Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging

被引:30
作者
Steinhardt, Rachel C. [1 ]
O'Neill, Jessica M. [1 ]
Rathbun, Colin M. [1 ]
McCutcheon, David C. [1 ]
Paley, Miranda A. [1 ]
Prescher, Jennifer A. [1 ,2 ,3 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92717 USA
[2] Univ Calif Irvine, Dept Mol Biol & Biochem, Irvine, CA 92717 USA
[3] Univ Calif Irvine, Dept Pharmaceut Sci, Irvine, CA 92717 USA
基金
美国国家卫生研究院;
关键词
bioluminescence imaging; C-H activation; luciferase; luciferin; Sonogashira coupling; IN-VIVO; FIREFLY LUCIFERASE; GENE-EXPRESSION; REPORTER APPLICATIONS; CATALYZED SYNTHESIS; CLICK CHEMISTRY; MOUSE MODELS; LIVING MICE; STEM-CELLS; RED;
D O I
10.1002/chem.201503944
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Herein, the synthesis and characterization of an alkyne-modified luciferin is reported. This bioluminescent probe was accessed using C-H activation methodology and was found to be stable in solution and capable of light production with firefly luciferase. The luciferin analogue was also cell permeant and emitted more redshifted light than d-luciferin, the native luciferase substrate. Based on these features, the alkynyl luciferin will be useful for a variety of imaging applications.
引用
收藏
页码:3671 / 3675
页数:5
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