publication . Article . 2017

Luciferase-Specific Coelenterazine Analogues for Optical Contamination-Free Bioassays

Ryo Nishihara; Masahiro Abe; Shigeru Nishiyama; Daniel Citterio; Koji Suzuki; Sung Bae Kim;
Open Access English
  • Published: 01 Apr 2017 Journal: Scientific Reports, volume 7 (issn: 2045-2322, eissn: 2045-2322, Copyright policy)
  • Publisher: Nature Publishing Group UK
Abstract
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, whi...
Subjects
mesheuropmc: eye diseasesgenetic structuressense organs
free text keywords: Article
17 references, page 1 of 2

Hastings, JW. Chemistries and colors of bioluminescent reactions. Gene. 1996; 173: 5-11 [PubMed] [DOI]

2.Shimomura, O. Bioluminescence. (World Scientific Publishing Co. Pte. Ltd, 2006).

Loening, AM, Wu, AM, Gambhir, SS. Red-shifted Renilla reniformis luciferase variants for imaging in living subjects. Nat. Methods. 2007; 4: 641-643 [PubMed] [DOI]

Yuan, J, Peng, LL, Bouma, BE, Tearney, GJ. Quantitative FRET measurement by high-speed fluorescence excitation and emission spectrometer. Optics Express. 2010; 18: 18839-18851 [PubMed] [DOI]

Gammon, STM, Leevy, WM, Gross, S, Gokel, GW, Piwnica-Worms, D. Spectral unmixing of multicolored bioluminescence emitted from heterogeneous biological sources. Anal. Chem.. 2006; 78: 1520-1527 [OpenAIRE] [PubMed] [DOI]

Shcherbakova, DM, Verkhusha, VV. Near-infrared fluorescent proteins for multicolor in vivo imaging. Nat. Methods. 2013; 10: 751-754 [OpenAIRE] [PubMed] [DOI]

Jathoul, AP, Grounds, H, Anderson, JC, Pule, MA. A Dual-Color Far-Red to Near-Infrared Firefly Luciferin Analogue Designed for Multiparametric Bioluminescence Imaging. Angew. Chem., Int. Ed.. 2014; 53: 13059-13063 [OpenAIRE] [DOI]

Loening, AM, Dragulescu-Andrasi, A, Gambhir, SS. A red-shifted Renilla luciferase for transient reporter-gene expression. Nat. Methods. 2010; 7: 5-6 [OpenAIRE] [PubMed] [DOI]

Nishihara, R. Bioluminescent coelenterazine derivatives with imidazopyrazinone C-6 extended substitution. Chem. Commun.. 2014; 51: 391-394 [DOI]

Kim, SB, Sato, M, Tao, H. Molecular Tension-Indexed Bioluminescent Probe for Determining Protein-Protein Interactions. Bioconjugate Chem. 2009; 20: 2324-2330 [DOI]

Kim, SB, Nishihara, R, Citterio, D, Suzuki, K. Genetically Encoded Molecular Tension Probe for Tracing Protein - Protein Interactions in Mammalian Cells. Bioconjugate Chem.. 2016; 27: 354-362 [DOI]

Kim, SB, Torimura, M, Tao, H. Creation of artificial luciferases for bioassays. Bioconjugate Chem.. 2013; 24: 2067-2075 [DOI]

Woo, JC, Howell, MH, Von Arnim, AG. Structure-function studies on the active site of the coelenterazine-dependent luciferase from Renilla. Protein Sci.. 2008; 17: 725-735 [OpenAIRE] [PubMed] [DOI]

Gealageas, R. Bioluminescent properties of obelin and aequorin with novel coelenterazine analogues. Anal Bioanal Chem. 2014; 406: 2695-2707 [OpenAIRE] [PubMed] [DOI]

Inouye, S. C6-Deoxy coelenterazine analogues as an efficient substrate for glow luminescence reaction of nanoKAZ: The mutated catalytic 19 kDa component of Oplophorus luciferase. Biochem. Biophys. Res. Comm.. 2013; 437: 23-28 [PubMed] [DOI]

17 references, page 1 of 2
Related research
Abstract
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, whi...
Subjects
mesheuropmc: eye diseasesgenetic structuressense organs
free text keywords: Article
17 references, page 1 of 2

Hastings, JW. Chemistries and colors of bioluminescent reactions. Gene. 1996; 173: 5-11 [PubMed] [DOI]

2.Shimomura, O. Bioluminescence. (World Scientific Publishing Co. Pte. Ltd, 2006).

