Chemical Modification of Hyaluronan and Their Biomedical Applications

Abstract

Hyaluronan, the extracellular matrix glycosaminoglycan, is an important structural component of many tissues playing a critical role in a variety of biological contexts. This makes hyaluronan, which can be biotechnologically produced in large scale, an attractive starting polymer for chemical modifications. This review provides a broad overview of different synthesis strategies used for modulating the biological as well as material properties of this polysaccharide. We discuss current advances and challenges of derivatization reactions targeting the primary and secondary hydroxyl groups or carboxylic acid groups and the N-acetyl groups after deamidation. In addition, we give examples for approaches using hyaluronan as biomedical polymer matrix and consequences of chemical modifications on the interaction of hyaluronan with cells via receptor-mediated signaling. Collectively, hyaluronan derivatives play a significant role in biomedical research and applications indicating the great promise for future innovative therapies.

Characteristics of Marine Biomaterials and Their Applications in Biomedicine

“…HA is an important component of the natural extracellular matrix, which mainly exists in animal connective tissue. Unlike other GAGs, HA is unsulfated and does not bind to proteins, and it is the only GAG without proteoglycan formation and sulfate group substitution [80]. The basic units of HA are GlcA and GlcNAc, which are linked by one to three glycosidic bonds.…”

Glycosaminoglycans: What Remains To Be Deciphered?

“…Native GAGs can be functionalized with specific target functional groups or labels. , Most of the structural modifications are chemoselective. They involve, for example, the derivatization of the carboxylate functionalities into amides and hydrazides carrying specific labels ( e.g ., fluorescent tags, bioactive moieties) or functional groups ( e.g ., double bonds, thiols, o -quinones etc.)…”

HYDRHA: Hydrogels of hyaluronic acid. New biomedical approaches in cancer, neurodegenerative diseases, and tissue engineering

“…Chemical modification involves three functional groups: the carboxyl group, the hydroxyl group, and the N-acetyl group [ 49 ]. The various chemical modification methods to obtain HA derivatives are detailed in various reviews [ [50] , [51] , [52] , [53] ]. In brief, chemical modifications of HA regarding the carboxyl group, include amidation, Ugi condensation, esterification, and oxidation [ [54] , [55] , [56] , [57] , [58] , [59] ].…”