Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages.
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.
Horikawa
Manabu
M
Suntory Institute for Bioorganic Research, Mishima-gun, Osaka 618-8503, Japan. horikawa@sunbor.or.jp
Tateda
Kazuhiro
K
Tuzuki
Etsu
E
Ishii
Yoshikazu
Y
Ueda
Chihiro
C
Takabatake
Tohru
T
Miyairi
Shinichi
S
Yamaguchi
Keizou
K
Ishiguro
Masaji
M
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
C109860:N-(3-oxododecanoyl)homoserine lactone; D006714:Homoserine; D015107:4-Butyrolactone