| Size | Price | Stock | Qty |
|---|---|---|---|
| 10g |
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| 25g | |||
| Other Sizes |
Purity: ≥98%
| Targets |
4-Hydroxyquinoline interacts with multiple molecular targets. It has been shown to promote tumor cell survival by suppressing anti-tumor immune responses via the AhR (Aryl hydrocarbon Receptor) in an autocrine/paracrine fashion. It is also a known inhibitor of monoamine oxidases (MAO-A and MAO-B) and serves as a core scaffold for IDO1 (indoleamine 2,3-dioxygenase 1) inhibitors. Its derivatives are reported to inhibit herpesvirus DNA polymerases and components of the electron transport chain, such as NDH-2 and the mitochondrial cytochrome bc1 complex.
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|---|---|
| ln Vitro |
4-Quinolone (Kynurine) promotes tumor cell survival and motility via autocrinely/paracrinely inhibiting anti-tumor immune responses via AhR. This mechanism is especially active in human brain tumors, where kynurenine production and TDO expression are both increased by AhR activation. TDO protein levels are extremely low in healthy human brains, but they rise with the aggressiveness of human brain tumors [3].
In vitro, 4-hydroxyquinoline and its derivatives demonstrate various activities. Modified analogues have shown promising antiproliferative activity against the human colorectal cancer cell line HCT116. Antibacterial and antifungal activities have been observed, with 2-alkyl-4-hydroxyquinolines isolated from marine Streptomyces showing potent inhibition of hyphal growth in Candida albicans with an IC50 of 11.4 µg/mL. At the enzymatic level, a 4-hydroxyquinoline-based IDO1 inhibitor was identified through in vitro enzyme activity assays, displaying an IC50 of approximately 37.78 μmol/L. |
| ln Vivo |
In vivo efficacy of 4-hydroxyquinoline derivatives has been demonstrated in various animal models. For instance, the derivative Y27 significantly prolonged the lifespan, and ameliorated proteinuria and renal lesions in MRL/lpr lupus model mice. This protective effect is linked to enhancing the suppressive capacity of CD4+CD25+ regulatory T (Treg) cells. In a Toxoplasma gondii infection model, the derivative 2-heptyl-4-hydroxyquinoline N-oxide (HQNO) significantly reduced the parasite burden in the peritoneal cavity of mice, demonstrating its potential as an antiparasitic agent.
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| Enzyme Assay |
A standard fluorescence spectrophotometric method is used to assess MAO-B inhibition. The protocol involves a reaction mixture at pH 7.4 (100 mM potassium phosphate buffer), containing human recombinant MAO-B, the test compound at various concentrations, and the substrate kynuramine. Kynuramine is non-fluorescent but is converted by MAO-B into the highly fluorescent product, 4-hydroxyquinoline. After an incubation period (e.g., 15-60 mins), the amount of fluorescent 4-hydroxyquinoline formed is measured. The compound's half-maximal inhibitory concentration (IC50) is calculated relative to a no-inhibitor control.
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| Cell Assay |
A typical cell-based assay also utilizes fluorescence detection to evaluate the impact of compounds on MAO-B activity in intact cells. This protocol often uses insect cell microsomes expressing human recombinant MAO-B. In this assay, the test compound, serially diluted, and the substrate kynuramine are added to the reaction mixture containing the MAO-B microsomes and incubated at room temperature for a defined period (e.g., 20 minutes). Following incubation, the fluorescence of the resulting 4-hydroxyquinoline is measured by fluorescence spectrophotometry. A dose-response curve is generated by comparing fluorescence intensity across different concentration groups to calculate the compound's IC50, quantifying its inhibitory effect on cellular MAO-B activity.