Loening, AM, Wu, AM, Gambhir, SS. Red-shifted Renilla reniformis luciferase variants for imaging in living subjects. Nat. Methods. 2007; 4: 641-643 [PubMed] [DOI]

Yuan, J, Peng, LL, Bouma, BE, Tearney, GJ. Quantitative FRET measurement by high-speed fluorescence excitation and emission spectrometer. Optics Express. 2010; 18: 18839-18851 [PubMed] [DOI]

Gammon, STM, Leevy, WM, Gross, S, Gokel, GW, Piwnica-Worms, D. Spectral unmixing of multicolored bioluminescence emitted from heterogeneous biological sources. Anal. Chem.. 2006; 78: 1520-1527 [OpenAIRE] [PubMed] [DOI]

Shcherbakova, DM, Verkhusha, VV. Near-infrared fluorescent proteins for multicolor in vivo imaging. Nat. Methods. 2013; 10: 751-754 [OpenAIRE] [PubMed] [DOI]

Jathoul, AP, Grounds, H, Anderson, JC, Pule, MA. A Dual-Color Far-Red to Near-Infrared Firefly Luciferin Analogue Designed for Multiparametric Bioluminescence Imaging. Angew. Chem., Int. Ed.. 2014; 53: 13059-13063 [OpenAIRE] [DOI]

Loening, AM, Dragulescu-Andrasi, A, Gambhir, SS. A red-shifted Renilla luciferase for transient reporter-gene expression. Nat. Methods. 2010; 7: 5-6 [OpenAIRE] [PubMed] [DOI]

Nishihara, R. Bioluminescent coelenterazine derivatives with imidazopyrazinone C-6 extended substitution. Chem. Commun.. 2014; 51: 391-394 [DOI]

Kim, SB, Sato, M, Tao, H. Molecular Tension-Indexed Bioluminescent Probe for Determining Protein-Protein Interactions. Bioconjugate Chem. 2009; 20: 2324-2330 [DOI]

Kim, SB, Nishihara, R, Citterio, D, Suzuki, K. Genetically Encoded Molecular Tension Probe for Tracing Protein - Protein Interactions in Mammalian Cells. Bioconjugate Chem.. 2016; 27: 354-362 [DOI]

Kim, SB, Torimura, M, Tao, H. Creation of artificial luciferases for bioassays. Bioconjugate Chem.. 2013; 24: 2067-2075 [DOI]

Woo, JC, Howell, MH, Von Arnim, AG. Structure-function studies on the active site of the coelenterazine-dependent luciferase from Renilla. Protein Sci.. 2008; 17: 725-735 [OpenAIRE] [PubMed] [DOI]

Gealageas, R. Bioluminescent properties of obelin and aequorin with novel coelenterazine analogues. Anal Bioanal Chem. 2014; 406: 2695-2707 [OpenAIRE] [PubMed] [DOI]

Inouye, S. C6-Deoxy coelenterazine analogues as an efficient substrate for glow luminescence reaction of nanoKAZ: The mutated catalytic 19 kDa component of Oplophorus luciferase. Biochem. Biophys. Res. Comm.. 2013; 437: 23-28 [PubMed] [DOI]

17 references, page 1 of 2
Related research
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publication . Article . 2017

Luciferase-Specific Coelenterazine Analogues for Optical Contamination-Free Bioassays

Ryo Nishihara; Masahiro Abe; Shigeru Nishiyama; Daniel Citterio; Koji Suzuki; Sung Bae Kim;