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| Other Sizes |
| Targets |
The primary molecular target of methyl alpha-D-mannopyranoside is the mannose-binding lectin family, including concanavalin A (Con A) and other plant lectins, as well as bacterial adhesins such as FimH on the surface of type-1 fimbriated E. coli. By binding to these lectin carbohydrate-recognition domains, the compound competitively inhibits the interaction between mannose-containing glycoproteins or mannose residues on cell surfaces and their cognate lectin receptors. This competitive binding mechanism underlies its utility in blocking bacterial adhesion to host epithelial cells and in eluting mannose-binding proteins from affinity matrices. The compound does not exhibit significant binding to non-lectin protein targets.
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| ln Vitro |
In vitro, methyl alpha-D-mannopyranoside shows potent inhibition of mannose-dependent bacterial adhesion. At concentrations of 1-50 mM, the compound effectively blocks the binding of E. coli to mannose-coated surfaces and to human uroepithelial cells in adhesion assays, with an IC50 typically in the low millimolar range. The compound is frequently used as a positive control in assays for novel FimH antagonists. In addition, it competitively inhibits concanavalin A (Con A)-mediated hemagglutination at concentrations of 6.25-25 mM. Furthermore, the compound has demonstrated utility in macrophage targeting studies, where mannose-conjugated nanoparticles functionalized with methyl alpha-D-mannopyranoside show enhanced uptake by mannose receptor-expressing macrophages, particularly relevant for tuberculosis inhalation therapy and other macrophage-targeted drug delivery approaches.
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| ln Vivo |
In vivo studies have confirmed that methyl alpha-D-mannopyranoside can reduce bacterial colonization in animal models of urinary tract infection (UTI). Oral or intraperitoneal administration at doses of 50-200 mg/kg reduces bladder and kidney bacterial loads in mice challenged with uropathogenic E. coli. The compound has also been evaluated in models of inhalational tuberculosis therapy, where methyl alpha-D-mannopyranoside-functionalized solid lipid nanoparticles (SLNs) demonstrate enhanced targeting to alveolar macrophages, improving the delivery of anti-tuberculosis drugs to the site of infection. These in vivo macrophage-targeting effects represent the primary pharmacological application of the compound, rather than direct therapeutic activity. Detailed dose-response and therapeutic efficacy data remain areas of active investigation.
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| Enzyme Assay |
A typical non-cellular lectin-binding inhibition assay for methyl alpha-D-mannopyranoside involves concanavalin A (Con A) binding to mannan. Con A (50 ug/mL in 10 mM HEPES buffer, pH 7.4, containing 0.1 mM CaCl2 and 0.1 mM MnCl2) is incubated with varying concentrations of the test compound (0-100 mM) for 30 min at room temperature. Mannan-coated 96-well plates are then blocked with 1% BSA in PBS for 1 h at 37degC. The Con A-inhibitor mixture is added to the wells and incubated for 1 h. After washing, bound Con A is detected using HRP-conjugated anti-Con A antibody or directly with an enzyme-labeled lectin detection system, followed by TMB substrate and absorbance reading at 450 nm. Alternatively, a hemagglutination inhibition assay using mannosylated red blood cells provides a visual or spectrophotometric readout. IC50 values are calculated from dose-response curves.
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| Cell Assay |
In vitro cell-based assays for methyl alpha-D-mannopyranoside are conducted using human bladder epithelial cell lines (e.g., T24, 5637) or macrophage cell lines (RAW 264.7, THP-1). Cells are cultured in RPMI-1640 or DMEM with 10% FBS at 37degC in 5% CO2 and seeded into 96-well plates at 1-2 × 10⁵ cells/well. Bacterial adhesion assays: uropathogenic E. coli (1 × 10⁷ CFU/well, pre-incubated with methyl alpha-D-mannopyranoside at 0-50 mM for 15 min) is added to cell monolayers and incubated for 1 h. After washing to remove non-adherent bacteria, adherent bacteria are quantified by plating serial dilutions or by measuring luciferase activity from labeled bacteria. Cytotoxicity is assessed using MTT or LDH release assays. For macrophage uptake studies, fluorescently labeled mannosylated nanoparticles are incubated with cells +/- free methyl alpha-D-mannopyranoside (25-100 mM) as a competitive inhibitor to confirm receptor-mediated uptake by flow cytometry or fluorescence microscopy.
