| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
4-Isothiocyanatophenyl α-D-Mannopyranoside is a mannose-based antigen delivery system that targets mannose-specific receptors and lectins, including the mannose receptor (CD206) on macrophages and dendritic cells. The isothiocyanate group enables covalent attachment to amine-containing macromolecules (e.g., proteins, dendrimers), creating neoglycoproteins and mannosylated carriers. These mannosylated constructs are used to deliver antigens to mannose receptor-expressing antigen-presenting cells for immunomodulation and vaccine development. The compound's mannose moiety is recognized by mannose-binding proteins.
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| ln Vitro |
In vitro, 4-Isothiocyanatophenyl α-D-Mannopyranoside is used as a reagent for the preparation of neoglycoproteins and mannosylated dendrimers. The compound's isothiocyanate group reacts with primary amines on proteins or other macromolecules under mild conditions to form stable thiourea linkages. The resulting mannosylated conjugates are used in binding studies to probe mannose-specific receptors and lectins. The compound has also been found to inhibit the growth of cancer cells and reduce inflammation and oxidative stress in cellular assays. However, its primary use is as a synthetic building block.
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| ln Vivo |
In vivo, 4-Isothiocyanatophenyl α-D-Mannopyranoside has been studied for its potential to modulate immune responses as part of mannosylated antigen delivery systems. Mannosylated conjugates prepared using this compound are used to target antigens to mannose receptor-expressing antigen-presenting cells, enhancing antigen uptake and presentation. This approach has potential applications in vaccine development and immunotherapy. However, the compound itself is not used as a therapeutic agent, and specific in vivo data for the compound alone are limited.
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| Enzyme Assay |
Non-cell-based assays for 4-Isothiocyanatophenyl α-D-Mannopyranoside involve characterization of its chemical reactivity and conjugation efficiency. The compound's isothiocyanate group reacts with primary amines, and the reaction is monitored by HPLC or LC-MS. The compound is used to prepare neoglycoproteins, and the efficiency of conjugation is assessed by SDS-PAGE, Western blot, or mass spectrometry. Binding of mannosylated conjugates to mannose-binding proteins or lectins is evaluated by ELISA or surface plasmon resonance. The compound's purity and identity are confirmed by NMR and MS.
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| Cell Assay |
Cellular assays for 4-Isothiocyanatophenyl α-D-Mannopyranoside are performed using mannose receptor-expressing cells such as macrophages or dendritic cells. Mannosylated conjugates prepared using the compound are added to cells, and receptor binding and uptake are measured by flow cytometry or fluorescence microscopy. Antigen presentation and T cell activation are evaluated in co-culture systems. The compound's effects on cancer cell growth, inflammation, and oxidative stress are assessed in cancer cell lines or immune cells by measuring cell viability, cytokine production, and ROS levels.
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| Animal Protocol |
In vivo experiments with 4-Isothiocyanatophenyl α-D-Mannopyranoside typically involve the use of mannosylated conjugates prepared from the compound. In animal models, mannosylated antigens or vaccines are administered to evaluate immune responses, including antibody titers, T cell activation, and protective efficacy. The compound's role is as a synthetic intermediate for preparing these conjugates. The compound itself is not administered to animals. Studies focus on the immunomodulatory effects of the mannosylated constructs.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties are not applicable to 4-Isothiocyanatophenyl α-D-Mannopyranoside as it is not a therapeutic agent. The compound is used as a chemical reagent for the synthesis of neoglycoproteins and mannosylated carriers. Its chemical stability, reactivity (isothiocyanate group), and solubility are characterized for synthetic applications. The compound is typically stored under dry, cool conditions to prevent hydrolysis of the isothiocyanate group. No PK data are available.
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| Toxicity/Toxicokinetics |
The toxicity of 4-Isothiocyanatophenyl α-D-Mannopyranoside has not been comprehensively evaluated as it is not a therapeutic agent. The compound is handled as a chemical reagent with standard laboratory safety precautions. Isothiocyanates are generally reactive and may be irritating to skin, eyes, and respiratory tract. The compound is for research use only and is not intended for human consumption. Safety data sheets recommend standard protective measures including gloves, lab coat, and eye protection when handling the compound.
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| References |
[1]. Lamptey RNL, et, al. Synthesis and Characterization of Fatty Acid Grafted Chitosan Polymeric Micelles for Improved Gene Delivery of VGF to the Brain through Intranasal Route. Biomedicines. 2022 Feb 19;10(2):493.
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| Additional Infomation |
4-Isothiocyanatophenyl α-D-Mannopyranoside (CAS# 96345-79-8) has the molecular formula C₁₃H₁₅NO₆S and a molecular weight of 313.33. It is also known as α-D-Mannopyranosylphenyl isothiocyanate and p-Isothiocyanatophenyl α-D-Mannopyranoside. The compound is used as a building block for preparing neoglycoproteins and mannosylated dendrimers for probing mannose-specific receptors and lectins. It is also a type of isothiocyanate compound found in plants and vegetables such as broccoli and Brussels sprouts and has been studied for potential anticancer, anti-inflammatory, and antioxidant activities. As of current knowledge, the compound is not approved as a therapeutic agent.
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| Molecular Formula |
C13H15NO6S
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| Molecular Weight |
313.33
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| Exact Mass |
313.062
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| CAS # |
96345-79-8
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| PubChem CID |
11023405
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| Appearance |
White to off-white solid powder
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| Melting Point |
180-181ºC
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| Index of Refraction |
1.659
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| LogP |
1
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
21
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| Complexity |
383
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| Defined Atom Stereocenter Count |
5
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| SMILES |
O(C1C=CC(N=C=S)=CC=1)[C@@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1
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| InChi Key |
RWANFUZQWINQBY-BNDIWNMDSA-N
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| InChi Code |
InChI=1S/C13H15NO6S/c15-5-9-10(16)11(17)12(18)13(20-9)19-8-3-1-7(2-4-8)14-6-21/h1-4,9-13,15-18H,5H2/t9-,10-,11+,12+,13+/m1/s1
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| Chemical Name |
(2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-(4-isothiocyanatophenoxy)oxane-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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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) |
DMSO: 250 mg/mL (797.88 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.64 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 20.8 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: ≥ 2.08 mg/mL (6.64 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1915 mL | 15.9576 mL | 31.9152 mL | |
| 5 mM | 0.6383 mL | 3.1915 mL | 6.3830 mL | |
| 10 mM | 0.3192 mL | 1.5958 mL | 3.1915 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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