose-dependent reduction in locomotor activity, consistent with enhanced central serotonergic signaling [3] |
| Enzyme Assay |
Purified rat brain MAO was mixed with reaction buffer containing [14C]serotonin (for MAO-A) or [14C]phenylethylamine (for MAO-B) as substrates. Isatin (Indoline-2,3-dione) was serially diluted (0.1-100 μM) and incubated with MAO and substrate at 37°C for 30 minutes. The reaction was terminated by adding hydrochloric acid, and radiolabeled CO2 (product of monoamine oxidation) was trapped and quantified by scintillation counting. Ki values were calculated using Lineweaver-Burk plots to confirm competitive inhibition [1]
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| Cell Assay |
SH-SY5Y neuroblastoma cells were cultured in DMEM/F12 medium supplemented with fetal bovine serum and antibiotics. Cells were seeded into 96-well plates (5×103 cells/well) or 6-well plates (1×105 cells/well) and treated with Isatin (Indoline-2,3-dione) (50-500 μM) for 6-24 hours. Cell viability was assessed by MTT assay [2]
Apoptosis was detected by Annexin V-FITC/PI staining and flow cytometry; mitochondrial membrane potential was measured with JC-1 dye. Caspase-3 activity was quantified using a colorimetric assay with a caspase-3-specific substrate [2] For necrosis assessment, cells were stained with propidium iodide (PI) alone (to detect plasma membrane rupture) and ATP levels were measured using a luciferase-based bioluminescent assay [2] |
| Animal Protocol |
Dissolved in DMSO; 100 mg/kg; i.p.
Albino rats of the Fisher strain Male Wistar rats (200-250 g) were randomized into groups (n=6 per group) and administered Isatin (Indoline-2,3-dione) (25, 50, 100 mg/kg) or vehicle (0.9% normal saline) via intraperitoneal injection. Two hours post-dosing, rats were euthanized, brains were dissected, and homogenized in ice-cold perchloric acid. Brain levels of serotonin (5-HT) and noradrenaline (NA) were quantified by HPLC with electrochemical detection [3] Locomotor activity was measured in an open-field apparatus for 30 minutes, starting 30 minutes after Isatin (Indoline-2,3-dione) administration. Total distance traveled and rearing frequency were recorded using automated activity monitors [3] |
| Toxicity/Toxicokinetics |
Toxicity Data
LC50 (Rat) > 5,200 mg/m³/4 hours |
| References |
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| Additional Infomation |
Isatin is an indole-dione, a 2,3-dione derivative of indole. It is an EC 1.4.3.4 (monoamine oxidase) inhibitor and also a plant metabolite. Indigo is an indole derivative, first obtained by Erdman and Laurent in 1841, and is a product of the oxidation of indigo dye with nitric acid and chromic acid. This compound is found in various plants, and the Schiff base of indigo has been studied for pharmaceutical applications. Indigo has been reported in Calanthe discolor, Capparis spinosa, and several other organisms with relevant data. Indigo is an indole-dione obtained by oxidizing indigo. It is a monoamine oxidase inhibitor, and its levels have been found in high amounts in the urine of patients with Parkinson's disease.
Indigo (indoline-2,3-dione) is an endogenous compound identified as a purified form of triphenylmethylnaphthalene, a naturally occurring monoamine oxidase (MAO) inhibitor[1] Its MAO inhibitory activity leads to an increase in the levels of monoamine neurotransmitters (serotonin, norepinephrine) in the brain, thereby promoting serotonergic regulation[1][3] In human neuroblastoma cells, Indigo (indoline-2,3-dione) through dose and The time-dependent shift in cytotoxicity from apoptosis (low concentration/short exposure) to necrosis (high concentration/long exposure) involves mitochondrial dysfunction and ATP depletion [2]. It is endogenously present in mammalian tissues (brain, blood, urine) and plays a role in regulating monoamine levels in the central nervous system (CNS) [1][3]. The compound’s dual inhibitory effect on MAO-A and MAO-B, as well as its endogenous nature, makes it a potential tool for studying monoamine metabolism and neurotoxicity [1][2][3]. |
| Molecular Formula |
C8H5NO2
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|---|---|---|
| Molecular Weight |
147.13
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| Exact Mass |
147.032
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| CAS # |
91-56-5
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| Related CAS # |
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| PubChem CID |
7054
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| Appearance |
Yellow to orange solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
360.3±52.0 °C at 760 mmHg
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| Melting Point |
193-195 °C (dec.)(lit.)
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| Flash Point |
171.7±30.7 °C
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| Vapour Pressure |
0.0±1.8 mmHg at 25°C
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| Index of Refraction |
1.679
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| LogP |
-0.17
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
212
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
JXDYKVIHCLTXOP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
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| Chemical Name |
1H-indole-2,3-dione
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| Synonyms |
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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 |
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| 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) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.75 mg/mL (18.69 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 27.5 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 | 6.7967 mL | 33.9836 mL | 67.9671 mL | |
| 5 mM | 1.3593 mL | 6.7967 mL | 13.5934 mL | |
| 10 mM | 0.6797 mL | 3.3984 mL | 6.7967 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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