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Brominated Luciferins Are Versatile Bioluminescent Probes
Author(s) -
Steinhardt Rachel C.,
Rathbun Colin M.,
Krull Brandon T.,
Yu Jason M.,
Yang Yuhang,
Nguyen Brian D.,
Kwon Jake,
McCutcheon David C.,
Jones Krysten A.,
Furche Filipp,
Prescher Jennifer A.
Publication year - 2017
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201600564
Subject(s) - bioluminescence , luciferase , luciferin , firefly protocol , luciferases , photoprotein , substrate (aquarium) , chemistry , mutant , enzyme , biochemistry , combinatorial chemistry , biophysics , biology , zoology , transfection , ecology , gene
We report a set of brominated luciferins for bioluminescence imaging. These regioisomeric scaffolds were accessed by using a common synthetic route. All analogues produced light with firefly luciferase, although varying levels of emission were observed. Differences in photon output were analyzed by computation and photophysical measurements. The brightest brominated luciferin was further evaluated in cell and animal models. At low doses, the analogue outperformed the native substrate in cells. The remaining luciferins, although weak emitters with firefly luciferase, were inherently capable of light production and thus potential substrates for orthogonal mutant enzymes.