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CONTACT US| Catalog Number | ACM9004540-7 |
| CAS | 9004-54-0 |
| Synonyms | Rheopolyglucine |
| IUPAC Name | 2,3,4,5-Tetrahydroxy-6-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexanal |
| Molecular Weight | 396.43 |
| Molecular Formula | C17H32O10 |
| Canonical SMILES | C(C1C(C(C(C(O1)OCC2C(C(C(C(O2)OCC(C(C(C(C=O)O)O)O)O)O)O)O)O)O)O)O |
| InChI | InChI=1S/C18H32O16/c19-1-5(21)9(23)10(24)6(22)3-31-17-16(30)14(28)12(26)8(34-17)4-32-18-15(29)13(27)11(25)7(2-20)33-18/h1,5-18,20-30H,2-4H2 |
| InChI Key | FZWBNHMXJMCXLU-UHFFFAOYSA-N |
| Melting Point | 483 °C |
| Purity | 98% |
| Appearance | White to off-white solid |
| Storage | Store at room temperature |
| Complexity | 625 |
| Covalently-Bonded Unit Count | 1 |
| Defined Atom Stereocenter Count | 0 |
| EC Number | 232-677-5 |
| Exact Mass | 504.16903493 |
| Heavy Atom Count | 34 |
| Hydrogen Bond Acceptor Count | 16 |
| Hydrogen Bond Donor Count | 11 |
| Monoisotopic Mass | 504.16903493 |
| Physical State | Solid |
| Rotatable Bond Count | 11 |
| Topological Polar Surface Area | 277 Ų |
Predescu AM, et al. Royal Society, 2018, 5(3), ISSN 2054-5703.
Dextran, a biocompatible, biodegradable, and water-soluble polysaccharide, is widely used in biomedical applications to coat nanoparticles. This coating prevents the agglomeration and toxicity of magnetic particles, enhancing their stability and compatibility for various medical uses.
Synthesis of Iron Oxide Nanoparticles
Iron oxide nanoparticles are synthesized using a controlled co-precipitation method. Ferrous ions (Fe2+) and ferric ions (Fe3+) are mixed in an alkaline solution as described in previous work based on the Massart method. The resulting suspension is centrifuged at 1200 rpm for 5 minutes, yielding a dark-brown precipitate. The precipitate is then separated using a magnet, ished with distilled water until the ish solution reached a pH of 7, and dried in an oven at 60℃.
Dextran Coating Process
Dextran solutions are prepared by mixing 2.5, 5, and 10 grams of dextran with 100 ml of deionized water. Each solution is then mixed with 1 gram of iron nanoparticles at 100℃ for 1 hour to achieve coating. After cooling to room temperature, the suspensions are centrifuged at 800 rpm for 15 minutes. The coated nanoparticles are separated using a magnet and ished with methanol. The samples are labeled as DINP 2.5 (1 g iron nanoparticles coated with 2.5 g dextran), DINP 5 (1 g iron nanoparticles coated with 5 g dextran), and DINP 10 (1 g iron nanoparticles coated with 10 g dextran).
By employing comprehensive characterization techniques such as XRD, SEM, TEM, FTIR, and SQUID magnetometry, the study successfully demonstrated the efficacy of dextran as a coating material for iron oxide nanoparticles, paving the way for their enhanced use in medical fields.
Sun H, et al. Biomacromolecules, 2010, 11(4), 848-854.
Dextran can be used to prepare shell-sheddable micelles based on dextran-SS-poly(ε-caprolactone) diblock copolymers for efficient intracellular release of doxorubicin.
The synthesis of dextran-SS-poly(ε-caprolactone) (Dextran-SS-PCL) copolymers is conducted through a multi-step process involving the following key stages:
Preparation of Dextran:
Dextran with a specified molecular weight is dissolved in an appropriate solvent to prepare a dextran solution.
Synthesis of Poly(ε-caprolactone) (PCL):
ε-Caprolactone is polymerized using a suitable initiator and catalyst to obtain PCL with the desired molecular weight and properties.
Conjugation of Dextran and PCL via Disulfide Linkages (SS):
The conjugation of dextran and PCL is achieved through the introduction of disulfide (SS) linkages. This involved reacting dextran with a thiol-containing compound to introduce thiol groups on the dextran chains.
The thiol-modified dextran is then reacted with PCL pre-polymers containing complementary functional groups, forming disulfide linkages between the two polymers.
Comprehensive characterization techniques, including NMR, FTIR, GPC, DSC, SEM, TEM, and DLS, confirmed the successful formation and desirable properties of the copolymers. The dextran-SS-PCL copolymers exhibit promising structural, thermal, and morphological characteristics, making them suitable for various biomedical applications, such as drug delivery and tissue engineering.
Qu X, et al. ACS Appl. Bio Mater, 2019, 2(4), 1456-1463.
Dextran can be used to combine it with cationic peptides for DNA and microRNA delivery.
