Analogs of Firefly Luciferin. III<sup>1</sup>

White, Emil H.; Wörther, Helmut; Field, George F.; McElroy, W. D.

doi:10.1021/jo01343a039

Cited by 49 publications

(18 citation statements)

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“…When we calculated oscillator strengths for a variety of known luciferins, we found that the values correlated with reported bioluminescent outputs (Table ). For example, d ‐luciferin analogues lacking electron‐donating groups at the 6′ position (and thus poor emitters) were predicted to have low oscillator strengths . By contrast, analogues with 6′‐amino substituents—and known light emitters—were predicted to have oscillator strengths on par with the native substrate.…”

Section: Figurementioning

confidence: 99%

Brominated Luciferins Are Versatile Bioluminescent Probes

et al. 2016

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We report a set of brominated luciferins for bioluminescence imaging. These regioisomeric scaffolds were accessed using a common synthetic route. All analogs produced light with firefly luciferase, although varying levels of emission were observed. Differences in photon output were analyzed via computation and photophysical measurements. The “brightest” brominated luciferin was further evaluated in cell and animal models. At low doses, the analog outperformed the native substrate in cells. The remaining luciferins, while weak emitters with firefly luciferase, were inherently capable of light production and thus potential substrates for orthogonal mutant enzymes.

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Section: Figurementioning

confidence: 99%

Brominated Luciferins Are Versatile Bioluminescent Probes

et al. 2016

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“…Miller and others have shown that luciferin variants containing a nitrogen atom in place of the exocyclic oxygen are efficiently processed by Fluc and emit red light. 9–11 In related work, Branchini and others have replaced the entire benzothiazole core of d -luciferin with quinoline, naphthalene, and coumarin units. These analogs emitted different colors of light with Fluc, but robust emission was only observed at elevated pH values.…”

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confidence: 99%

Expedient Synthesis of Electronically Modified Luciferins for Bioluminescence Imaging

et al. 2012

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Bioluminescence imaging with luciferase enzymes requires access to light-emitting, small molecule luciferins. Here, we describe a rapid method to synthesize d-luciferin, the substrate for firefly luciferase (Fluc), along with a novel set of electronically modified analogs. Our procedure utilizes a relatively rare, but synthetically useful dithiazolium reagent to generate heteroaromatic scaffolds in a divergent fashion. Two of the luciferin analogs produced with this approach emit light with Fluc in vitro and in live cells. Collectively, our work increases the number of substrates that can be used for bioluminescence imaging and provides a general strategy for synthesizing new collections of luciferins.

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“…Although many analogs of luciferin have been synthesized (30)(31)(32), only the 6-amino and the 4-hydroxy compounds are substrates for the luciferase-catalyzed reaction. Both these compounds produce red light, again indicating enolization does not occur prior to light emission.…”

Section: Luciferin and Analogsmentioning

confidence: 99%