Conjugation of bile esters to cellulose by olefin cross-metathesis: A strategy for accessing complex polysaccharide structures

Dong, Yifan; Novo, Diana C.; Mosquera-Giraldo, Laura I.; Taylor, Lynne S.; Edgar, Kevin J.

doi:10.1016/j.carbpol.2019.05.061

Cited by 11 publications

(4 citation statements)

References 62 publications

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“…The use of polysaccharides as a building block in the construction of micelles presents many advantages as compared to synthetic polymers such as PEG and poly(N-isopropylacrylamide) (PNIPAAm), including low immunogenicity, compatibility with various tissues, and biodegradability [ 51 , 52 , 53 ]. Moreover, tailoring the functionalization of the polysaccharide backbone enables control over polymer solubility and responsiveness to stimuli such as pH or temperature.…”

Section: Polysaccharides In the Construction Of Nanocarriersmentioning

confidence: 99%

“…Moreover, tailoring the functionalization of the polysaccharide backbone enables control over polymer solubility and responsiveness to stimuli such as pH or temperature. Many polysaccharides contain free hydroxyl groups, facilitating functionalization with carboxylic acid or hydroxyl-containing drugs like cholesterol [ 51 , 52 , 53 ]. Table 1 summarizes the various nanocarriers formed by polysaccharide-based amphiphilic block copolymers reported in the literature.…”

Section: Polysaccharides In the Construction Of Nanocarriersmentioning

confidence: 99%

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Polysaccharides as a Hydrophilic Building Block of Amphiphilic Block Copolymers for the Conception of Nanocarriers

Lu,

2024

Pharmaceutics

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Polysaccharides are gaining increasing attention for their relevance in the production of sustainable materials. In the domain of biomaterials, polysaccharides play an important role as hydrophilic components in the design of amphiphilic block copolymers for the development of drug delivery systems, in particular nanocarriers due to their outstanding biocompatibility, biodegradability, and structural versatility. The presence of a reducing end in polysaccharide chains allows for the synthesis of polysaccharide-based block copolymers. Compared with polysaccharide-based graft copolymers, the structure of block copolymers can be more precisely controlled. In this review, the synthesis methods of polysaccharide-based amphiphilic block copolymers are discussed in detail, taking into consideration the structural characteristics of polysaccharides. Various synthetic approaches, including reductive amination, oxime ligation, and other chain-end modification reactions, are explored. This review also focuses on the advantages of polysaccharides as hydrophilic blocks in polymeric nanocarriers. The structure and unique properties of different polysaccharides such as cellulose, hyaluronic acid, chitosan, alginate, and dextran are described along with examples of their applications as hydrophilic segments in the synthesis of amphiphilic copolymers to construct nanocarriers for sustained drug delivery.

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Section: Polysaccharides In the Construction Of Nanocarriersmentioning

confidence: 99%

Section: Polysaccharides In the Construction Of Nanocarriersmentioning

confidence: 99%

Polysaccharides as a Hydrophilic Building Block of Amphiphilic Block Copolymers for the Conception of Nanocarriers

Lu,

2024

Pharmaceutics

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“…The methodology was utilized to conjugate cholesterol to cellulose polymer, with the intent to solubilize otherwise water-insoluble drugs (Dong et al, 2019 ). The method of amorphous solid dispersion of drugs with the cholesterol-derivatized cellulose was adopted to retain a supersaturated amounts of the drug in the dispersion.…”

Section: Introductionmentioning

confidence: 99%

Glycoconjugations of Biomolecules by Chemical Methods

Sarkar

Jayaraman

2020

Front. Chem.

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Bioconjugations under benign aqueous conditions have the most promise to covalently link carbohydrates onto chosen molecular and macromolecular scaffolds. Chemical methodologies relying on C-C and C-heteroatom bond formations are the methods of choice, coupled with the reaction conditions being under aqueous milieu. A number of methods, including metal-mediated, as well as metal-free azide-alkyne cyclo-addition, photocatalyzed thiol-ene reaction, amidation, reductive amination, disulfide bond formation, conjugate addition, nucleophilic addition to vinyl sulfones and vinyl sulfoxides, native chemical ligation, Staudinger ligation, olefin metathesis, and Suzuki-Miyaura cross coupling reactions have been developed, in efforts to conduct glycoconjugation of chosen molecular and biomolecular structures. Within these, many methods require pre-functionalization of the scaffolds, whereas methods that do not require such pre-functionalization continue to be few and far between. The compilation covers synthetic methodology development for carbohydrate conjugation onto biomolecular and biomacromolecular scaffolds. The importance of such glycoconjugations on the functional properties is also covered.

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“…These studies showed that CM is mild, fast, functional grouptolerant, efficient (with high yields and conversions), and selective for synthesis of cellulose derivatives with brush architectures. Those brushes may bear a diverse set of functional groups (Dong & Edgar, 2015;Dong, Novo, Mosquera-Giraldo, Taylor, & Edgar, 2019), (Meng, Matson, & Edgar, 2014).…”

Section: Introductionmentioning

confidence: 99%