Vizantin, 6,6′-bis-O-(3-nonyldodecanoyl)-α,α′-trehalose, has been developed as a safe immunostimulator on the basis of a structure–activity relationship study with trehalose 6,6′-dicorynomycolate. Our recent study indicated that vizantin acts as an effective Toll-like receptor-4 (TLR4) partial agonist to reduce the lethality of an immune shock caused by lipopolysaccharide (LPS). However, because vizantin has low solubility in water, the aqueous solution used in in vivo assay systems settles out in tens of minutes. Here, vizantin was chemically modified in an attempt to facilitate the preparation of an aqueous solution of the drug. This paper describes the concise synthesis of a water-soluble vizantin analogue in which all the hydroxyl groups of the sugar unit were replaced by sulfates. The vizantin derivative displayed micelle-forming ability in water and potent TLR-4 partial agonist activity.

Vizantin，6,6'-双-O- (3-壬基十二酰基)-α,α'-海藻糖，基于海藻糖 6,6'-二角霉菌酸酯的结构-活性关系研究，已被开发为一种安全的免疫刺激剂。我们最近的研究表明，Vizantin 作为一种有效的 Toll 样受体 4 (TLR4) 部分激动剂，可降低脂多糖 (LPS) 引起的免疫休克的致死率。然而，由于维赞汀在水中的溶解度较低，体内测定系统中使用的水溶液在数十分钟内就会沉降。在此，对维赞汀进行了化学修饰，试图促进药物水溶液的制备。本文描述了水溶性 Vizantin 类似物的简明合成，其中糖单元的所有羟基都被硫酸盐取代。Vizantin 衍生物在水中表现出胶束形成能力和有效的 TLR-4 部分激动剂活性。