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US 2026/0224755 A1Published application
Imidazopyrazine derivatives, process for preparation thereof, and their uses as luciferins
AssigneesInstitut Pasteur, Centre National De La Recherche Scientifique
InventorsYves-Louis JANIN, Eloi Paul COUTANT, Vincent HERVIN, Glwadys GAGNOT, Yves JACOB, Sophie GOYARD, Thierry ROSE
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Abstract
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.
Claims21
A method of in vivo imaging for detecting cells that express luciferase in an animal, the method comprising:
- (a) preparing a solution of a substrate in a buffer, the substrate comprising:
- (i) a compound of formula:
- wherein:
- R1 represents H;
- R2 represents a phenyl, optionally, comprising up to two substituents, each independently selected from C1-C6 alkyl, C3-C7 cycloalkyl, C6-C10 aryl, C5-C10 heteroaryl, halogen, —CF3, —CN, —ORi, —OSO3H, —NRiRii, guanidinyl, and —C(═O)ORa;
- R3 represents a benzyl substituted by one or two substituents, each independently selected from —F and CF3;
- R4 represents H;
- Z represents a furanyl, optionally, comprising up to two substituents, each independently selected from C1-C6 alkyl, C3-C7 cycloalkyl, C6-C10 aryl, C5-C10 heteroaryl, halogen, —CF3, —CN, —ORi, —OSO3H, —NRiRii, guanidinyl, and —C(═O)ORa;
- R5 represents C(═O)Ra or C(═O)ORa;
- Ri and Rii each independently represent H, C1-C6 alkyl, C3-C10 cycloalkyl, aralkyl, or together with the nitrogen atom to which they are attached to form a C4-C7 heterocycloalkyl;
- and
- Ra represents H, C1-C6 alkyl, C3-C7 cycloalkyl, C6-C10 aryl, or aralkyl;
- or
- (ii) a corresponding imidazopyrazinone compound of the above that does not comprise an R5 moiety,
- wherein the solution of the substrate is prepared from the compound of the formula after removal of the R5 or the compound of the formula that does not comprise R5;
- (b) administering the solution of the substrate to the animal, wherein the substrate upon contact with the luciferase generates bioluminescence;
- and
- (c) detecting bioluminescence in the animal, wherein the bioluminescence indicates presence of the cells that express luciferase in the animal.
15 more elements
A method of detecting expression of a protein that is fused to a luciferase in a sample, the method comprising:
- (a) preparing a solution of a substrate in a buffer, the substrate comprising:
- (i) a compound of formula:
- wherein:
- R1 represents H;
- R2 represents a phenyl, optionally, comprising up to two substituents, each independently selected from —CH3, —F, —Cl, —O(C1-C6 alkyl), —OH, —NH2, —NH(C1-C6 alkyl), and —N(C1-C6 alkyl)2;
- R3 represents a benzyl substituted by one or two substituents, each independently selected from —F and CF3;
- R4 represents H;
- Z represents a furanyl, optionally, comprising up to two substituents, each independently selected from —CH3, —F, and —CF3;
- and
- R5 represents C(═O)Ra or C(═O)ORa;
- or
- (ii) a corresponding imidazopyrazinone compound that does not comprise an R5 moiety,
- wherein the solution of the substrate is prepared from the compound of the formula after removal of the R5 or the compound of the formula that does not comprise R5;
- (b) contacting the solution of the substrate with the sample, wherein the substrate, upon interaction with the luciferase in the sample, generates luminescence;
- and
- (c) detecting the luminescence, wherein the luminescence indicates presence of the protein in the sample.
13 more elements
A method of performing cell infectibility diagnosis for a virus carrying a luciferase in a cell sample, the method comprising:
- (a) preparing a solution of a substrate in a buffer, the substrate comprising:
- (i) a compound of formula:
- wherein:
- R1 represents H;
- R2 represents a phenyl, optionally, comprising up to two substituents, each independently selected from —CH3, —F, —Cl, —O(C1-C6 alkyl), —OH, —NH2, —NH(C1-C6 alkyl), and —N(C1-C6 alkyl)2;
- R3 represents a benzyl substituted by one or two substituents, each independently selected from —F and CF3;
- R4 represents H;
- Z represents a furanyl, optionally, comprising up to two substituents, each independently selected from —CH3, —F, and —CF3;
- and
- R5 represents C(═O)Ra or C(═O)ORa;
- or
- (ii) a corresponding imidazopyrazinone compound that does not comprise an R5 moiety,
- wherein the preparing comprises preparing the solution of the substrate comprising the compound of the formula after removal of the R5 or preparing the solution of the substrate comprising the compound of the formula that does not comprise R5;
- (b) contacting the solution of the substrate with cell sample, wherein the substrate, upon interaction with the luciferase, generates luminescence;
- and
- (c) detecting the luminescence, wherein the luminescence indicates presence of the virus in and out of the cells.
13 more elements
Dependencies are inferred from the claim text.