A comparative study of boron-containing and boron-omitted capsaicinoids

IF 1 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Canadian Journal of Chemistry Pub Date : 2023-06-26 DOI:10.1139/cjc-2023-0043
Giao N. Ngô, SunMin Park, Hailey M. Stack, J. Rourke, Jennifer A. Melanson, S. Westcott
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Abstract

This study reports the synthesis and characterization of a limited number of novel boron-containing and boron-omitted capsaicinoids, providing 12 unique substrates. We have previously reported boron-containing capsaicinoids that showed improved bioactivity compared to capsaicin itself but have yet to test a series of analogous boron-omitted substrates as a direct comparison. The boron-containing capsaicinoids bear a pinacolboronate ester (Bpin) group, which was incorporated using an iridium-catalyzed hydroboration reaction. We report that although nearly all compounds display moderate cytotoxic activity that bests that of capsaicin against human colon HCT116 cancer cells, the activity of our boron-omitted capsaicinoids surpasses that of the boron-containing analogues.
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含硼辣椒素与不含硼辣椒素的比较研究
本研究报道了有限数量的新型含硼和不含硼辣椒素的合成和表征,提供了12种独特的底物。我们以前报道过含硼辣椒素与辣椒素本身相比具有更好的生物活性,但尚未测试一系列类似的不含硼的底物作为直接比较。含硼辣椒素含有一个双硼酸酯(Bpin)基团,该基团是通过铱催化的硼氢化反应结合而成的。我们报告说,尽管几乎所有化合物对人类结肠HCT116癌细胞的细胞毒活性都优于辣椒素,但我们的不含硼的辣椒素的活性超过了含硼的类似物。
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来源期刊
Canadian Journal of Chemistry
Canadian Journal of Chemistry 化学-化学综合
CiteScore
1.90
自引率
9.10%
发文量
99
审稿时长
1 months
期刊介绍: Published since 1929, the Canadian Journal of Chemistry reports current research findings in all branches of chemistry. It includes the traditional areas of analytical, inorganic, organic, and physical-theoretical chemistry and newer interdisciplinary areas such as materials science, spectroscopy, chemical physics, and biological, medicinal and environmental chemistry. Articles describing original research are welcomed.
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