Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging

被引:29
|
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
相关论文
共 50 条
  • [1] Expedient synthesis of luciferin analogs for orthogonal bioluminescence imaging
    McCutcheon, Dave C.
    Paley, Miranda A.
    Steinhardt, Rachel C.
    Prescher, Jennifer A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [2] Multicomponent Bioluminescence Imaging with a π-Extended Luciferin
    Yao, Zi
    Zhang, Brendan S.
    Steinhardt, Rachel C.
    Mills, Jeremy H.
    Prescher, Jennifer A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (33) : 14080 - 14089
  • [3] Bioluminescence imaging in mice with synthetic luciferin analogues
    Ji, Xincai
    Adams, Spencer T., Jr.
    Miller, Stephen C.
    CHEMICAL TOOLS FOR IMAGING, MANIPULATING, AND TRACKING BIOLOGICAL SYSTEMS: DIVERSE METHODS BASED ON OPTICAL IMAGING AND FLUORESCENCE, 2020, 640 : 165 - 183
  • [4] Orthogonal Luciferase-Luciferin Pairs for Bioluminescence Imaging
    Jones, Krysten A.
    Porterfield, William B.
    Rathbun, Colin M.
    McCutcheon, David C.
    Paley, Miranda A.
    Prescher, Jennifer A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (06) : 2351 - 2358
  • [5] A luciferin analogue generating near-infrared bioluminescence achieves highly sensitive deep-tissue imaging
    Kuchimaru, Takahiro
    Iwano, Satoshi
    Kiyama, Masahiro
    Mitsumata, Shun
    Kadonosono, Tetsuya
    Niwa, Haruki
    Maki, Shojiro
    Kizaka-Kondoh, Shinae
    NATURE COMMUNICATIONS, 2016, 7
  • [6] Constructing firefly luciferin bioluminescence probes for in vivo imaging
    Yang, Xingye
    Qin, Xiaojun
    Ji, Huimin
    Du, Lupei
    Li, Minyong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (07) : 1360 - 1372
  • [7] A luciferin analogue generating near-infrared bioluminescence achieves highly sensitive deep-tissue imaging
    Takahiro Kuchimaru
    Satoshi Iwano
    Masahiro Kiyama
    Shun Mitsumata
    Tetsuya Kadonosono
    Haruki Niwa
    Shojiro Maki
    Shinae Kizaka-Kondoh
    Nature Communications, 7
  • [8] A synthetic luciferin improves bioluminescence imaging in live mice
    Evans, Melanie S.
    Chaurette, Joanna P.
    Adams, Spencer T., Jr.
    Reddy, Gadarla R.
    Paley, Miranda A.
    Aronin, Neil
    Prescher, Jennifer A.
    Miller, Stephen C.
    NATURE METHODS, 2014, 11 (04) : 393 - +
  • [9] A synthetic luciferin improves bioluminescence imaging in live mice
    Evans M.S.
    Chaurette J.P.
    Adams Jr. S.T.
    Reddy G.R.
    Paley M.A.
    Aronin N.
    Prescher J.A.
    Miller S.C.
    Nature Methods, 2014, 11 (4) : 393 - 395
  • [10] Confocal Bioluminescence Imaging for Living Tissues with a Caged Substrate of Luciferin
    Hattori, Mitsuru
    Kawamura, Genki
    Kojima, Ryosuke
    Kamiya, Mako
    Urano, Yasuteru
    Ozawa, Takeaki
    ANALYTICAL CHEMISTRY, 2016, 88 (12) : 6231 - 6238