| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
IC50: 64.4 µg/mL (α-glucosidase); 130.5 µg/mL (α-amylase)[1]
2-Hydroxyquinoline (carbostyril) targets alpha-glucosidase, an enzyme that breaks down carbohydrates into simple sugars in the small intestine. By inhibiting alpha-glucosidase, it delays carbohydrate digestion and reduces postprandial blood glucose levels. It also inhibits alpha-amylase (IC50 = 130.5 ug/mL), another carbohydrate-digesting enzyme. Additionally, 2-hydroxyquinoline is a specific inhibitor of plaque paraoxonase 1 (PON1), an enzyme associated with high-density lipoprotein (HDL) that has antioxidant properties. It has been studied for its potential antidiabetic effects. |
|---|---|
| ln Vitro |
In vitro, 2-Hydroxyquinoline is a potent inhibitor of alpha-glucosidase with an IC50 of 64.4 ug/mL. It also inhibits alpha-amylase with an IC50 of 130.5 ug/mL. The compound has the potential for research into diabetes. It is a natural product found in various plants. It also acts as a specific inhibitor of plaque paraoxonase 1 (PON1). No detailed cellular activity data (e.g., glucose uptake in Caco-2 cells, or effects on insulin secretion) are reported in the search results. The compound is a chemical tool for studying carbohydrate metabolism and diabetes.
|
| ln Vivo |
No specific in vivo activity data for 2-Hydroxyquinoline are reported in the search results. As an alpha-glucosidase inhibitor, it has potential for evaluation in animal models of diabetes, such as streptozotocin (STZ)-induced diabetic rats or mice, or in db/db mice. The compound could be administered orally at doses of 10-100 mg/kg before a starch load, and postprandial blood glucose levels would be measured. The compound‘s effect on HbA1c, insulin sensitivity, and body weight could also be assessed. However, no such data are provided.
|
| Enzyme Assay |
The binding of 2-Hydroxyquinoline to alpha-glucosidase is measured by standard in vitro enzyme activity assays using alpha-glucosidase from Saccharomyces cerevisiae or rat intestinal acetone powder. The compound is incubated with the enzyme and the substrate p-nitrophenyl-alpha-D-glucopyranoside (pNPG). After incubation, the reaction is stopped, and the amount of p-nitrophenol released is measured spectrophotometrically at 405 nm. The IC50 of 64.4 ug/mL is calculated from dose-response curves (1-1000 ug/mL). The inhibition of alpha-amylase (IC50 = 130.5 ug/mL) is measured using porcine pancreatic alpha-amylase and starch as a substrate, with the reducing sugar product quantified by the DNS method or by a chromogenic assay. The inhibition of PON1 can be measured using paraoxon as a substrate and measuring the release of p-nitrophenol at 405 nm.
|
| Cell Assay |
No cellular experiments for 2-Hydroxyquinoline are described in the search results. For cellular alpha-glucosidase inhibition studies, Caco-2 human intestinal epithelial cells are seeded in 6- or 24-well plates. Cells are treated with 2-Hydroxyquinoline at concentrations of 1-1000 ug/mL for 1-4 hours. The cells are then lysed, and alpha-glucosidase activity in the lysate is measured using the pNPG substrate. For glucose uptake studies, cells are treated with the compound and then incubated with 2-deoxyglucose (2-DG); glucose uptake is measured using a fluorescent 2-DG analog. Cytotoxicity is assessed by MTT or LDH assays. No such data are provided.
|
| Animal Protocol |
No animal experiments for 2-Hydroxyquinoline are described in the search results. For in vivo evaluation of antidiabetic activity, 6-8-week-old male Sprague-Dawley rats or C57BL/6 mice would be used. Diabetes is induced by a single intraperitoneal injection of streptozotocin (STZ, 45-65 mg/kg). After diabetes is confirmed (blood glucose >250 mg/dL), animals are treated with 2-Hydroxyquinoline orally (10-200 mg/kg) once daily for 2-4 weeks. Blood glucose levels are measured at various time points (0, 1, 2, 4, 6, 8, 12, 24 hours after dosing) by tail prick. An oral glucose tolerance test (OGTT) is performed: after an overnight fast, animals receive an oral glucose load (2 g/kg), and blood glucose is measured at 0, 30, 60, 90, and 120 minutes. Body weight, food and water intake, and HbA1c levels are monitored. At the study endpoint, blood is collected for lipid profile and insulin levels, and the pancreas is harvested for histology and insulin immunostaining.
