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Imidazo[1,2-alpha]pyrazin-3(7H)-one derivatives

Blue-to-red emission shiftCoelenterazineIntact cell imagingNovel luciferase substrateStructural modification


The invention relates to imidazo[1,2-alpha]pyrazin-3(7H)-one derivatives comprising an hetero-atom and their use as chemiluminescent and/or bioluminescent reagents.

Technical features

The structural modification proposed can be incorporated (easy variation in the synthesis procedure) into known structures and selected to be the preferred compounds for both basic and industrial research. These findings endow coelenterazine with an improved red-shifted photoemission in bioluminescence maintaining lipofilicity, stability and enzymatic binding properties of the original molecules. However, the efficiency and sensibility to Ca2+ depends on the interactions of the particular compound in the enzymatic binding pocket and the environment involved. Indeed, the bivalent sulfur and selenium atoms are bioisosteres of the methylene group. The invention is a new photochemical entity obtained by modification of the methylene (-CH2-) in position C-8 of the imidazo[1,2-alpha]pyrazin-3(7H)-one nucleus, while the other substituents in position C-2, C-5 and C-6 are preserved.

Possible Applications

  • Basic and industrial research;
  • Custom structural modifications;
  • Novel luminescent reagent;
  • Novel luciferase substrate;
  • Luminescent ELISA kit.


  • Improved red-shifted emission;
  • Predictable chemical properties;
  • Intact cell analysis;
  • Whole animal analysis.