Brominated Luciferins Are Versatile Bioluminescent Probes

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.

doi:10.1002/cbic.201600564

Title: Brominated Luciferins Are Versatile Bioluminescent Probes

Journal Article · Thu Dec 08 00:00:00 EST 2016 · ChemBioChem: a European journal of chemical biology

DOI:https://doi.org/10.1002/cbic.201600564· OSTI ID:1423816

Steinhardt, Rachel C. ^[1]; Rathbun, Colin M. ^[1]; Krull, Brandon T. ^[1]; Yu, Jason M. ^[1]; Yang, Yuhang ^[1]; Nguyen, Brian D. ^[1]; Kwon, Jake ^[1]; McCutcheon, David C. ^[1]; Jones, Krysten A. ^[2]; Furche, Filipp ^[1];

^[3]

Univ. of California, Irvine, CA (United States). Dept. of Chemistry
Univ. of California, Irvine, CA (United States). Dept. of Molecular Biology and Biochemistry
Univ. of California, Irvine, CA (United States). Dept. of Chemistry; Univ. of California, Irvine, CA (United States). Dept. of Pharmaceutical Sciences

Here, 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.

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Research Organization:: Univ. of California, Irvine, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Institutes of Health (NIH)

Grant/Contract Number:: SC0008694

OSTI ID:: 1423816

Journal Information:: ChemBioChem: a European journal of chemical biology, Vol. 18, Issue 1; ISSN 1439-4227

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 32 works

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Pyridone Luciferins and Mutant Luciferases for Bioluminescence Imaging Zhang, Brendan S.; Jones, Krysten A.; McCutcheon, David C. ChemBioChem, Vol. 19, Issue 5 https://doi.org/10.1002/cbic.201700542	journal	January 2018
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