Beyond D-luciferin: expanding the scope of bioluminescence imaging in vivo

Adams, Spencer T.; Miller, Stephen J.

doi:10.1016/j.cbpa.2014.07.003

Cited by 123 publications

(96 citation statements)

References 61 publications

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“…1 Synthetic analogues containing amine or alkylamine donors are also luminogenic and can offer advantages for in vivo imaging. 2,3 However, to date most firefly luciferin substrates and “caged” sensors have been synthesized from 6-amino or 6-hydroxy benzothiazoles, placing inherent restrictions on the nature of the electron-donating 6′-functionality.…”

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confidence: 99%

Rapid Access to a Broad Range of 6′-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors

et al. 2017

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Light-emitting firefly luciferin analogues contain electron-donating groups in the 6′-position, but the scope of known 6′-substitution remains narrow. A two-step route to a broad range of 6′-substituted luciferin analogues was developed to fill this void and enable more extensive study of the 6′-functionality. This chemistry allowed direct access to “caged” amide and bright azetidine analogues, but also revealed thioether inhibitors and unexpectedly luminogenic aryl amine derivatives.

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confidence: 99%

Rapid Access to a Broad Range of 6′-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors

et al. 2017

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“…The most red-shifted luciferin analogues to date[16] are based upon amino derivatives (Figure 1 b), for example cyclic aminoluciferin ( 3 a : λ max =599 nm; 3 b : λ max =607 nm),[17] seleno- d -aminoluciferin ( 4 : λ max =600 nm),[18] and a rationally designed 4-(dimethylamino)phenyl derivative conjugated to a thiazoline group ( 5 : λ max =675 nm). [19] In particular cyclic aminoluciferin derivative 3 a has been shown to give improved bioluminescence imaging compared to luciferin (LH 2 ; 1 ) at dilute concentrations where the intracellular concentration of the luciferin or analogue is limiting.…”

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confidence: 99%

A Dual‐Color Far‐Red to Near‐Infrared Firefly Luciferin Analogue Designed for Multiparametric Bioluminescence Imaging

et al. 2014

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Red-shifted bioluminescent emitters allow improved in vivo tissue penetration and signal quantification, and have led to the development of beetle luciferin analogues that elicit red-shifted bioluminescence with firefly luciferase (Fluc). However, unlike natural luciferin, none have been shown to emit different colors with different luciferases. We have synthesized and tested the first dual-color, far-red to near-infrared (nIR) emitting analogue of beetle luciferin, which, akin to natural luciferin, exhibits pH dependent fluorescence spectra and emits bioluminescence of different colors with different engineered Fluc enzymes. Our analogue produces different far-red to nIR emission maxima up to λmax=706 nm with different Fluc mutants. This emission is the most red-shifted bioluminescence reported without using a resonance energy transfer acceptor. This improvement should allow tissues to be more effectively probed using multiparametric deep-tissue bioluminescence imaging.

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“…Another way to enhance the performance of bioluminescent reporter systems is by modification of the luciferase substrates, which has yielded substrates showing increased brightness, a reduced sensitivity for autooxidation, different spectral properties, or enhanced bioavailability (Jiang, Du, & Li, 2016). Also, a range of "caged" substrates have been developed that can be used to report on the presence of specific enzymes such as β-galactosidase, glycosidase, and caspases (Adams & Miller, 2014;Jiang et al, 2016). Most BRET-sensors developed to date are based on Renilla luciferase or its improved variants such as the brighter RLuc8.…”

Section: Luciferases For Integration In Bret-sensorsmentioning

confidence: 99%