New red-shifted coelenterazine analogues with an extended electronic conjugation

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• 作者：Germano Giuliani ; Paola Molinari ; Giulia Ferretti ; Andrea Cappelli ; Maurizio Anzini ; Salvatore Vomero ; Tommaso Costa
• 关键词：Bioluminescence ; Coelenterazine ; Red-shift ; 2Y-System ; Renilla Luciferase
• 刊名：Tetrahedron Letters
• 出版年：2012
• 出版时间：19 September, 2012
• 年：2012
• 卷：53
• 期：38
• 页码：5114-5118
• 全文大小：520 K

文摘

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.