Glycol chitosan

Catalog	ACM123938863-1
CAS	123938-86-3
Description	degree of polymerization ≥400
Synonyms	Glycol chitin, deacetylated
Molecular Weight	82685.58
Canonical SMILES	N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COCCO)O[C@H]1O[C@@H]2[C@@H](COCCO)O[C@@H](O[C@@H]3[C@@H](COCCO)O[C@@H](O)[C@H](N)[C@H]3O)[C@H](N)[C@H]2O.[n]
Purity	96%
Appearance	Solid
Application	Glycol chitosan increases membrane permeability and leakage in Glycine max Harosoy 63w cells.
Storage	storage temp. -20°C
Assay	≥60% (titration)
Form	crystalline
MDL Number	MFCD00131218
Packaging	500 mg in poly bottle 1, 5 g in poly bottle

Case Study

Tumor Targeting Strategies of Glycol Chitosan Nanoparticles

Ryu, Ju Hee, et al. Advanced Materials, 2020, 32(51), 2002197.

Glycol chitosan nanoparticles (CNPs) have been considered as excellent tumor targeting nanocarriers for many years. Many studies have developed pH-sensitive GC-CNPs to achieve different responses to the acidic tumor environment.
· GC-histidine nanoparticles for pH-sensitive release of anticancer drugs: The self-assembled histidine-coated CNPs were developed through hydrophobic interactions between the components. These histidine-CNPs were effective at encapsulating hydrophobic anticancer drugs. When the imidazole group of the histidine became protonated in the acidic environment of tumor extracellular matrices (ECM) or endosomes, it turned hydrophilic, leading to the disassembly of the histidine-CNPs and the subsequent release of the loaded drugs.
· GC-diethylaminopropyl nanoparticles for drug release under acidic conditions: Another pH-sensitive component was the 3-diethylaminopropyl group, which has a pKa range of 7.0-7.3. 3-Diethylaminopropyl isothiocyanate was chemically bonded to the amine groups of GC, producing self-assembled CNPs in a manner similar to the previous study. The diethylaminopropyl groups became protonated in acidic conditions, causing the nanoparticles to disintegrate and release the hydrophobic drug doxorubicin (DOX).
· GC-PDPA nanoparticles for estrone delivery under acidic conditions: PDPA-modified CNPs functioned in a similar manner as the earlier examples. The goal was to deliver estrone, a ligand targeting the overexpressed estrogen receptor (ER), as a chemotherapeutic agent for breast cancer. When the diisopropyl tertiary amines were protonated at a pH lower than 6.3, the PDPA-CNPs lost their structural integrity and released estrone at the target sites.

Preparation of Cross-Linked Hydrogels Based on Glycol Chitosan

Tripodo, G., et al. Carbohydrate polymers, 2018, 198, 124-130.

Glycol chitosan (GCS) was cross-linked with polyethylene glycol diglycidyl ether (PEGDE) to successfully prepare a series of GCS-PEG scaffolds that can be used as wound dressing materials (after cross-linking) or in situ molding materials. By controlling the degree of cross-linking, the obtained scaffolds showed macroscopic pores and adjustable swelling in water. In addition, the GCS-PEG scaffolds showed significant antibacterial activity against Staphylococcus aureus and obvious pro-angiogenic activity.
Preparation of GCS-PEG scaffolds
· Precise quantities of GCS were dissolved in double-distilled water to create homogeneous dispersions at two specified concentrations: 10 mg/mL (1 wt/vol%) and 20 mg/mL (2 wt/vol%). These dispersions were designated as GCS1% and GCS2%, respectively.
· A calculated volume of PEGDE was then incorporated into the GCS solutions, followed by vortex mixing for 1 minute to achieve optimal homogenization. For each GCS solution-1 wt/vol% or 2 wt/vol%-PEGDE was added to create varying molar ratios of PEGDE to GCS, corresponding to 8%, 16%, 33%, or 50% (expressed as moles of PEGDE per mole of GCS repetitive units).
· The samples were named according to their GCS concentration and PEG to GCS ratio, resulting in designations such as: GCS1%-PEG8%, GCS1%-PEG16%, GCS1%-PEG33%, GCS1%-PEG50%, GCS2%-PEG8%, GCS2%-PEG16%, GCS2%-PEG33%, and GCS2%-PEG50%.
· The resulting GCS-PEG gels underwent a washing process with three 20 mL water rinses, were freeze-dried, and subsequently characterized.