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| Animal Protocol |
In vivo animal studies for methyl alpha-D-mannopyranoside are typically performed using C57BL/6 mice (female, 6-8 weeks old, 18-22 g). For urinary tract infection models, mice are transurethrally inoculated with 1 × 10⁸ CFU of uropathogenic E. coli CFT073 under light anesthesia. Methyl alpha-D-mannopyranoside is administered either orally (50-200 mg/kg) or intraperitoneally (25-100 mg/kg) once daily for 3-5 days. At study termination (24 h after final treatment), mice are euthanized, bladders and kidneys are harvested, homogenized, and plated onto selective agar for CFU enumeration. Reduction in bacterial burden is calculated relative to vehicle-treated controls. For macrophage-targeting studies, fluorescently labeled methyl alpha-D-mannopyranoside-functionalized nanoparticles are administered intratracheally or intravenously, and tissue distribution (lung, liver, spleen) is analyzed by fluorescence imaging or flow cytometry. Appropriate animal ethics approval is required.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of methyl alpha-D-mannopyranoside have been evaluated primarily through computational ADMET modeling and in silico drug-likeness predictions. The compound is a small hydrophilic sugar analog (MW 194.18) expected to have low passive permeability across biological membranes due to its polar nature. Absorption following oral administration is predicted to be moderate to low. Distribution is likely limited to the extracellular space and aqueous compartments, with minimal intracellular penetration. The compound is not expected to be a substrate for major CYP450 enzymes. Renal excretion of the intact compound is the primary elimination pathway. In silico predictions suggest a favorable drug-likeness profile with low predicted toxicity. Experimental pharmacokinetic data in animals or humans are limited; the compound is primarily used as a research tool rather than a therapeutic agent.
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| Toxicity/Toxicokinetics |
Toxicological data for methyl alpha-D-mannopyranoside indicate low toxicity consistent with a simple sugar analog. In acute toxicity studies, the compound is well tolerated at doses up to 2,000 mg/kg orally in rodents with no observed mortality or significant adverse effects. No evidence of genotoxicity has been reported in standard bacterial reverse mutation (Ames) assays. The compound is not expected to cause skin or eye irritation. Chronic toxicity studies are limited, as methyl alpha-D-mannopyranoside is not intended for systemic therapeutic use in humans. It is considered a relatively safe biochemical reagent when handled according to standard laboratory safety practices. For research use only; not for human consumption or therapeutic administration. Precautionary measures include avoiding inhalation and direct contact with skin and eyes.
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| References | |
| Additional Infomation |
Methyl α-D-mannoside is a methylmannoside with an α-configuration at the terminal carbon atom. It is both a methylmannoside and an α-D-mannoside. Methyl α-D-mannopyranoside has been reported to exist in Lilium pumilum and Lilium tenuifolium, and relevant data are available.
Methyl alpha-D-mannopyranoside is not approved as a pharmaceutical drug for human use. It is primarily employed as a research reagent and laboratory tool in glycobiology, lectin binding studies, and carbohydrate chemistry. Its primary mechanism involves acting as a competitive inhibitor of mannose-binding lectins, including bacterial adhesins and plant lectins such as Con A. The compound has been used to elute mannose-binding proteins from lectin affinity columns and as a positive control in assays designed to identify novel FimH inhibitors. It has also been explored for macrophage-targeting drug delivery systems, particularly for inhalation therapy in tuberculosis treatment, where mannose-functionalized carriers enhance uptake by pulmonary macrophages via mannose receptor-mediated endocytosis. No clinical trials or regulatory approvals exist for this compound as a drug. For research use only; not intended for diagnostic or therapeutic applications in humans. |
| Molecular Formula |
C7H14O6
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|---|---|
| Molecular Weight |
194.18
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| Exact Mass |
194.079
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| CAS # |
617-04-9
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| PubChem CID |
101798
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
389.1±42.0 °C at 760 mmHg
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| Melting Point |
193-196ºC
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| Flash Point |
189.1±27.9 °C
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| Vapour Pressure |
0.0±2.0 mmHg at 25°C
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| Index of Refraction |
1.548
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| LogP |
-2.69
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
13
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| Complexity |
163
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| Defined Atom Stereocenter Count |
5
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| SMILES |
CO[C@@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
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| InChi Key |
HOVAGTYPODGVJG-VEIUFWFVSA-N
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| InChi Code |
InChI=1S/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3-,4-,5+,6+,7+/m1/s1
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| Chemical Name |
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol
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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) |
H2O: ≥ 100 mg/mL (514.99 mM)
DMSO: 100 mg/mL (514.99 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.87 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (12.87 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (12.87 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.1499 mL | 25.7493 mL | 51.4986 mL | |
| 5 mM | 1.0300 mL | 5.1499 mL | 10.2997 mL | |
| 10 mM | 0.5150 mL | 2.5749 mL | 5.1499 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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