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.
authors.affiliation: Department of Chemistry, University of California, Irvine, Irvine, CA, USA.
authors.forename: Rachel C
authors.initials: RC
authors.lastname: Steinhardt
authors.affiliation: Department of Chemistry, University of California, Irvine, Irvine, CA, USA.
authors.forename: Jessica M
authors.initials: JM
authors.lastname: O'Neill
authors.affiliation: Department of Chemistry, University of California, Irvine, Irvine, CA, USA.
authors.forename: Colin M
authors.initials: CM
authors.lastname: Rathbun
authors.affiliation: Department of Chemistry, University of California, Irvine, Irvine, CA, USA.
authors.forename: David C
authors.initials: DC
authors.lastname: McCutcheon
authors.affiliation: Department of Chemistry, University of California, Irvine, Irvine, CA, USA.
authors.forename: Miranda A
authors.initials: MA
authors.lastname: Paley
authors.affiliation: Department of Chemistry, University of California, Irvine, Irvine, CA, USA. jpresche@uci.edu.|Department of Molecular Biology & Biochemistry, University of California, Irvine, Irvine, CA, USA. jpresche@uci.edu.|Department of Pharmaceutical Sciences, University of California, Irvine, Irvine, CA, USA. jpresche@uci.edu.
authors.forename: Jennifer A
authors.identifier: http://orcid.org/0000-0002-9250-4702
authors.initials: JA
authors.lastname: Prescher
mesh_terms: D052160:Benzothiazoles / Q000737:chemistry*; D003952:Diagnostic Imaging; D049454:Firefly Luciferin / Q000737:chemistry*; D007700:Kinetics; D008156:Luciferases / Q000737:chemistry*; D049409:Luciferases, Firefly / Q000737:chemistry* / Q000378:metabolism; D008163:Luminescent Measurements
chemical_list: D052160:Benzothiazoles; C532924:D-luciferin; D049454:Firefly Luciferin; D008156:Luciferases; D049409:Luciferases, Firefly
keywords: C−H activation; Sonogashira coupling; bioluminescence imaging; luciferase; luciferin