磷酸缩水甘油酯作为潜在抗癌药物的合成、生物学和电化学评价。

IF 2.1 4区 化学 Q2 CHEMISTRY, ORGANIC
Beilstein Journal of Organic Chemistry Pub Date : 2025-09-15 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.148
Almaz A Zagidullin, Emil R Bulatov, Mikhail N Khrizanforov, Damir R Davletshin, Elvina M Gilyazova, Ivan A Strelkov, Vasily A Miluykov
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引用次数: 0

摘要

有机磷化合物具有多种生物活性,在合成有机化学和制药领域有着重要的应用。在本研究中,我们通过氯膦氧化物或氯氧磷与甘油三酯在碱的存在下缩合,合成了三种新型的磷酸缩水甘油三酯1-3,得到了纯度高、收率中至优异的产品。在人成纤维细胞(HSF)、前列腺癌(PC-3)和乳腺癌(MCF7)细胞系上使用MTT试验评估了它们的细胞毒性潜力,揭示了对癌细胞的中度优先细胞毒性,特别是在MCF7的情况下。此外,利用线性扫描伏安法(LSV)研究了人血清白蛋白(HSA)的烷基化特性。电化学结果表明,这些化合物有效地修饰白蛋白,突出了它们作为活性抗癌剂的潜力。这些发现对磷酸缩水甘油酯的合成、细胞毒活性和生化反应性提供了重要的见解,强调了它们在抗癌药物发现和药物研究中作为先导结构的潜力。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Synthesis, biological and electrochemical evaluation of glycidyl esters of phosphorus acids as potential anticancer drugs.

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 1-3 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.

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来源期刊
CiteScore
4.90
自引率
3.70%
发文量
167
审稿时长
1.4 months
期刊介绍: The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
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