title: Synthesis and evaluation of a cyclopropane derivative of DHMEQ.
abstract: Dehydroxymethylepoxyquinomycin (DHMEQ, 1) is well known to inhibit nuclear factor-kappa B (NF-κB), which is closely associated with immune, inflammatory, and apoptotic processes as an inducible transcription factor. The inhibitory effect seems to be the result of the ring opening of an epoxide of 1 with Cys(38) of p65. We have synthesized an analog 4 containing a cyclopropanated quinol skeleton and examined its ability to inhibit NF-κB. Surprisingly, 4 showed no remarkable NF-κB inhibitory activity as determined through expression of cyclooxygenase-2 (COX-2) in an RAW264.7 macrophage cell line.
authors.affiliation: Department of Applied Chemistry, Kogakuin University.
authors.forename: Eiko
authors.initials: E
authors.lastname: Yasui
authors.forename: Kan
authors.initials: K
authors.lastname: Takayama
authors.forename: Takahiro
authors.initials: T
authors.lastname: Nakago
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Takeda
authors.forename: Yasutada
authors.initials: Y
authors.lastname: Imamura
authors.forename: Shinji
authors.initials: S
authors.lastname: Nagumo
mesh_terms: D000818:Animals; D001549:Benzamides / Q000737:chemistry* / Q000494:pharmacology*; D002478:Cells, Cultured; D003512:Cyclohexanones / Q000737:chemistry* / Q000494:pharmacology*; D051546:Cyclooxygenase 2 / Q000096:biosynthesis; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000494:pharmacology*; D051379:Mice; D016328:NF-kappa B / Q000037:antagonists & inhibitors*
chemical_list: D001549:Benzamides; D003512:Cyclohexanones; D003521:Cyclopropanes; D016328:NF-kappa B; C464444:dehydroxymethylepoxyquinomicin; D051546:Cyclooxygenase 2