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A new promising approach to the development of red-shifted coelenterazine analogues was described. In order to alter the photochemical properties of native coelenterazine, we have designed and synthesized analogues bearing a new electron-rich structure. The spectroscopic results obtained, in the presence of the target enzyme (Renilla Luciferase), show a bathochromic emission shift of the entire class of new derivatives. Among them, the 2-benzyl-8-(4- chlorophenylthio)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one (8) shows an emission at 510 nm and uncommon slow kinetic decay. © 2012 Elsevier Ltd. All rights reserved.

Giuliani, G., Molinari, P., Ferretti, G., Cappelli, A., Anzini, M., Vomero, S., et al. (2012). New red-shifted coelenterazine analogues with an extended electronic conjugation. TETRAHEDRON LETTERS, 53(38), 5114-5118 [10.1016/j.tetlet.2012.07.041].

New red-shifted coelenterazine analogues with an extended electronic conjugation

Giuliani, Germano;Cappelli, Andrea;Anzini, Maurizio;Vomero, Salvatore;
2012-01-01

Abstract

A new promising approach to the development of red-shifted coelenterazine analogues was described. In order to alter the photochemical properties of native coelenterazine, we have designed and synthesized analogues bearing a new electron-rich structure. The spectroscopic results obtained, in the presence of the target enzyme (Renilla Luciferase), show a bathochromic emission shift of the entire class of new derivatives. Among them, the 2-benzyl-8-(4- chlorophenylthio)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one (8) shows an emission at 510 nm and uncommon slow kinetic decay. © 2012 Elsevier Ltd. All rights reserved.
2012
TETRAHEDRON LETTERS
Giuliani, G., Molinari, P., Ferretti, G., Cappelli, A., Anzini, M., Vomero, S., et al. (2012). New red-shifted coelenterazine analogues with an extended electronic conjugation. TETRAHEDRON LETTERS, 53(38), 5114-5118 [10.1016/j.tetlet.2012.07.041].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/41852
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