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

Bioconjugate Chemistry
Ryo NishiharaSung Bae Kim

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 molecula...Continue Reading

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Citations

Dec 7, 2018·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Sung Bae KimKoji Suzuki
Apr 9, 2019·Chembiochem : a European Journal of Chemical Biology·Masahiro AbeKoji Suzuki
Nov 26, 2019·Chemistry : a European Journal·Eloi P CoutantYves L Janin
Mar 3, 2020·Frontiers in Bioengineering and Biotechnology·Duong LeJyothi U Menon
Feb 21, 2019·Annual Review of Analytical Chemistry·Hsien-Wei Yeh, Hui-Wang Ai
Oct 24, 2020·Photochemistry and Photobiology·Germano GiulianiFabrizia Cesca
Jan 28, 2021·Scientific Reports·Shota TamakiShojiro Maki
Sep 24, 2020·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Sung-Bae Kim, Ramasamy Paulmurugan
Mar 7, 2021·International Journal of Molecular Sciences·Ryohei Saito-MoriyaHiroshi Aoyama
Nov 26, 2020·Bioconjugate Chemistry·Ryo NishiharaRyoji Kurita

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