Synthesis of the novel (±)-2-methoxy-6-icosynoic acid--a fatty acid that induces death of neuroblastoma cells.
Synthesis of the novel (±)-2-methoxy-6-icosynoic acid--a fatty acid that induces death of neuroblastoma cells.
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DOI：
10.1016/j.chemphyslip.2013.04.004
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发表时间：
2013-07
影响因子：
3.4
通讯作者：
Carballeira NM
中科院分区：
文献类型：
--
作者：
Orellano EA;Cartagena MM;Rosado K;Carballeira NM
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 SHSY5Y 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) towards 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.
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DOI：
10.3181/0808-mr-250
发表时间：
2009-02
期刊：
Experimental biology and medicine (Maywood, N.J.)
影响因子：
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