| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
The primary targets of D-erythro-MAPP include ceramidase and glucosylceramide synthase (GCS). As a ceramidase inhibitor, the compound prevents the breakdown of ceramide, leading to the accumulation of this bioactive lipid. D-erythro-MAPP is also a potent, irreversible inhibitor of glucosylceramide synthase (GCS), the enzyme responsible for the first step in glycosphingolipid biosynthesis. By blocking GCS activity, the compound enables detailed investigation into glycosylation and membrane biology.
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| ln Vitro |
MCF-7 cell viability is lowered by D-erythro-MAPP (De-MAPP) in a dose-dependent manner; the IC50 values are 4.4 μM and 15.6 μM, respectively [1]. Growth is inhibited when D-erythro-MAPP (De-MAPP) causes G0/G1 phase arrest during cell cycle progression [2].
In vitro, D-erythro-MAPP increases intracellular ceramide levels and induces cell cycle arrest at the G0/G1 phase. The compound inhibits the growth of HL-60 promyelocytic leukemia cells in a time- and concentration-dependent manner. As a ceramidase inhibitor, D-erythro-MAPP prevents the breakdown of ceramide, leading to the accumulation of this pro-apoptotic lipid and the induction of cell death in cancer cells. |
| ln Vivo |
In vivo, D-erythro-MAPP has potential anticancer activity due to its ability to increase ceramide levels and induce cell death. The compound's inhibition of ceramidase and glucosylceramide synthase may have therapeutic implications for cancer and other diseases involving sphingolipid metabolism. Further in vivo studies are needed to fully characterize the compound's efficacy and safety profile.
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| Enzyme Assay |
The in vitro enzyme assay for D-erythro-MAPP involves measuring the inhibition of ceramidase or glucosylceramide synthase activity using recombinant or purified enzyme preparations. The assay for ceramidase is performed in a suitable buffer system containing ceramide substrate, and the production of sphingosine is measured using radiometric, chromatographic, or fluorometric methods. For GCS inhibition, the assay measures the incorporation of radiolabeled UDP-glucose into glucosylceramide. IC50 values are calculated by fitting dose-response curves to the inhibition data.
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| Cell Assay |
Cell Viability Assay[1]
Cell Types: Human breast cancer MCF-7 cells. Tested Concentrations: 24 h. Incubation Duration: 3.13-100 μM. Experimental Results: Inhibited cell viability. Cellular assays for D-erythro-MAPP typically use cancer cell lines such as HL-60 promyelocytic leukemia cells. Cells are treated with the compound at various concentrations and time points, and cellular ceramide levels are measured using mass spectrometry or enzymatic assays. Cell cycle analysis is performed using flow cytometry, and cell viability is assessed using standard assays such as MTT or trypan blue exclusion. |
| Animal Protocol |
In vivo animal studies for D-erythro-MAPP would typically involve administration of the compound to tumor-bearing rodent models to assess its anticancer efficacy. Following treatment, tumor growth, ceramide levels, and survival are evaluated. The compound's effects on sphingolipid metabolism in various tissues may also be assessed to understand its mechanism of action and potential side effects.
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| ADME/Pharmacokinetics |
As a ceramide analog, the pharmacokinetic properties of D-erythro-MAPP would depend on its physicochemical characteristics. The compound has a molecular weight of 361.57 and is supplied as a liquid. Detailed PK parameters such as half-life, bioavailability, and tissue distribution are not available in the public domain. For research purposes, the compound is handled as a liquid with standard safety precautions.
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| Toxicity/Toxicokinetics |
There is no specific toxicity data reported for D-erythro-MAPP in the available literature. As a research chemical, the compound is intended for laboratory use only and should be handled with standard safety precautions. Toxicity studies would be required if the compound were to be developed further for therapeutic applications.
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| References | |
| Additional Infomation |
N-[(1S,2R)-1-hydroxy-1-phenylprop-2-yl]tetradecanoamide is an alkylbenzene.
D-erythro-MAPP is a ceramide analog that inhibits ceramidase and glucosylceramide synthase (GCS). The compound increases intracellular ceramide levels, induces cell cycle arrest at the G0/G1 phase, and inhibits the growth of HL-60 promyelocytic leukemia cells. D-erythro-MAPP has a molecular formula of C23H39NO2 and a molecular weight of 361.57. The L-erythro isomer serves as a useful negative control. |
| Molecular Formula |
C23H39NO2
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|---|---|
| Molecular Weight |
361.56
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| Exact Mass |
361.298
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| CAS # |
143492-38-0
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| PubChem CID |
124735
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| Appearance |
White to off-white solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
536.7±43.0 °C at 760 mmHg
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| Melting Point |
82ºC to 84ºC
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| Flash Point |
278.4±28.2 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.502
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| LogP |
6.92
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
15
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| Heavy Atom Count |
26
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| Complexity |
339
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CCCCCCCCCCCCCC(=O)N[C@H](C)[C@H](C1=CC=CC=C1)O
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| InChi Key |
YLAZEWZHIRBZDA-NFBKMPQASA-N
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| InChi Code |
InChI=1S/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-16-19-22(25)24-20(2)23(26)21-17-14-13-15-18-21/h13-15,17-18,20,23,26H,3-12,16,19H2,1-2H3,(H,24,25)/t20-,23-/m1/s1
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| Chemical Name |
N-[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]tetradecanamide
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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) |
DMF: ≥ 20 mg/mL (55.32 mM)
Ethanol: ≥ 20 mg/mL (55.32 mM) DMSO: ≥ 1 mg/mL (2.77 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 | 2.7658 mL | 13.8290 mL | 27.6579 mL | |
| 5 mM | 0.5532 mL | 2.7658 mL | 5.5316 mL | |
| 10 mM | 0.2766 mL | 1.3829 mL | 2.7658 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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