Facile synthesis of deuterated and [14C]labeled analogs of vanillin and curcumin for use as mechanistic and analytical tools
Facile synthesis of deuterated and [14C]labeled analogs of vanillin and curcumin for use as mechanistic and analytical tools
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DOI：
10.1002/jlcr.3102
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发表时间：
2013-12-01
影响因子：
1.8
通讯作者：
Schneider, Claus
中科院分区：
文献类型：
--
作者：
Gordon, Odaine N.;Graham, Leigh A.;Schneider, Claus
姜黄素是一种具有抗氧化、抗炎和抗肿瘤活性的膳食二酚。我们描述了合成[C-14（2）]姜黄素（4 mCi/mmol）、[d（6）]姜黄素、[d（3）]姜黄素、[C-13（5）]姜黄素和[d（6）]二环己基丙酮（姜黄素的主要氧化代谢产物）的简便方法。我们还描述了标记的结构单元[C-14]香草醛、[d（3）]香草醛和[C-13（5）]乙酰丙酮的合成。标记产物的总摩尔产率为香草醛52（[C-14]）和47%（[d（3）]），姜黄素25（[C-14（2）]）和27%（[d（6）]）。该化合物可用作生物转化研究中的放射性示踪剂，并可用作药代动力学分析中基于质谱的定量的同位素标准。版权所有（c）2013约翰威利父子有限公司
Curcumin is a dietary diphenol with antioxidant, antinflammatory, and antitumor activity. We describe facile procedures for the synthesis of [C-14(2)]curcumin (4mCi/mmol), [d(6)]curcumin, [d(3)]curcumin, [C-13(5)]curcumin, and [d(6)]bicyclopentadione, the major oxidative metabolite of curcumin. We also describe synthesis of the labeled building blocks [C-14]vanillin, [d(3)]vanillin, and [C-13(5)]acetylacetone. The overall molar yields of the labeled products were 52 ([C-14]) and 47% ([d(3)]) for vanillin and 25 ([C-14(2)]) and 27% ([d(6)]) for curcumin. The compounds can be used as radiotracers in biotransformation studies and as isotopic standards for mass spectrometry-based quantification in pharmacokinetic analyses. Copyright (c) 2013 John Wiley & Sons, Ltd.