Imidazopyrazine derivatives, process for preparation thereof, and their uses as luciferins
The present invention is in the field of bioluminescence in biology and/or medicine. In particular, the invention provides imidazopyrazine derivatives, processes for preparation thereof, and their uses as luciferins.
1 . A composition comprising:
(a) a compound of formula:
wherein:
R 1 represents H;
R 2 represents a phenyl, optionally, comprising two substituents, each independently selected from —CH 3 , —F, —Cl, —OH, and —NH 2 ;
R 3 represents a benzyl comprising one or two substituents, each independently selected from —F and —CF 3 ;
R 4 represents H;
Z represents a furanyl, optionally, comprising one substituent selected from —CH 3 and —F;
R 5 represents —C(═O)R a or —C(═O)OR a ;
R a represents H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 6 -C 10 aryl, or aralkyl; or
(b) a corresponding imidazopyrazinone compound of the above that does not comprise an R 5 moiety.
2 . The composition of claim 1 , wherein:
the R 2 comprises two substituents, each independently selected from —F and —NH 2 ;
the R 3 comprises one substituent of —F; and
the Z represents the furanyl.
3 . The composition of claim 1 , wherein the compound is selected from:
4 . A method of detecting and/or measuring an enzymatic activity of luciferase in a sample, the method comprising contacting the compound of the composition of claim 1 with the sample, wherein the contacting comprises contacting the compound comprising R 5 with the sample after removal of the R 5 or contacting the compound that does not comprise R 5 with the sample, and detecting the luminescence signal, wherein the luminescence signal correlates to the presence of enzymatic activity of the luciferase in the sample.
5 . The method of claim 4 , wherein the luciferase is derived from an Oplophorus luciferase.
6 . The method of claim 5 , wherein the Oplophorus luciferase is a nanoKAZ luciferase.