Chemical Synthesis and Anti-Inflammatory Activity of Bikunin Associated Chondroitin Sulfate 24-mer
Author(s) -
Sherif Ramadan,
Tianlu Li,
Weizhun Yang,
Jicheng Zhang,
Zahra Rashidijahanabad,
Zibin Tan,
Narayanan Parameswaran,
Xuefei Huang
Publication year - 2020
Publication title -
acs central science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 4.893
H-Index - 76
eISSN - 2374-7951
pISSN - 2374-7943
DOI - 10.1021/acscentsci.9b01199
Subject(s) - chondroitin sulfate , proinflammatory cytokine , chemistry , proteoglycan , glycan , inflammation , monosaccharide , biochemistry , glycobiology , glycosaminoglycan , chondroitin , immunology , glycoprotein , medicine , extracellular matrix
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.
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