Art. -Nr.: HY-W001542

5-Hydroxyoxindole

Name: 5-Hydroxyoxindole
Brand: MedChemExpress
SKU: HY-W001542
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5-Hydroxyoxindole is an endogenous compound and a Uric acid (HY-B2130) analog. 5-Hydroxyoxindole selectively inhibits rat MAO-A. 5-Hydroxyoxindole scavenges DPPH radicals, inhibits lipid peroxidation, suppresses hydrogen peroxide-induced intracellular oxidative stress, and reduces ERK activity. 5-Hydroxyoxindole can be used in research on leukemia and neuroblastoma.

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Reinheit : 95.09%
CAS. Nr.: 3416-18-0
Formel: C₈H₇NO₂
Molecular Weight:149.15

Speicherung:

Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month

5-Hydroxyoxindole Chemical Structure

CAS. Nr.: 3416-18-0

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Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target

^[1]^[2]

Human Endogenous Metabolite

MAO-A

Alle Endogenous Metabolite Isoform-spezifische Produkte anzeigen :

Alle Monoamine Oxidase Isoform-spezifische Produkte anzeigen :

MAO-A
MAO-B

Alle ERK Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
N1E-115	EC50	21.2 μM	EC50 for inhibition of N1E-115 cell proliferation assessed by [3H]thymidine incorporation after 20 hrs exposure and 4 hrs labeling. EC50 for inhibition of N1E-115 cell proliferation assessed by [3H]thymidine incorporation after 20 hrs exposure and 4 hrs labeling.	11006132
BALB/3T3	EC50	15.0 μM	EC50 for inhibition of BALB/c3T3 cell proliferation assessed by [3H]thymidine incorporation after 20 hrs exposure and 4 hrs labeling. EC50 for inhibition of BALB/c3T3 cell proliferation assessed by [3H]thymidine incorporation after 20 hrs exposure and 4 hrs labeling.	11006132
PC-12	EC50	54.7 μM	EC50 for inhibition of PC12 cell proliferation assessed by [3H]thymidine incorporation after 20 hrs exposure and 4 hrs labeling. EC50 for inhibition of PC12 cell proliferation assessed by [3H]thymidine incorporation after 20 hrs exposure and 4 hrs labeling.	11006132
HL-60	EC50	58.2 μM	EC50 for inhibition of HL60 cell proliferation assessed by [3H]thymidine incorporation after 20 hrs exposure and 4 hrs labeling. EC50 for inhibition of HL60 cell proliferation assessed by [3H]thymidine incorporation after 20 hrs exposure and 4 hrs labeling.	11006132
NIH3T3	EC50	34.8 μM	EC50 for inhibition of NIH 3T3 cell proliferation assessed by [3H]thymidine incorporation after 20 hrs exposure and 4 hrs labeling. EC50 for inhibition of NIH 3T3 cell proliferation assessed by [3H]thymidine incorporation after 20 hrs exposure and 4 hrs labeling.	11006132

In Vitro

Anti-cancerApoptosisOxidative StressOthers

Anti-cancer

5-Hydroxyoxindole (20 h) inhibits the proliferation of N1E-115, BALB/c3T3, BBC, PC12, HL60, and NIH 3T3 cells, with the lowest EC₅₀ of 15.0 µM in BALB/c3T3 cells^[3].

Anti-cancer

Apoptosis

5-Hydroxyoxindole (72 h) induces apoptotic nuclear morphology in N1E-115 cells, including DNA fragmentation and chromatin condensation^[3].

Oxidative Stress

5-Hydroxyoxindole (0.25-1.00 mM) scavenges DPPH radicals in cell-free assays, with a second-order rate constant of 9.2 M^-1·s^-1^[4].
5-Hydroxyoxindole (20 min) inhibits lipid peroxidation in rat liver microsome/tert-butyl hydroperoxide assays^[4].
5-Hydroxyoxindole (100 μM; 60 min) shows no significant iron-induced pro-oxidant effect in the cell-free formaldehyde generation assay^[4].
5-hydroxyoxindole inhibits tert-butyl hydroperoxide-induced lipid peroxidation in rat liver microsomes, with an IC₅₀ of 300 μM^[5].

Others

5-Hydroxyoxindole (1 pM-0.01 M) is a selective inhibitor of MAO-A in rat brain nonsynaptic mitochondria, with an IC₅₀ of 56.8 μM for MAO-A and an IC₅₀ of 1.3 mM for MAO-B^[2].
5-Hydroxyoxindole (0-100 µM; 5 min) inhibits ERK activity in N1E-115 lysates, reaching 20% inhibition at 60 µM^[3].
5-Hydroxyoxindole (0-100 µM; 5 min) strongly reduces ERK2 phosphorylation in N1E-115 cells at 10 µM, whereas ERK1 phosphorylation is only minimally affected^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Proliferation Assay^[3]

Cell Line:

N1E-115, BALB/c3T3, BBC, PC12, HL60, and NIH 3T3 cells
Concentration:

Concentration-response for EC₅₀ determination
Incubation Time:

20 h (exposure); 4 h (thymidine incorporation)
Result:

EC₅₀ values were 21.2 µM in N1E-115, 15.0 µM in BALB/c3T3, and 19.4 µM in BBC cells.
Additional EC50 values were 54.7 µM in PC12, 58.2 µM in HL60, and 34.8 µM in NIH 3T3 cells.
At 0.1 mM, cell proliferation was reduced by 80% compared with controls.