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| Animal Protocol |
Taking Y27 in a systemic lupus erythematosus (SLE)-like mouse model as an example, the procedure is as follows: Female MRL/lpr mice (10-week old) are treated orally by gavage with Y27 for 10 weeks. Various endpoints are monitored during and after treatment to evaluate efficacy: survival rate, severity of proteinuria and renal lesions (assessed by blood urea nitrogen, serum creatinine, and renal histopathology), determination of CD4+CD25+Foxp3+ Treg cell percentages in peripheral blood leukocytes by flow cytometry, and measurement of anti-double-stranded DNA antibodies levels in serum. A similar protocol is applied in a chronic graft-versus-host disease (GVHD) mouse model for 12 weeks to evaluate the renoprotective effects.
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| ADME/Pharmacokinetics |
Computational predictions indicate favorable absorption and distribution properties for 4-hydroxyquinoline. admetSAR models predict high human intestinal absorption (100%), good Caco-2 permeability (86.39%), and satisfactory oral bioavailability (80%), suggesting good oral absorption. The compound is also predicted to be able to cross the blood-brain barrier (68.79%) and may localize in mitochondria. Furthermore, as the fluorescent product of the MAO-B reaction, 4-hydroxyquinoline is also used as a substrate or product to assess the drug metabolism process in plasma or tissues.
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| Toxicity/Toxicokinetics |
4-Hydroxyquinoline is hazardous to both human operators and the environment. According to its safety data sheet (SDS), direct contact can cause irritation, as it is harmful if swallowed and causes skin, eye, and respiratory tract irritation. Furthermore, it is very toxic to aquatic life with long-lasting effects (H410), indicating high ecotoxicity. Therefore, strict safety protocols must be followed when handling this compound in a research laboratory, and proper waste disposal is crucial to prevent environmental contamination.
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| References |
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| Additional Infomation |
4-Quinolone is a quinolone compound in which 1,4-dihydroquinoline is substituted with an oxygen group at the 4-position. It is a tautomer of quinoline-4-ol. 4-Hydroxyquinolone has been reported to exist in Glycosmis parviflora and Glycosmis citrifolia, and relevant data are available for reference.
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| Molecular Formula |
C9H12N2O
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|---|---|
| Molecular Weight |
164.21
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| Exact Mass |
145.052
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| CAS # |
611-36-9
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| Related CAS # |
611-36-9;
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| PubChem CID |
69141
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| Appearance |
White to light brown solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
313.0±15.0 °C at 760 mmHg
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| Melting Point |
200-202 °C(lit.)
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| Flash Point |
143.1±20.4 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.691
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| LogP |
2.45
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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 |
198
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C2C(=C1)C(=O)C=CN2
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| InChi Key |
PMZDQRJGMBOQBF-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H7NO/c11-9-5-6-10-8-4-2-1-3-7(8)9/h1-6H,(H,10,11)
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| Chemical Name |
4-Hydroxyquinoline
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| Synonyms |
4-Hydroxyquinoline 4 Hydroxyquinoline 4Hydroxyquinoline Kynurine
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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 |
| 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) |
DMSO : ~100 mg/mL (~688.90 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (17.22 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 (17.22 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (17.22 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.0898 mL | 30.4488 mL | 60.8976 mL | |
| 5 mM | 1.2180 mL | 6.0898 mL | 12.1795 mL | |
| 10 mM | 0.6090 mL | 3.0449 mL | 6.0898 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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT02153541 | NOT YET RECRUITING | Drug: Antipyrine-benzocaine otic solution Other: Glycerin with Oxyquinoline Sulfate |
Asthma | Global United Pharmaceutical Corporation | 2023-04-01 | Phase 2 |
| NCT04492501 | COMPLETED | Procedure: Therapeutic Plasma exchange Biological: Convalescent Plasma Drug: Tocilizumab |
ARDS Covid19 Critical Illness Cytokine Release Syndrome |
UNICEF | 2020-04-01 | Not Applicable |
| NCT01429012 | WITHDRAWN | Biological: Mesenchymal Stem Cells Other: Culture medium without MSC. |
Nonunion Fracture | University of Liege | 2012-11 | Phase 2 |
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