Zagidullin Almaz A, Bulatov Emil R, Khrizanforov Mikhail N, Davletshin Damir R, Gilyazova Elvina M, Strelkov Ivan A, Miluykov Vasily A
Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of Russian Academy of Sciences, Arbuzov Street 8, Kazan, 420088, Russia.
Institute of Fundamental Medicine and Biology, Kazan Federal University, Kremlyovskaya Street 18, Kazan, 420008, Russia.
Beilstein J Org Chem. 2025 Sep 15;21:1909-1916. doi: 10.3762/bjoc.21.148. eCollection 2025.
Organophosphorus compounds are important in synthetic organic chemistry and pharmaceutical applications due to their diverse biological activities. In this study, we synthesized three novel glycidyl esters of phosphorus acids - via the condensation of chlorophosphine oxides or phosphorus oxychloride with glycidol in the presence of a base, obtaining products with high purity and moderate to excellent yields. Their cytotoxic potential was evaluated using the MTT assay on human fibroblasts (HSF), prostate cancer (PC-3), and breast cancer (MCF7) cell lines, revealing moderate preferential cytotoxicity toward cancer cells, particularly in the case of MCF7. Additionally, linear sweep voltammetry (LSV) studies on human serum albumin (HSA) were conducted to investigate their alkylating properties. The electrochemical results suggest that these compounds effectively modify albumin, highlighting their potential as reactive anticancer agents. These findings provide important insights into the synthesis, cytotoxic activity, and biochemical reactivity of glycidyl esters of phosphorus acids, underscoring their potential as lead structures for further development in anticancer drug discovery and pharmaceutical research.
有机磷化合物因其多样的生物活性在有机合成化学和药物应用中具有重要意义。在本研究中，我们通过在碱存在下使氯氧化膦或三氯氧磷与缩水甘油醇缩合，合成了三种新型磷酸缩水甘油酯，得到了高纯度且产率适中至优异的产物。使用MTT法对人成纤维细胞（HSF）、前列腺癌（PC - 3）和乳腺癌（MCF7）细胞系评估了它们的细胞毒性潜力，结果显示对癌细胞具有中等程度的优先细胞毒性，尤其是对MCF7细胞。此外，还对人血清白蛋白（HSA）进行了线性扫描伏安法（LSV）研究，以研究它们的烷基化性质。电化学结果表明这些化合物能有效修饰白蛋白，突出了它们作为活性抗癌剂的潜力。这些发现为磷酸缩水甘油酯的合成、细胞毒性活性和生化反应性提供了重要见解，强调了它们作为抗癌药物发现和药物研究中进一步开发的先导结构的潜力。
