Chemical studies on the chiral indanone derivatives as the inhibitor of Renilla luciferase

The bioluminescence reaction of coelenterazine involves an oxidative proces s. To investigate the reaction mechanism, we synthesized three mechanism-ba sed inhibitors with an indanone core structure. The inhibitors exhibited th e competitive inhibition of the Renilla luciferase reaction. The (-)-4-benz yl-2-(4-hydroxybenzyl)-2-hydroxymethyl-6-(4-hydroxyphenyl)-indan-1-one show ed the significant enantio-selectivity of the inhibition and its absolute c onfiguration was assigned as the R-configuration. These inhibitors could be useful probes to study the catalytic environment in the coelenterazine-luc iferase reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.