Effects of sulfate group in red seaweed polysaccharides on anticoagulant activity and cytotoxicity

• Published in: Carbohydrate polymers Vol. 101; pp. 776 - 785
• Main Authors: Liang, Wanai, Mao, Xuan, Peng, Xiaohui, Tang, Shunqing
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 30.01.2014; Elsevier
• Subjects: Agarose; Anticoagulant; anticoagulant activity; Anticoagulants - chemistry; Anticoagulants - pharmacology; Anticoagulants - toxicity; Applied sciences; Biological and medical sciences; Blood. Blood coagulation. Reticuloendothelial system; Carrageenan; cell proliferation; Cell Proliferation - drug effects; Cytotoxicity; Exact sciences and technology; Human Umbilical Vein Endothelial Cells - cytology; Human Umbilical Vein Endothelial Cells - drug effects; Humans; macroalgae; Medical sciences; Molecular Weight; Natural polymers; Oligosaccharide; Partial Thromboplastin Time; Pharmacology. Drug treatments; Physicochemistry of polymers; Polysaccharides - chemistry; Polysaccharides - pharmacology; Polysaccharides - toxicity; Prothrombin Time; Seaweed - chemistry; Starch and polysaccharides; Structure-Activity Relationship; sulfates; Sulfates - chemistry; Sulfation; Cytotoxicity; Anticoagulant; Carrageenan; Oligosaccharide; Agarose; Sulfation; Biological properties; Endothelial cell; Molecular structure; In vitro; Sulfatation; Chemical modification; Activity concentration relation; Structure activity relation; Prothrombin time; Preparation; Organic sulfate; Partial thromboplastin time; Oside polymer
• ISSN: 0144-8617; 1879-1344; 1879-1344
• DOI: 10.1016/j.carbpol.2013.10.010

•We prepared kinds of red seaweed polysaccharide derivatives by chemical modification.•A comprehensive exploration combining various influencing factors together was investigated.•The substitution position is the most important influencing factor on bioactivity of red seaweed glycans.•The anticoagulant effect of the substitution positions follows the sequence: A-2, G-2>G-4>G-6.•The cytotoxic effect of the substitution positions follows the sequence: G-6>G-4>G-2>A-2. In this paper, the structural effects of two main red seaweed polysaccharides (agarose and carrageenan) and their sulfated derivatives on the anticoagulant activity and cytotoxicity were investigated. The substitution position rather than the substitution degree of sulfate groups shows the biggest impact on both the anticoagulant activity and the cell proliferation. Among them, C-2 of 3,6-anhydro-α-d-Galp is the most favorable position for substitution, whereas C-6 of β-d-Galp is the most disadvantageous. Moreover, the secondary structures of glycans also play a key role in biological activities. These demonstrations warrant that the red seaweed polysaccharides should be seriously considered in biomedical applications after carefully tailoring the sulfate groups.