Development of phenyl oligoene-type firefly luciferin analogues with extended π-electronic conjugation for near-infrared bioluminescence

2021 ◽  
Author(s):  
Genta Kamiya ◽  
Nobuo Kitada ◽  
Ryohei Saito-Moriya ◽  
Rika Obata ◽  
Satoshi Iwano ◽  
...  
Keyword(s):  
Near Infrared ◽  
Firefly Luciferin

scholarly journals Berichtigung: A Dual-Color Far-Red to Near-Infrared Firefly Luciferin Analogue Designed for Multiparametric Bioluminescence Imaging

2015 ◽  
Vol 127 (6) ◽  
pp. 1718-1718
Author(s):  
Amit P. Jathoul ◽  
Helen Grounds ◽  
James C. Anderson ◽  
Martin A. Pule
Keyword(s):  
Near Infrared ◽  
Bioluminescence Imaging ◽  
Dual Color ◽  
Firefly Luciferin

scholarly journals Development of near‐infrared firefly luciferin analogue reacted with wild‐type and mutant luciferases

Chirality ◽  
2020 ◽  
Vol 32 (7) ◽  
pp. 922-931 ◽  
Author(s):  
Nobuo Kitada ◽  
Ryohei Saito ◽  
Rika Obata ◽  
Satoshi Iwano ◽  
Kazuma Karube ◽  
...  
Keyword(s):  
Near Infrared ◽  
Wild Type ◽  
Firefly Luciferin

scholarly journals Corrigendum: A Dual-Color Far-Red to Near-Infrared Firefly Luciferin Analogue Designed for Multiparametric Bioluminescence Imaging

2015 ◽  
Vol 54 (6) ◽  
pp. 1698-1698 ◽  
Author(s):  
Amit P. Jathoul ◽  
Helen Grounds ◽  
James C. Anderson ◽  
Martin A. Pule
Keyword(s):  
Near Infrared ◽  
Bioluminescence Imaging ◽  
Dual Color ◽  
Firefly Luciferin

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

2014 ◽  
Vol 126 (48) ◽  
pp. 13275-13279 ◽  
Author(s):  
Amit P. Jathoul ◽  
Helen Grounds ◽  
James C. Anderson ◽  
Martin A. Pule
Keyword(s):  
Near Infrared ◽  
Bioluminescence Imaging ◽  
Dual Color ◽  
Firefly Luciferin

Toward bioluminescence in the near-infrared region: Tuning the emission wavelength of firefly luciferin analogues by allyl substitution

2018 ◽  
Vol 59 (12) ◽  
pp. 1087-1090 ◽  
Author(s):  
Nobuo Kitada ◽  
Tsuyoshi Saitoh ◽  
Yuma Ikeda ◽  
Satoshi Iwano ◽  
Rika Obata ◽  
...  
Keyword(s):  
Near Infrared ◽  
Infrared Region ◽  
Emission Wavelength ◽  
Firefly Luciferin ◽  
Near Infrared Region ◽  
Allyl Substitution

Synthesis and luminescence properties of biphenyl-type firefly luciferin analogs with a new, near-infrared light-emitting bioluminophore

Tetrahedron ◽  
2013 ◽  
Vol 69 (46) ◽  
pp. 9726-9734 ◽  
Author(s):  
Chihiro Miura ◽  
Masahiro Kiyama ◽  
Satoshi Iwano ◽  
Kazuto Ito ◽  
Rika Obata ◽  
...  
Keyword(s):  
Near Infrared ◽  
Infrared Light ◽  
Luminescence Properties ◽  
Near Infrared Light ◽  
Light Emitting ◽  
Firefly Luciferin

scholarly journals A Very Bright Far-Red Bioluminescence Emitting Combination Based on Engineered Railroad Worm Luciferase and 6′-Amino-Analogs for Bioimaging Purposes

2020 ◽  
Vol 22 (1) ◽  
pp. 303
Author(s):  
Vadim R. Viviani ◽  
Vanessa R. Bevilaqua ◽  
Daniel R. de Souza ◽  
Gabriel F. Pelentir ◽  
Michio Kakiuchi ◽  
...  
Keyword(s):  
Near Infrared ◽  
Catalytic Efficiency ◽  
Firefly Luciferase ◽  
Site Directed Mutagenesis ◽  
Directed Mutagenesis ◽  
Bacterial Cells ◽  
Mammalian Tissues ◽  
Absorption Of Light ◽  
Firefly Luciferin

Beetle luciferases produce bioluminescence (BL) colors ranging from green to red, having been extensively used for many bioanalytical purposes, including bioimaging of pathogen infections and metastasis proliferation in living animal models and cell culture. For bioimaging purposes in mammalian tissues, red bioluminescence is preferred, due to the lower self-absorption of light at longer wavelengths by hemoglobin, myoglobin and melanin. Red bioluminescence is naturally produced only by Phrixothrix hirtus railroad worm luciferase (PxRE), and by some engineered beetle luciferases. However, Far-Red (FR) and Near-Infrared (NIR) bioluminescence is best suited for bioimaging in mammalian tissues due to its higher penetrability. Although some FR and NIR emitting luciferin analogs have been already developed, they usually emit much lower bioluminescence activity when compared to the original luciferin-luciferases. Using site-directed mutagenesis of PxRE luciferase in combination with 6′-modified amino-luciferin analogs, we finally selected novel FR combinations displaying BL ranging from 636–655 nm. Among them, the combination of PxRE-R215K mutant with 6′-(1-pyrrolidinyl)luciferin proved to be the best combination, displaying the highest BL activity with a catalytic efficiency ~2.5 times higher than the combination with native firefly luciferin, producing the second most FR-shifted bioluminescence (650 nm), being several orders of magnitude brighter than commercial AkaLumine with firefly luciferase. Such combination also showed higher thermostability, slower BL decay time and better penetrability across bacterial cell membranes, resulting in ~3 times higher in vivo BL activity in bacterial cells than with firefly luciferin. Overall, this is the brightest FR emitting combination ever reported, and is very promising for bioimaging purposes in mammalian tissues.

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

2014 ◽  
Vol 53 (48) ◽  
pp. 13059-13063 ◽  
Author(s):  
Amit P. Jathoul ◽  
Helen Grounds ◽  
James C. Anderson ◽  
Martin A. Pule
Keyword(s):  
Near Infrared ◽  
Bioluminescence Imaging ◽  
Dual Color ◽  
Firefly Luciferin

Development of simple firefly luciferin analogs emitting blue, green, red, and near-infrared biological window light

Tetrahedron ◽  
2013 ◽  
Vol 69 (19) ◽  
pp. 3847-3856 ◽  
Author(s):  
Satoshi Iwano ◽  
Rika Obata ◽  
Chihiro Miura ◽  
Masahiro Kiyama ◽  
Kazutoshi Hama ◽  
...  
Keyword(s):  
Near Infrared ◽  
Firefly Luciferin

ChemInform Abstract: Synthesis and Luminescence Properties of Biphenyl-Type Firefly Luciferin Analogues with a New, Near-Infrared Light-Emitting Bioluminophore.

ChemInform ◽  
2014 ◽  
Vol 45 (11) ◽  
pp. no-no
Author(s):  
Chihiro Miura ◽  
Masahiro Kiyama ◽  
Satoshi Iwano ◽  
Kazuto Ito ◽  
Rika Obata ◽  
...  
Keyword(s):  
Near Infrared ◽  
Infrared Light ◽  
Luminescence Properties ◽  
Near Infrared Light ◽  
Light Emitting ◽  
Firefly Luciferin
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