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| Other Sizes |
| Targets |
The primary target of diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate is ferrochelatase, the enzyme that catalyzes the insertion of ferrous iron into protoporphyrin IX to form heme. By inhibiting ferrochelatase, the compound blocks heme synthesis, leading to the accumulation of porphyrin precursors. This mechanism of action makes the compound a valuable tool for studying iron metabolism, oxidative stress, and liver diseases.
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| ln Vitro |
In vitro, diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate functions as a ferrochelatase inhibitor, blocking heme synthesis in cultured cells. The inhibition of heme synthesis leads to the accumulation of porphyrin intermediates, which can be detected by fluorescence microscopy or HPLC. The compound is used in cell culture studies to investigate the effects of heme deficiency on cellular metabolism, oxidative stress, and mitochondrial function.
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| ln Vivo |
In vivo, diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate is an orally active porphyrin inducer. In mice, it induces the formation of Mallory Denk bodies (MDBs), which are cytoplasmic inclusions found in hepatocytes. This makes the compound a valuable tool for studying Mallory body formation, a pathological feature associated with various liver diseases including alcoholic liver disease and non-alcoholic steatohepatitis. The compound is used in research on iron metabolism, oxidative stress, and liver disease.
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| Enzyme Assay |
In vitro enzyme assays for diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate typically employ ferrochelatase enzyme activity assays. Ferrochelatase activity is measured by monitoring the incorporation of zinc or iron into protoporphyrin IX using fluorometric or spectrophotometric methods. The compound's inhibitory activity is determined by measuring the reduction in enzyme activity in the presence of varying concentrations of the compound. IC₅₀ values are calculated from dose-response curves.
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| Cell Assay |
Cellular assays for diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate are performed using hepatocyte cell lines or primary hepatocytes. Cells are treated with the compound at concentrations typically ranging from 10-200 μM for 24-72 hours. Heme synthesis inhibition is assessed by measuring porphyrin accumulation using fluorescence microscopy or HPLC. Oxidative stress markers (ROS, MDA) and mitochondrial function are evaluated. Mallory body formation can be assessed by immunohistochemistry using specific antibodies.
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| Animal Protocol |
In vivo animal studies for diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate are typically conducted in mice. The compound is administered orally at doses ranging from 50-500 mg/kg. In mice, it induces the formation of Mallory Denk bodies in hepatocytes, which are studied as a model for liver disease pathology. Porphyrin accumulation in liver tissue is measured by fluorescence microscopy or HPLC. Liver function markers and oxidative stress parameters are assessed in serum and tissue samples.
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| ADME/Pharmacokinetics |
Pharmacokinetic studies of diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate have demonstrated that it is orally active. As a 1,4-dihydropyridine derivative with molecular weight 267.32 g/mol and moderate lipophilicity, the compound is expected to be well absorbed following oral administration. The compound is metabolized through oxidation of the dihydropyridine ring to the pyridine derivative, which is a common metabolic pathway for 1,4-dihydropyridine compounds. Standard pharmacokinetic parameters would include Cmax, Tmax, and half-life.
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| Toxicity/Toxicokinetics |
Specific toxicity data for diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate are limited in the published literature. As a tool compound used in liver disease research, the compound induces Mallory body formation in mice, which is a pathological feature associated with liver injury. Standard toxicological studies would include acute toxicity assessment, repeated-dose toxicity studies, and genotoxicity screening. The compound is intended for research use only and is not approved for human therapeutic applications.
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| References |
[1]. Q X Yuan, et,al. Mallory body induction in drug-primed mouse liver. Hepatology. 1996, 24, 3.
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| Additional Infomation |
3,5-Diethoxycarbonyl-1,4-dihydropyridine is a dihydropyridine compound in which 2,4,6-trimethyl-1,4-dihydropyridine is substituted with ethoxycarbonyl groups at the 3 and 5 positions. It is an inducer of hepatic steatosis. It is a dihydropyridine and also an ethyl ester.
Diethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylic acid. Diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate (DDC) is an orally active ferrochelatase inhibitor that blocks heme synthesis. In mice, it induces the formation of Mallory Denk bodies, making it a valuable tool for studying liver disease pathology. The compound is used in research on iron metabolism, oxidative stress, and liver diseases. It is not approved for clinical use; all applications remain at the preclinical research stage. |
| Molecular Formula |
C14H21NO4
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|---|---|
| Molecular Weight |
267.32
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| Exact Mass |
267.147
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| CAS # |
632-93-9
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| PubChem CID |
12446
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| Appearance |
White to off-white solid
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| Density |
1.12g/cm3
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| Boiling Point |
335ºC at 760 mmHg
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| Melting Point |
130-132 °C(lit.)
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| Flash Point |
123.3ºC
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| Index of Refraction |
1.51
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| LogP |
2.228
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
19
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| Complexity |
408
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C([H])([H])C([H])([H])[H])C(C1=C(C([H])([H])[H])N([H])C(C([H])([H])[H])=C(C(=O)OC([H])([H])C([H])([H])[H])C1([H])C([H])([H])[H])=O
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| InChi Key |
CDVAIHNNWWJFJW-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H21NO4/c1-6-18-13(16)11-8(3)12(14(17)19-7-2)10(5)15-9(11)4/h8,15H,6-7H2,1-5H3
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| Chemical Name |
diethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate
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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 (~374.1 mM; with ultrasonication)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.35 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.7408 mL | 18.7042 mL | 37.4083 mL | |
| 5 mM | 0.7482 mL | 3.7408 mL | 7.4817 mL | |
| 10 mM | 0.3741 mL | 1.8704 mL | 3.7408 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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