Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages

Manabu Horikawa; Kazuhiro Tateda; Etsu Tuzuki; Yoshikazu Ishii; Chihiro Ueda; Tohru Takabatake; Shinichi Miyairi; Keizou Yamaguchi; Masaji Ishiguro

doi:10.1016/j.bmcl.2006.01.054

Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages

Bioorg Med Chem Lett. 2006 Apr 15;16(8):2130-3. doi: 10.1016/j.bmcl.2006.01.054. Epub 2006 Feb 7.

Authors

Manabu Horikawa¹, Kazuhiro Tateda, Etsu Tuzuki, Yoshikazu Ishii, Chihiro Ueda, Tohru Takabatake, Shinichi Miyairi, Keizou Yamaguchi, Masaji Ishiguro

Affiliation

¹ Suntory Institute for Bioorganic Research, Mishima-gun, Osaka 618-8503, Japan. horikawa@sunbor.or.jp

PMID: 16460931
DOI: 10.1016/j.bmcl.2006.01.054

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone / analogs & derivatives*
4-Butyrolactone / chemical synthesis
4-Butyrolactone / pharmacology
Apoptosis / drug effects*
Cells, Cultured
Homoserine / analogs & derivatives*
Homoserine / chemical synthesis
Homoserine / pharmacology
Hydrophobic and Hydrophilic Interactions
Macrophages / cytology
Macrophages / drug effects*
Pseudomonas / drug effects
Pseudomonas / metabolism
Structure-Activity Relationship

Substances

N-(3-oxododecanoyl)homoserine lactone
Homoserine
4-Butyrolactone