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昆布多糖乙酰酯的合成、构象分析及抗病毒活性。

Laminarin acetyl esters: Synthesis, conformational analysis and anti-viral effects.

机构信息

Guangzhou Jinan Biomedicine Research and Development Center, Institute of Biomedicine, Guangdong Provincial Key Laboratory of Virology, College of Life Science and Technology, Jinan University, Guangzhou, China.

Guangzhou Jinan Biomedicine Research and Development Center, Institute of Biomedicine, Guangdong Provincial Key Laboratory of Virology, College of Life Science and Technology, Jinan University, Guangzhou, China.

出版信息

Int J Biol Macromol. 2022 Sep 1;216:528-536. doi: 10.1016/j.ijbiomac.2022.06.208. Epub 2022 Jul 7.

DOI:10.1016/j.ijbiomac.2022.06.208
PMID:35809670
Abstract

Chemical modification of polysaccharides is important for expanding their applications and gaining new insights into their structure-property relationships. Here we reported the synthesis, characterization, and anti-viral activities of laminarin acetyl derivatives. The chemical structure and chain conformation of acetylated laminarin were characterized by FT-IR, H NMR, AFM, UV-vis spectrum, and induced circular dichroism based on a modified Congo Red assay (ICD-CR assay). The inhibition effect of laminarin and its acetyl derivatives on HSV-1 was evaluated by viral plaque assay and virus-associated DNA/protein change. Acetylation modification was found to trigger the conformation transition of laminarin from triple helix to single helix, and the extent of transition can be tuned by the degree of substitution. The single helical acetylated laminarins were found to be stable in neutral aqueous solution and exhibited no cytotoxicity. However, the acetylated laminarin exhibited declined antiviral activity after modification.

摘要

多糖的化学修饰对于拓展其应用范围和深入了解其结构-性能关系非常重要。在这里,我们报道了岩藻多糖乙酰衍生物的合成、表征和抗病毒活性。通过傅里叶变换红外光谱(FT-IR)、核磁共振氢谱(H NMR)、原子力显微镜(AFM)、紫外可见光谱和基于改良刚果红检测法(ICD-CR assay)的诱导圆二色性(induced circular dichroism),对乙酰化岩藻多糖的化学结构和链构象进行了表征。通过病毒斑减少法和病毒相关 DNA/蛋白变化,评估了岩藻多糖及其乙酰衍生物对单纯疱疹病毒 1 型(HSV-1)的抑制作用。乙酰化修饰被发现会引发岩藻多糖从三螺旋到单螺旋的构象转变,而转变的程度可以通过取代度来调节。单螺旋乙酰化岩藻多糖在中性水溶液中稳定,且无细胞毒性。然而,乙酰化修饰后,岩藻多糖的抗病毒活性下降。

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