Azide- and Dye-Conjugated Coelenterazine Analogues
for a Multiplex Molecular Imaging Platform
Version 2 2018-05-16, 13:58
Version 1 2018-05-16, 13:55
Posted on 2018-05-16 - 13:58
Native
coelenterazine (nCTZ) is a common substrate to most marine
luciferases and photoproteins. In this study, nine novel dye- and
azide-conjugated CTZ analogues were synthesized by conjugating a series
of fluorescent dyes or an azide group to the C-2 or C-6 position of
the nCTZ backbone to obtain bulkiness-driven substrate specificity
and potential chemiluminescence/bioluminescence resonance energy transfer
(C/BRET). The investigation on the optical properties revealed that
azide-conjugated CTZs emit greatly biased bioluminescence to ALucs
and ca. 130 nm blue-shifted bioluminescence with RLuc8.6 in living
animal cells or lysates. The corresponding kinetic study explains
that azide-conjugated CTZ exerts higher catalytic efficiency than
nCTZ. Nile red-conjugated CTZ completely showed red-shifted CRET spectra
and characteristic BRET spectra with artificial luciferase 16 (ALuc16).
No or less spectral overlap occurs among [Furimazine–NanoLuc],
[6-N3-CTZ–ALuc26], [6-pi-OH-CTZ–RLuc8.6],
and [6-N3-CTZ–RLuc8.6] pairs, because of the substrate-driven
luciferase specificity and color shifts, providing a crosstalk-free
multiplex bioassay platform. The unique bioluminescence system appends
a new toolbox to bioassays and multiplex molecular imaging platforms.
This study is the first example that systematically synthesized fluorescent
dye-conjugated CTZs and applied them for a bioluminescence assay system.
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Nishihara, Ryo; Hoshino, Emi; Kakudate, Yoshiki; Kishigami, Satoshi; Iwasawa, Naoko; Sasaki, Shin-ichi; et al. (2018). Azide- and Dye-Conjugated Coelenterazine Analogues
for a Multiplex Molecular Imaging Platform. ACS Publications. Collection. https://doi.org/10.1021/acs.bioconjchem.8b00188
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AUTHORS (12)
RN
Ryo Nishihara
EH
Emi Hoshino
YK
Yoshiki Kakudate
SK
Satoshi Kishigami
NI
Naoko Iwasawa
SS
Shin-ichi Sasaki
TN
Takahiro Nakajima
MS
Moritoshi Sato
SN
Shigeru Nishiyama
DC
Daniel Citterio
KS
Koji Suzuki
SK
Sung Bae Kim
KEYWORDS
bioluminescence system appendsRLuc 8.6Multiplex Molecular Imaging Platform Native coelenterazineazide-conjugated CTZsbioluminescence assay systemDye-Conjugated Coelenterazine AnaloguesC -2imaging platformsanimal cellssubstrate-driven luciferase specificitybulkiness-driven substrate specificityNile red-conjugated CTZC -6 positionazide-conjugated CTZ analoguesdye-conjugated CTZsluciferase 16marine luciferasesBRET spectraazide groupnovel dyeazide-conjugated CTZcolor shiftscrosstalk-free multiplex bioassay platform130 nm blue-shifted bioluminescencenCTZ backbonered-shifted CRET spectra