Synthesis of Dextran-Peptide Conjugates
1.5 g of dextran and 1.35 g of DMAP are weighed, added to a 100 mL flask, and dissolved in 20 mL of DMSO under a nitrogen atmosphere for 20 minutes. 2 mL of GMA is added. The mixture is stirred at 25 ℃ under nitrogen for 4 days. To neutralize the DMAP and stop the reaction, an equimolar amount of concentrated HCl is added. The mixture is dialyzed using a 7K MWCO membrane against deionized water at 25 ℃ for 4 days and lyophilized to produce Dex-MA powder.
Next, a solution of 40 mg peptide in water is mixed with 22 μL of 200 mM TCEP in a 1.5 mL tube for 5 minutes. To neutralize TCEP and trifluoroacetic acid, 80 μL of 1 M NaOH is added.
Dex-MA is dissolved in 70 μL of water at 25 ℃ for 10 minutes, and then mixed with the peptide solution. The mixtures are incubated at 25 ℃ for 2 days after adjusting the pH to 7.5, purified using a Zebra Spin Desalting Column, and lyophilized.
Preparation of Dextran-Peptide/siRNA Complexes
A siRNA stock solution (2 μg/μL) is prepared using nuclease-free water and diluted to 1 μM in PBS. Dextran-peptide is dissolved in DI water to make a 1 mg/mL stock solution and further diluted in PBS to the required concentrations, based on the desired N/P ratio (molar ratio of arginine residues in the dextran-peptide vector to phosphate groups in siRNA). The dextran-peptides/siRNA complexes are formed by mixing equal volumes of dextran-peptides and siRNA at different N/P ratios, keeping the siRNA concentration at 1 μM. The solutions are incubated at 25 ℃ for 20 minutes to ensure complete interaction between the peptide and RNA molecules.
Jin R, et al. Biomaterials, 2007, 28, 2791-2800.
Jin R, et al. Colloids and Surfaces B: Biointerfaces, 2017, 158, 47-56.
Jin R, et al. ACS Appl. Polym. Mater. 2021, 3(11), 5999-6007.
Dextran can be used to synthesize clickable dextran-doxorubicin prodrugs (CDPs) for solid tumor chemotherapy.
Synthesis of Dex-PNC
Dextran (5.0 g) is dissolved in DMF (500 mL with LiCl) at 90℃ under nitrogen. After cooling to 0℃, PNC (2.2 g) and pyridine (0.9 g) are added. The reaction is conducted overnight. Dex-PNC is precipitated in cold ethanol, filtered, ished with ethanol and diethyl ether, and dried in a vacuum oven.
Synthesis of Carbazate-Dextran (Dex-NHNH2)
Dex-PNC (1.5 g) in anhydrous DMF (8 mL) is reacted with tert-butyl carbazate (0.46 g) and pyridine (374 μL) for 2 days under nitrogen. The product (Dex-NHNHBoc) is precipitated in ethanol and dried under vacuum. Dex-NHNHBoc (1.0 g) is dissolved in 50% deionized water/TFA (10 mL) overnight, neutralized to pH 7.0, purified by ultrafiltration, and freeze-dried to obtain Dex-NHNH2 as a white foam.
Synthesis of CDPs
Dextran derivatives with clickable groups are prepared by coupling DBCO-NHS or N3-PEG-NHS with Dex-NHNH2 via carbodiimide chemistry. For DDB5 synthesis, DBCO-NHS (30 mg) in DMSO (1 mL) is mixed with Dex-NHNH2 (150 mg) in DMSO/water (1 mL). The mixture is stirred under nitrogen at room temperature for 2 days, dialyzed, and freeze-dried to yield DDB5 as a solid powder.
DOX/HCl (14 mg) is mixed with triethylamine (10 μL) in DMSO (2 mL) and stirred overnight in the dark. DDB5 (20 mg) in DMSO (2 mL) is then added and reacted for 3 days in the dark. The mixture is dialyzed against DMSO and deionized water, then freeze-dried to obtain DDB5/DOX3 as a red powder.
What is dextran derived from?
Dextran is derived from the condensation of glucose, originally derived from wine.
How does IUPAC define dextrans?
IUPAC defines dextrans as branched poly-α-d-glucosides of microbial origin with glycosidic bonds predominantly C-1 → C-6.
What are the lengths of dextran chains?
Dextran chains can vary in length from 3 to 2000 kilodaltons.
What is the main chain of the dextran polymer composed of?
The main chain of the dextran polymer is composed of α-1,6 glycosidic linkages between glucose monomers.
How is dextran different from dextrin?
Dextran is characterized by its branching structure with α-1,3 linkages, while dextrin is a straight chain glucose polymer tethered by α-1,4 or α-1,6 linkages.
Which bacteria are involved in the production of dextran?
Dextran is produced from sucrose by certain lactic acid bacteria, including Leuconostoc mesenteroides and Streptococcus mutans.
What are the medicinal uses of dextran?
Dextran is used medicinally as an antithrombotic, to reduce blood viscosity, and as a volume expander in hypovolaemia.
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