Western Blot Analysis^[3]

Cell Line:

N1E-115 cells
Concentration:

0, 10, 30, 60, and 100 µM
Incubation Time:

5 min (pre-exposure); 5 min (FCS stimulation)
Result:

At 10 µM, ERK2 phosphorylation was strongly reduced.
In contrast, ERK1 phosphorylation was little affected.

Related Protocols :

Chemical Information

CAS. Nr. 3416-18-0
Appearance Solid
Molecular Weight 149.15
Formel C₈H₇NO₂
Color Light brown to brown
SMILES

O=C1NC2=C(C=C(O)C=C2)C1
Structure Classification
- Alkaloids
- Indole Alkaloids
- Phenols
- Monophenols
Initial Source
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 100 mg/mL (670.47 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

6.7047 mL

33.5233 mL

67.0466 mL

5 mM

1.3409 mL

6.7047 mL

13.4093 mL

10 mM

0.6705 mL

3.3523 mL

6.7047 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Working solution concentration: 0.22 mg/mL

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (279 KB)
SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
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GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Niino T, et al. A 5-hydroxyoxindole derivative attenuates LPS-induced inflammatory responses by activating the p38-Nrf2 signaling axis. Biochemical Pharmacology. 2018 Sep 1;155:182-97.

[2]. Crumeyrolle-Arias M, et al. Inhibition of brain mitochondrial monoamine oxidases by the endogenous compound 5-hydroxyoxindole. Biochemical pharmacology. 2004 Mar 01;67(5):977-9.

[3]. Cane A, et al. The endogenous oxindoles 5-hydroxyoxindole and isatin are antiproliferative and proapoptotic. Biochemical and biophysical research communications. 2000 Sep 16;276(1):379-84.

[4]. Yasuda D, et al. Preparation and antioxidant/pro-oxidant activities of 3-monosubstituted 5-hydroxyoxindole derivatives. Journal of clinical biochemistry and nutrition. 2016;59(3):165-73.

[5]. Yasuda D, et al. Antioxidant activities of 5-hydroxyoxindole and its 3-hydroxy-3-phenacyl derivatives: the suppression of lipid peroxidation and intracellular oxidative stress. Bioorganic & medicinal chemistry. 2013 Dec 15;21(24):7709-14.

[6]. Peesh P, et al. Benefits of equilibrium between microbiota- and host-derived ligands of the aryl hydrocarbon receptor after stroke in aged male mice. Nature communications. 2025 Feb 19;16(1):1767.

[7]. Dwivedi MK, et al. Evaluation of ethnopharmacologically selected Vitex negundo L. for In vitro antimalarial activity and secondary metabolite profiling. Journal of ethnopharmacology. 2021 Jul 15;275:114076.

[8]. Crumeyrolle-Arias M, et al. Endogenous oxidized indoles share inhibitory potency against [3H] isatin binding in rat brain. InNeuropsychiatric Disorders An Integrative Approach 2007 Jan 1 (pp. 29-34). Vienna: Springer Vienna.

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	6.7047 mL	33.5233 mL	67.0466 mL	167.6165 mL
	5 mM	1.3409 mL	6.7047 mL	13.4093 mL	33.5233 mL
	10 mM	0.6705 mL	3.3523 mL	6.7047 mL	16.7617 mL
	15 mM	0.4470 mL	2.2349 mL	4.4698 mL	11.1744 mL
	20 mM	0.3352 mL	1.6762 mL	3.3523 mL	8.3808 mL
	25 mM	0.2682 mL	1.3409 mL	2.6819 mL	6.7047 mL
	30 mM	0.2235 mL	1.1174 mL	2.2349 mL	5.5872 mL
	40 mM	0.1676 mL	0.8381 mL	1.6762 mL	4.1904 mL
	50 mM	0.1341 mL	0.6705 mL	1.3409 mL	3.3523 mL
	60 mM	0.1117 mL	0.5587 mL	1.1174 mL	2.7936 mL
	80 mM	0.0838 mL	0.4190 mL	0.8381 mL	2.0952 mL
	100 mM	0.0670 mL	0.3352 mL	0.6705 mL	1.6762 mL

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5-Hydroxyoxindole

Alle Endogenous Metabolite Isoform-spezifische Produkte anzeigen

Alle Monoamine Oxidase Isoform-spezifische Produkte anzeigen

Alle ERK Isoform-spezifische Produkte anzeigen