Bioluminescent coelenterazine derivatives with imidazopyrazinone C-6 extended substitution

Nishihara, Ryo; Suzuki, Hideyuki; Hoshino, Emi; Suganuma, Sakura; Sato, Moritoshi; Saitoh, Tohru; Nishiyama, Shigeru; Iwasawa, Naoko; Citterio, Daniel; Suzuki, Kôji

doi:10.1039/c4cc06886f

Cited by 42 publications

(39 citation statements)

References 31 publications

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“…Separately, we showed that RLuc8 and RLuc8.6-535 emit significant bioluminescence with C-6 position-modified CTZ analogues 9 . This precedent study inspired us to synthesize unique CTZ analogues modified at the C-2 and/or C-6 positions.…”

Section: Methodsmentioning

confidence: 82%

Luciferase-Specific Coelenterazine Analogues for Optical Contamination-Free Bioassays

Nishihara

Abe

Nishiyama

et al. 2017

Sci Rep

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Spectral overlaps among the multiple optical readouts commonly cause optical contamination in fluorescence and bioluminescence. To tackle this issue, we created five-different lineages of coelenterazine (CTZ) analogues designed to selectively illuminate a specific luciferase with unique luciferase selectivity. In the attempt, we found that CTZ analogues with ethynyl or styryl groups display dramatically biased bioluminescence to specific luciferases and pHs by modifying the functional groups at the C-2 and C-6 positions of the imidazopyradinone backbone of CTZ. The optical contamination-free feature was exemplified with the luciferase-specific CTZ analogues, which illuminated anti-estrogenic and rapamycin activities in a mixture of optical probes. This unique bioluminescence platform has great potential for specific and high throughput imaging of multiple optical readouts in bioassays without optical contamination.

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Section: Methodsmentioning

confidence: 82%

Luciferase-Specific Coelenterazine Analogues for Optical Contamination-Free Bioassays

Nishihara

Abe

Nishiyama

et al. 2017

Sci Rep

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“…24 Live-Cell Image of COS-7 Cells Carrying TP2.4. A bioluminescence imaging was conducted with living COS-7 cells carrying TP2.4 in a 6-channel microslide (μ-slide VI 0.4 , ibidi) ( Figure 5).…”

Section: Bioconjugate Chemistrymentioning

confidence: 99%

Genetically Encoded Molecular Tension Probe for Tracing Protein–Protein Interactions in Mammalian Cells

et al. 2015

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Optical imaging of protein-protein interactions (PPIs) facilitates comprehensive elucidation of intracellular molecular events. We demonstrate an optical measure for visualizing molecular tension triggered by any PPI in mammalian cells. Twenty-three kinds of candidate designs were fabricated, in which a full-length artificial luciferase (ALuc) was sandwiched between two model proteins of interest, e.g., FKBP and FRB. One of the designs greatly enhanced the bioluminescence in response to varying concentrations of rapamycin. It is confirmed with negative controls that the elevated bioluminescence is solely motivated from the molecular tension. The probe design was further modified toward eliminating the C-terminal end of ALuc and was found to improve signal-to-background ratios, named "a combinational probe". The utilities were elucidated with detailed substrate selectivity, bioluminescence imaging of live cells, and different PPI models. This study expands capabilities of luciferases as a tool for analyses of molecular dynamics and cell signaling in living subjects.

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“…[32,40*] Ring-closing metathesis and carbene insertions have also been used to produce a series of conformationally restricted and pi-extended coelenterazines. [41–43] Many these probes exhibited red-shifted emission or other desirable photophysical properties.…”

Section: Engineering Orthogonal Luciferase-luciferin Pairsmentioning

confidence: 99%

Advances in bioluminescence imaging: new probes from old recipes

Yao

Zhang

Prescher

2018

Current Opinion in Chemical Biology

102

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Bioluminescent probes are powerful tools for visualizing biology in live tissues and whole animals. Recent years have seen a surge in the number of new luciferases, luciferins, and related tools available for bioluminescence imaging. Many were crafted using classic methods of optical probe design and engineering. Here we highlight recent advances in bioluminescent tool discovery and development, along with applications of the probes in cells, tissues, and organisms. Collectively, these tools are improving in vivo imaging capabilities and bolstering new research directions.

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Bioluminescent coelenterazine derivatives with imidazopyrazinone C-6 extended substitution

Cited by 42 publications

References 31 publications

Luciferase-Specific Coelenterazine Analogues for Optical Contamination-Free Bioassays

Luciferase-Specific Coelenterazine Analogues for Optical Contamination-Free Bioassays

Genetically Encoded Molecular Tension Probe for Tracing Protein–Protein Interactions in Mammalian Cells

Advances in bioluminescence imaging: new probes from old recipes

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