New silibinin phosphodiester glyco-conjugates were synthesized by efficient phosphoramidite chemistry and were fully characterized by 2D-NMR. A wide-ranging study focused on the determination of their pKa and E° values as well as on their radical scavenging activities by different assays (DPPH, ABTS⁺ and HRSA) was conducted. The new glyco-conjugates are more water-soluble than silibinin, and their radical scavenging activities are higher than those of silibinin. The conjugation therefore improves both the water solubilities and antioxidant activities of the flavonolignan moieties. The serum stability was evaluated under physiological conditions, and the glyco-conjugates degraded with half-lives of 40–70 h, making them useful in pro-drug approaches. We started by treating androgen-dependent prostate cancer (PCa) LNCaP cells and then expanded our studies to androgen-independent PCa PC3 and DU145 cells. In most cases, the new derivatives significantly reduced both total and live cell numbers, albeit at different levels. Anti-HIV activities were evaluated and the glucosamine-phosphate silibinin derivative showed higher activity (IC₅₀ = 73 μM) than silibinin.

通过高效的亚磷酰胺化学合成了新的水飞蓟宾磷酸二酯糖缀合物，并通过 2D-NMR 对其进行了充分表征。进行了一项范围广泛的研究，重点是确定它们的 pKa 和E ° 值以及通过不同的测定法（DPPH、ABTS ⁺和 HRSA）确定它们的自由基清除活性。新的糖缀合物比水飞蓟宾更易溶于水，其自由基清除活性高于水飞蓟宾。因此，缀合改善了黄酮木脂素部分的水溶性和抗氧化活性。在生理条件下评估血清稳定性，糖缀合物降解的半衰期为 40-70 小时，使其可用于前药方法。我们首先治疗雄激素依赖性前列腺癌 (PCa) LNCaP 细胞，然后将我们的研究扩展到雄激素非依赖性 PCa PC3 和 DU145 细胞。在大多数情况下，新的衍生物显着减少了总细胞数和活细胞数，尽管水平不同。评估了抗 HIV 活性，并且氨基葡萄糖-磷酸水飞蓟宾衍生物显示出比水飞蓟宾更高的活性 (IC ₅₀  = 73 μM)。