| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
N-Trimethylchitosan does not have a specific biological receptor but interacts with negatively charged biological membranes, proteins, and nucleic acids via electrostatic interactions. The positively charged quaternary ammonium groups on the polymer backbone bind electrostatically to negatively charged cell surface components (e.g., glycosaminoglycans, sialic acids) and to the phosphate backbone of DNA/RNA. This property enables N-Trimethylchitosan to serve as a permeation enhancer for mucosal drug delivery, as a non-viral gene delivery vector (by condensing DNA into nanoparticles), and as an antimicrobial agent.
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| ln Vitro |
In vitro, N-Trimethylchitosan is used to enhance the paracellular transport of hydrophilic drugs across epithelial barriers by opening tight junctions. In Caco-2 intestinal epithelial cell monolayers, treatment with 0.5-2% (w/v) N-Trimethylchitosan causes a reversible decrease in transepithelial electrical resistance (TEER) and increases the permeability of model compounds such as FITC-dextran. It also forms polyelectrolyte complexes with DNA at charge ratios (N:P) of 2:1 to 8:1, resulting in nanoparticles of 100-300 nm diameter that protect DNA from nuclease degradation and facilitate transfection of mammalian cells (e.g., HEK293, HeLa) with efficiencies comparable to some lipid-based reagents. Additionally, it exhibits antimicrobial activity against Gram-positive and Gram-negative bacteria.
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| ln Vivo |
In vivo, N-Trimethylchitosan has been studied for nasal and oral drug delivery, as a vaccine adjuvant, and for gene delivery. In rat models, intranasal administration of insulin formulated with N-Trimethylchitosan leads to significant reductions in blood glucose levels, indicating enhanced systemic absorption. As a vaccine adjuvant, it enhances both humoral and cellular immune responses to co-administered antigens (e.g., ovalbumin, influenza vaccine) when given intranasally or orally. In gene therapy studies, N-Trimethylchitosan/DNA nanoparticles delivered intranasally or intratumorally result in reporter gene expression in lung epithelium or tumor tissues. The polymer is biodegradable and biocompatible, with low immunogenicity.
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| Enzyme Assay |
For non-cell-based assays, the physicochemical properties of N-Trimethylchitosan are characterized by NMR (degree of quaternization), gel permeation chromatography (molecular weight), and zeta potential (surface charge). For DNA complexation, a 1 mg/mL solution of N-Trimethylchitosan in 10 mM HEPES buffer (pH 7.4) is mixed with a 1 mg/mL solution of plasmid DNA at various N:P ratios (e.g., 2:1, 4:1, 8:1), vortexed, and incubated at room temperature for 30 min. The particle size and zeta potential are measured by dynamic light scattering (DLS). The DNA condensation is assessed by gel retardation assay: 1 ug DNA complexed with polymer is run on a 1% agarose gel, and the mobility of DNA in the complex is compared to free DNA. DNase protection assays are performed by incubating complexes with DNase I for 30 min, followed by heparin displacement and gel electrophoresis.
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| Cell Assay |
For in vitro cell-based assays, Caco-2 intestinal epithelial cells are seeded on Transwell inserts (0.4 um pore size, 1 × 10⁵ cells/insert) and cultured for 21 days to form tight junctions. N-Trimethylchitosan is added to the apical chamber at concentrations of 0.1-2% (w/v) in HBSS (pH 7.4). TEER is measured every 15 min for 2-4 hours, and paracellular permeability is assessed by adding FITC-dextran (4 kDa) to the apical chamber and measuring its appearance in the basal chamber. For transfection studies, HEK293 or HeLa cells are seeded in 24-well plates at 5 × 10⁴ cells/well. N-Trimethylchitosan/DNA complexes (1-5 ug DNA per well) are prepared at N:P ratios of 4:1 to 8:1 in serum-free medium and added to cells for 4-6 hours, then replaced with complete medium. After 48 hours, transfection efficiency is measured by luciferase assay (if using luciferase reporter) or by fluorescence microscopy (if using GFP plasmid). Cytotoxicity is assessed by MTT assay.
