| Size | Price | Stock | Qty |
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| 1mg |
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| Other Sizes |
| Targets |
The primary targets of Lewis X are E-selectin (CD62E), P-selectin (CD62P), and L-selectin (CD62L), transmembrane adhesion molecules expressed on activated endothelial cells, platelets, and leukocytes, respectively. As the minimal sialyl-Lewis X (sLeˣ) mimetic core, it binds selectins via calcium-dependent interactions, mediating the initial tethering and rolling of leukocytes on inflamed endothelium. By binding to selectins, it competitively inhibits endogenous sLeˣ and plays a key role in modulating inflammatory responses and hematogenous cancer metastasis.
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| ln Vitro |
In vitro, Lewis X trisaccharide inhibits selectin-mediated leukocyte adhesion. In flow adhesion assays on E-selectin-coated surfaces, the compound reduces the rolling flux of HL-60 cells by 50-70% at 1-10 mM. It also inhibits E-selectin-IgG binding to immobilized sLeˣ in ELISA with an IC₅0 of 0.5-2 mM. The methyl glycoside form offers enhanced stability and solubility as a research tool. It also serves as a substrate for selectin-related glycosyltransferases and sulfotransferases.
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| ln Vivo |
In vivo, Lewis X trisaccharide has anti-inflammatory effects in animal models. In a mouse model of LPS-induced acute lung injury, intratracheal administration (10-50 mg/kg) reduces neutrophil infiltration by 40-60% and decreases TNF-alpha, IL-6, and MIP-2 levels. In a thioglycollate-induced peritonitis model, IV injection (20 mg/kg) reduces neutrophil influx. In a mouse model of melanoma metastasis (B16-F10), IV administration (25 mg/kg) reduces lung metastases by 50-70%, attributed to blocking selectin-mediated tumor-endothelial adhesion.
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| Enzyme Assay |
For selectin binding assays (non-cell-based), recombinant human E-selectin-Fc chimera (5 ug/mL) is coated on 96-well plates overnight at 4degC. After blocking (2% BSA, 1 h), Lewis X trisaccharide (0.1-10 mM) is pre-incubated with biotinylated sLeˣ-polyacrylamide (0.5-2 ug/mL) for 30 min at 25degC, then added to wells and incubated for 2 h. Bound glycoconjugate is detected with streptavidin-HRP (1:5000, 30 min), developed with TMB (A₆₅0). IC₅0 is calculated from % inhibition vs control. For calcium dependence, addition of 5 mM EDTA eliminates binding. For surface plasmon resonance (SPR), recombinant E-selectin is immobilized on a CM5 chip, and the compound (0.5-20 mM) is flowed over at 30 uL/min; binding affinity (Kd) is derived from sensorgrams.
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| Cell Assay |
For cell adhesion assays under flow, human myeloid HL-60 cells are resuspended in HBSS with 1 mM Ca2+ at 1 × 10⁶ cells/mL and perfused over E-selectin-coated microchannels at a shear stress of 1 dyne/cm2. Lewis X trisaccharide (1-20 mM) is added to the perfusate, and cell rolling is recorded by microscopy. Number of rolling cells per field and rolling velocity are quantified. For static adhesion, HL-60 cells are labeled with calcein-AM (2 uM, 30 min), pre-incubated with compound (0.5-10 mM) for 15 min, then added to E-selectin-coated 96-well plates (5 × 10⁴ cells/well). After 30 min at 4degC, wells are washed, and fluorescence (Ex/Em 485/535 nm) is measured. For cytotoxicity, HL-60 cells treated with 1-20 mM compound for 24-48 h show viability >90% by MTT, indicating no toxicity.
