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Comprehensive synthesis and anticoagulant evaluation of a diverse fucoidan library
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Comprehensive synthesis and anticoagulant evaluation of a diverse fucoidan library
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Journal Article
Comprehensive synthesis and anticoagulant evaluation of a diverse fucoidan library
2025
Overview
Fucoidan, a sulfated glycan derived from brown algae, has garnered significant attention for its anticoagulant properties. However, the structural complexity and heterogeneity of naturally extracted fucoidan have hindered a comprehensive understanding of its structure-activity relationship, limiting the development of fucoidan-based anticoagulant drugs. To address this challenge, we synthesize a diverse library of 58 distinct fucoidans with multiple contiguous 1,2-
cis
glycosidic bonds, ranging from disaccharides to dodecasaccharides, using a highly efficient preactivation-based one-pot glycosylation strategy. This library includes compounds with various sulfation patterns (2,3-
O
-
di-
, 3,4-
O
-
di-
, and 2,3,4-
O
-
tri
-sulfation) encompassing nearly all possible fucoidan structures. In vitro anticoagulant assays demonstrate that both molecular size and degree of sulfation play crucial roles in anticoagulant potency. Notably, compounds
29
,
30
,
37
, and
58
significantly prolong human plasma activated partial thromboplastin time (APTT), comparable to the effect of enoxaparin, without affecting prothrombin time (PT) or thrombin time (TT). This selective inhibition of the intrinsic coagulation pathway suggests a reduced risk of bleeding, highlighting the therapeutic potential of these fucoidans as safer anticoagulant agents.
Fucoidan is a sulfated glycan with anticoagulant properties, but its structural complexity and heterogeneity hinders understanding of its structure-activity relationship. Here, the authors synthesize a diverse library of 58 distinct fucoidans with multiple contiguous 1,2-
cis
glycosidic bonds and various sulfation patterns, and investigate their anticoagulant activity.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
Subject
/ 140/58
/ Algae
/ Anticoagulants - chemical synthesis
/ Anticoagulants - pharmacology
/ Blood Coagulation - drug effects
/ Fucoidan
/ Glycan
/ Humanities and Social Sciences
/ Humans
/ Polysaccharides - chemical synthesis
/ Polysaccharides - pharmacology
/ Science
/ Structure-Activity Relationship
/ Thrombin
