Department of Chemistry, University of Puerto Rico, Rio Piedras campus, PO Box 23346, San Juan, PR 00931-3346.
Chem Phys Lipids. 2013 Jul-Aug;172-173:14-9. doi: 10.1016/j.chemphyslip.2013.04.004. Epub 2013 May 3.
The first total synthesis for the novel fatty acid (±)-2-methoxy-6-icosynoic acid was accomplished in seven steps and in a 14% overall yield starting from 2-(4-bromobutoxy)-tetrahydro-2H-pyran. The title compound displayed an EC50=23±1 μM against the human SH-SY5Y neuroblastoma cell line and an EC50=26±1 μM against the human adenocarcinoma cervix cell line (HeLa) after 48 h of exposure. The corresponding non-methoxylated analog 6-icosynoic acid did not display cytotoxicity (EC50>500 μM) toward the studied cell lines as well as the 2-methoxyicosanoic acid (EC50>300 μM). The critical micelle concentration (CMC=20-30 μM) for the (±)-2-methoxy-6-icosynoic acid was also determined. It was found that α-methoxylation decreases the CMC of a fatty acid.
新型脂肪酸(±)-2-甲氧基-6-二十碳烯酸的全合成首次在 7 步反应中以 2-(4-溴丁氧基)-四氢-2H-吡喃为原料,以 14%的总收率完成。标题化合物在暴露 48 小时后对人神经母细胞瘤细胞系(SH-SY5Y)的 EC50=23±1 μM,对人宫颈癌细胞系(HeLa)的 EC50=26±1 μM。相应的非甲氧基类似物 6-二十碳烯酸对所研究的细胞系没有显示出细胞毒性(EC50>500 μM),2-甲氧基二十烷酸(EC50>300 μM)也是如此。(±)-2-甲氧基-6-二十碳烯酸的临界胶束浓度(CMC=20-30 μM)也被确定。结果发现,α-甲氧基化降低了脂肪酸的 CMC。