Ring-Fused Firefly Luciferins: Expanded Palette of Near-Infrared Emitting Bioluminescent Substrates

Ikeda, Yoshikazu; Nomoto, Takahiro; Hiruta, Yuki; Nishiyama, Nobuhiro; Citterio, Daniel

doi:10.1021/acs.analchem.9b04562

Cited by 36 publications

(27 citation statements)

References 39 publications

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“…Moreover, Ikeda et al synthesized NIRLuc2 based on AkaLumine, with a fused N-hetero ring (like CycLuc1). NIRLuc2 exhibits wavelength at 683 nm (Km = 1.05 μM in Table 2) [83]. However, unlike AkaLumine, NIRLuc2 is soluble in PBS (-) containing 5% DMSO.…”

Section: Luciferin Analogues That Produce Nir Lightmentioning

confidence: 99%

“…However, unlike AkaLumine, NIRLuc2 is soluble in PBS (-) containing 5% DMSO. The authors then performed BLI, using NIRLuc2 on a subcutaneous tumor mouse model after intraperitoneal administration, revealing that the luminescence intensity of NIRLuc2 is approximately seven-fold that of DLH2 and similar to that of AkaLumine [83].…”

Section: Luciferin Analogues That Produce Nir Lightmentioning

confidence: 99%

“…The solubilities of AkaLumine in PBS and ultra-pure water are very poor, and thus usability was limited for in vivo imaging [58,83]. Therefore, TokeOni [58] and seMpai [82], the hydrochloric acid salt of AkaLumine and N-atom containing AkaLumine derivative, respectively, were prepared with the aim of improving water solubility.…”

Section: Development Of Tokeoni (Akalumine-hcl)mentioning

confidence: 99%

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How to Select Firefly Luciferin Analogues for In Vivo Imaging

Saito-Moriya

Nakayama²,

Kamiya

et al. 2021

IJMS

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Bioluminescence reactions are widely applied in optical in vivo imaging in the life science and medical fields. Such reactions produce light upon the oxidation of a luciferin (substrate) catalyzed by a luciferase (enzyme), and this bioluminescence enables the quantification of tumor cells and gene expression in animal models. Many researchers have developed single-color or multicolor bioluminescence systems based on artificial luciferin analogues and/or luciferase mutants, for application in vivo bioluminescence imaging (BLI). In the current review, we focus on the characteristics of firefly BLI technology and discuss the development of luciferin analogues for high-resolution in vivo BLI. In addition, we discuss the novel luciferin analogues TokeOni and seMpai, which show potential as high-sensitivity in vivo BLI reagents.

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Section: Luciferin Analogues That Produce Nir Lightmentioning

confidence: 99%

Section: Luciferin Analogues That Produce Nir Lightmentioning

confidence: 99%

Section: Development Of Tokeoni (Akalumine-hcl)mentioning

confidence: 99%

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How to Select Firefly Luciferin Analogues for In Vivo Imaging

Saito-Moriya

Nakayama²,

Kamiya

et al. 2021

IJMS

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“…10,11 Scientists have harnessed this technology to track cells, 12,13 monitor cell-cell interactions, 14,15 and serve as a reporter gene. 16 Beyond D-luciferin, a variety of NIR-light emitting luciferins have been developed, 13,17,18 which can be adapted for ABS applications. The most common design is to chemically modify the luciferin with a trigger such that luciferase does not recognize the luciferin until it is unmasked.…”

Section: Bioluminescencementioning

confidence: 99%

New directions of activity-based sensing forin vivoNIR imaging

2021

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“…Альтернативным подходом к изменению цвета люминесценции является модификация D-люциферина. На сегодняшний день разработан широкий спектр аналогов D-люциферина, приводящих к спектральному сдвигу люминесценции люцифераз жесткокрылых, в том числе в ближний инфракрасный диапазон длин волн [23][24][25].…”

Section: люциферазы светлячковunclassified

Palette of Luciferases: Natural Biotools for New Applications in Biomedicine

2020

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Optoanalytical methods based on using genetically encoded bioluminescent enzymes,luciferases, allow one to obtain highly sensitive signals, are non-invasive, and require no external irradiation. Bioluminescence is based on the chemical reaction of oxidation of a low-molecular-weight substrate (luciferin) by atmospheric oxygen, which is catalyzed by an enzyme (luciferase). Relaxation of the luciferin oxidation product from its excited state is accompanied by a release of a quantum of light, which can be detected as an analytical signal.The ability to express luciferase genes in various heterological systems and high quantum yields of luminescence reactions have made these tools rather popular in biology and medicine. Amongseveral naturally available luciferases, a few have been found to be useful for practicalapplication. Luciferase size, the wavelength of its luminescence maximum, enzyme thermostability, optimal pH of the reaction, and the need for cofactors areparameters that may differ for luciferases from different groups of organisms, and this fact directly affects the choice of the application area for each enzyme. It is quite important to overview the whole range of currently available luciferases based ontheir biochemical properties before choosing one bioluminescent probe suitable for a specific application.

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Ring-Fused Firefly Luciferins: Expanded Palette of Near-Infrared Emitting Bioluminescent Substrates

Cited by 36 publications

References 39 publications

How to Select Firefly Luciferin Analogues for In Vivo Imaging

How to Select Firefly Luciferin Analogues for In Vivo Imaging

New directions of activity-based sensing forin vivoNIR imaging

Palette of Luciferases: Natural Biotools for New Applications in Biomedicine

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