Medicinal Chemistry Department, CSIR-Central Institute of Medicinal and Aromatic Plants, Lucknow 226015, India.
Parasitology Division, CSIR-Central Drug Research Institute, Lucknow-226031, India.
Curr Top Med Chem. 2019;19(14):1191-1200. doi: 10.2174/1568026619666190618141450.
Lymphatic filariasis is one of the chronic diseases in many parts of the tropics and sub-tropics of the world despite the use of standard drugs diethylcarbamazine and ivermectin because they kill microfilaries and not the adult parasites. Therefore, new leads with activity on adult parasites are highly desirable.
Anti-filarial lead optimization by semi-synthetic modification of glycyrrhetinic acid (GA).
The GA was first converted into 3-O-acyl derivative, which was further converted into 12 amide derivatives. All these derivatives were assessed for their antifilarial potential by parasite motility assay. The binding affinity of active GA derivatives on trehalose-6-phosphate phosphatase (Bm-TPP) was assessed by molecular docking studies.
Among 15 GA derivatives, GAD-2, GAD-3, and GAD-4 were found more potent than the GA and standard drug DEC. These derivatives reduced the motility of Brugia malayi adult worms by up to 74% while the GA and DEC reduced only up to 49%. Further, GA and most of its derivatives exhibited two times more reduction in MTT assay when compared to the standard drug DEC. These derivatives also showed 100% reduction of microfilariae and good interactions with Bm-TPP protein.
The present study suggests that 3-O-acyl and linear chain amide derivatives of glycyrrhetinic acid may be potent leads against B. malayi microfilariae and adult worms. These results might be helpful in developing QSAR model for optimizing a new class of antifilarial lead from a very common, inexpensive, and non toxic natural product.
尽管使用了标准药物乙胺嗪和伊维菌素,但淋巴丝虫病仍是世界上许多热带和亚热带地区的慢性疾病之一,因为这些药物只能杀死微丝蚴,而不能杀死成虫寄生虫。因此,人们非常希望能有新的针对成虫寄生虫的药物。
通过半合成修饰甘草次酸(GA)来优化抗丝虫药物。
首先将 GA 转化为 3-O-酰基衍生物,然后进一步转化为 12 个酰胺衍生物。通过寄生虫运动试验评估所有这些衍生物的抗丝虫活性。通过分子对接研究评估活性 GA 衍生物与海藻糖-6-磷酸磷酸酶(Bm-TPP)的结合亲和力。
在 15 个 GA 衍生物中,GAD-2、GAD-3 和 GAD-4 比 GA 和标准药物 DEC 更有效。这些衍生物可使盘尾丝虫成虫的运动能力降低高达 74%,而 GA 和 DEC 仅降低了 49%。此外,与标准药物 DEC 相比,GA 和其大多数衍生物在 MTT 测定中显示出高达两倍的减少。这些衍生物还对微丝蚴表现出 100%的减少,并且与 Bm-TPP 蛋白有良好的相互作用。
本研究表明,甘草次酸的 3-O-酰基和直链酰胺衍生物可能是对抗盘尾丝虫微丝蚴和成虫的有效先导化合物。这些结果可能有助于从非常常见、廉价且无毒的天然产物中开发出针对新型抗丝虫药物的 QSAR 模型。