Physicochemical Properties
| Molecular Formula | C12H24N2O9 |
| Molecular Weight | 340.32696 |
| Exact Mass | 340.148 |
| CAS # | 148411-57-8 |
| PubChem CID | 16213812 |
| Appearance | Light yellow to yellow solid powder |
| LogP | -5.2 |
| Hydrogen Bond Donor Count | 8 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 23 |
| Complexity | 390 |
| Defined Atom Stereocenter Count | 10 |
| SMILES | C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)N)O)CO)N)O)O)O |
| InChi Key | QLTSDROPCWIKKY-PMCTYKHCSA-N |
| InChi Code | InChI=1S/C12H24N2O9/c13-5-9(19)10(4(2-16)21-11(5)20)23-12-6(14)8(18)7(17)3(1-15)22-12/h3-12,15-20H,1-2,13-14H2/t3-,4-,5-,6-,7-,8-,9-,10-,11-,12+/m1/s1 |
| Chemical Name | (2R,3S,4R,5R,6S)-5-amino-6-[(2R,3S,4R,5R,6R)-5-amino-4,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-2-(hydroxymethyl)oxane-3,4-diol |
| HS Tariff Code | 2934.99.9001 |
| 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) |
Biological Activity
| ln Vitro | Chitosan oligosaccharides (COS) represent a class of natural polymers that not only have physical and chemical properties such as water solubility and low viscosity, but also have good pharmacological properties, including good pharmacokinetics and safety and a variety of beneficial biological properties. active and has therapeutic promise for a range of illnesses. Activation of AMPK and suppression of inflammatory signaling pathways (including NF-κB and MAPK pathways) are regarded to be the key mechanisms underlying the numerous effects of chitosan oligosaccharide (COS), including anti-inflammatory, anti-cancer, and anti-diabetic actions. COS can stop many phases of cancer growth by regulating multiple signaling proteins/pathways, including NF-κB, AMPK, mTOR, caspase-3, CD147, MMP-2, MMP-9, and VEGF. In vitro investigations have demonstrated that chitosan oligosaccharide (COS) can trigger mortality in a range of cancer cell types, including ascites, bladder cancer, prostate cancer, lung cancer, liver cancer, leukemia, cervical cancer, and colorectal cancer. The IC50 value of chitosan oligosaccharide (COS)-induced cytotoxicity is 25 μg/mL-50 μg/mL, depending on the cancer cell type [1]. |
| ln Vivo | In lung tissue and bronchoalveolar lavage fluid of mice, the oral treatment of chitosan oligosaccharide (16 mg/kg/day) reduces the production of proinflammatory cytokines involved in allergic reactions (i.e., IL-4, IL-13, and TNF-α). In a rat model of autoimmune anterior uveitis brought on by immunization with bovine melanin-related antigen, the anti-inflammatory impact of chitosan oligosaccharide (COS) on lymphocyte activation has finally been reported [1]. Chitosan oligosaccharide (COS) prevents the macroscopic appearance of mouse skin caused by UV light. There are a few superficial creases when compared to the smooth, hairless mice in the normal control group that had healthy back skin. Following ten weeks of UV exposure, the model's skin showed signs of erythema, dryness, thickening, drooping, and coarse wrinkles. It even took on a faintly wrinkled, leather-like appearance. It has been demonstrated that UV radiation causes photoaging of the skin surface because the visual scores of mice with flesh-colored lesions were considerably higher (p<0.05) than those of the normal control group [2]. |
| References |
[1]. Chitosan oligosaccharide: Biological activities and potential therapeutic applications. Pharmacol Ther. 2017 Feb;170:80-97. [2]. Anti-photoaging effects of chitosan oligosaccharide in ultraviolet-irradiated hairless mouse skin. Exp Gerontol. 2018 Mar;103:27-34. |
| Additional Infomation | Beta-D-glucosaminyl-(1->4)-beta-D-glucosamine is a beta-D-glucosaminyl-(1->4)-D-glucosamine having beta-configuration at the reducing end anomeric centre. |
Solubility Data
| Solubility (In Vitro) |
H2O : ~50 mg/mL DMSO : ~50 mg/mL |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (Infinity 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 (Infinity 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (Infinity 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 100 mg/mL (Infinity mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9383 mL | 14.6916 mL | 29.3832 mL | |
| 5 mM | 0.5877 mL | 2.9383 mL | 5.8766 mL | |
| 10 mM | 0.2938 mL | 1.4692 mL | 2.9383 mL |