Two series of novel coelenterazine analogues (alkynes and triazoles) with imidazopyrazinone C-6 extended substitution have been designed and synthesized successfully for the extension of bioluminescent substrates. After extensive evaluation, some compounds display excellent bioluminescence properties compared with DeepBlueC in cellulo, thus becoming potential molecules for bioluminescence techniques.

No abstract

The first dual bioluminescent and chemiluminescent sensor for detecting highly toxic thiophenols has been developed. Such a probe was designed by using a coelenterazine analogue as the luminophore and dinitrophenyl ether as the recognition moiety. It should be noted that this probe displayed good sensitivity and selectivity toward thiophenols, and has been effectively applied for the quantitative detection of thiophenols in aqueous media and complex biological samples.

The prodrug or caged-luciferin strategy affords an excellent platform for persistent bioluminescence imaging. In the current work, we designed and synthesized ten novel pro-substrates for Renilla luciferase by introducing ester protecting groups of different sizes into the carbonyl group of the free luciferin 1. Taking advantage of intracellular esterases, lipases, and nucleophilic substances, the ester protecting groups were hydrolyzed, resulting in the release of a free luciferin and a bioluminescence signal turn-on. Among the tested pro-substrates, the butyryloxymethyl luciferin 7 exhibited low cytotoxicity and a prolonged luminescence signal both in cellulo and in vivo. Therefore, the butyryloxymethyl luciferin 7 can act as a promising substrate for noninvasive extended imaging in diagnostic and therapeutic fields.

A set of high and efficient caged luciferin derivatives exhibited low cytotoxicity and prolonged bioluminescence in vitro and in vivo.