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| 5mg |
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| Targets |
(2S)-2-Amino-1-hydroxyoctadecan-3-one is not a drug but a metabolic intermediate; its biological role is mediated by its involvement in sphingolipid biosynthesis and signaling pathways. It is a substrate for sphingolipid biosynthesis, specifically for enzymes like ceramide synthase. The compound is also known to be a marker for the activation of cysteine proteases (caspases), and it induces cell death. In apoptosis, it activates caspases and triggers mitochondrial apoptotic pathways by reducing the expression of anti-apoptotic Bcl-2, increasing the expression of pro-apoptotic Bax, and promoting the release of cytochrome c from mitochondria. This leads to the activation of caspases-9 and -3, culminating in cell death. As an intermediate in ceramide synthesis, it contributes to the generation of pro-apoptotic ceramides, which play a central role in stress responses and programmed cell death.
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| ln Vitro |
The in vitro activity of (2S)-2-Amino-1-hydroxyoctadecan-3-one is centered on its role in inducing cell death through caspase activation. Studies in cancer cell lines have demonstrated that this compound induces apoptosis by activating caspases and triggering mitochondrial apoptotic pathways. Mechanistically, it reduces the expression of the anti-apoptotic protein Bcl-2 while increasing the expression of the pro-apoptotic protein Bax. This shifts the balance toward apoptosis and promotes the release of cytochrome c from the mitochondria into the cytosol. Once in the cytosol, cytochrome c activates caspase-9, which in turn activates the executioner caspase-3, leading to the characteristic morphological and biochemical features of apoptosis. The compound's ability to induce cell death is concentration- and time-dependent.
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| ln Vivo |
In vivo studies of (2S)-2-Amino-1-hydroxyoctadecan-3-one are limited, as it is primarily a research tool for studying sphingolipid metabolism and apoptosis. It is not administered as a therapeutic agent. However, the compound has been studied in mouse models of cancer. For instance, administration of the compound (as the hydrochloride salt) at a dose of 25 mg/kg/day for 10 days was shown to inhibit tumor growth in H22 tumor-bearing mice (a hepatocellular carcinoma model) by inducing apoptosis of tumor cells. The mechanism involved the activation of caspases and the regulation of Bcl-2 family proteins. No significant toxicity was reported at this dose, indicating that the compound may have a reasonable safety window for anti-cancer applications in preclinical models.
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| Enzyme Assay |
Cell-free assays for studying the caspase-activating potential of (2S)-2-Amino-1-hydroxyoctadecan-3-one typically involve measuring its effects on purified caspases or on mitochondrial fractions. A protocol for measuring caspase-3 activity in cell lysates: (1) Treat cells with the compound for 24-48 hours. (2) Harvest cells and lyse in a buffer containing 50 mM HEPES (pH 7.4), 5 mM CHAPS, 5 mM DTT, and 1 mM EDTA. (3) Centrifuge at 15,000×g for 20 minutes and collect the supernatant (protein lysate). (4) Quantify protein concentration using the Bradford method. (5) In a 96-well plate, mix 50-100 ug of protein lysate with 100 uL of assay buffer (50 mM HEPES, pH 7.4, 100 mM NaCl, 0.1% CHAPS, 10 mM DTT). (6) Add a fluorogenic caspase-3 substrate, such as Ac-DEVD-AMC (50 uM). (7) Incubate at 37degC for 1-2 hours. (8) Measure fluorescence using a microplate reader with excitation at 360 nm and emission at 460 nm. (9) The increase in fluorescence is proportional to caspase-3 activity. For negative controls, include a caspase-3-specific inhibitor (e.g., Ac-DEVD-CHO).
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| Cell Assay |
A standard cellular protocol for evaluating the pro-apoptotic activity of (2S)-2-Amino-1-hydroxyoctadecan-3-one in cancer cell lines: (1) Culture human cancer cells (e.g., HeLa cervical, H22 hepatoma, MCF-7 breast) in DMEM with 10% FBS at 37degC in 5% CO2. (2) Seed cells into 6-well plates at a density of 5×10⁵ cells per well. (3) Prepare a 10 mM stock solution of the compound (as the free base or hydrochloride salt) in DMSO. (4) Dilute the stock in culture medium to final concentrations of 5, 10, 25, 50, and 100 uM (final DMSO ≤0.5%). (5) Treat cells for 24-48 hours. (6) For MTT viability assay: seed cells in 96-well plates (5,000-10,000 cells/well), treat, add 20 uL of 5 mg/mL MTT, incubate 4 hours, dissolve in DMSO, and read at 570 nm. (7) For apoptosis detection: stain treated cells with FITC-conjugated annexin V and propidium iodide (PI) following the manufacturer's protocol, then analyze by flow cytometry to quantify early apoptotic (annexin V+/PI-) and late apoptotic/necrotic (annexin V+/PI+) populations. (8) For Western blotting: lyse cells in RIPA buffer, run SDS-PAGE, and probe with antibodies against cleaved caspase-3, cleaved caspase-9, Bcl-2, Bax, and cytochrome c (using cytosolic and mitochondrial fractions).
