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七种肝素和硫酸乙酰肝素类似物三糖的合成与生物学特征分析。

Synthesis and Biological Profiling of Seven Heparin and Heparan Sulphate Analogue Trisaccharides.

机构信息

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.

Department of Molecular and Nanopharmaceutics, Faculty of Pharmacy, University of Debrecen, Nagyerdei Körút 98, H-4032 Debrecen, Hungary.

出版信息

Biomolecules. 2024 Aug 25;14(9):1052. doi: 10.3390/biom14091052.

DOI:10.3390/biom14091052
PMID:39334821
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11429564/
Abstract

Researchers are paying increasing attention to the strongly negatively charged heteropolysaccharides in cells, in the extracellular matrix or in the cell wall. Examples of such molecules are glycosaminoglycans (e.g., heparin, heparan sulphate). It is well known from the literature that heparin and its derivatives have anti-inflammatory, angiogenic, metastatic and growth factor inhibitory activity. Herein, we present the efficient synthesis of six non-glycosaminoglycan (Glc-GlcA-Glc-sequenced) and one heparin-related (GlcN-GlcA-Glc-sequenced) trisaccharides with various functional group patterns. The anti-inflammatory, antioxidant and cell growth-inhibitory/cytotoxic effects of the synthesized compounds were tested. Among the investigated molecules, we have found some derivatives with a promising anti-inflammatory and antioxidant effect.

摘要

研究人员越来越关注细胞、细胞外基质或细胞壁中带强负电荷的杂多糖。此类分子的例子有糖胺聚糖(例如肝素、硫酸乙酰肝素)。文献中已知肝素及其衍生物具有抗炎、血管生成、转移和生长因子抑制活性。在此,我们展示了六种非糖胺聚糖(Glc-GlcA-Glc 序列)和一种肝素相关(GlcN-GlcA-Glc 序列)三糖的高效合成,它们具有各种功能基团模式。测试了合成化合物的抗炎、抗氧化和抑制细胞生长/细胞毒性作用。在所研究的分子中,我们发现一些具有有前途的抗炎和抗氧化作用的衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/8017cdd7682e/biomolecules-14-01052-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/300714567132/biomolecules-14-01052-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/74caefd1c001/biomolecules-14-01052-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/a109070302a1/biomolecules-14-01052-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/cd7a1dccad8a/biomolecules-14-01052-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/28aaadca5ac8/biomolecules-14-01052-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/1aafea3f3ec5/biomolecules-14-01052-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/cc6a24e90d1c/biomolecules-14-01052-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/c482131d1c8d/biomolecules-14-01052-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/0c553018ea7f/biomolecules-14-01052-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/701aaa669c98/biomolecules-14-01052-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/fb3f1aa0136a/biomolecules-14-01052-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/7c6c8d2f7c2a/biomolecules-14-01052-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/8017cdd7682e/biomolecules-14-01052-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/300714567132/biomolecules-14-01052-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/74caefd1c001/biomolecules-14-01052-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/a109070302a1/biomolecules-14-01052-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/cd7a1dccad8a/biomolecules-14-01052-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/28aaadca5ac8/biomolecules-14-01052-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/1aafea3f3ec5/biomolecules-14-01052-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/cc6a24e90d1c/biomolecules-14-01052-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/c482131d1c8d/biomolecules-14-01052-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/0c553018ea7f/biomolecules-14-01052-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/701aaa669c98/biomolecules-14-01052-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/fb3f1aa0136a/biomolecules-14-01052-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/7c6c8d2f7c2a/biomolecules-14-01052-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cfb4/11429564/8017cdd7682e/biomolecules-14-01052-g008.jpg

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3
Sulfated polysaccharides effectively inhibit SARS-CoV-2 in vitro.
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Cell Discov. 2020 Jul 24;6(1):50. doi: 10.1038/s41421-020-00192-8. eCollection 2020.
4
Characterization of heparin and severe acute respiratory syndrome-related coronavirus 2 (SARS-CoV-2) spike glycoprotein binding interactions.肝素与严重急性呼吸综合征相关冠状病毒 2(SARS-CoV-2)刺突糖蛋白结合相互作用的表征。
Antiviral Res. 2020 Sep;181:104873. doi: 10.1016/j.antiviral.2020.104873. Epub 2020 Jul 10.
5
Specificity of glycosaminoglycan-protein interactions.糖胺聚糖-蛋白相互作用的特异性。
Curr Opin Struct Biol. 2018 Jun;50:101-108. doi: 10.1016/j.sbi.2017.12.011. Epub 2018 Feb 9.
6
Biological activities and pharmaceutical applications of polysaccharide from natural resources: A review.天然资源多糖的生物活性及药学应用:综述。
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7
Targeting heparin and heparan sulfate protein interactions.靶向肝素和硫酸乙酰肝素蛋白相互作用。
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