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| Targets |
Methyl 13-cis-4-oxoretinoate acts as a retinoic acid receptor (RAR) agonist. By binding to and activating RARs, it modulates gene expression involved in cell differentiation, proliferation, and apoptosis. Its activity as a retinoid metabolite suggests it may play a role in the biological effects of retinoids in neuroblastoma and other tissues. The compound is related to 13-cis-retinoic acid (isotretinoin), a well-known retinoid used in dermatology and oncology, and its 4-oxo metabolite is an important intermediate in retinoid metabolism.
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| ln Vitro |
In vitro, methyl 13-cis-4-oxoretinoate activates retinoic acid receptors (RARs) in cell-based reporter assays. It has been studied in neuroblastoma cells as a retinoid metabolite. Its activity is characterized by concentration-dependent RAR activation, induction of differentiation markers, and inhibition of cell proliferation in various cell lines. As a retinoid, it likely exhibits similar in vitro activities to other RAR agonists, including induction of differentiation in leukemia and neuroblastoma cells and modulation of keratinocyte differentiation.
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| ln Vivo |
In vivo, methyl 13-cis-4-oxoretinoate is promising for research in dermatological diseases and cancers. As a retinoid, it may exhibit similar in vivo effects to other retinoids, including induction of differentiation, inhibition of tumor growth, and modulation of immune responses. However, detailed in vivo studies specifically on this compound are limited. Its identification as a metabolite in neuroblastoma suggests it may contribute to the biological activity of retinoids in this tumor type.
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| Enzyme Assay |
In vitro enzyme/receptor binding studies for methyl 13-cis-4-oxoretinoate typically involve radioligand binding assays using recombinant retinoic acid receptors (RARα, RARβ, RARγ) or RXR receptors. Competitive binding experiments with labeled retinoic acid are performed to determine binding affinity (Ki) at the different receptor subtypes. Transactivation assays in cells transfected with RAR or RXR expression vectors and reporter genes are used to measure agonist activity. Standard protocols involve incubating cells with increasing concentrations of the compound and measuring luciferase or other reporter activity.
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| Cell Assay |
In vitro cellular assays for methyl 13-cis-4-oxoretinoate include studies using neuroblastoma cell lines, keratinocytes, or other retinoid-responsive cells. Cells are treated with serial dilutions of the compound, and differentiation is assessed by morphological changes and expression of differentiation markers (e.g., cytokeratins in keratinocytes, neuronal markers in neuroblastoma). Proliferation is measured by [3H]-thymidine incorporation or cell counting. Apoptosis is quantified by flow cytometry with Annexin V/PI staining. Reporter assays using RAR-responsive luciferase constructs are also employed.
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| Animal Protocol |
In vivo animal studies for methyl 13-cis-4-oxoretinoate would typically involve mouse models of cancer (e.g., neuroblastoma xenografts) or dermatological diseases (e.g., psoriasis-like skin inflammation). Animals are treated with the compound via oral or intraperitoneal administration, and tumor growth, skin differentiation, or inflammation is assessed. However, specific published in vivo studies for this particular compound are limited. Related retinoids have well-established in vivo efficacy, and this compound is expected to show similar activity in relevant models.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of methyl 13-cis-4-oxoretinoate are expected to be similar to other retinoid esters, with good oral absorption and extensive metabolism. As a methyl ester, it may be hydrolyzed to the active acid form (13-cis-4-oxoretinoic acid) in vivo. Retinoids are highly protein-bound, distribute widely in tissues, and are metabolized in the liver via cytochrome P450 enzymes. The compound has a molecular weight of 328.20 g/mol and a molecular formula of C21H28O3. Detailed PK parameters would require specific studies.
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| Toxicity/Toxicokinetics |
Toxicological data for methyl 13-cis-4-oxoretinoate are likely similar to other retinoids, which are known teratogens and can cause significant side effects including mucocutaneous dryness, headache, hepatotoxicity, hyperlipidemia, and bone toxicity. Retinoids are strictly contraindicated during pregnancy due to severe teratogenic effects. Long-term use requires monitoring of liver function, lipid levels, and bone density. The compound is intended for research use only and has not been approved for clinical therapeutic use.
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| Additional Infomation |
Methyl 13-cis-4-oxoretinoate is a research compound used to study retinoid biology and metabolism. It is identified as a metabolite of 13-cis-retinoic acid in neuroblastoma, suggesting potential relevance to the pharmacology of isotretinoin. Its activity as an RAR agonist makes it a useful tool for studying retinoid signaling pathways. The compound is being investigated for potential applications in dermatology and oncology, though it is not currently approved for human use. It is available for research purposes from chemical suppliers.
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| Molecular Formula |
C21H28O3
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| Molecular Weight |
328.452
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| Exact Mass |
328.204
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| CAS # |
71748-57-7
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| Related CAS # |
71748-57-7
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| PubChem CID |
10471728
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
4.87
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
24
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| Complexity |
653
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC1=C(C(CCC1=O)(C)C)C=CC(=CC=CC(=CC(=O)OC)C)C
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| InChi Key |
VTSFDGSDUILKPM-ZTXQEUQPSA-N
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| InChi Code |
InChI=1S/C21H28O3/c1-15(8-7-9-16(2)14-20(23)24-6)10-11-18-17(3)19(22)12-13-21(18,4)5/h7-11,14H,12-13H2,1-6H3/b9-7+,11-10+,15-8+,16-14-
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| Chemical Name |
Methyl (2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)nona-2,4,6,8-tetraenoate
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| Synonyms |
Methyl 13-cis-4-Oxoretinoate Methyl 13cis4Oxoretinoate Methyl 13 cis 4 Oxoretinoate 4-Keto-13-cis-Retinoic Acid Methyl ester 4 Keto 13 cis Retinoic Acid Methyl ester
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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) |
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
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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 | 3.0446 mL | 15.2230 mL | 30.4460 mL | |
| 5 mM | 0.6089 mL | 3.0446 mL | 6.0892 mL | |
| 10 mM | 0.3045 mL | 1.5223 mL | 3.0446 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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