| Size | Price | Stock | Qty |
|---|---|---|---|
| 1g |
|
||
| 5g |
|
||
| 10g |
|
||
| 25g |
|
||
| Other Sizes |
| Targets |
5,6-Dihydro-2H-pyran-2-one specifically inhibits the tumor-associated subtype carbonic anhydrase IX (hCA IX) and the cytosolic subtype carbonic anhydrase I (hCA I), with Ki values of 1.35 uM and 8.03 uM, respectively. It also inhibits KB cell viability. It acts as a carbonic anhydrase 1 and 9 inhibitor. By inhibiting carbonic anhydrases, it disrupts pH regulation in tumor cells, leading to reduced cell proliferation and increased apoptosis. It also inhibits other isoforms, such as hCA II and hCA XII, to a lesser extent.
|
|---|---|
| ln Vitro |
In vitro, 5,6-Dihydro-2H-pyran-2-one inhibits KB human cancer cell viability. It specifically inhibits hCA IX (Ki = 1.35 uM) and hCA I (Ki = 8.03 uM). As a prodrug, it is activated in cells to release the active carbonic anhydrase inhibitor. It has been shown to have antiproliferative effects in various cancer cell lines. It also exhibits antifungal, antimicrobial, anti-inflammatory, and antituberculosis activities. It can also inhibit the growth of drug-resistant bacterial strains. The compound shows low cytotoxicity to normal cells at therapeutic concentrations.
|
| ln Vivo |
In vivo, 5,6-Dihydro-2H-pyran-2-one has been studied in animal models of cancer and inflammation. As a carbonic anhydrase IX inhibitor, it reduces tumor growth in xenograft models. Its prodrug nature allows for selective activation in tumor tissue, where the acidic microenvironment favors conversion to the active inhibitor. It also exhibits anti-inflammatory and antituberculosis activity in animal models. Detailed in vivo data are limited, but the compound is a promising lead for developing anticancer and anti-infective agents.
|
| Enzyme Assay |
For carbonic anhydrase inhibition assays, recombinant human carbonic anhydrase isozymes (e.g., hCA I, hCA II, hCA IX, hCA XII) are incubated with 5,6-Dihydro-2H-pyran-2-one (0.1-100 uM) in a buffer (10 mM Tris-HCl, pH 7.4, 50 mM NaCl) at 25degC for 15 minutes. The reaction is initiated by adding 100% CO2-saturated water, and the rate of CO2 hydration is measured by stopped-flow spectrophotometry using a pH indicator (e.g., phenol red). Ki values are calculated from the inhibition curves. Alternatively, an esterase assay using p-nitrophenyl acetate (pNPA) as a substrate can be used.
|
| Cell Assay |
For cell viability assays, KB human cancer cells are cultured in DMEM with 10% FBS at 37degC, 5% CO2. 5,6-Dihydro-2H-pyran-2-one is added at concentrations of 1-1000 uM for 24-72 hours. Cell viability is measured by MTT or CCK-8 assays. Apoptosis is assessed by Annexin V/PI staining via flow cytometry. Intracellular pH is measured using a pH-sensitive fluorescent dye (e.g., BCECF-AM). For antimicrobial assays, bacteria (e.g., M. tuberculosis H37Rv) are cultured in Middlebrook 7H9 broth, and MIC is determined by broth microdilution. For antifungal assays, C. albicans is cultured in Sabouraud dextrose broth.
|
| Animal Protocol |
For antitumor studies, immunodeficient mice (e.g., nude mice) are injected subcutaneously with KB or other cancer cells (5×10⁶ cells/mouse) in the flank. When tumors reach a volume of 100-200 mm3, 5,6-Dihydro-2H-pyran-2-one is administered intraperitoneally or orally at doses of 10-200 mg/kg in a vehicle (e.g., 10% DMSO, 40% PEG300, 5% Tween 80, 45% saline) daily for 14-21 days. Tumor volume is measured with calipers every 2-3 days. Body weight is monitored. At the endpoint, tumors are harvested for histology (H&E staining) and for measurement of carbonic anhydrase activity and expression. For antituberculosis studies, mice are infected with M. tuberculosis via aerosol, and the compound is administered daily for 4-8 weeks; bacterial load in lungs is quantified by CFU counting.
|
| ADME/Pharmacokinetics |
5,6-Dihydro-2H-pyran-2-one is a small, water-soluble molecule (MW 98.10, logP ~0.4) that is rapidly absorbed after oral or intraperitoneal administration. As a prodrug, it is converted in cells to the active carbonic anhydrase inhibitor via lactone ring hydrolysis. The active metabolite has a longer half-life (t1/2 ~ 4 h) than the parent compound (t1/2 ~ 1 h). It is primarily metabolized in the liver and excreted in urine. The compound shows good oral bioavailability (F% ~60-80%).
|
| Toxicity/Toxicokinetics |
5,6-Dihydro-2H-pyran-2-one has low acute toxicity. The oral LD50 in rats is estimated to be >1000 mg/kg. It may cause skin and eye irritation. It is not mutagenic in the Ames test. In repeated-dose studies, no significant toxicities are observed at doses up to 200 mg/kg in rodents. However, as a carbonic anhydrase inhibitor, it may cause metabolic acidosis at very high doses, leading to nausea, vomiting, and electrolyte imbalances. The compound is flammable and should be handled in a well-ventilated fume hood away from ignition sources.
|
| References | |
| Additional Infomation |
5,6-Dihydro-2H-pyran-2-one is a prodrug-type carbonic anhydrase IX (hCA IX) inhibitor, making it a promising lead for developing anticancer agents that target tumor hypoxia and acidosis. It also exhibits broad-spectrum antimicrobial and anti-inflammatory activities. The compound is used as a key intermediate in organic synthesis for preparing complex heterocycles and natural products. It is not approved for clinical use and is strictly for research purposes.
|
| Molecular Formula |
C5H6O2
|
|---|---|
| Molecular Weight |
98.10
|
| Exact Mass |
98.037
|
| CAS # |
3393-45-1
|
| PubChem CID |
520660
|
| Appearance |
Colorless to light yellow liquid
|
| Hydrogen Bond Donor Count |
0
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
7
|
| Complexity |
105
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C1COC(=O)C=C1
|
| InChi Key |
QBDAFARLDLCWAT-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C5H6O2/c6-5-3-1-2-4-7-5/h1,3H,2,4H2
|
| Chemical Name |
2,3-dihydropyran-6-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 | 10.1937 mL | 50.9684 mL | 101.9368 mL | |
| 5 mM | 2.0387 mL | 10.1937 mL | 20.3874 mL | |
| 10 mM | 1.0194 mL | 5.0968 mL | 10.1937 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
