title: Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages.
abstract: The synthesis of the analogs of N-3-oxododecanoyl-L-homoserine lactone (1) and their structure-activity relationship for the apoptotic induction in macrophages, P388D1 cells, are described. It was revealed that the position of the oxo group in the acyl side chain in addition to the presence of the L-homoserine lactone unit is crucial for the apoptosis-inducing activity. Furthermore, the long acyl side chains with hydrophobic distal ends are preferable for the activity.
authors.affiliation: Suntory Institute for Bioorganic Research, Mishima-gun, Osaka 618-8503, Japan. horikawa@sunbor.or.jp
authors.forename: Manabu
authors.initials: M
authors.lastname: Horikawa
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Tateda
authors.forename: Etsu
authors.initials: E
authors.lastname: Tuzuki
authors.forename: Yoshikazu
authors.initials: Y
authors.lastname: Ishii
authors.forename: Chihiro
authors.initials: C
authors.lastname: Ueda
authors.forename: Tohru
authors.initials: T
authors.lastname: Takabatake
authors.forename: Shinichi
authors.initials: S
authors.lastname: Miyairi
authors.forename: Keizou
authors.initials: K
authors.lastname: Yamaguchi
authors.forename: Masaji
authors.initials: M
authors.lastname: Ishiguro
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects*; D002478:Cells, Cultured; D006714:Homoserine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D057927:Hydrophobic and Hydrophilic Interactions; D008264:Macrophages / Q000166:cytology / Q000187:drug effects*; D011549:Pseudomonas / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: C109860:N-(3-oxododecanoyl)homoserine lactone; D006714:Homoserine; D015107:4-Butyrolactone