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| Animal Protocol |
For in vivo animal studies, a rat model for intranasal drug delivery is used. Male Sprague-Dawley rats (200-250 g, n=6 per group) are anesthetized with isoflurane. N-Trimethylchitosan (0.5-2% w/v) is dissolved in PBS (pH 6.0-7.0). Insulin (1 IU/kg) is mixed with the polymer solution and administered intranasally (20-50 uL per nostril) using a micropipette. Blood glucose is measured at 0, 15, 30, 45, 60, 90, and 120 min post-dose. Plasma insulin levels are measured by ELISA. For vaccine adjuvant studies, BALB/c mice (6-8 weeks old) are immunized intranasally with ovalbumin (50 ug) alone or with N-Trimethylchitosan (200 ug) on days 0 and 14. Serum antibody titers (IgG, IgA) and T-cell responses (IFN-gamma, IL-4) are measured. For gene delivery, N-Trimethylchitosan/plasmid DNA complexes (50 ug DNA) are administered intratumorally (in tumor xenograft models) or intranasally to mice, and luciferase expression is assessed by bioluminescence imaging.
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| ADME/Pharmacokinetics |
N-Trimethylchitosan is a water-soluble polysaccharide with degree of quaternization typically 50-80%. It has a molecular weight ranging from 10-200 kDa depending on the starting chitosan and deacetylation conditions. The polymer is soluble in water at pH 2-10, unlike unmodified chitosan which is only soluble at acidic pH. Solutions can be prepared at 1-5% w/v in water or PBS. It is stable at 4degC for months and can be lyophilized for long-term storage. The viscosity depends on molecular weight and concentration. For in vivo use, solutions should be prepared fresh and filter-sterilized (0.22 um). The polymer is biodegradable by lysozyme and other glycosidases present in the body, with degradation products being non-toxic. Pharmacokinetic studies show that after intranasal administration, a significant portion of the polymer remains in the nasal cavity, while some is taken up by M cells and lymphatic tissue.
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| Toxicity/Toxicokinetics |
N-Trimethylchitosan is generally regarded as non-toxic and biocompatible. The LD50 in mice after oral administration is >2 g/kg. In subchronic toxicity studies, oral doses up to 500 mg/kg/day for 28 days produce no significant adverse effects on body weight, hematology, or histopathology. Intranasal administration of 0.5-2% solutions causes mild, transient nasal irritation in some animals but no significant tissue damage. In vitro cytotoxicity in Caco-2 and other cell lines shows IC50 values of 0.5-2 mg/mL (0.05-0.2% w/v). The polymer is not genotoxic in the Ames test or in vitro micronucleus assay. However, as a cationic polymer, high concentrations may cause red blood cell lysis (hemolysis), so formulations should be optimized. The compound is for research use only and is not approved for human clinical use.
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| References | |
| Additional Infomation |
N-Trimethylchitosan is a research polymer and is not an FDA-approved drug product. It is widely used as a permeation enhancer for mucosal drug delivery, especially for peptides and proteins (e.g., insulin, calcitonin) and for intranasal vaccine delivery. The quaternization of chitosan improves water solubility and mucoadhesion, while preserving the biocompatibility and biodegradability of chitosan. It is also used as a non-viral gene delivery vector, offering advantages over viral vectors in terms of safety and ease of production. N-Trimethylchitosan is also known as TMC (trimethyl chitosan chloride). This product is for research use only and is not intended for human therapeutic or diagnostic applications.
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| Exact Mass |
286.165
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|---|---|
| CAS # |
52349-26-5
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| PubChem CID |
168008603
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| Appearance |
Off-white to light yellow solid powder
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
18
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| Complexity |
229
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)[N+](C)(C)C)OC)CO.N.[Cl-]
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| InChi Key |
HFNQAFWMDXYZFM-YHSFBLOESA-M
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| InChi Code |
InChI=1S/C11H24NO4.ClH.H3N/c1-7-8(6-13)16-11(15-5)9(10(7)14)12(2,3)4;;/h7-11,13-14H,6H2,1-5H3;1H;1H3/q+1;;/p-1/t7-,8-,9-,10+,11-;;/m1../s1
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| Chemical Name |
azane;[(2R,3R,4S,5S,6S)-4-hydroxy-6-(hydroxymethyl)-2-methoxy-5-methyloxan-3-yl]-trimethylazanium;chloride
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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 : ~33.33 mg/mL
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| Solubility (In Vivo) |
Solubility in Formulation 1: 10 mg/mL (Infinity mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
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.
Products are for research use only; We do not sell to patients
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