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Azide- And Dye-Conjugated Coelenterazine Analogues for a Multiplex Molecular Imaging Platform

Azide- And Dye-Conjugated Coelenterazine Analogues for a Multiplex Molecular Imaging Platform

Ryo Nishihara, Emi Hoshino, Yoshiki Kakudate, Satoshi Kishigami, Naoko Iwasawa, Shin-Ichi Sasaki, Takahiro Nakajima, Moritoshi Sato, Shigeru Nishiyama, Daniel Citterio, Koji Suzuki, Sung Bae Kim

Bioconjug Chem. 2018 Jun 20;29(6):1922-1931.

PMID: 29767512

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP55779481	Coelenterazine, native		55779-48-1	Price

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