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1
Oversulfated chondroitin sulfate: impact of a heparin impurity, associated with adverse clinical events, on low-molecular-weight heparin preparation.过硫酸化硫酸软骨素：一种与不良临床事件相关的肝素杂质对低分子量肝素制剂的影响。
J Med Chem. 2008 Sep 25;51(18):5498-501. doi: 10.1021/jm800785t.
2
Oversulfated chondroitin sulfate interaction with heparin-binding proteins: new insights into adverse reactions from contaminated heparins.过度硫酸化硫酸软骨素与肝素结合蛋白的相互作用：对受污染肝素不良反应的新见解。
Biochem Pharmacol. 2009 Aug 1;78(3):292-300. doi: 10.1016/j.bcp.2009.04.012. Epub 2009 Apr 21.
3
Molecular profiling of heparinase-I resistant glycosaminoglycans in contaminated heparins. Comparative studies with uncontaminated heparin and porcine oversulfated chondroitin sulfate.受污染肝素中抗肝素酶-I糖胺聚糖的分子谱分析。与未受污染肝素和猪硫酸皮肤素的对比研究。
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4
Assessment of oversulfated chondroitin sulfate in low molecular weight and unfractioned heparins diffusion ordered nuclear magnetic resonance spectroscopy method.低分子量肝素和未分级肝素中过度硫酸化硫酸软骨素的评估：扩散排序核磁共振光谱法
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Quality assessment of unfractionated heparin using 1H nuclear magnetic resonance spectroscopy.使用氢核磁共振波谱法对普通肝素进行质量评估。
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Lessons learned from the contamination of heparin.从肝素污染事件中吸取的教训。
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Crude Heparin Preparations Unveil the Presence of Structurally Diverse Oversulfated Contaminants.粗制肝素制剂揭示了结构多样的过硫酸化污染物的存在。
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Description of hypersensitivity adverse events following administration of heparin that was potentially contaminated with oversulfated chondroitin sulfate in early 2008.描述 2008 年初肝素给药后可能因污染而过硫酸化硫酸软骨素引起的超敏反应不良事件。
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Analysis of pharmaceutical heparins and potential contaminants using (1)H-NMR and PAGE.采用（1）H-NMR 和 PAGE 分析药物肝素及其潜在污染物。
J Pharm Sci. 2009 Nov;98(11):4017-26. doi: 10.1002/jps.21729.

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[Advances in heparin structural analysis by chromatography technologies].[色谱技术在肝素结构分析中的进展]
Se Pu. 2023 Feb;41(2):107-121. doi: 10.3724/SP.J.1123.2022.07020.
2
Crude Heparin Preparations Unveil the Presence of Structurally Diverse Oversulfated Contaminants.粗制肝素制剂揭示了结构多样的过硫酸化污染物的存在。
Molecules. 2019 Aug 17;24(16):2988. doi: 10.3390/molecules24162988.
3
Precise Structure and Anticoagulant Activity of Fucosylated Glycosaminoglycan from : Analysis of Its Depolymerized Fragments.岩藻糖基化糖胺聚糖的精细结构和抗凝血活性：其解聚片段分析。
Mar Drugs. 2019 Mar 27;17(4):195. doi: 10.3390/md17040195.
4
Synthetic oligosaccharides can replace animal-sourced low-molecular weight heparins.合成寡糖可以替代动物源的低分子量肝素。
Sci Transl Med. 2017 Sep 6;9(406). doi: 10.1126/scitranslmed.aan5954.
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New Applications of Heparin and Other Glycosaminoglycans.肝素和其他糖胺聚糖的新应用。
Molecules. 2017 May 6;22(5):749. doi: 10.3390/molecules22050749.
6
The design and synthesis of new synthetic low-molecular-weight heparins.新型合成低分子量肝素的设计与合成
J Thromb Haemost. 2016 Jun;14(6):1135-45. doi: 10.1111/jth.13312. Epub 2016 Apr 15.
7
In vitro and in vivo characterization of a reversible synthetic heparin analog.一种可逆合成肝素类似物的体外和体内特性研究
Thromb Res. 2016 Feb;138:121-129. doi: 10.1016/j.thromres.2015.12.007. Epub 2015 Dec 10.
8
A purification process for heparin and precursor polysaccharides using the pH responsive behavior of chitosan.一种利用壳聚糖的pH响应特性对肝素和前体多糖进行纯化的方法。
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9
De novo synthesis of a narrow size distribution low-molecular-weight heparin.窄尺寸分布低分子量肝素的从头合成。
Glycobiology. 2014 May;24(5):476-86. doi: 10.1093/glycob/cwu016. Epub 2014 Mar 13.
10
Homogeneous low-molecular-weight heparins with reversible anticoagulant activity.具有可逆抗凝活性的均一低分子量肝素。
Nat Chem Biol. 2014 Apr;10(4):248-50. doi: 10.1038/nchembio.1459. Epub 2014 Feb 23.