|
| ADME/Pharmacokinetics |
2-Hydroxyquinoline (C₉H₇NO, MW = 145.16, purity ≥98%, CAS 59-31-4) is a white to light yellow to light orange powder or crystalline solid. The melting point is 194-201degC. For storage, the compound should be kept at room temperature or 4degC, sealed, and protected from light. For in vitro use, stock solutions in DMSO (10-50 mM) can be prepared and stored at -20degC for up to 1 month or at -80degC for up to 6 months. The compound is soluble in DMSO and ethanol. For in vivo use, it can be formulated in 5% DMSO / 5% Tween-80 / 90% saline, or 0.5% methylcellulose/0.1% Tween-80, or as a suspension in water. No detailed PK parameters (oral bioavailability, Cmax, Tmax, half-life) are reported.
|
| Toxicity/Toxicokinetics |
Toxicity Summary
If a patient begins to experience potential symptoms of tendinitis or tendon rupture, it is recommended to immediately discontinue quinolone medications and avoid using the affected joint. These symptoms may include tendon pain, swelling, or inflammation. Furthermore, if serious adverse reactions occur, such as Stevens-Johnson syndrome, toxic epidermal necrolysis, hepatotoxicity, or allergic reactions, it is also recommended to discontinue quinolone medications and immediately initiate supportive care. No specific toxicity data for 2-Hydroxyquinoline are reported in the search results. As a research-grade compound, it is not intended for human or veterinary use. Standard laboratory safety precautions for handling chemicals should be followed, including the use of gloves, lab coat, and safety goggles. 2-Hydroxyquinoline has been reported to have antimicrobial, antifungal, and antioxidant activities. The compound is a natural product and may have low acute toxicity. However, no LD50 or formal toxicology studies are available. |
| References | |
| Additional Infomation |
Quinoline-2-ol is a monohydroxyquinoline with a hydroxyl substituent at the 2-position. It is an intermediate metabolite produced during the microbial degradation of quinolines and can serve as a xenobiotic metabolite for bacteria. It is a tautomer of quinoline-2(1H)-one. It has been reported that 2-hydroxyquinoline is present in Glycosmis pentaphylla, Houttuynia cordata, and Aconitum ferox, and relevant data are available for reference.
2-Hydroxyquinoline (carbostyril, 1H-quinolin-2-one) is a nitrogen-containing heterocyclic compound and a natural product found in various plants, including Houttuynia cordata (fish mint), Aconitum ferox (Indian aconite), and Glycosmis pentaphylla. It is a quinoline derivative with a hydroxyl group at the 2-position, which exists in tautomeric equilibrium with the oxo form (quinolin-2(1H)-one). 2-Hydroxyquinoline has been studied for its alpha-glucosidase and alpha-amylase inhibitory activities, making it a potential lead compound for the treatment of type 2 diabetes. It also inhibits paraoxonase 1 (PON1), an enzyme involved in the antioxidant properties of HDL. The compound has potential for diabetes research. It is for research use only and has not received regulatory approval for any indication. |
| Molecular Formula |
C9H7NO
|
|---|---|
| Molecular Weight |
145.16
|
| Exact Mass |
145.052
|
| CAS # |
59-31-4
|
| PubChem CID |
6038
|
| Appearance |
Solid powder
|
| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
352.9±15.0 °C at 760 mmHg
|
| Melting Point |
198-199 °C(lit.)
|
| Flash Point |
167.2±20.4 °C
|
| Vapour Pressure |
0.0±0.8 mmHg at 25°C
|
| Index of Refraction |
1.691
|
| LogP |
1.95
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
1
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
11
|
| Complexity |
198
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=C1C=CC2C=CC=CC=2N1
|
| InChi Key |
LISFMEBWQUVKPJ-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C9H7NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h1-6H,(H,10,11)
|
| Chemical Name |
1H-quinolin-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 (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.8890 mL | 34.4448 mL | 68.8895 mL | |
| 5 mM | 1.3778 mL | 6.8890 mL | 13.7779 mL | |
| 10 mM | 0.6889 mL | 3.4445 mL | 6.8890 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.
Link: https://clinicaltrials.gov/ct2/show/NCT07452588
Conditions:Infectious Keratitis|Adjuvant Treatment Bacterial Infectious Keratitis|Sodium Chloride 5% SolutionLink: https://clinicaltrials.gov/ct2/show/NCT04615702
Conditions:Acute PancreatitisLink: https://clinicaltrials.gov/ct2/show/NCT00331916
Conditions:Bacterial ConjunctivitisProducts are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
