Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging

Rachel C. Steinhardt; Jessica M. O'Neill; Colin M. Rathbun; David C. McCutcheon; Miranda A. Paley; Jennifer A. Prescher

doi:10.1002/chem.201503944

Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging

Rachel C. Steinhardt, Jessica M. O'Neill, Colin M. Rathbun, David C. McCutcheon, Miranda A. Paley, Jennifer A. Prescher

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	3671-3675
Number of pages	5
Journal	Chemistry - A European Journal
Volume	22
Issue number	11
DOIs	https://doi.org/10.1002/chem.201503944
State	Published - Mar 7 2016
Externally published	Yes

Keywords

C-H activation
Sonogashira coupling
bioluminescence imaging
luciferase
luciferin

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201503944

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title = "Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging",

abstract = "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.",

keywords = "C-H activation, Sonogashira coupling, bioluminescence imaging, luciferase, luciferin",

author = "Steinhardt, {Rachel C.} and O'Neill, {Jessica M.} and Rathbun, {Colin M.} and McCutcheon, {David C.} and Paley, {Miranda A.} and Prescher, {Jennifer A.}",

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T1 - Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging

AU - Steinhardt, Rachel C.

AU - O'Neill, Jessica M.

AU - Rathbun, Colin M.

AU - McCutcheon, David C.

AU - Paley, Miranda A.

AU - Prescher, Jennifer A.

PY - 2016/3/7

Y1 - 2016/3/7

N2 - 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.

AB - 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.

KW - C-H activation

KW - Sonogashira coupling

KW - bioluminescence imaging

KW - luciferase

KW - luciferin

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SN - 0947-6539

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EP - 3675

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 11

ER -

Design and Synthesis of an Alkynyl Luciferin Analogue for Bioluminescence Imaging

Abstract

Keywords

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