title: Synthetic Routes to Coelenterazine and Other Imidazo[1,2-a]pyrazin-3-one Luciferins: Essential Tools for Bioluminescence-Based Investigations.
abstract: In the last few decades, bioluminescent systems based on the expression of a luciferase and the addition of a luciferin to monitor the emission of light have become very important tools for biological investigations. A growing proportion of these systems use coelenterazine or analogues of imidazo[1,2-a]pyrazine luciferins along with photoproteins or luciferases from sea creatures such as Aequorea, Renilla, Gaussia or Oplophorus. Central to the success of these tools are the synthetic pathways developed not only to prepare the naturally occurring luciferins, but also to design altered compounds that exhibit improved bioluminescence. Current work is indeed focused on the design of systems exhibiting extended luminescence ("glow" systems) or redshifted wavelengths, as well as constructions better adapted to conditions in cells or in vivo. This review describes the synthetic pathways used to prepare imidazo[1,2-a]pyrazine luciferins along with the research efforts aimed at preparing analogues even better suited to the design of assays.
authors.affiliation: Unité Mixte de Recherche 3523, CNRS, 28 rue du Dr. Roux, 75724 Paris Cedex 15 (France).|Unité de Chimie et Biocatalyse, Département de Biologie Structurale et Chimie, Institut Pasteur, 28 rue du Dr. Roux, 75724 Paris Cedex 15 (France).
authors.forename: Eloi P
authors.initials: EP
authors.lastname: Coutant
authors.affiliation: Unité Mixte de Recherche 3523, CNRS, 28 rue du Dr. Roux, 75724 Paris Cedex 15 (France). yves.janin@pasteur.fr.|Unité de Chimie et Biocatalyse, Département de Biologie Structurale et Chimie, Institut Pasteur, 28 rue du Dr. Roux, 75724 Paris Cedex 15 (France). yves.janin@pasteur.fr.
authors.forename: Yves L
authors.initials: YL
authors.lastname: Janin
mesh_terms: D049454:Firefly Luciferin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D008156:Luciferases / Q000378:metabolism*; D049449:Luminescence; D008163:Luminescent Measurements; D008164:Luminescent Proteins / Q000737:chemistry; D011719:Pyrazines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D007093:Imidazoles; D008164:Luminescent Proteins; D011719:Pyrazines; C017144:coelenterazine; D049454:Firefly Luciferin; D008156:Luciferases
keywords: heterocycles; luciferins; luminescence; natural products; photoproteins