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Chemical Synthesis and Anti-Inflammatory Activity of Bikunin Associated Chondroitin Sulfate 24-mer.

ABSTRACT: Bikunin, a chondroitin sulfate (CS) proteoglycan clinically used to treat acute inflammation and sepsis, contains a CS chain with more than 20 monosaccharide units. To understand the function of the CS chain of bikunin, synthesis of long CS chains is needed. After exploring multiple glycosylation approaches and protective group chemistry, we report herein the successful generation of the longest CS chain to date (24-mer) in an excellent overall yield on a multi-mg scale. The anti-inflammatory activities of both bikunin and the synthetic 24-mer were determined, and the results demonstrate that both the glycan and the core protein are important for anti-inflammatory activities of bikunin by reducing macrophage production of proinflammatory cytokines.

SUBMITTER: Ramadan S

PROVIDER: S-EPMC7318065 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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Chemical Synthesis and Anti-Inflammatory Activity of Bikunin Associated Chondroitin Sulfate 24-mer.

Ramadan Sherif S Li Tianlu T Yang Weizhun W Zhang Jicheng J Rashidijahanabad Zahra Z Tan Zibin Z Parameswaran Narayanan N Huang Xuefei X

ACS central science 20200601 6

Bikunin, a chondroitin sulfate (CS) proteoglycan clinically used to treat acute inflammation and sepsis, contains a CS chain with more than 20 monosaccharide units. To understand the function of the CS chain of bikunin, synthesis of long CS chains is needed. After exploring multiple glycosylation approaches and protective group chemistry, we report herein the successful generation of the longest CS chain to date (24-mer) in an excellent overall yield on a multi-mg scale. The anti-inflammatory ac ...[more]

PMID: 32607438

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