Computational investigation into the fluorescence of luciferin analogues

Abstract

Luciferin analogues that display bioluminescence at specific wavelengths can broaden the scope of imaging and biological assays, but the need to design and synthesize many new analogues can be time-consuming. Employing a collection of previously synthesized and characterized aminoluciferin analogues, we demonstrate that computational TD-DFT methods can accurately reproduce and further explain the experimentally measured fluorescence wavelengths. The best computational approach yields a correlation with experiment of r = 0.98, which we expect to guide and accelerate the further development of luciferin analogues.

Coumarin luciferins and mutant luciferases for robust multi-component bioluminescence imaging

“…This strong agreement between CouLuc-1 uorescence and bioluminescence is consistent with other pi-extended and amino luciferins. 28,38,59 Engineering complementary luciferases for CouLuc-1s…”

The Fluorescent Properties of pH‐Independent Cypridina Oxyluciferin Derivatives

“…[18][19][20][21] Reactive oxygen species have been found to be associated with the pathology of many diseases. [22][23][24][25] As we known, the most widely applied substrates which can reaction with molecular oxygen are firefly luciferin and coelenterazine, unfortunately, firefly luciferin requires the addition of magnesium ion and ATP to trigger light emission, [26][27][28][29][30][31][32][33] the process leading the light emission of coelenterazine requires the presence of calcium ion as cofactors, [34][35][36][37] which potentially leads to complex protocols in bioanalysis. For this reason, the co-factors independent cypridina bioluminescence has attracted considerable attention from biologists and chemists.…”

Coumarin Luciferins and Mutant Luciferases for Robust Multicomponent Bioluminescence Imaging

“…This strong correlation between CouLuc-1 fluorescence and bioluminescence is consistent with other piextended and amino luciferins. 28,39,58 CouLuc-1 fluorescence was also strongly influenced by solvent and pH (Figure S7, Table S2). In polar aprotic solvents, both amino CouLuc-1s were more blue-shifted (up to 170 nm) than in protic or aqueous environments.…”