Preparation of Low Molecular Weight Heparin from a Remodeled Bovine Intestinal Heparin

Sultan N.  Baytas; Sony S.  Varghese; Weihua  Jin; Yanlei  Yu; Peng  He; Marc  Douaisi; Fuming  Zhang; Paul  Brodfuehrer; Ke  Xia; Jonathan S.  Dordick; Robert J.  Linhardt

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Preparation of Low Molecular Weight Heparin from a Remodeled Bovine Intestinal Heparin

机译：重塑牛肠肝素低分子量肝素的制备

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Bovine intestinal heparins are structurally distinct from porcine intestinal heparins and exhibit lower specific anticoagulant activity (units/mg). The reduced content of N -sulfo, 3-O -sulfo glucosamine, the central and critical residue in heparin’s antithrombin III binding site, is responsible for bovine intestinal heparin’s reduced activity. Previous studies demonstrate that treatment of bovine intestinal heparin with 3-O -sulfotransferase in the presence of 3′-phosphoadenosine-5′-phosphosulfate afforded remodeled bovine heparin with an enhanced activity reaching the United States Pharmacopeia’s requirements. Starting from this remodeled bovine intestinal heparin, we report the preparation of a bovine intestinal low molecular weight heparin having the same structural properties and anti-factor IIa and anti-factor Xa activities of Enoxaparin. Moreover, this bovine intestinal heparin-derived “Enoxaparin” showed comparable platelet factor-4 binding affinity, suggesting that it should exhibit similarly low levels of heparin induced thrombocytopeneia, HIT.

机译：牛肠肝素在结构上不同于猪肠肝素，并表现出较低的抗凝活性（单位/mg）。N-磺基、3-O-磺基葡萄糖胺是肝素抗凝血酶III结合位点的中心和关键残基，其含量降低是导致牛肠道肝素活性降低的原因。以前的研究表明，在3′-磷酸腺苷-5′-磷酸硫酸盐存在下，用3-O-磺基转移酶处理牛肠道肝素，可提供具有增强活性的重组牛肝素，达到美国药典的要求。从这种重组的牛肠道肝素出发，我们报道了一种具有与依诺肝素相同的结构特性和抗因子IIa和抗因子Xa活性的牛肠道低分子肝素的制备。此外，这种牛肠道肝素衍生的“依诺肝素”显示出类似的血小板因子-4结合亲和力，这表明它应该表现出类似的低水平肝素诱导的血小板减少症，HIT。

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来源
《Journal of Medicinal Chemistry》 |2021年第4期|共12页
作者
Sultan N. Baytas; Sony S. Varghese; Weihua Jin; Yanlei Yu; Peng He; Marc Douaisi; Fuming Zhang; Paul Brodfuehrer; Ke Xia; Jonathan S. Dordick; Robert J. Linhardt;
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作者单位

Department of Chemistry &

Chemical Biology Rensselaer Polytechnic Institute;

Center for Biotechnology and Interdisciplinary Studies Rensselaer Polytechnic Institute;

Center for Biotechnology and Interdisciplinary Studies Rensselaer Polytechnic Institute;

Department of Chemistry &

Chemical Biology Rensselaer Polytechnic Institute;

Department of Chemistry &

Chemical Biology Rensselaer Polytechnic Institute;

Center for Biotechnology and Interdisciplinary Studies Rensselaer Polytechnic Institute;

Center for Biotechnology and Interdisciplinary Studies Rensselaer Polytechnic Institute;

Center for Biotechnology and Interdisciplinary Studies Rensselaer Polytechnic Institute;

Center for Biotechnology and Interdisciplinary Studies Rensselaer Polytechnic Institute;

Center for Biotechnology and Interdisciplinary Studies Rensselaer Polytechnic Institute;

Department of Chemistry &

Chemical Biology Rensselaer Polytechnic Institute;

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正文语种 eng
中图分类药学;
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1. Comparison of low-molecular-weight-heparin and unfractionated heparin for acute PTE [J] . CHEN Li-ying, YING Ke-jing, HONG Wu-jun, 浙江大学学报（英文版）（B辑：生物医学和生物技术） . 2005,第012期
2. Studies of Oral Preparation of Low Molecular Weight Heparin [J] . 无中国药学（英文版） . 1995,第001期
3. Preparation of low molecular weight heparins from bovine and ovine heparins using nitrous acid degradation [J] . Xie Shaoshuai, Guan Yudong, Zhu Peipei, Carbohydrate Polymers: Scientific and Technological Aspects of Industrially Important Polysaccharides . 2018,第期

机译：使用亚硝酸降解从牛和绵羊肝素的低分子量肝素的制备
4. Efficacy of Intracolonic Administration of Low-Molecular-Weight Heparin CB-01-05, Compared to Other Low-Molecular-Weight Heparins and Unfractionated Heparin, in Experimentally Induced Colitis in Rat [J] . Giuseppe Celasco, Luigi Moro, Roberta Bozzella, Digestive Diseases and Sciences . 2008,第12期

机译：与其他低分子肝素和普通肝素相比，低分子肝素CB-01-05结肠内给药对大鼠实验性结肠炎的疗效
5. Efficacy of intracolonic administration of low-molecular-weight heparin CB-01-05, compared to other low-molecular-weight heparins and unfractionated heparin, in experimentally induced colitis in rat. [J] . Celasco G, Moro L, Bozzella R, Digestive Diseases and Sciences . 2008,第12期

机译：与其他低分子量肝素和普通肝素相比，结肠内施用低分子量肝素CB-01-05在大鼠实验性结肠炎中的功效。
6. Carbopol C934 increases the intestinal absorption of low molecular weight heparin (LMWH) in rats and pigs [C] . M.Thanou, M.T.Nihot, G.Borchard, International symposium on controlled release of bioactive materials . 2000

机译：Carbopol C934增加了大鼠和猪的低分子量肝素（LMWH）的肠道吸收
7. Synthesis and characterization of sugar based low molecular weight gelators and the preparation of chiral sulfinamides. [D] . Mangunuru, Hari Prasad Reddy. 2014

机译：糖基低分子量胶凝剂的合成，表征以及手性亚磺酰胺的制备。
8. Low molecular weight protamine (LMWP) as nontoxic heparin/low molecular weight heparin antidote (I): Preparation and characterization [O] . Li-Chien Chang, Hsiao-Feng Lee, ZhiQiang Yang, 2001

机译：低分子量鱼精蛋白（LMWP）作为无毒肝素/低分子量肝素解毒剂（I）：制备和表征
9. Low molecular weight protamine (LMWP) as nontoxic heparin/low molecular weight heparin antidote (I): Preparation and characterization [O] . Chang, Li-Chien, Lee, Hsiao-Feng, Yang, ZhiQiang, 2001

机译：低分子量鱼精蛋白（LMWP）作为无毒肝素/低分子量肝素解毒剂（I）：制备和表征
10. Methods for Preparing Low Molecular Weight Heparin with Modified Heparinase III. [R] . Liu, D., Pojasek, K., Shriver, Z., 2006

机译：用改良的肝素酶III制备低分子肝素的方法。

Preparation of Low Molecular Weight Heparin from a Remodeled Bovine Intestinal Heparin

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