A series of eight novel phosphatidylcholines containing cinnamic or 3-methoxycinnamic acids (3a-b, 5a-b, 9a-b, 10a-b) at sn-1 and/or sn-2 positions were synthesized and tested for their antiproliferative activity in an in vitro model against representative six human cancer cell lines (MV4-11, A549, MCF-7, LoVo, LoVo/DX, HepG2) and a normal cell line BALB/3T3. The structures of the new compounds were confirmed by spectral analysis. Biological evaluation revealed that all the tested conjugates exhibited higher antitumor activity than the corresponding free aromatic acids. Compounds 3b and 9b turned out to be the most active, with IC₅₀ values of 32.1 and 30.5 μM against the LoVo/DX and MV4-11 cell lines, respectively. Studies of the mechanism of the antitumor action were carried out for 1-palmitoyl-2-cinnamoyl-sn-glycero-3-phosphocholine (5a), and it was shown to be active toward almost all the tested types of cancer cells, showing that this compound could effectively arrest the cell cycle in G2/M and decrease the mitochondrial membrane potential of leukemia MV4-11 cells. The obtained results proved that the strategy of the incorporation of cinnamic and 3-methoxycinnamic acids into phospholipids could expand their potential application in industry, as well as could improve their antiproliferative activity and selectivity toward cancer cell lines.

中文翻译：

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具有有效抗增殖活性的肉桂酸和 3-甲氧基肉桂酸磷脂酰胆碱的合成和生物学评价†

合成了一系列在sn -1 和/或sn -2 位点含有肉桂酸或 3-甲氧基肉桂酸（3a-b、5a-b、9a-b、10a-b）的八种新型磷脂酰胆碱，并测试了它们的抗增殖活性。针对代表性六种人类癌细胞系（MV4-11、A549、MCF-7、LoVo、LoVo/DX、HepG2）和正常细胞系 BALB/3T3 的体外模型。新化合物的结构通过光谱分析得到证实。生物学评价表明，所有测试的缀合物均比相应的游离芳香酸表现出更高的抗肿瘤活性。化合物3b和9b被证明是最有活性的，针对 LoVo/DX 和 MV4-11 细胞系的IC _{50值分别为 32.1 和 30.5 μM。}对 1-棕榈酰-2-肉桂酰-sn-甘油-3-磷酸胆碱 ( 5a )的抗肿瘤作用机制进行了研究，结果表明它对几乎所有测试类型的癌细胞都有活性，表明该化合物可以有效地将细胞周期阻滞在 G2/M 期，并降低白血病 MV4-11 细胞的线粒体膜电位。所得结果证明，将肉桂酸和3-甲氧基肉桂酸掺入磷脂中的策略可以扩大其在工业上的潜在应用，并可以提高其抗增殖活性和对癌细胞系的选择性。