Synthesis and characterization of a novel glycoconjugated macromolecule

Mi, Fwu Long; Yu, Shu Huei; Peng, Chih Kang; Sung, Hsing‐Wen; Shyu, Shin Shing; Liang, Hsiang Fa; Huang, Mei Feng; Wang, Chee Chan

doi:10.1016/j.polymer.2006.04.005

Cited by 17 publications

(5 citation statements)

References 36 publications

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“…14). -D-Galaktopyranosyl units are important for targeting drug-delivery system into liver cancer cells [52]. These conjugated molecules exposed activity against Escherichia coli and Staphylococcus aureus.…”

Section: Antibacterial Activitymentioning

confidence: 99%

Recent Advances in Drugs and Prodrugs Design of Chitosan

Vinšová¹,

Vavříková

2008

CPD

109

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The aim of this review is to outline the recent advances in chitosan molecular modeling, especially its usage as a prodrug or drug in a field of antibacterial, anticarcinogenic and antioxidant activity. Polymeric materials like peptides, polysaccharides and other natural products have recently attracted attention as biodegradabile drug carriers. They can optimize clinical drug application, minimize the undesirable drug properties and improve drug efficiency. They are used for the slow release of effective components as depot forms, to improve membrane permeability, solubility and site-specific targeting. Chitosan is such a prospective cationic polysaccharide which has shown number of functions in many fields, including bio medicinal, pharmaceutical, preservative, microbial and others. This article discusses the structure characteristics of chitosan, a number of factors such as degree of polymerization, level of deacetylation, types of quarternisation, installation of various hydrophilic substituents, metal complexation, and combination with other active agents. Biodegradable, non-toxic and non-allergenic nature of chitosan encourages its potential use as a carrier for drug delivery systems in all above mentioned targets. The use of chitosan prodrug conjugates is aimed at the site-specific transport to the target cells use, for example, a spacer tetrapeptide Gly-Phe-Leu-Gly, promotion of drug incorporation into cells via endocytosis, hybridization or synergism of two types of drugs or a drug with a bioactive carrier. The design of chitosan macromolecule prodrugs is also discussed.

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Section: Antibacterial Activitymentioning

confidence: 99%

Recent Advances in Drugs and Prodrugs Design of Chitosan

Vinšová¹,

Vavříková

2008

CPD

109

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“…Chitosan is a nonphysiologic glycosaminoglycan that has been demonstrated to be biocompatible, – to accelerate wound healing, , has antimicrobial properties, – and supports the growth and function of osteoblasts and chondrocytes. , It is therefore a potentially useful biomaterial for use in the preparation of photopolymerizable hydrogels as tissue engineering constructs and drug delivery matrices. Photopolymerizable chitosan derivatives have been prepared previously through styrenation and methacrylation using reactive aldehyde intermediates .…”

Section: Introductionmentioning

confidence: 99%

Methacrylated Glycol Chitosan as a Photopolymerizable Biomaterial

et al. 2007

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Glycol chitosan is a derivative of chitosan that is soluble at neutral pH and possesses potentially useful biological properties. With the goal of obtaining biocompatible hydrogels for use as tissue engineering scaffolds or drug delivery depots, glycol chitosan was converted to a photopolymerizable prepolymer through graft methacrylation using glycidyl methacrylate in aqueous media at pH 9. N-Methacrylation was verified by both (1)H NMR and (13)C NMR. The degree of N-methacrylation, measured via (1)H NMR, was easily varied from 1.5% to approximately 25% by varying the molar ratio of glycidyl methacrylate to glycol chitosan and the reaction time. Using a chondrocyte cell line, the N-methacrylated glycol chitosan was found to be noncytotoxic up to a concentration of 1 mg/mL. The prepolymer was cross-linked in solution using UV light and Irgacure 2959 photoinitiator under various conditions to yield gels of low sol content ( approximately 5%), high equilibrium water content (85-95%), and thicknesses of up to 6 mm. Cross-polarization magic-angle spinning (13)C solid state NMR verified the complete conversion of the double bonds in the gel. Chondrocytes seeded directly onto the gel surface, populated the entirety of the gel and remained viable for up to one week. The hydrogels degraded slowly in vitro in the presence of lysozyme at a rate that increased as the cross-link density of the gels decreased.

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“…Chitosan, shown in Figure 1(A), is the term given to the family of cationic polysaccharides consisting of N‐ acetyl D ‐ glucosamine and D ‐ glucosamine residues coupled through a β (1‐4) (glycosidic) linkage, where the degree of N‐ acetylation is less than 50% 1, 2. Chitosan has been demonstrated to be biocompatible,3–5 to accelerate wound healing,6, 7 to possess antimicrobial properties,8–11 and to support the growth and function of osteoblasts and chondrocytes 12, 13. These favorable properties are believed to be due in part to the free amine groups along its backbone.…”

Section: Introductionmentioning

confidence: 99%

Structure, depolymerization, and cytocompatibility evaluation of glycol chitosan

Knight

Shapka

Amsden

2007

J Biomedical Materials Res

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Glycol chitosan, a water soluble chitosan derivative being investigated as a new biomaterial, was fractionated via two different methods. Initial characterization of the glycol chitosan with (1)H NMR spectroscopy illustrated the presence of both secondary and tertiary amine groups, contradictory to its widely accepted structure. Fractionation of glycol chitosan with nitrous acid resulted in a significant reduction in the number average molecular weight, specifically, from 170 to approximately 7 kDa for a pH 3 and below. However, the reaction altered its chemical structure, as the secondary amine groups were converted to N-nitrosamines, which are potentially carcinogenic. An increase in the pH of the reaction limited this formation, but not entirely. Free radical degradation initiated with potassium persulfate was not as effective at reducing the molecular weight as the nitrous acid approach, yielding molecular weights around 12 kDa under the same molar ratio of degrading species, but did retain the structural integrity of the glycol chitosan. Additionally, control of the molecular weight appears feasible with potassium persulfate. When assessed in vitro for cytocompatibility, the polymer exhibited no toxicity on monolayer-cultured chondrocytes, and in fact stimulated cell growth at low concentrations.

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Synthesis and characterization of a novel glycoconjugated macromolecule

Cited by 17 publications

References 36 publications

Recent Advances in Drugs and Prodrugs Design of Chitosan

Recent Advances in Drugs and Prodrugs Design of Chitosan

Methacrylated Glycol Chitosan as a Photopolymerizable Biomaterial

Structure, depolymerization, and cytocompatibility evaluation of glycol chitosan

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