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| Animal Protocol |
A standard protocol for evaluating the anti-tumor activity of (2S)-2-Amino-1-hydroxyoctadecan-3-one in a mouse xenograft model: (1) Culture H22 hepatoma cells or another cancer cell line. (2) Subcutaneously inject 2×10⁶ to 5×10⁶ cells into the right flank of 6-8 week old male BALB/c nude mice. (3) When tumors reach an average volume of 100-150 mm3 (approximately 7-10 days post-inoculation), randomize mice into groups (n=6-10 per group). (4) Formulate the compound in a suitable vehicle, such as PBS with 5% DMSO and 5% Tween 80. (5) Administer the compound by intraperitoneal (IP) injection daily at a dose of 25 mg/kg body weight. Control groups receive an equal volume of vehicle. (6) Measure tumor volumes with calipers every 2-3 days, using the formula V = (length × width2)/2. (7) Record body weights twice weekly as a measure of toxicity. (8) After 10-14 days of treatment, euthanize mice, excise tumors, and weigh them. (9) Fix tumors in 10% formalin for histopathological examination (H&E staining and TUNEL assay for apoptosis detection). (10) Collect tumor tissue for Western blotting to assess caspase-3 activation and Bcl-2/Bax expression.
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| ADME/Pharmacokinetics |
Quantitative pharmacokinetic data for (2S)-2-Amino-1-hydroxyoctadecan-3-one are limited. As a sphingolipid intermediate, it is rapidly metabolized in vivo. The molecular weight is 299.49, and the compound has a logP value indicative of moderate lipophilicity (the free base is likely highly lipophilic). It is relatively insoluble in water but can be dissolved in DMSO or ethanol and further diluted in aqueous buffers with the aid of detergents or carrier proteins (e.g., BSA). For storage, the powder (typically the hydrochloride salt) should be kept at -20degC in a tightly sealed container, protected from light and moisture. It is stable under these conditions for up to 3 years. Stock solutions in DMSO can be stored at -80degC for up to 6 months. For in vivo experiments, the compound is often formulated in PBS containing up to 5-10% DMSO and 5% Tween 80 to enhance solubility.
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| Toxicity/Toxicokinetics |
The toxicity profile of (2S)-2-Amino-1-hydroxyoctadecan-3-one has been evaluated in animal models at therapeutic doses. In H22 tumor-bearing mice, daily intraperitoneal administration of 25 mg/kg for 10 days did not result in significant body weight loss or other observable signs of toxicity, suggesting a favorable safety margin at this dose for anti-cancer applications. No data are available regarding acute toxicity (LD50), subchronic toxicity, or target organ toxicity. As the compound induces apoptosis through caspase activation, it could theoretically cause cell death in normal proliferating tissues such as bone marrow and intestinal epithelium if administered at high doses. However, preclinical studies suggest that cancer cells may be more sensitive to its pro-apoptotic effects due to their dysregulated apoptotic machinery. Standard safety precautions for handling potential cytotoxic agents should be followed.
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| Additional Infomation |
(2S)-2-Amino-1-hydroxyoctadecan-3-one (CAS 18944-28-0) is a bioactive sphingolipid metabolite that is an intermediate in sphingolipid biosynthesis. It is also known as 3-dehydrosphinganine, 3-ketodihydrosphingosine, or (2S)-2-amino-1-hydroxy-3-octadecanone. Sphingolipids are essential components of cell membranes and also function as potent signaling molecules regulating cell growth, differentiation, and apoptosis. Ceramide, a central sphingolipid metabolite, is a well-established pro-apoptotic second messenger. As an intermediate in the ceramide synthesis pathway, this compound contributes to the generation of ceramides. In addition, the compound itself can induce cell death through activation of caspases and the mitochondrial apoptotic pathway. It has been reported to inhibit tumor growth in H22 hepatoma mouse models. The compound is used in research as a tool to study sphingolipid metabolism, apoptosis, and cancer biology. It is not an FDA-approved drug and has no clinical trial history.
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| Molecular Formula |
C18H37NO2
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| Molecular Weight |
299.49
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| CAS # |
18944-28-0
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| Appearance |
Typically exists as solids at room temperature
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| LogP |
5.859
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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 | 3.3390 mL | 16.6950 mL | 33.3901 mL | |
| 5 mM | 0.6678 mL | 3.3390 mL | 6.6780 mL | |
| 10 mM | 0.3339 mL | 1.6695 mL | 3.3390 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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