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| Targets |
Chitin synthase inhibitor 4 targets chitin synthase (CHS), an enzyme that is essential for the synthesis of chitin, a key component of the fungal cell wall. By inhibiting CHS, the compound disrupts cell wall formation, leading to abnormal hyphal growth, cell content leakage, cell wall degradation, and plasmolysis. This mechanism is specific to fungi and is not toxic to plants or mammals, making it an attractive target for fungicide development.
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| ln Vitro |
With EC50 values of 2.47 μg/mL and 0.71 μg/mL for Sclerotinia sclerotiorum and Staphylococcus apillum, respectively, chitin synthase inhibitor 4 has strong antifungal efficacy [1]. Staphylococcus api and Sclerotinia sclerotiorum are effectively inhibited by chitin synthase inhibitor 4 (50 μg/mL), with respective inhibition rates of 90.3% and 88.7% [1]. The use of chitin synthase inhibitor 4 (1 μg/mL) will cause aberrant hyphal growth, limit hyphal growth, reduce cell content, and cause cell wall disintegration and plasmolysis [1]. Polyantibin D and chitin synthase are both inhibited by chitin synthase inhibitor 4 (50 μM; 3 h), with respective inhibition rates of 63.84% and 68.08% [1].
In vitro, Chitin synthase inhibitor 4 shows potent antifungal activity. It has EC50 values of 0.71 μg/mL against V. mali and 2.47 μg/mL against S. sclerotiorum. At 1 μg/mL, it blocks hyphae growth, resulting in abnormal growth and inducing cell content decrease, cell wall degradation, and plasmolysis. It also shows good inhibitory activity against chitin synthase and polyoxin D, with inhibition rates of 68.08% and 63.84%, respectively. |
| ln Vivo |
Chitin synthase inhibitor 4 (50 μg/mL) shows strong therapeutic and preventive benefits on Sclerotinia sclerotiorum without noticeable phytotoxicity [1]. Chitin synthase inhibitor 4 has modest acute toxicity and no risk of carcinogenesis or mutagenic damage [1].
In vivo, Chitin synthase inhibitor 4 shows strong therapeutic and preventive benefits on Sclerotinia sclerotiorum at 50 μg/mL without noticeable phytotoxicity. This demonstrates its potential as an effective and safe agricultural fungicide. |
| Enzyme Assay |
A cell-free assay for Chitin synthase inhibitor 4 involves measuring its inhibition of chitin synthase enzymatic activity. Recombinant chitin synthase is incubated with a substrate (UDP-N-acetylglucosamine) in the presence of varying concentrations of the compound. The incorporation of N-acetylglucosamine into chitin is measured, and the IC50 is calculated. Specific IC50 values are not provided in the available sources.
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| Cell Assay |
Cellular assays for Chitin synthase inhibitor 4 typically involve assessing its antifungal activity against fungal cultures. Fungi, such as V. mali and S. sclerotiorum, are incubated with varying concentrations of the compound, and the minimum inhibitory concentration (MIC) or EC50 is determined. The compound's effects on hyphal morphology can be observed microscopically.
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| Animal Protocol |
Animal/Disease Models: Salmonella typhimurium in rats [1]
Doses: According to the acute oral toxicity of chemicals - Acute toxicity classification method Route of Administration: po (oral gavage) Experimental Results: According to the toxicity classification standard, the acute toxicity is 3.58, carcinogenic toxicity, mutagenic toxicity is negative. In vivo animal experiments for Chitin synthase inhibitor 4 are not applicable as it is a fungicide intended for agricultural use on plants, not for animal models. |
| ADME/Pharmacokinetics |
Chitin synthase inhibitor 4 has a molecular formula of C20H15FN4O and a molecular weight of 346.36 g/mol. Specific pharmacokinetic properties are not applicable as it is a fungicide. It is a solid.
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| Toxicity/Toxicokinetics |
Toxicity data indicate it has modest acute toxicity and no risk of carcinogenesis or mutagenic damage. It shows no noticeable phytotoxicity.
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| References |
[1]. Zhang X, et al. Synthesis, Antifungal Activity, and 3D-QASR of Novel 1,2,3,4-Tetrahydroquinoline Derivatives Containing a Pyrimidine Ether Scaffold as Chitin Synthase Inhibitors. J Agric Food Chem. 2022 Jul 21.
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| Additional Infomation |
Chitin synthase inhibitor 4 (CAS: 2755847-31-3) is a chitin synthase inhibitor with antimicrobial and fungicidal activity. It is also known as Compound 4fh. The compound has potent antifungal activity against V. mali and S. sclerotiorum and is a candidate fungicide for agricultural use. It is not a therapeutic drug and is strictly for research purposes.
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| Molecular Formula |
C20H15FN4O
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|---|---|
| Molecular Weight |
346.357707262039
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| Exact Mass |
346.122
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| CAS # |
2755847-31-3
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| PubChem CID |
164886638
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
4.3
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
26
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| Complexity |
523
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1CC2=CC=CC=C2N(C1)C3=C(C(=NC=N3)OC4=CC=CC=C4C#N)F
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| InChi Key |
NBUUFZOGDLIBJX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C20H15FN4O/c21-18-19(25-11-5-8-14-6-1-3-9-16(14)25)23-13-24-20(18)26-17-10-4-2-7-15(17)12-22/h1-4,6-7,9-10,13H,5,8,11H2
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| Chemical Name |
2-[6-(3,4-dihydro-2H-quinolin-1-yl)-5-fluoropyrimidin-4-yl]oxybenzonitrile
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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 (~288.72 mM)
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| 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 | 2.8872 mL | 14.4358 mL | 28.8717 mL | |
| 5 mM | 0.5774 mL | 2.8872 mL | 5.7743 mL | |
| 10 mM | 0.2887 mL | 1.4436 mL | 2.8872 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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