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2-methoxylated fatty acids in marine sponges: defense mechanism against mycobacteria?
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The first total synthesis of the marine fatty acid (+/-)-2-methoxy-13-methyltetradecanoic acid: a cytotoxic fatty acid to leukemia cells.海洋脂肪酸（±）-2-甲氧基-13-甲基十四烷酸的首次全合成：一种对白血病细胞具有细胞毒性的脂肪酸。
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6
Ranking the toxicity of fatty acids on Jurkat and Raji cells by flow cytometric analysis.通过流式细胞术分析对脂肪酸对Jurkat细胞和Raji细胞的毒性进行排名。
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Facile total synthesis and antimicrobial activity of the marine fatty acids (Z)-2-methoxy-5-hexadecenoic acid and (Z)-2-methoxy-6-hexadecenoic acid.海洋脂肪酸（Z）-2-甲氧基-5-十六碳烯酸和（Z）-2-甲氧基-6-十六碳烯酸的简便全合成及其抗菌活性
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10
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新型系列2-甲硫基脂肪酸的合成及其对人K-562和U-937白血病细胞系的毒性

Synthesis of a novel series of 2-methylsulfanyl fatty acids and their toxicity on the human K-562 and U-937 leukemia cell lines.

作者信息

Carballeira Néstor M, Miranda Carlos, Orellano Elsie A, González Fernando A

机构信息

Department of Chemistry, University of Puerto Rico, San Juan 00931-3346.

出版信息

Lipids. 2005 Oct;40(10):1063-8. doi: 10.1007/s11745-005-1470-5.

DOI:10.1007/s11745-005-1470-5
PMID:16382579
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1618881/
Abstract

The hitherto unknown 2-methylsulfanyldecanoic acid and 2-methylsulfanyldodecanoic acid were synthesized from methyl decanoate and methyl dodecanoate, respectively, through the reaction of lithium diisopropylamide and dimethyldisulfide in THF followed by saponification with potassium hydroxide in ethanol. Both alpha-methylsulfanylated FA were cytotoxic to the human chronic myelogenous leukemia K-562 and the human histiocytic lymphoma U-937 cell lines with EC50 values in the 200-300 microM range, which makes them more cytotoxic to these cell lines than decanoic and/or dodecanoic acid. The cytotoxicity of the studied FA toward K-562 followed the order 2-SCH3-12:0 > 2-SCH3-10:0 > 10:0 > 12:0 > 2-OCH3-12:0, whereas toward U-937 the cytotoxicity was 2-SCH3-10:0 > 2-SCH3-12:0 > 12:0 > 10:0 > 2-OCH3-12:0. These results indicate that the alpha-methylsulfanyl substitution increases the cytotoxicity of the C10 and C12 FA toward the studied leukemia cell lines.

摘要

迄今未知的2-甲硫基癸酸和2-甲硫基十二酸分别由癸酸甲酯和十二酸甲酯合成，方法是在四氢呋喃中使二异丙基酰胺锂与二甲基二硫反应，然后在乙醇中用氢氧化钾皂化。两种α-甲硫基化脂肪酸对人慢性粒细胞白血病K-562和人组织细胞淋巴瘤U-937细胞系均具有细胞毒性，其半数有效浓度（EC50）值在200 - 300微摩尔范围内，这使得它们对这些细胞系的细胞毒性比癸酸和/或十二酸更强。所研究的脂肪酸对K-562细胞的细胞毒性顺序为2-SCH3-12:0 > 2-SCH3-10:0 > 10:0 > 12:0 > 2-OCH3-12:0，而对U-937细胞的细胞毒性顺序为2-SCH3-10:0 > 2-SCH3-12:0 > 12:0 > 10:0 > 2-OCH3-12:0。这些结果表明，α-甲硫基取代增加了C10和C12脂肪酸对所研究白血病细胞系的细胞毒性。