Tetraacetylphytosphingosine
Based on 1 Customer Validation
Tetraacetylphytosphingosine is a sphingolipid metabolite produced by phytosphingosine acetylation. Tetraacetylphytosphingosine exerts its inhibitory action on angiogenesis through the inhibition of MAPK activation and intracellular calcium increase. Tetraacetylphytosphingosine induces apoptosis in HaCaT cells.
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- Pureté : 99.90%
- CAS No.: 13018-48-9
- Formule: C26H47NO7
- Masse moléculaire:485.65
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Stockage:
4°C, sealed storage, away from moisture and light
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
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Activité biologique
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Chemical Information
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Solvant et solubilité
- Protocole
- Pureté et documentation
- Références
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Help & FAQs
Activité biologique
Description
In Vitro
Tetraacetylphytosphingosine (TAPS; 5 μM; 24 h) markedly decreases VEGF-induced chemotactic migration and capillary-like tube formation in HUVEC. Tetraacetylphytosphingosine significantly inhibits VEGF-induced proteolytic enzyme production, including MMP-2, urokinase-type plasminogen activator (uPA) and plasminogen activator inhibitor-1 (PAI-1). Tetraacetylphytosphingosine also suppresseS VEGF-induced phosphorylation of p42/44 extracellular signal-regulated kinase and c-JNK[1].
In addition, Tetraacetylphytosphingosine abolished VEGF-induced intracellular calcium increase[1].
In HaCaT cells, Tetraacetylphytosphingosine co-treatment synergistically increases the level of UVB-induced apoptosis via caspase activation by regulating the level of pro-apoptotic Bax and anti-apoptotic Bcl-2[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
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Cell Line:HUVEC
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Concentration:5 μM
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Incubation Time:24 h
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Result:Markedly inhibits VEGF-induced proteolytic enzyme production, including MMP-2, uPA and PAI-1.
Chemical Information
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CAS No. 13018-48-9
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Appearance Solid
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Masse moléculaire 485.65
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Formule C26H47NO7
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Color White to off-white
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SMILES
CCCCCCCCCCCCCC[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H](NC(C)=O)COC(C)=O
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Structure Classification
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Initial Source
Hansenula ciferri
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Livraison
Room temperature in continental US; may vary elsewhere.
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Stockage
4°C, sealed storage, away from moisture and light
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
Solvant et solubilité
In Vitro:
DMSO : 25 mg/mL (51.48 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocole
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Human pluripotent stem cell endothelial-cell differentiation
Human pluripotent stem cell endothelial differentiation is based on stepwise developmental patterning: early activation of WNT/GSK3β inhibition promotes mesodermal or vascular progenitor entry, followed by endothelial specification using VEGF-related signaling, BMP4, FGF2, Notch modulation, or cAMP depending on the published protocol. Endothelial differentiation is read out by acquisition of CD31, CD34, VE-cadherin/CD144, KDR/VEGFR2, vWF, Tie2, NOS3, acetylated LDL uptake, tube/network formation, barrier function, and in vivo vessel-forming capacity where tested.
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Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
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TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
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Vascular/Branching Fractal Analysis
Vascular/branching fractal analysis quantifies the geometric complexity of vessel trees or vascular networks from segmented 2D images, commonly by converting vessels into binary and/or skeletonized maps and estimating fractal dimension using box-counting or related approaches. Fractal dimension is interpreted as an image-derived readout of vascular branching complexity, space filling, or density, and has been applied to retinal photographs, fluorescein angiography, OCT angiography, capillary perfusion maps, and in vitro Matrigel angiogenesis networks. The assay readout is generated from vessel-positive pixels after image preprocessing, vessel segmentation, binarization, and optional skeletonization; reported outputs include fractal dimension, vessel density, branchpoint density, endpoint density, vessel length density, tortuosity, and generation-based branching metrics when VESGEN-style analysis is used. The biological interpretation is limited to quantitative vascular patterning and s
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Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
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Endothelial Tube Formation Assay
Endothelial tube formation assay evaluates the ability of endothelial cells to attach, migrate, align, and organize into capillary-like networks when cultured on gelled basement membrane extract or Matrigel; the readout is the morphology and quantity of tube-like networks, which reflects an in vitro endothelial morphogenesis step related to angiogenesis. Basement membrane extract/Matrigel provides laminin-rich extracellular matrix cues that support endothelial differentiation into capillary-like structures, but it can contain biologically active growth factors, so growth-factor-reduced matrix is preferred when testing defined angiogenic stimulators or inhibitors.
