Tojo Toshifumi, Maeda Rika, Kondo Takeshi, Yuasa Makoto
Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan.
Bioorg Med Chem Lett. 2023 Mar 15;84:129191. doi: 10.1016/j.bmcl.2023.129191. Epub 2023 Feb 18.
Recently, ω-3 fatty acids have been revealed to having cancer cell growth suppressibility. It is necessary to analyze the mechanism of cancer cell growth suppressibility and to impart selective cancer cell accumulation when creating anticancer drugs based on ω-3 fatty acids. Therefore, it is necessarily essential to introduce a luminescent molecule or a molecule which have a drug delivery function into ω-3 fatty acids, and the position of introduction is the ω-3 fatty acids' carboxyl group. On the other hand, whether the ω-3 fatty acids' cancer cell growth suppressibility is maintained when the ω-3 fatty acids' carboxyl groups are converted to other structures, such as ester groups, is unclear. In this work, a derivative was synthesized wherein the α-linolenic acid carboxyl group, one of the ω-3 fatty acids, was converted to an ester group and evaluated the cancer cell growth suppressibility, as well as the amount of cancer cell uptake. As a result, it was suggested that the ester group derivatives presented the same functionality as α-linolenic acid, and the ω-3 fatty acid carboxyl group is a flexible functional group, which can be structurally modified in terms of functionality to cancer cells.
最近，ω-3脂肪酸已被发现具有抑制癌细胞生长的能力。在基于ω-3脂肪酸开发抗癌药物时，有必要分析其抑制癌细胞生长的机制，并实现对癌细胞的选择性富集。因此，有必要将发光分子或具有药物递送功能的分子引入ω-3脂肪酸中，引入位置为ω-3脂肪酸的羧基。另一方面，当ω-3脂肪酸的羧基转化为其他结构（如酯基）时，其抑制癌细胞生长的能力是否得以维持尚不清楚。在这项工作中，合成了一种衍生物，其中ω-3脂肪酸之一的α-亚麻酸羧基被转化为酯基，并评估了其对癌细胞生长的抑制能力以及癌细胞摄取量。结果表明，酯基衍生物表现出与α-亚麻酸相同的功能，并且ω-3脂肪酸羧基是一个灵活的官能团，在对癌细胞的功能方面可以进行结构修饰。
