Preparation of O-acylated low-molecular-weight carrageenans with potent anti-HIV activity and low anticoagulant effect
Preparation of O-acylated low-molecular-weight carrageenans with potent anti-HIV activity and low anticoagulant effect
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DOI：
10.1016/s0144-8617(99)00083-1
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发表时间：
2000-02-01
影响因子：
11.2
通讯作者：
Nakagawa, Y
中科院分区：
文献类型：
--
作者：
Yamada, T;Ogamo, A;Nakagawa, Y
在亚铁离子、抗坏血酸和乙二胺四乙酸存在下，在室温下使用超声处理进行 lambda 和 kappa-角叉菜胶的解聚。将每种解聚角叉菜胶的四丁基铵(TBA)盐溶解在N,N-二甲基甲酰胺(DMF)中，并在二甲基氨基吡啶和三丁胺作为催化剂存在下，在室温下用羧酸酐酰化。将酰化角叉菜胶的TEA盐溶解在DMF中并通过吡啶三氧化硫硫酸化。每种制剂的抗HIV活性在MT-4细胞感染HTLV-III B的系统中测定。由低丁酰化或低己酰化衍生物制备的硫酸化样品比用作参考的硫酸葡聚糖具有更高的抗HIV活性。这些制剂的抗凝活性通过测量活化部分凝血活酶时间（APTT）来确定。取代度为1.1-1.5的h-卡拉胶丁酰化衍生物的抗凝活性为6.7-8.5单位/mg，明显低于硫酸葡聚糖(avg.mel.wt.0.7 X 10(4))的23.4单位/mg。该结果清楚地表明取代的酰基对抗凝血活性的降低作用。这些制剂的溶血活性可以忽略不计。 (C) 2000 Elsevier Science Ltd. 保留所有权利。
Depolymerization of lambda and kappa-carrageenan was performed using ultrasonication at room temperature in the presence of ferrous ions, ascorbic acid and ethylenediaminetetraacetic acid. Tetrabutylammonium (TBA) salts of each depolymerized carrageenan were dissolved in N,N-dimethylformamide (DMF) and acylated by carboxylic acid anhydride at room temperature in the presence of dimethylaminopyridine and tributylamine as catalysts. The TEA salts of acylated carrageenans were dissolved in DMF and sulfated by pyridine-sulfur trioxide. The anti-HIV activities of each preparation were determined in a system in which MT-4 cells were infected with HTLV-III B. Sulfated samples prepared from low butanoylated or low hexanoylated derivatives had higher anti-HIV activities than dextran sulfate used as reference. Anticoagulant activity of these preparations was determined from the measurement of activated partial thromboplastin time (APTT). The butanoylated derivatives of h-carrageenan with a degree of substitution of 1.1-1.5 had anticoagulant activities of 6.7-8.5 unit/mg, which were distinctly lower than that of dextran sulfate (avg. mel. wt. 0.7 X 10(4)), 23.4 unit/mg. This result indicated clearly the decreasing effect of the substituted acyl group on anticoagulant activity. Hemolytic activity of these preparations was negligible. (C) 2000 Elsevier Science Ltd. All rights reserved.