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Calcium Spark Assay
Calcium sparks are localized, transient increases in intracellular calcium concentration ([Ca2+]i) that occur in cardiac myocytes and represent elementary events underlying excitation-contraction coupling. These events are generated by the coordinated opening of clusters of ryanodine receptors (RyRs) on the sarcoplasmic reticulum membrane, leading to a brief release of Ca2+ into the cytosol. The detection and analysis of calcium sparks provide insights into the mechanisms of calcium handling and signaling in cardiac cells. Imaging techniques using fluorescent calcium indicators such as Fluo-3 are employed to visualize these subcellular calcium transients with high spatial and temporal resolution. The protocol is based on established methodologies described in primary literature for both experimental measurement and automated analysis of calcium sparks.
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Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
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Ca2+ Staining Technique
Ca2+ staining is an experimental technique that utilizes specific fluorescent probes (such as Fluo-4 AM, Fura-2, etc.) to qualitatively or quantitatively detect dynamic changes in intracellular Ca2+ concentrations; this is achieved by monitoring the changes in fluorescent signals generated when these probes bind to free intracellular calcium ions. The underlying principle relies primarily on the presence of chelating groups within the probe's molecular structure that possess high affinity for calcium ions.
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Endothelial Cell Migration/Angiogenic Sprouting Assay
Endothelial cell migration and angiogenic sprouting assays are in vitro (and partially ex vivo-adapted) functional models that quantify the ability of endothelial cells to undergo coordinated migration, extracellular matrix invasion, and multicellular organization into capillary-like sprouts in response to pro-angiogenic stimuli such as VEGF, bFGF, or conditioned microenvironments. These assays are used to model early angiogenic events including tip-cell formation, directional migration, and lumen-like sprout extension, which collectively reflect angiogenic activation and vascular morphogenesis processes observed in vivo.
Pureté et documentation
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Fiche technique (269 KB)
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SDS (399 KB)
- English - EN (399 KB)
- Français - FR (399 KB)
- Deutsch - DE (399 KB)
- Norwegian - NO (399 KB)
- Español - ES (399 KB)
- Swedish - SV (399 KB)
- Italian - IT (399 KB)
- Korean - KR (399 KB)
- Portuguese - PT (399 KB)
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Instruction de manipulation (2659 KB)
Références
[1]. Yoo Bin Kwon, et al. Anti-angiogenic effect of tetraacetyl-phytosphingosine. Exp Dermatol. 2007 Apr;16(4):311-7. [Content Brief]
[2]. H J Kim, et al. Potentiation of UVB-induced apoptosis by novel phytosphingosine derivative, tetraacetyl phytosphingosine in HaCaT cell and mouse skin. Apoptosis. 2004 Jul;9(4):449-56. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 2.0591 mL | 10.2955 mL | 20.5910 mL | 51.4774 mL |
| 5 mM | 0.4118 mL | 2.0591 mL | 4.1182 mL | 10.2955 mL | |
| 10 mM | 0.2059 mL | 1.0295 mL | 2.0591 mL | 5.1477 mL | |
| 15 mM | 0.1373 mL | 0.6864 mL | 1.3727 mL | 3.4318 mL | |
| 20 mM | 0.1030 mL | 0.5148 mL | 1.0295 mL | 2.5739 mL | |
| 25 mM | 0.0824 mL | 0.4118 mL | 0.8236 mL | 2.0591 mL | |
| 30 mM | 0.0686 mL | 0.3432 mL | 0.6864 mL | 1.7159 mL | |
| 40 mM | 0.0515 mL | 0.2574 mL | 0.5148 mL | 1.2869 mL | |
| 50 mM | 0.0412 mL | 0.2059 mL | 0.4118 mL | 1.0295 mL |
Tetraacetylphytosphingosine Related Classifications
HY-138875 Related Classifications
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