本文引用的文献

1
Oversulfated chondroitin sulfate is a contaminant in heparin associated with adverse clinical events.过度硫酸化硫酸软骨素是肝素中的一种污染物，与不良临床事件相关。
Nat Biotechnol. 2008 Jun;26(6):669-75. doi: 10.1038/nbt1407. Epub 2008 Apr 23.
2
Contaminated heparin associated with adverse clinical events and activation of the contact system.受污染的肝素与不良临床事件及接触系统激活相关。
N Engl J Med. 2008 Jun 5;358(23):2457-67. doi: 10.1056/NEJMoa0803200. Epub 2008 Apr 23.
3
2003 Claude S. Hudson Award address in carbohydrate chemistry. Heparin: structure and activity.2003年碳水化合物化学领域克劳德·S·哈德逊奖获奖致辞。肝素：结构与活性
J Med Chem. 2003 Jun 19;46(13):2551-64. doi: 10.1021/jm030176m.
4
Heparin-protein interactions.肝素-蛋白质相互作用
Angew Chem Int Ed Engl. 2002 Feb 1;41(3):391-412. doi: 10.1002/1521-3773(20020201)41:3<390::aid-anie390>3.0.co;2-b.
5
Further evidence that periodate cleavage of heparin occurs primarily through the antithrombin binding site.进一步的证据表明，肝素的高碘酸盐裂解主要通过抗凝血酶结合位点发生。
Carbohydr Res. 2002 Nov 19;337(21-23):2239-43. doi: 10.1016/s0008-6215(02)00229-x.
6
Conformational changes and anticoagulant activity of chondroitin sulfate following its O-sulfonation.硫酸软骨素O-磺化后的构象变化及抗凝血活性
Carbohydr Res. 1998 Jan;306(1-2):35-43. doi: 10.1016/s0008-6215(97)10060-x.
7
Biochemistry and pharmacology of low molecular weight heparin.低分子量肝素的生物化学与药理学
Semin Hematol. 1997 Oct;34(4 Suppl 4):2-8.
8
Molecular weight measurements of low molecular weight heparins by gel permeation chromatography.通过凝胶渗透色谱法测定低分子量肝素的分子量
Thromb Haemost. 1997 Apr;77(4):668-74.
9
Oligosaccharide composition of heparin and low-molecular-weight heparins by capillary electrophoresis.通过毛细管电泳法分析肝素及低分子量肝素的寡糖组成
Anal Biochem. 1993 Aug 15;213(1):120-7. doi: 10.1006/abio.1993.1394.
10
More to "heparin" than anticoagulation.肝素的作用远不止抗凝。
Thromb Res. 1994 Jul 1;75(1):1-32. doi: 10.1016/0049-3848(94)90136-8.

过硫酸化硫酸软骨素：一种与不良临床事件相关的肝素杂质对低分子量肝素制剂的影响。

Oversulfated chondroitin sulfate: impact of a heparin impurity, associated with adverse clinical events, on low-molecular-weight heparin preparation.

作者信息

Zhang Zhenqing, Weïwer Michel, Li Boyangzi, Kemp Melissa M, Daman Tyler H, Linhardt Robert J

机构信息

Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, New York 12180, USA.

出版信息

J Med Chem. 2008 Sep 25;51(18):5498-501. doi: 10.1021/jm800785t.

DOI:10.1021/jm800785t
PMID:18754653
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2630253/
Abstract

Heparin, a widely used anticoagulant, is being rapidly displaced by low-molecular-weight heparins. Recently, certain lots of heparin have been associated with anaphylactoid-type reactions resulting from contamination with oversulfated chondroitin sulfate. This impurity has also contaminated low-molecular-weight heparins obtained by chemical and enzymatic depolymerization of heparin. The sensitivity of oversulfated chondroitin sulfate to five different depolymerization processes similar to ones used in preparing low-molecular-weight heparins is reported.

摘要

肝素是一种广泛使用的抗凝剂，正迅速被低分子量肝素所取代。最近，某些批次的肝素与因硫酸皮肤素过度硫酸化污染而导致的类过敏反应有关。这种杂质也污染了通过肝素化学和酶解聚获得的低分子量肝素。本文报道了硫酸皮肤素过度硫酸化对五种不同解聚过程的敏感性，这些过程类似于制备低分子量肝素时所使用的过程。