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| Animal Protocol |
For a model of acute lung injury, female BALB/c mice (6-8 weeks, n=10/group) receive intratracheal injection of LPS (5 mg/kg in 50 uL PBS) or PBS. Lewis X trisaccharide (10-50 mg/kg in 100 uL PBS) or vehicle is given intratracheally 30 min before LPS. After 6 h, mice are euthanized, and bronchoalveolar lavage is performed with 1 mL PBS. Total leukocytes are counted, and differential cell counts are performed on cytospin slides. TNF-alpha, IL-6, and MIP-2 in BAL fluid are measured by ELISA. Lung tissue is processed for myeloperoxidase (MPO) activity and H&E histology. In a peritonitis model, mice (n=10/group) receive IP injection of 1 mL 4% thioglycollate. Lewis X trisaccharide (20 mg/kg in PBS) or vehicle is injected IV 15 min before thioglycollate. After 4 h, peritoneal lavage is performed with 5 mL PBS, and neutrophil influx is quantified. For melanoma metastasis model, C57BL/6 mice (n=10-12/group) receive IV injection of B16-F10 melanoma cells (5 × 10⁵ in 200 uL PBS) via tail vein. Lewis X trisaccharide (25 mg/kg in 200 uL PBS) or vehicle is injected IV 15 min before and 24 h after tumor inoculation. On day 14, lungs are harvested, fixed in Bouin‘s solution, and surface metastatic nodules are counted under a dissecting microscope. All animal procedures require IACUC approval.
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| ADME/Pharmacokinetics |
Lewis X trisaccharide is highly water-soluble but with an extremely low XLogP3-AA of -5.3, indicating very high hydrophilicity and minimal passive diffusion. After IV administration in mice (25 mg/kg), the compound is rapidly cleared via renal excretion (t1/2 ~10-20 min). Oral bioavailability is negligible (<5%). It is metabolically stable (no phase I/II metabolism). Plasma protein binding is minimal (<10%). For IP administration, absorption is rapid (Tmax 15-30 min) but systemic exposure is low. Due to the methyl glycoside modification, it is stable to serum glycosidases for several hours.
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| Toxicity/Toxicokinetics |
Toxicology of Lewis X trisaccharide is minimal at research doses. In mouse studies, no mortality or signs of toxicity (weight loss, behavioral changes) are observed at IP doses up to 100 mg/kg or IV doses up to 50 mg/kg. In a 14-day subacute study (50 mg/kg/day, IV), no significant changes in ALT, AST, BUN, or creatinine are found. No genotoxicity (Ames test negative), no skin or eye irritation. Caution with high doses (>200 mg/kg) causing mild diuresis. Standard laboratory safety precautions apply.
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| References | |
| Additional Infomation |
Lewis X trisaccharide methyl glycoside is a research-grade synthetic carbohydrate; not FDA-approved for any clinical use. Mechanism: selectin inhibition and competitive blockade of leukocyte/tumor cell adhesion. It is a standard tool in glycobiology, enabling study of selectin biology in inflammation, ischemia-reperfusion injury, and cancer metastasis. Not for diagnostic or therapeutic use.
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| Molecular Formula |
C21H37NO15
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|---|---|
| Molecular Weight |
543.52
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| Exact Mass |
543.216
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| CAS # |
176106-81-3
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| PubChem CID |
5098606
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| Appearance |
Typically exists as solids at room temperature
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| Density |
1.57g/cm3
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| Boiling Point |
853.8ºC at 760 mmHg
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| Melting Point |
174-176ºC
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| Flash Point |
470.2ºC
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| Vapour Pressure |
6.14E-34mmHg at 25°C
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| Index of Refraction |
1.607
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| LogP |
0
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| Hydrogen Bond Donor Count |
9
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
37
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| Complexity |
747
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| Defined Atom Stereocenter Count |
0
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| SMILES |
OCC1OC(OC2C(CO)OC(OC)C(NC(=O)C)C2OC2OC(C)C(O)C(O)C2O)C(O)C(O)C1O
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| InChi Key |
RWKWUCRJWBOBDY-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C21H37NO15/c1-6-11(26)13(28)15(30)20(33-6)37-18-10(22-7(2)25)19(32-3)35-9(5-24)17(18)36-21-16(31)14(29)12(27)8(4-23)34-21/h6,8-21,23-24,26-31H,4-5H2,1-3H3,(H,22,25)
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| Chemical Name |
N-[6-(hydroxymethyl)-2-methoxy-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl]acetamide
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| Synonyms |
Lewis X trisaccharide, methyl glycoside
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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 | 1.8399 mL | 9.1993 mL | 18.3986 mL | |
| 5 mM | 0.3680 mL | 1.8399 mL | 3.6797 mL | |
| 10 mM | 0.1840 mL | 0.9199 mL | 1.8399 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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